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Vacation Rentals in Pittsfield, MA and nearby

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All 30 Rentals in the Pittsfield Area
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From
$130
Per Night
1 / 20
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Pittsfield
3 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
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From
$171
Per Night
1 / 14
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Pittsfield
3 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$100
Per Night
1 / 8
Pittsfield
1 Bedroom, 1 Bathroom, Sleeps 5
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The following rentals are within 10 miles of Pittsfield, Massachusetts.

From
$150
Per Night
1 / 21
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Lenox
4 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
Details Reviews (18) Make Inquiry
Amenities & Details
  • Washer
  • Stereo System
  • Parking
  • Refrigerator
  • Stove
  • Microwave
  • DVD Player
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Located on a quiet side street in the charming Berkshire town of Lenox, Gartner House is a great place to call home while exploring this scenic, historical, and culturally rich area of Western Massachusetts. Walk to breakfast, lunch or dinner at one of the town's many charming restaurants, explore... View all property information
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5 of 5 stars Reviewed October 22, 2014
We spent the weekend at the Gartner House in Lenox to visit my son at Shakespeare and Company. From my first contact with Deb, she was friendly and helpful. It is evident...
4 of 5 stars Reviewed October 20, 2014
I visited Lenox on a girls leaf peeping trip in mid-October. We found this house to be cozy & warm. It is very quaint & centrally located. It was nice to have most of the comforts...
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From
$225
Per Night
1 / 11
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Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Make Inquiry
Amenities & Details
  • Grill
  • Microwave
  • Dishwasher
  • Dryer
  • Refrigerator
  • Hot Tub
  • TV
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Bentley Brook is a ski in/ski out resort located at the base of Jiminy Peak ski resort. On-site Amenities Include: Heated Indoor/Outdoor Pool (year round), 3 hot tubs, 'Get out & Play ' children's program, 3 tennis courts, game room, exercise equipment, sauna, theater with nightly movies.. At... View all property information
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From
$242
Per Night
1 / 15
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Lenox
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • Fireplace
  • Dryer
  • VCR
  • Refrigerator
  • Parking
  • Grill
  • Stereo System
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
In the heart of Lenox, this 2 BR plus study (can be used as a 3BR) house offers the best of both worlds. On nearly 2 park-like acres, the house is a peaceful place for rest and relaxation. But there's much to do nearby. The town center of Lenox is within easy walking distance so you'll be close... View all property information
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From
$400
Per Night
1 / 24
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Lenox
4 Bedrooms, 2 Bathrooms, Sleeps 10
Details Make Inquiry
Amenities & Details
  • Washer
  • Grill
  • Dishwasher
  • Stove
  • Parking
  • Hot Tub
  • Microwave
  • Fireplace
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
220+ Acres W\ Tennis Cts, Indoor / Outdoor Pool, Canoe, Fishing Boat, Hot Tub. New first time rental of 4 BR, 2BA, Cape Cod style, sleeps 10-12. New fully equipped kitchen w/ center island, indoor and outdoor barbecues, wine cooler, 2 fireplaces, large deck with 8 person hot tub and super seating... View all property information
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From
$155
Per Night
1 / 10
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Lanesboro
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (12) Make Inquiry
Amenities & Details
  • Ceiling Fans
  • Stove
  • Internet Access
  • Swingset
  • Microwave
  • VCR
  • Refrigerator
  • Safe
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
If you’ve driven by, you’ve wondered about the story of this beautiful stone building. Built in 1832 as a one-room schoolhouse – a function it served until 1950 -- this charming and historic building has been given new life as a vacation getaway. It is perfect for romantic weekends or family... View all property information
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5 of 5 stars Reviewed July 7, 2014
We were lucky to happen upon this gem, and highly recommend it to families visiting the area of Mt. Greylock. Great on a rainy day, and interesting for all given the history of...
5 of 5 stars Reviewed May 30, 2014
We have stayed in several vacation rentals, and this one was extremely charming. The very first time I saw this one I just knew we had to vacation here while we were in The...
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From
$179
Per Night
1 / 16
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Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Washer
  • Hot Tub
  • Microwave
  • DVD Player
  • Refrigerator
  • Stove
  • Sauna
  • Pool
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
A fully furnished and nicely appointed 2br/2ba suite. There's a full kitchen, living room with sofa sleeper, king bed in master bedroom, 2nd bedroom has either a king bed or two queen size beds(varies), washer/dryer, private balcony with mountain or valley views. Everything you need on your... View all property information
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4 of 5 stars Reviewed October 25, 2014
Lovely place with pool, spa, gym, and movie theater. Units are a bit noisy between floors but otherwise nice and quiet. We had the unfortunate experience of having three small...
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From
$135
Per Night
1 / 11
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Richmond
3 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (4) Make Inquiry
Amenities & Details
  • VCR
  • Dishwasher
  • Grill
  • Washer
  • Stove
  • Refrigerator
  • Microwave
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Fantastic spot for families and for those looking for a quiet getaway. Come have some summer fun, enjoy the autumn colors or play in the snow. This year round cottage is the perfect spot for those who enjoy outdoor activities. The house is on a private dead end road, has a wonderful lake view... View all property information
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From
$134
Per Night
1 / 13
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Hancock
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Washer
  • Fireplace
  • Dishwasher
  • Parking
  • DVD Player
  • Refrigerator
  • Gym
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Luxury condo in hancock, ma ....Three bedrooms, loft, 2 baths, living room, kitchen with dining area, a/c, deck w/grill et al, heated pool, tennis court, mountain view. Near williamstown theater, clark art museum, tanglewood and three local golf courses. View all property information
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From
$145
Per Night
1 / 16
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Hancock
1 Bedroom, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Grill
  • Dishwasher
  • Safe
  • TV
  • Microwave
  • Fireplace
  • Patio
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Low long term rates. Call $2500/mo for 3 months. Free Electric Vehicle Charging Station! (240V 40A no J1772) Thanksgiving Special - Nov 24 - Dec 1 - $500 Christmas Special - Dec 20 - Dec 27 - $800 Ski Season Dec 1 - Mar 31 $8000 April $50/nt Summer Cultural May 26, 2014 - Seot 2, 2014 $7500 Summer... View all property information
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5 of 5 stars Reviewed October 16, 2014
This property is perfect for people with pets. Serene setting with a gorgeous view. The hosts, Tom and Susan, were gracious and very helpful. Highly recommended if your travels...
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From
$200
Per Night
1 / 19
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Cheshire
2 Bedrooms, 1 Bathroom, Sleeps 5
Details Make Inquiry
Amenities & Details
  • Microwave
  • Stove
  • VCR
  • Patio
  • Parking
  • Refrigerator
  • Garage
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Comfortable house situated on the shore of Hoosac Lake with beautiful, long views stretching across the large lake. It's fully furnished, with cable TV, stereo, and high-speed Internet. There's a big kitchen, with a central island for dining. The expansive living/dining room and attached study,... View all property information
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From
$450
Per Night
1 / 20
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Richmond
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Fireplace
  • Stove
  • Grill
  • Garage
  • Washer
  • Dishwasher
  • Refrigerator
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Newly furnished 3 bedroom (with AC) & 2 1/2 bath single family home with stunning deck and in ground pool nestled in the quiet countryside opposite a horse farm. Situated minutes from West Stockbridge convenience stores and restaurants. Property is on 2 quiet tree lined acres with an enclosed... View all property information
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From
$500
Per Night
1 / 18
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Hinsdale
4 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
Details Make Inquiry
Amenities & Details
  • Dryer
  • Stove
  • Grill
  • Microwave
  • Parking
  • DVD Player
  • Refrigerator
  • Hot Tub
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
The best place in the world to watch the sunset! Set up high on a hill and nestled amidst the pine trees, this four year old, private and spacious contemporary home overlooks Lake Ashmere (across the road) in Hindsdale. The great room with cathedral ceilings and a wall of windows overlooking the... View all property information
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From
$150
Per Night
1 / 15
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Dalton
5 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Inquiry
Amenities & Details
  • # Of Bathrooms
  • Number Of Bedrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
The Cottage at Holiday Farm is a gorgeous place to spend the month, week or a mini-break weekend. Centered in the heart of a real, working farm there are miles of wooded trails and farm roads right outside the door. You can wander the farm, enjoy seasonal sports activities from cross-country skiing... View all property information
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From
$225
Per Night
1 / 14
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Hancock
4 Bedrooms, 2 Bathrooms, Sleeps 10
Details Reviews (3) Make Inquiry
Amenities & Details
  • Garage
  • DVD Player
  • Microwave
  • Fireplace
  • Hot Tub
  • Washer
  • Stove
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Come and enjoy our beautiful mountain retreat - A home for every season. This charming home away from home is a wonderful place for family, friends and romance. Only 3 minutes from Jiminy Peak! With over 2200 square feet, this new country home has plenty of space for everyone yet a very cozy... View all property information
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From
$250
Per Night
1 / 12
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Lenox
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Ceiling Fans
  • Washer
  • Stove
  • Dishwasher
  • DVD Player
  • Dryer
  • Grill
  • Garage
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Charming, spacious and comfortable 1860's farmhouse adjacent to wildlife sanctuary. Cozy country decor with original wide plank floors, lovely views and outdoor dining or lounging on porch or deck. Walking distance to hiking trails in Pleasant Valley Wildlife Preserve or Kennedy Park. Quiet and... View all property information
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From
$300
Per Night
1 / 12
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Washington
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Guest Count
  • # Of Bathrooms
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Shingle style, timber frame, passive solar, Berkshie 'Cottage' Built along side of Coles Brook, the manor is a retreat destination any time of the year. The seclusion and tranquility of the custom built home and site are unique and comforting for family gatherings and weekend getaways. View all property information
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From
$130
Per Night
1 / 8
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Hinsdale
3 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
Details Make Inquiry
Amenities & Details
  • Washer
  • Parking
  • TV
  • Refrigerator
  • Safe
  • VCR
  • Stereo System
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Located on 19 acres of forest and a creek, mixing modern and traditional with a charming two story wall of windows overlooking a back deck. This comfortable furnished home has two bedrooms with an additional open loft area for a third bedroom, two baths, all hardwood floors, and contains a large... View all property information
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From
$250
Per Night
1 / 7
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Lenox
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Satellite TV
  • Air Conditioning
  • Stove
  • Central Heating
  • Grill
  • Microwave
  • Fireplace
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
This cozy cottage located in the heart of the Berkshires is located just 5 minutes fom Tanglewood, Shakespeare and Company, Lenox center, and Stockbridge bowl. If the wind is blowing in the right direction, you can hear the Boston Symphony rehearsing. My home was built in the 1940s, and offers all... View all property information
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From
$250
Per Night
1 / 14
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Lenox
2 Bedrooms, 1 Bathroom, Sleeps 5
Details Make Inquiry
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
This summer cottage built in the 1950's has recently been completely renovated from stem to stern to bring it up to date with the most current design standards. It is a 2-bedroom, 1-bathroom space with a beautiful backyard for grilling. There is also an amazing dining room surrounded by windows... View all property information
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From
$275
Per Night
1 / 18
Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (7) Make Inquiry
Amenities & Details
  • Microwave
  • Satellite TV
  • Refrigerator
  • Stove
  • Hot Tub
  • VCR
  • Dryer
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
On-site Amenities Include: Heated Indoor/Outdoor Pool (year round), Alpine Slide (warmer months), Berkshire Express Chairlift to Summit Lodge during ski season. The Berkshire Express provides scenic rides during warmer months. Bentley Brook is situated Slope Side for SKI/IN - SKI/OUT all winter... View all property information
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5 of 5 stars Reviewed August 1, 2013
Really nice accommodations & the staff was amazing, going out of their way to help in any way possible. Easy access to Jiminy Peak, which was full of activities for the...
5 of 5 stars Reviewed January 31, 2013
We spent time at Bentley Brook with "Kids" and the "Grands". Loved the 2BR, 2B with full K and really nice LR. Immaculate, extremely well equipped and spacious. The convenience...
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From
$140
Per Night
1 / 7
Richmond
3 Bedrooms, 1 Bathroom, Sleeps 7
Details Reviews (1) Make Inquiry
Amenities & Details
  • Satellite TV
  • TV
  • DVD Player
  • Microwave
  • Terrace
  • Balcony
  • Refrigerator
  • Internet Access
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
The Berkshires, in Western Massachusetts, are known as center of cultural activities, including but not limited to Tanglewood (the summer home of the Boston Symphony Orchestra), Shakespeare Theatre Festival, Jacobs Pillow, Williamstown Theatre Festival, plus numerous recreational opportunities for... View all property information
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2 of 5 stars Reviewed September 10, 2014
I recently rented this vacation rental with a couple friends to go to Tanglewood and Kripalu. While the house has a lot of potential, it has been very poorly maintained. The...
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From
$250
Per Night
1 / 10
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Richmond
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Number Of Bedrooms
  • Guest Count
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
In 1832, Josiah Loomis bought a parcel of land 'and the structures thereon', along what was then known as 'Massachusetts Turnpike No. 10,' the toll road between Albany, NY and Hartford, CT. Josiah Loomis, when he owned this property, could never have imagined what it would look like 180 years... View all property information
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From
$72
Per Night
1 / 27
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Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (2) Make Inquiry
Amenities & Details
  • Dryer
  • Iron
  • Hairdryer
  • Central Heating
  • Towels Provided
  • Air Conditioning
  • Safe
  • Sauna
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
The Two-Bedroom Condos are the ultimate Hancock, Massachusetts vacation retreat. Apart from two ultra-spacious private bedrooms and two oversized bathrooms, take advantage of the washer and dryer and fully equipped kitchen for additional travel savings. Create fun filled memories just minutes from... View all property information
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4 of 5 stars Reviewed September 18, 2014
What a pleasant and wonderful stay. This is the second Wyndham resort we have stayed at. We had asked for a room on the top floor with a view and that was exacly what we got...
4 of 5 stars Reviewed August 19, 2014
The condo has a full kitchen and living room, making it pleasant to gather with family and/or friends in the evening or on a rainy day.
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From
$250
Per Night
1 / 7
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Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Two Bedroom Ski Condo at base of Jiminy Peak. Renovated kitchen, fireplace, deck and a large livingroom with vaulted ceilings. Rent from the owner and save. View all property information
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Inquire for rates
1 / 4
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Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Grill
  • Dishwasher
  • Washer
  • Garage
  • Parking
  • Stove
  • Safe
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Cozy ranch home 3 miles away from Jiminy Peak Ski Resort. Near MASS MOCA, Clark Art Institute, Williams College Contemperary Museum of Art, Williamstown Theatre Festival, Tanglewood, shopping, golf courses. Wrap around deck with beautiful mountain views. Family room with full wet bar & flat screen... View all property information
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4 of 5 stars Reviewed August 11, 2013
Aside from the excessive amount of men's shirts in the closets (closets and drawers had not been emptied so storage space was minimal), the full trash bins and dirty dishes...
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1 / 12
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Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Reviews (1) Make Inquiry
Amenities & Details
  • Dishwasher
  • Parking
  • Refrigerator
  • Air Conditioning
  • Safe
  • Satellite TV
  • Stove
  • Balcony
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
7 hour drive from NYC and neighboring New Jersey, Wyndham Bentley Brook is the best place to ski in New England. This two bedroom Condo has 2 large bedrooms, two baths, kitchen/dining room with seating for up to 6 people. No need to hang your ski clothes to dry when you get in off the slopes, it... View all property information
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4 of 5 stars Reviewed July 21, 2014
The condo was great - clean, roomy, stocked with expected items (towels, linens, shampoos, etc.) - my kids felt that it was very hotel-like. Location was perfect for us, although...
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1 / 9
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Hancock
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Refrigerator
  • Air Conditioning
  • Microwave
  • Internet Access
  • Parking
  • Dishwasher
  • Hot Tub
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This is an amazing 2 Bedroom Condo located in the heart of Berkshires.. On site amenities include, Pool and Game Room. Full Kitchen, 2 Baths and a large Living Room. Western Mass known for its rich culture, which will allow to enjoy close by Jaunts like, Norman Rockwell Museum, Tanglewood etc..... View all property information
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  • Pet friendly (6)
  • Smoking allowed (0)

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  • Internet (22)
  • Other outdoor space (22)
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