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Vacation Rentals in Pittsfield, MA and nearby

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All 47 Rentals in the Pittsfield Area
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From
$150
Per Night
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1 / 20
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Pittsfield
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
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From
$100
Per Night
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1 / 8
Pittsfield
1 Bedroom, 1 Bathroom, Sleeps 5
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The following rentals are within 10 miles of Pittsfield, Massachusetts.

From
$250
Per Night
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1 / 19
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West Stockbridge
5 Bedrooms, 2 Bathrooms, Sleeps 12
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From
$229
Per Night
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1 / 4
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Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • DVD Player
  • Safe
  • Dishwasher
  • Washer
  • Refrigerator
  • Garage
  • Grill
  • Stove
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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From
$300
Per Night
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1 / 25
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Lee
3 Bedrooms, 2 Bathrooms, Sleeps 5
Details Reviews (2) Make Inquiry
Amenities & Details
  • Ceiling Fans
  • Washer
  • Fireplace
  • DVD Player
  • Dryer
  • Refrigerator
  • TV
  • Hot Tub
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
** Rental is only available for 2 week minimum during the summer (July - August) Special Summer Deal -- Rent for the Season (July and August) and get either the last week in June OR the first week in September for half price! This adorable cottage has all the ingredients for the ultimate retreat... View all property information
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From
$325
Per Night
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1 / 21
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Lee
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
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Amenities & Details
  • Garage
  • Washer
  • Refrigerator
  • DVD Player
  • Fireplace
  • Grill
  • Patio
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Enjoy all the Berkshires has to offer in our new (2014) restoration and outstanding renovation of the historic South Lee Schoolhouse. Perched on a hillside just across the road from the Housatonic River and Beartown State Forest in the hamlet of South Lee, just outside of Stockbridge, the 1892... View all property information
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From
$250
Per Night
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1 / 14
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Lenox
2 Bedrooms, 1 Bathroom, Sleeps 5
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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
  • 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
$360
Per Night
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1 / 33
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Lee
5 Bedrooms, 3 Bathrooms, Sleeps 11
Bookings
Details Reviews (8) Make Inquiry
Amenities & Details
  • Dishwasher
  • Washer
  • DVD Player
  • Stove
  • Refrigerator
  • Deck
  • Grill
  • Stereo System
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Beautiful house surrounded by protected woodland and a small beaver pond behind your backyard. All kinds of birds and wildlife. 5 Bedrooms, 2.5 baths, brand new kitchen, open living/dining room, laundry room. Wood stove that can function as a fireplace. 3 heating zones for comfort. All new... View all property information
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4 of 5 stars Reviewed September 27, 2014
We went there for a golf buddy trip and it was the perfect place for us in the Berkshires. Place was very clean, and had all the comforts of home. Robin is super friendly and...
5 of 5 stars Reviewed September 3, 2014
This is a wonderful home! Robin has taken care with the furnishing and finishings, which are a nice blend of antique and modern. Her love of the home and region is apparent...
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From
$450
Per Night
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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
$145
Per Night
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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
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1 / 8
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Lee
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
Details Reviews (1) Make Inquiry
Amenities & Details
  • Hairdryer
  • Hot Tub
  • Grill
  • Fax
  • Internet Access
  • Fireplace
  • Stereo System
  • Garage
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
The Writer's Room is at the top of the stairs on the right. This handsome room is made completely of wood. Ceilings are higher and there's a sitting area in the big dormer. dormer faces east and get the morning sun! The floors are wide plank cherry milled from the property. the walls are pine.... View all property information
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5 of 5 stars Reviewed June 17, 2014
We have taken the Writer's Room each Summer for about three years now. We find the Lodge to be authentic New England... our natural wood room to the rest of the house. It is...
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From
$450
Per Night
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1 / 17
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Lee
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
Details Reviews (1) Make Inquiry
Amenities & Details
  • Fireplace
  • Dishwasher
  • Stereo System
  • Hot Tub
  • Dryer
  • Refrigerator
  • Stove
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
handsome and welcoming, this authentic Berkshire lodge will make you feel like you`re in an old fashioned Christmas card! fireplace blazing, wood floors post and beam, hand planed planks. in the kitchen the floor is marble slabs from the famous lee marble quarry. Daniel Chester French, the designer... View all property information
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5 of 5 stars Reviewed June 12, 2014
I had several summer months here, it never disappoints. Full of nature's bounty, hospitable host, friendly vacationers. Very close to all the best of the Berkshires, Tanglewood...
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From
$150
Per Night
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1 / 4
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Lee
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
Details Reviews (1) 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
first floor queensized bed, bath with shower. floors are wood ceiling has exposed beams and is furnished with oak antiques and a big wingbacked chair.built in bookshelf was from a companionway on a wooden sailing vessel owned by a sea captain that owned and ran the lodge back at the turn of the... View all property information
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5 of 5 stars Reviewed June 17, 2014
And I hope to stay here again in the future. I feel very comfortable here - good privacy, the house is huge, rustic charm, generally very quiet. The property is massive - and the...
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$200
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1 / 7
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Lee
1 Bedroom, 1 Bathroom, Sleeps 6
Booking
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
  • x
About this property
sleeps 4 can combine with writer's room for large suite, private entrance. fireplace or windowed woodstove, ceiling fans cathedral ceiling, terrace with seating, pasture and forest views. windows line both sides of room and feels like a treehouse. beautiful wood floors and soft carpets make you... View all property information
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From
$200
Per Night
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1 / 12
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Lee
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Fireplace
  • Porch
  • Internet Access
  • TV
  • Grill
  • Air Conditioning
  • Microwave
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
cute cozy cottage, screened porch with views, close to everything, sleeps 4 . nice yard with big old trees and soft grass. gas bbq, just one mile to stockbridge center , Berkshire theatre festival. 5 miles to tanglewood, lenox , kripalu. 10 minutes to great barrington. bath has shower. full... View all property information
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From
$125
Per Night
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1 / 10
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Lee
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Make Inquiry
Amenities & Details
  • Outdoor Dining Area
  • Grill
  • Parking
  • Hot Tub
  • Balcony
  • Internet Access
  • Linens Provided
  • Shared Yard
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
the garden room is a small room with a full sized bed. everything is floral, even the closet walls. it 's a sweet room with even a wood stove. it has an entrance to the courtyard just outside in the hall, the bath may be shared depending on the situation. bath has shower and lovely old sink. bath... View all property information
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From
$175
Per Night
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1 / 2
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Lee
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Inquiry
Amenities & Details
  • Number Of Bedrooms
  • Guest Count
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Sunny, light , bright and wide! the queens room is one of the biggest rooms and has private ensuite bathroom with tub/shower. 2 big closets, large writing desk, comfy conversation area, 2 dressers full sized bed. a section of the room has original ceilings so persons taller than 6'2' would be... View all property information
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From
$375
Per Night
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1 / 5
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Lee
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Grill
  • Dishwasher
  • Gym
  • Parking
  • Microwave
  • Refrigerator
  • DVD Player
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
I have a corner unit first floor 2-bed resort presidential suite in beautiful Berkshires! Just 2 hours drive down the Mass Pike from Boston. It's July 4th week and James Taylor will be playing at Tanglewood. This is one of the most sought after concerts every year and you wouldn't want to miss it!... View all property information
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From
$250
Per Night
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1 / 14
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West Stockbridge
3 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
Details Reviews (5) Make Inquiry
Amenities & Details
  • Deck
  • Fireplace
  • Dryer
  • Grill
  • Parking
  • Stove
  • Ceiling Fans
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Located in West Stockbridge minutes from everything . Nestled in the Berkshire Mountains. Convenient yet Private Visit our web-site at aberkshirehome The Berkshires is a world unto itself. It is scenic beauty married to cultural bounty. It is urban sophistication in an idyllic, rural setting.... View all property information
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5 of 5 stars Reviewed November 2, 2014
Had an outstanding couple of weeks staying here; place was quiet, peaceful and not too far from civilization. All the amenities and space you could wish for and Cassandra and her...
5 of 5 stars Reviewed August 25, 2014
We were excited to get away from NYC and stay in the Berkshires! It was a wonderful stay at this home! So spacious, comfortable, lots of thoughtful gestures for our stay! We...
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From
$400
Per Night
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1 / 24
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Lenox
4 Bedrooms, 2 Bathrooms, Sleeps 10
Booking
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Amenities & Details
  • Dishwasher
  • DVD Player
  • Gym
  • Washer
  • Refrigerator
  • Fireplace
  • TV
  • Grill
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
$750
Per Night
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1 / 7
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Lee
5 Bedrooms, 5 Bathrooms, Sleeps 12
Details Make Inquiry
Amenities & Details
  • Number Of Bedrooms
  • # Of Bathrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
--Brand new 3400 sq ft Lee home in a private lake community, Berkshires --Situated on 4 wooded acres on a quiet country road --Pristine home features two master bedroom suites plus 3 additional bedrooms, 5 bathrooms --Spacious living room with vaulted ceiling & skylights --Fully equipped kitchen,... View all property information
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From
$200
Per Night
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1 / 16
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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
$134
Per Night
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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
$300
Per Night
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1 / 12
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Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 1
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Safe
  • Refrigerator
  • Microwave
  • Hot Tub
  • Parking
  • Stove
  • Dishwasher
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Wyndham Bentley Brook Ski-In Ski Out Wyndham Bentley Brook Resort Ski-In Ski-Out at Jiminy Peak at Wyndham Bentley Brook Resort. Beginners or Experts, we have -programs designed for all levels. After a couple days of skiing, you want to venture out and hit local attractions like, Barrington... 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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From
$150
Per Night
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1 / 21
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Lenox
4 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
Details Reviews (19) Make Inquiry
Amenities & Details
  • Grill
  • VCR
  • Refrigerator
  • Microwave
  • Washer
  • TV
  • Parking
  • DVD Player
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 January 3, 2015
Ski trip in Berkshires and this place was perfect. Gave us nice options to do on off days. Debra was great with any issues that came up and was very helpful and responsive...
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...
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From
$157
Per Night
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1 / 9
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Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 1
Details Make Inquiry
Amenities & Details
  • Guest Count
  • Number Of Bedrooms
  • # Of Bathrooms
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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From
$500
Per Night
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1 / 18
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Hinsdale
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
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
$242
Per Night
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1 / 15
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Lenox
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • Fireplace
  • Dryer
  • VCR
  • Microwave
  • Refrigerator
  • 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
$135
Per Night
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1 / 11
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Richmond
3 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (4) Make Inquiry
Amenities & Details
  • Dryer
  • Grill
  • DVD Player
  • Dishwasher
  • Washer
  • Microwave
  • TV
  • Refrigerator
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
$175
Per Night
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1 / 10
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Lanesboro
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (12) Make Inquiry
Amenities & Details
  • Ceiling Fans
  • VCR
  • Central Heating
  • Internet Access
  • Microwave
  • Playground
  • 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
$125
Per Night
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1 / 8
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West Stockbridge
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Stove
  • Fireplace
  • Satellite TV
  • Washer
  • Dryer
  • Refrigerator
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Cozy and modern two bedroom and one bath vacation home with lake nearby Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living... View all property information
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5 of 5 stars Reviewed December 18, 2013
We stayed at this home in Housatonic, which is part of Great Barrington, the Smithsonian pic for best small town in the USA. I hope you all don't however as one of the best...
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From
$189
Per Night
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Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Patio
  • Washer
  • Microwave
  • DVD Player
  • Refrigerator
  • Dryer
  • Stereo System
  • Dishwasher
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
$200
Per Night
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1 / 19
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Cheshire
2 Bedrooms, 1 Bathroom, Sleeps 5
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Amenities & Details
  • TV
  • Patio
  • Stove
  • Garage
  • Refrigerator
  • Microwave
  • Washer
  • DVD Player
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
$600
Per Night
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Lee
2 Bedrooms, 2 Bathrooms, Sleeps 5
Details Reviews (3) Make Inquiry
Amenities & Details
  • Hot Tub
  • Stove
  • Microwave
  • DVD Player
  • Sauna
  • Gym
  • Safe
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Prime week 2br 2ba Berkshire Oak & Spruce resort time share. Full amenities indoor and outdoor pools. Tennis, basketball, mini golf, game room, movie theater on resort. A short drive to tangle wood, lakes etc. View all property information
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3 of 5 stars Reviewed October 14, 2014
We were in the older condos that need new furnishings, tvs, appliances, etc. I recommend trying to get into the newer condos; but not the older units; thus my rating below...
4 of 5 stars Reviewed July 14, 2014
My wife and I spent a restful week at The Oak and Spruce resort in the Berkshires. The unit was roomy and had a large master bedroom with jacuzzi and shower.The second bedroom had...
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From
$140
Per Night
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1 / 11
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Hinsdale
3 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
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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
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1 / 10
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Lee
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
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Amenities & Details
  • Washer
  • Refrigerator
  • Dryer
  • Patio
  • Grill
  • Porch
  • Stove
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Renovated Victorian cottage up on a hill, one block from the center of downtown Lee. Country charm with in-town convenience. Fully equipped with an eye towards comfort. Open plan living room/dining room, hardwood floors throughout. Three bedrooms (two queen, one full) with new mattresses - all... View all property information
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From
$225
Per Night
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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
$300
Per Night
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Washington
4 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Guest Count
  • Number Of Bedrooms
  • # Of Bathrooms
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
$250
Per Night
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Lenox
3 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
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Amenities & Details
  • Playground
  • Dishwasher
  • Garage
  • Grill
  • Refrigerator
  • Stove
  • DVD Player
  • Washer
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
$299
Per Week
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1 / 5
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Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (1) Make Inquiry
Amenities & Details
  • DVD Player
  • Grill
  • Microwave
  • Stove
  • Hot Tub
  • Safe
  • Refrigerator
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Fantastic Value at over 50% off the retail rates! Great Fall Season pricing of only $299 for each entire week's stay! No other fees due! We own this timeshare and can't use it this year! March 20-27th and March 27 to April 3, 2015.-. 2 bedroom, 2 bath, sleeps 6 Fully furnished with cooking... View all property information
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5 of 5 stars Reviewed February 16, 2015
Didn't go late enough for the Fall Foliage, but even as the leaves were just turning this was a lovely resort to visit. We go to the Highlands of Scotland every other year where...
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$250
Per Night
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Hancock
2 Bedrooms, 1 Bathroom, Sleeps 6
Booking
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Amenities & Details
  • Hairdryer
  • Central Heating
  • Ceiling Fans
  • Microwave
  • Linens Provided
  • Dishwasher
  • Refrigerator
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • 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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From
$250
Per Night
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1 / 11
Lee
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (2) Make Inquiry
Amenities & Details
  • Dishwasher
  • TV
  • Stove
  • Stereo System
  • Refrigerator
  • Parking
  • Dryer
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Experience a little of old New England. Our vacation rental is a charming historic family farmhouse apartment with lots of room and comfort,2100Sq.ft., situated on 22 acres. Built in 1782, our farm was famous for breeding Plymouth Barred Rock chickens. In the 1800's, one of these barred rock... View all property information
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4 of 5 stars Reviewed June 18, 2013
This property was a great home base for our brief visit to the Berkshires. Plenty of space and well equipped. We especially enjoyed the beautiful property, whether sitting on the...
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From
$140
Per Night
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1 / 7
Richmond
3 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
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
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1 / 10
Richmond
3 Bedrooms, 2 Bathrooms, Sleeps 8
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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
  • 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
$300
Per Night
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1 / 18
Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (8) Make Inquiry
Amenities & Details
  • TV
  • Air Conditioning
  • Microwave
  • Washer
  • Dishwasher
  • Dryer
  • Stove
  • Sauna
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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4 of 5 stars Reviewed January 26, 2015
Always a great trip for Friends and family. Easy quick park and party. They have a movie theater activities for kids all day long indoor outdoor swimming pool hot cider coffee and...
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...
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From
$72
Per Night
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1 / 27
Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (2) Make Inquiry
Amenities & Details
  • Dryer
  • Guest Count
  • 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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$300
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New Lebanon, NY
5 Bedrooms, 5 Bathrooms, Sleeps 5
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Amenities & Details
  • Guest Count
  • Short Term Rentals...
  • Number Of Bedrooms
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
This home sits on 10 private acres in the beautiful Berkshire mountains. Greeted by friendly wood carved bears, the entire estate consists of a 3 BR main house with 3.5 baths, two bedroom pool house with 1 bath, and 1 bedroom garage apartment with 1 bath. All units are available but this listings... View all property information
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Suitability

  • Wheelchair access (7)
  • Elder access (18)
  • Suitable for children (5)
  • Pet friendly (13)
  • Smoking allowed (0)

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  • Internet (35)
  • Other outdoor space (34)
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