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Vacation Rentals in Pittsfield, VT and nearby

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All 125 Rentals in the Pittsfield Area
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From
$400
Per Night
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1 / 16
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Pittsfield
5 Bedrooms, 2 Bathrooms, Sleeps 11
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From
$150
Per Night
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1 / 27
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Pittsfield
4 Bedrooms, 1 Bathroom, Sleeps 9
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From
$130
Per Night
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1 / 19
Pittsfield
2 Bedrooms, 1 Bathroom, Sleeps 8
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From
$352
Per Night
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1 / 8
Pittsfield
3 Bedrooms, 2 Bathrooms, Sleeps 20
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Amenities & Details
  • Hairdryer
  • Guest Count
  • Balcony
  • Telephone
  • Mountain Views
  • Terrace
  • Number Of Bedrooms
  • Stereo System
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Come ski Killington and Pico Peak mountains while staying in this lovely Vermont Chalet located only 7 miles and a 15-minute drive from the Killington access roads. This beautiful Vermont Chalet is located on the side of a high mountain right off picturesque Route VT-100, and it enjoys a peaceful,... View all property information
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The following rentals are within 10 miles of Pittsfield, Vermont.

From
$220
Per Night
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1 / 23
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Killington
3 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Fireplace
  • Parking
  • Refrigerator
  • Stove
  • Dishwasher
  • Gym
  • DVD Player
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Ski In Ski Out 3 bedroom, 3 bath Townhouse in Sunrise Village Spacious 3 level townhouse with 2 master bedroom each with queen beds and private baths with a Jacuzzi tub and shower, all bedrooms on different levels. Main floor has open floor plan with living room with wood burning fireplace (free... View all property information
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5 of 5 stars Reviewed December 19, 2014
This house is very comfortable and well appointed. The bedrooms are large yet cozy for those seeking a quiet spot. Two of the bathrooms have jet tubs and the house has washer and...
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From
$400
Per Night
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1 / 11
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Killington
3 Bedrooms, 2 Bathrooms, Sleeps 10
Bookings
Details Make Inquiry
Amenities & Details
  • Stove
  • Grill
  • DVD Player
  • Fireplace
  • TV
  • Hot Tub
  • Washer
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
I only accept payment through the FLIPKEY System. Upscale spacious 3 bedroom Townhouse Condo with family room. Sunrise Mountain Village - 2300 ft elevation. Ski-in/ski-out. All of the comforts of home. The location and accommodations are excellent. This three bedroom town house condo (three levels)... View all property information
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From
$105
Per Night
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1 / 11
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Killington
7 Bedrooms, 3 Bathrooms, Sleeps 24
Bookings
Details Reviews (5) Make Inquiry
Amenities & Details
  • Microwave
  • TV
  • Hot Tub
  • Washer
  • DVD Player
  • Grill
  • Stove
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
The Killington Mountain Retreat is a vacation home located just off the main access road in Killington, Vermont. This three-floor, 7 bedroom home is fully equipped and furnished. In addition to the bedrooms, there is a large kitchen, living room, game room, media room, mud room and large outdoor... View all property information
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5 of 5 stars Reviewed December 8, 2014
Great place to get away with a group of friends or other couples with kids. The house is very spacious and has room to sleep a large group. It is set up in a very convenient...
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From
$85
Per Night
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1 / 14
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Killington
4 Bedrooms, 2 Bathrooms, Sleeps 12
Bookings
Details Reviews (5) Make Inquiry
Amenities & Details
  • Washer
  • Stove
  • Microwave
  • DVD Player
  • Parking
  • Dishwasher
  • Hot Tub
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
The Cabin at Killington is the perfect place to spend your Killington vacation. Located just off the main access road in Killington, VT (close to the Killington Market), the house is less than 2 miles to the mountain and close to all the stores, bars and restaurants. It's the perfect vacation spot... View all property information
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5 of 5 stars Reviewed August 13, 2013
The house was spacious, clean and had all the necessaties. Overall we had a great time. The only drawback is that you share the house with another unit, and if they stay up...
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From
$250
Per Night
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1 / 18
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Killington
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (3) Make Inquiry
Amenities & Details
  • Fireplace
  • Dishwasher
  • Washer
  • Stove
  • Parking
  • DVD Player
  • Hot Tub
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Our updated and contemporary Killington trailside condo is perfect for a family or couples getaway! Featuring 2 en-suite bedrooms with full private baths, living room with fireplace & queen sleeper, remodeled & fully appointed kitchen, high speed WIFI internet, dining area, laundry and balcony... View all property information
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5 of 5 stars Reviewed December 23, 2014
Overall: Great place to stay, which is why I gave it a 5. It was quiet, and felt like you were at home. Cleanliness: All in all, it was clean. Aside from the fact that there...
4 of 5 stars Reviewed October 11, 2014
We travel to Killington yearly and stay at the better hotels on the mountain. This year we decided to bring our three children along. Through past experience, we knew that two...
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From
$540
Per Night
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1 / 55
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Killington
3 Bedrooms, 2 Bathrooms, Sleeps 14
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Amenities & Details
  • Washer
  • TV
  • Fireplace
  • Hot Tub
  • Dishwasher
  • Refrigerator
  • DVD Player
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
The Tanglewood Estate at Killington is a 3 bedroom, 2.5 bathroom luxury home located in the Green Mountains of Killington, Vermont. This home is just off the main access road and close to all the bars, restaurants and shops of Killington and just miles to the slopes. This home features a... View all property information
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From
$400
Per Night
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1 / 12
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Killington
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
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Amenities & Details
  • Stove
  • Dishwasher
  • Microwave
  • Grill
  • DVD Player
  • Gym
  • Hot Tub
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
I only accept payment through the FLIPKEY System. Charming one-bedroom condo at Sunrise Mountain Village - 2300 ft elevation - Ski/in-ski/off location - the ski lift is literally right next to the condo - it couldn't be more convenient. TV's are available in the living room and bedroom. Large... View all property information
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From
$170
Per Night
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1 / 27
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Killington
8 Bedrooms, 4 Bathrooms, Sleeps 24
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Amenities & Details
  • Refrigerator
  • Washer
  • Grill
  • Fireplace
  • Patio
  • Microwave
  • Dishwasher
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
The Cabin at Killington is the perfect place to spend your Killington vacation. Located just off the main access road in Killington, VT (close to the Killington Market), the house is less than 2 miles to the mountain and close to all the stores, bars and restaurants. It's the perfect vacation spot... View all property information
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From
$85
Per Night
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1 / 14
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Killington
4 Bedrooms, 2 Bathrooms, Sleeps 12
Bookings
Details Make Inquiry
Amenities & Details
  • DVD Player
  • Refrigerator
  • Parking
  • Washer
  • Hot Tub
  • Dishwasher
  • Stove
  • Fireplace
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
The Cabin at Killington is the perfect place to spend your Killington vacation. Located just off the main access road in Killington, VT (close to the Killington Market), the house is less than 2 miles to the mountain and close to all the stores, bars and restaurants. It's the perfect vacation spot... View all property information
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From
$190
Per Night
View Details
1 / 4
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Killington
1 Bedroom, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • DVD Player
  • Microwave
  • Refrigerator
  • Washer
  • Gym
  • Fireplace
  • Satellite TV
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
About this property
Perfect family or couples ski vacation week from December 28, 2014 thru January 4, 2015. Nestled in the rolling Green Mountains of Vermont, this resort is one minute away from Killington Ski Resorts fastest Gondola. Enjoy the experience of great restaurants, the best skiing in the east, heated... View all property information
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From
$138
Per Night
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1 / 12
Killington
2 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Deck
  • Internet Access
  • TV
  • Wi-Fi
  • Gym
  • Linens Provided
  • Parking
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Killington, Vermont- Whiffletree: Whiffletree Condominiums are centrally located in the heart of Killington's main basin area. In winter, a shuttle runs to Snowshed lodge, only 1/2 mile away, and enjoy ski home access provided if there is enough natural snow. These neat and tidy 2 BR/1BA... View all property information
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From
$350
Per Night
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1 / 10
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Killington
3 Bedrooms, 2 Bathrooms, Sleeps 10
Bookings
Details Make Inquiry
Amenities & Details
  • TV
  • Stove
  • Dryer
  • Gym
  • Washer
  • Microwave
  • Hot Tub
  • VCR
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Conviently located in Pinnacle’s E building on Killington grounds, a 3 bedroom, 2 bath townhouse condo can sleep 10 people and has all the amenities of home. A free shuttle that loops every 15min picks you up right at the end of the building (50yds from the front door) to take you to the main... View all property information
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From
$500
Per Night
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1 / 18
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Mendon
7 Bedrooms, 6 Bathrooms, Sleeps 20
Bookings
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Amenities & Details
  • Parking
  • Dishwasher
  • Grill
  • DVD Player
  • Washer
  • Microwave
  • Patio
  • Hot Tub
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
New Large 7 Bedroom 6.5 Bathroom home with large wrap around deck, with Mountain Views, and easy access. View all property information
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From
$650
Per Night
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1 / 17
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Mendon
5 Bedrooms, 3 Bathrooms, Sleeps 16
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Amenities & Details
  • Fireplace
  • Microwave
  • Washer
  • Hot Tub
  • Grill
  • Dishwasher
  • TV
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This Charming Home has Gorgeous Mountain Views, overlooking it's own Pond with water wheel house. A beautiful Marble front fireplace in Dinning Room, and wood stove in Livingroom. On a tar road with straight in driveway on US Route 4 about three minutes to Pico Ski Area and about seven minutes to... View all property information
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From
$150
Per Night
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1 / 4
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Killington
2 Bedrooms, 1 Bathroom, Sleeps 3
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Amenities & Details
  • Waterfront
  • Microwave
  • Central Heating
  • Dishwasher
  • Washer
  • Deck
  • Mountain Views
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Our Killington apartment is the perfect all-season getaway located in the mountains of Killington, VT. During the winter Killington offers some of the best skiing and riding in the Northeast. The spring and summer bring beautiful scenery and mountain breezes that are the perfect escape from the... View all property information
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From
$280
Per Night
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1 / 12
Killington
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (1) Make Inquiry
Amenities & Details
  • TV
  • Satellite TV
  • Hot Tub
  • Sauna
  • Wi-Fi
  • Gym
  • Dishwasher
  • Deck
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Killington, Vermont- Sunrise Complex Enjoy one of Killington’s few Ski on Ski off developments. As a guest put it “Staying at Sunrise you can have it all.” Sunrise is an ideal area for families, couples, and groups who want to get away from the crowds of Killington's main mountain. Enjoy access to... View all property information
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5 of 5 stars Reviewed September 24, 2014
Several times I had questions about the unit and the owner was an email away. I always received a quick response and she was very willing to help or work with me on our check-out...
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From
$800
Per Night
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1 / 10
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Chittenden
5 Bedrooms, 4 Bathrooms, Sleeps 18
Booking
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Amenities & Details
  • Parking
  • Air Conditioning
  • Deck
  • Dishwasher
  • DVD Player
  • Stove
  • Fireplace
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Enjoy over 4,500 square feet of luxury mountain living featuring 5 bedrooms and 3 full and 2 half baths - plus over 700 square ft of mahogany deck and screened porch and 3 fireplaces. Take a left out your front door and the Mountain Top Inn & Resort is a short walk away. Take a right and you enter... View all property information
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From
$500
Per Night
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1 / 5
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Chittenden
3 Bedrooms, 4 Bathrooms, Sleeps 6
Details Reviews (1) Make Inquiry
Amenities & Details
  • Patio
  • Dishwasher
  • Stove
  • Porch
  • Grill
  • DVD Player
  • Microwave
  • Stereo System
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Enjoy this spectacular spacious, open-plan, single level home; furnished with antiques and fine furniture. You'll be just a short walk to all activities and to the Main Lodge. Incomparable panoramic views of the lake and Green Mountain National Forest. Very private setting. Cable television... View all property information
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5 of 5 stars Reviewed June 9, 2014
White Birches is a beautiful home well appointed to mirror the surrounding environment. We stayed there for a few days during the kids February vacation. White Birches is...
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From
$800
Per Night
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1 / 9
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Chittenden
4 Bedrooms, 4 Bathrooms, Sleeps 12
Booking
Details Reviews (1) Make Inquiry
Amenities & Details
  • Stereo System
  • Dishwasher
  • Parking
  • DVD Player
  • Stove
  • Grill
  • Fireplace
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
'The Jewel' features the best of a classic mountain lodge: soaring spaces, fascinating design elements and understated elegance all blending seamlessly in its idyllic environment - complete with spectacular Green Mountain vistas. 4,400 square feet of living space on two levels featuring 4 guest... View all property information
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From
$400
Per Night
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1 / 6
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Chittenden
4 Bedrooms, 2 Bathrooms, Sleeps 10
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Amenities & Details
  • Guest Count
  • # Of Bathrooms
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Beautiful 4 bedroom chalet home with great views of the mountains. Ideal for riding, skiing, and hiking enthusiasts, this chalet offers quick access to the trails. 2 bedrooms each with a Queen bed, one bedroom with 2 Twin beds and one bedroom with 2 sets of bunk beds...great for the kids! 2 Full... View all property information
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From
$240
Per Night
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1 / 20
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Barnard
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Ceiling Fans
  • Refrigerator
  • Fireplace
  • Grill
  • Parking
  • Stove
  • Dishwasher
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
'Sanctuary' describes this green-built, two-story log home perfectly. Peaceful, quiet, nestled on a wooded mountainside in Vermont, it's the superlative setting to escape the noise of everyday life. A fully furnished screened back porch, complete with soft patio lights, padded porch swing, and... View all property information
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5 of 5 stars Reviewed November 3, 2014
In early October I stayed at Heidi's place with two of my sisters and our spouses. What an awesome place! When we arrived, there were lights on and a welcoming note left by...
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From
$450
Per Night
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1 / 20
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Killington
3 Bedrooms, 3 Bathrooms, Sleeps 6
Booking
Details Make Inquiry
Amenities & Details
  • Microwave
  • Safe
  • Dishwasher
  • Washer
  • Refrigerator
  • Gym
  • Fireplace
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Convenient location awaits...Just 3 hours from Boston, 4 hours from NYC and 1.5 hours from Burlington, VT & Concord, NH 'The Woods', Killington's premier destination spa and resort, awaits you this Ski Season! We have a spacious, multi-level, 3 bedroom, 3.5 bath plus loft townhouse. The condo is... View all property information
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From
$99
Per Night
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1 / 5
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Barnard
Studio, 1 Bathroom, Sleeps 2
Details Reviews (3) Make Inquiry
Amenities & Details
  • # Of Bathrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Charming studio cabin in an apple orchard, with stone fireplace, bath with shower, kitchenette, sleeps two, short walk to Silver Lake and quintessential Vermont village center. View all property information
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5 of 5 stars Reviewed July 27, 2014
This cabin is as warm and welcoming as its owner! Barnard is a quaint town in Vermont with access to one of the cleanest lakes in the state, a general store (with great ice cream...
5 of 5 stars Reviewed July 26, 2014
Thank you Doreen for the wonderful hospitality and the opportunity to stay in the red cabin. I absolutely loved the comfort and simplicity of the cabin. I couldn't ask for a...
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From
$200
Per Night
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1 / 16
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Rochester
4 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
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Amenities & Details
  • Number Of Bedrooms
  • # Of Bathrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Spacious four bedroom home with river front access and beautiful mountain views. It's a short walk to the quaint village of Rochester, VT. with cafes, pubs and shopping. The house comfortably sleeps six with complete kitchen and bed linens provided. Come see the fall foliage or ski one of four... View all property information
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4 of 5 stars Reviewed January 6, 2015
We stayed at Linda's wonderful Home in Rochester from 31 Dec to 4 Jan 2015 (skiing at Killington). It is an older property, but had so many unique features (and some wonderful...
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From
$125
Per Night
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1 / 15
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Killington
1 Bedroom, 1 Bathroom, Sleeps 6
Booking
Details Reviews (1) Make Inquiry
Amenities & Details
  • Hot Tub
  • Microwave
  • Sauna
  • Fireplace
  • Dishwasher
  • TV
  • Satellite TV
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
As an architect and designer by trade, we have been working to bring our condo up to the 21st century, while maintaining the coziness that you find in a mountain getaway. The bedroom features a brand new Queen sized bed and a television. The living space features a custom designed Full Sized... View all property information
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4 of 5 stars Reviewed January 4, 2015
The condo was VERY CLEAN and stocked with all the essentials you need. For a pet friendly condo this was top notch! After a long day of skiing it was nice to be able to access the...
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From
$275
Per Night
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1 / 10
Killington
4 Bedrooms, 2 Bathrooms, Sleeps 10
Details Make Inquiry
Amenities & Details
  • Guest Count
  • Number Of Bedrooms
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Snow King - Four bedroom Townhouse just minutes to Killington Base Lodges. This property is can also be rented with Snow Queen if available. Main Level Fully equipped Kitchen - dishwasher, microwave Dining Area seat 6 Bar with seating for 3 Living room with 46' Flat screen TV VCR/DVD player Propane... View all property information
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From
$2,295
Per Week
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1 / 7
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Killington
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Microwave
  • TV
  • Dishwasher
  • Stereo System
  • Parking
  • Stove
  • Dryer
  • Fireplace
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Ski the largest and best sow-making mountain in the Eastern USA. Steps from amazing bars and restaurants. Wonderful 2 bedr. - 2 baths duplex- sleep 6. Fireplace (free wood), 2 flat screen TVs, free internet and local calls and fully equipped kitchen. Located right on the Killington Access Road.... View all property information
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From
$300
Per Night
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1 / 11
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Killington
4 Bedrooms, 2 Bathrooms, Sleeps 9
Details Make Inquiry
Amenities & Details
  • Fireplace
  • Washer
  • Refrigerator
  • Parking
  • Grill
  • TV
  • Dishwasher
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Just minutes from the slopes, the Sundowner is the perfect place to wind down from a great day skiing/snowboarding. Enjoy apres ski with friends and family in the hot tub while enjoying a colorful sunset, the views of Pico's mountaintop trails or an unexpected snow squall. The main level... View all property information
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From
$375
Per Night
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1 / 10
Killington
4 Bedrooms, 2 Bathrooms, Sleeps 10
Details Reviews (8) Make Inquiry
Amenities & Details
  • Dishwasher
  • Hot Tub
  • Fireplace
  • Refrigerator
  • Parking
  • DVD Player
  • Stove
  • VCR
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
About this property
The Dew Drop Inn, Winter Ski House is Charming & Cozy. It is in the valley surrounded by Scenic Mountain Views. There is an Outdoor Hot Tub in the back of the house. It is 1 mile from Killington's worlds famous high speed 'Skyeship Base Lodge GONDOLA' (8 passenger- hi speed Gondola that takes... View all property information
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5 of 5 stars Reviewed February 27, 2015
Thank you so much for letting us stay at The Dew Drop Inn! It was such an amazing time and everyone had only the best things to say about your place. It was even better than...
5 of 5 stars Reviewed February 23, 2015
The property is clean, well maintained and very comfortable; the showers are hot and powerful, the fire is toasty and the hot tub is great. There was plenty of room for 10...
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From
$550
Per Night
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1 / 18
Killington
5 Bedrooms, 3 Bathrooms, Sleeps 12
Booking
Details Reviews (8) Make Inquiry
Amenities & Details
  • Washer
  • Refrigerator
  • Fireplace
  • Grill
  • Parking
  • Microwave
  • Hot Tub
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This house on Killington has it all. With scenic mountain views in all directions, this contemporary 14-room home is located on Sunrise Mountain, one of Killington's six peaks. It's just a 50-yard walk to the ski trail that provides direct access to Killington's 200 slopes and trails. The home is... View all property information
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5 of 5 stars Reviewed January 30, 2015
Great location (ski in, and almost ski out). Nicely furnished especially kitchen. Spacious, surprisingly so from outside appearance. Well maintained. Owner easy to work with.
5 of 5 stars Reviewed February 19, 2014
I found a perfect house to stay in for my family and friends for our Christmas holiday break. Was exactly what I was looking for: cozy and warm and close to the trails which was a...
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From
$170
Per Night
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1 / 19
Killington
3 Bedrooms, 2 Bathrooms, Sleeps 9
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Amenities & Details
  • Fireplace
  • DVD Player
  • Linens Provided
  • TV
  • Satellite TV
  • Wi-Fi
  • Gym
  • Internet Access
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
The region's best kept secret, the North Side Condominiums are located in a private setting directly across from the Pico Ski Area! In addition to a great location, for skiing, hiking, and local activities these properties have great floor plans and amenities that you and your company will be sure... View all property information
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From
$2,500
Per Night
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1 / 62
Killington
12 Bedrooms, 12 Bathrooms, Sleeps 30
Details Reviews (1) Make Inquiry
Amenities & Details
  • Number Of Bedrooms
  • # Of Bathrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Killington Big House is a large luxury vacation rental house renovated in 2011 and fully upgraded, located in Killington, Vermont, that can accommodate family get-togethers, corporate retreats or large groups of up to 30 persons. With a total of 12 bedrooms and 12 bathrooms, big groups can “Come... View all property information
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5 of 5 stars Reviewed January 5, 2014
What a wonderful place for our group of 19 four families in total. We are skiers ( most of us) and always stay on the mountain this was the first time we would have to drive to...
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From
$500
Per Night
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1 / 20
Rochester
5 Bedrooms, 2 Bathrooms, Sleeps 19
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Amenities & Details
  • Patio
  • Hot Tub
  • DVD Player
  • Refrigerator
  • Grill
  • Microwave
  • TV
  • Fireplace
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
**CALL FOR REDUCED PRICE FOR SCHOOL VACATION WEEK 2/16-20 AND 2/22 AND AFTER** Situated on 10 beautiful acres with two ponds, a brook with a water hole, and views of the Green Mountains. Inside, you will find a warm spacious atmosphere, where a large family or group will feel right at home... View all property information
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From
$278
Per Night
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1 / 9
Killington
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (1) Make Inquiry
Amenities & Details
  • Washer
  • Satellite TV
  • Fireplace
  • Parking
  • Patio
  • Dryer
  • Wi-Fi
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
3 Bedroom/2 bath (sleeps 8) Nicely Decorated Slopeside Pico Condo! Walk to the Slopes! Great Views! On Site Sports Center, Wood Burning Fireplace, WiFi and Washer/Dryer. Spend a great family vacation in the Killington Valley away from the crowds of big mountain skiing & riding. Enjoy the laid back,... View all property information
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5 of 5 stars Reviewed January 22, 2014
For MLK Weekend my boyfriend and three other couples stayed in this 3 bedroom/2 bath condo. Truly a ski-in/ski-out to Pico Mountain, wewalked two minutes to the lifts. The condo...
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From
$278
Per Night
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1 / 15
Killington
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (1) Make Inquiry
Amenities & Details
  • Dishwasher
  • TV
  • Refrigerator
  • Fireplace
  • Microwave
  • Dryer
  • DVD Player
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Three Bedroom Slopeside (sleeps 8) Beautifully Decorated Condo at Pico Ski Resort! Ski home right to your back door! Spend a great family vacation in the Killington Valley away from the crowds of big mountain skiing & riding. Enjoy the laid back, quiet atmosphere of Pico Mountain featuring 50... View all property information
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5 of 5 stars Reviewed January 25, 2014
Booked this condo for MLK weekend to share with 6 friends. It was perfect. There was enough space for us to hang comfortably. The condo had a stocked (utensils, pots, pants...
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From
$192
Per Night
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1 / 24
Killington
1 Bedroom, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Towels Provided
  • DVD Player
  • Fireplace
  • Deck
  • Linens Provided
  • Satellite TV
  • Hot Tub
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
A truly unique Vermont log cabin, tucked quietly away so you may enjoy the soothing sounds of nature and the brook from the porch. Don’t let the privacy fool you, this property is located on Dean Hill Road and a mile from the Killington Access road. You will enjoy luxuries and exquisite... View all property information
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From
$325
Per Night
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1 / 17
Killington
3 Bedrooms, 3 Bathrooms, Sleeps 10
Details Reviews (2) Make Inquiry
Amenities & Details
  • DVD Player
  • Microwave
  • Dishwasher
  • Wi-Fi
  • Hot Tub
  • Fireplace
  • Parking
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
3 Bedroom Plus Loft Private Home on Ski Trail with Hot Tub! Start your ski day on the Great Eastern ski trail which is in the back yard. The living room has floor to ceiling windows offering panoramic views. The upper level loft, which has a bedroom with a private bath, overlooks the living room.... View all property information
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4 of 5 stars Reviewed December 31, 2013
coz the owners themselves were the ones who'll see what your needs are, attends to whatever concerns you have and from time to time gave us tips on the wheres, whats & hows in...
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From
$135
Per Night
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1 / 7
Killington
2 Bedrooms, 2 Bathrooms, Sleeps 7
Details Reviews (1) Make Inquiry
Amenities & Details
  • Parking
  • Dishwasher
  • Microwave
  • TV
  • DVD Player
  • Paper Towels...
  • Linens Provided
  • Wi-Fi
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
2 Bedroom/2 Bathroom Northbrook Townhouse (sleeps 7). Economical and convenient location! Only 3.5 miles from Killington Ski Resort Snowshed Base Lodge Area. Main Level Living room w/Queen sofa bed, 25' TV/DVD Dining area seats 6 Large Stone Fireplace with Gas Burner Kitchen - Electric Stove -... View all property information
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2 of 5 stars Reviewed January 19, 2015
I have stayed at this property numerous times with no issues. It is adequate and comfortable. What is unforgivable is my most recent dealings with the property manager...
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From
$125
Per Night
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1 / 10
Killington
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Refrigerator
  • Parking
  • Satellite TV
  • Stove
  • Hairdryer
  • TV
  • Patio
  • Wi-Fi
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
1 Bedroom updated Edgemont Condo (sleeps 4) - This property is exceptionally decorated. Wood stove, with radiant heated floors. Enjoy the 50' flat screen HDTV in the living room. Ski right home when you stay at Edgemont...located at the end of a trail coming from Snowshed. Or take advantage of the... View all property information
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From
$587
Per Night
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1 / 18
Killington
3 Bedrooms, 2 Bathrooms, Sleeps 10
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Amenities & Details
  • # Of Bathrooms
  • Number Of Bedrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Enjoy this newly Furnished two bedroom plus loft private home with outdoor hot tub. This wonderful property is close to everything - skiing, nightlife, restaurants and golf in the summer months. Main Level Kitchen - Fully Equipped Dining Area - Seats 10 Living Room - beautiful wood burning... View all property information
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From
$200
Per Night
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1 / 29
Killington
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • TV
  • Linens Provided
  • Towels Provided
  • Fireplace
  • DVD Player
  • Deck
  • Satellite TV
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Mountainside Lodge is an incredible 3000 square feet of living space with a huge living room, open floor plan, large kitchen, large field stone fireplace (gas) and wrap around deck make this hideaway ideal for your group. Mountainside Lodge is a country home with plenty of room. On the main level... View all property information
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From
$875
Per Night
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1 / 12
Killington
5 Bedrooms, 3 Bathrooms, Sleeps 18
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Amenities & Details
  • # Of Bathrooms
  • Guest Count
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Beautiful Renovated Country home with restored pine floors, 5 bedrooms with flat screen TV's in each. Gorgeous fireplace with large flat screen TV. Main Level Kitchen - fully equipped kitchen - gas cooking stove Microwave Dishwasher All new stainless Steel Appliances Living room with large wood... View all property information
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From
$140
Per Night
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1 / 7
Killington
1 Bedroom, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Parking
  • Wi-Fi
  • Dryer
  • Satellite TV
  • DVD Player
  • Washer
  • Microwave
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
1 Bedroom Plus Loft (sleeps 6) across from Pico Mountain! The region's best kept secret, the Northside Condos are located in a secluded setting directly across for the Pico Ski Area and just a short drive to the main Killington base lodges. This clean comfortable unit features stunning views of... View all property information
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From
$595
Per Night
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1 / 14
Killington
3 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Wi-Fi
  • Toaster
  • Guest Count
  • # Of Bathrooms
  • Number Of Bedrooms
  • TV
  • Microwave
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Come Stay minutes from Killington Ski Area in a nicely furnished home just seconds from Killington's Skyship Base Lodge. The first floor has a large eat-in kitchen, living room, library that has a custom built full size Murphy bed to make the first floor private bedroom, laundry room, and full... View all property information
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From
$225
Per Night
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1 / 18
Killington
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Washer
  • Microwave
  • Dryer
  • Parking
  • Hot Tub
  • DVD Player
  • Fireplace
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
2 Bedroom/2 Bath (sleeps 6) Village Unit at the Woods Resort & Spa -- Located on Killington’s Access Road. Guests are only a stone’s throw from all that Killington has to offer. Featuring a whirlpool tub, wood burning fireplace, equipped kitchen, washer/dryer and high speed internet connection,... View all property information
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From
$139
Per Night
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1 / 20
Killington
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • # Of Bathrooms
  • Gym
  • TV
  • DVD Player
  • Number Of Bedrooms
  • Shared Outdoor Pool...
  • Deck
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Killington, Vermont-Pico The small mountain charm of Pico Mountain, In the winter you will enjoy a family friendly mountain and the convenience of walking or skiing to the slopes offering 48 trails and 7 lifts for a fun filled day of skiing or snowboarding. Also, onsite you can have access to the... View all property information
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Suitability

  • Wheelchair access (3)
  • Elder access (11)
  • Suitable for children (10)
  • Pet friendly (23)
  • Smoking allowed (1)

Amenities

  • Other outdoor space (96)
  • Fireplace (88)
  • Parking (79)
  • Internet (63)
  • Hot Tub (59)
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