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$300

3 BR / 2 BA / Sleeps 5

2 Reviews

$300

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Perfect Getaway for Body, Mind and Soul

Lee cottage
3 BR / 2 BA / Sleeps 5 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

** 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 for body, mind and …
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Washing Machine
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(2)

Great getaway!

Left on Feb 12, 2012 for a stay in August 2011

We had the most amazing time. This adorable home is so close to everything and yet is feels very private and secluded. It provided a perfect balance for relaxation and adventure. One of the best parts for us was the awesome lake. We certainly hope to come back very soon!

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$300

2 BR / 2 BA / Sleeps 6

9 Reviews

$300

Inquire

Wyndham Bentley Brook at Jiminy Peak

Hancock resort
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent9 Reviews

Details

Reviews

(9)

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 long. Jiminy Peak …
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(9)

Fall Colors

Left on Oct 04, 2011 for a stay in October 2011

Great location and they really work to keep the place well kept and painted. The beds are very comfortable. Unfortunately the walls are paper thin and the bedrooms butt up against each other. We could hear the conversations of the couple next door without listening-even ear-plugs didn't help. The kitchen has no cabinet to store spices or groceries. Water pressure in showers was very weak. There …

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$175

3 BR / 2 BA / Sleeps 7

13 Reviews

$175

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Berkshires House, 40 wooded acres, Lake Frontage

Monterey house
3 BR / 2 BA / Sleeps 7 | Quick view
Excellent13 Reviews

Details

Reviews

(13)

Charming house with the feeling of a cottage, set on a knoll with adjacent cathedral-like pine forest. ** Stone fireplace, woodstove, beautiful kitchen with modern appliances (gas stove, microwave, refrigerator with water/ice dispenser, dishwasher, breadmaker, crockpot, blender, etc.) ** Cathedral-ceiling living area…
  • Waterfront
  • Ocean or water views
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(13)

Awesome Venue!

Left on Jul 17, 2012 for a stay in June 2012

The Hill Cottage is absolutely charming. It is nestled in the forest surrounded by soaring, magnificent pines on a private country road. The atmosphere is very tranquil and peaceful. The cottage is spacious, clean, and well stocked.It is very comfortable and inviting. The cottage is rustic with attractive wide pine floors and knotty pine walls, yet it has very modern amenities including a Jacuzzi…

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$200

2 BR / 2 BA / Sleeps 8

Wyndham Bentley Brook Jiminy Peak ski in/out - Berkshires vacation rentals
1 / 16

$200

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Wyndham Bentley Brook Jiminy Peak ski in/out

Hancock condo
2 BR / 2 BA / Sleeps 8 | Quick view

Details

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 Jiminy - Alpine Slide (…
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

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$129

1 BR / 2 BA / Sleeps 4

Berkshires Resort Apartment - Berkshires vacation rentals
1 / 12

$129

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Berkshires Resort Apartment

South Lee condo
1 BR / 2 BA / Sleeps 4 | Quick view

Details

RIght off the Mass Pike Exit 2, Berkshire family vacation condo with full kitchen and all amenities.Take in Boston Symphony at Tanglewood and dance at Jacob's Pillow, theatre at Shakespeare & Company, Yoga at Kripalu, a spa day at Canyon Ranch, the Norman Rockwell Museum, Hancock Shaker Village, Edith Wharton's The …
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$185

1 BR / 1 BA / Sleeps 2

3 Reviews

$185

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The Smith Farm Homestead

Alford B&B
1 BR / 1 BA / Sleeps 2 | Quick view
Excellent3 Reviews

Details

Reviews

(3)

The Smith Homestead in Alford Massachusetts has been homesteaded and farmed by our family for the past two centuries. Located on one of the nicest settings in the Berkshires, with 30 acres of fields and woods, and the crystal clear Alford Brook running through, we are central to all the cultural events and outdoor …
  • Waterfront
  • Ocean or water views
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Wireless Internet

Details

Reviews

(3)

Beautiful

Left on Apr 09, 2013 for a stay in March 2013

Five stars! Perfect location for a getaway. A quick ride into the beautiful downtown Great Barrington. I have had many good night rests in this room. The hillside view is spectacular. And the best cup of coffee around.

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$200

1 BR / 1 BA / Sleeps 2

1 Reviews

$200

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Writer's Room at Chestnut Lodge

Lee B&B
1 BR / 1 BA / Sleeps 2 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

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. there's a double bed, a…
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

vintage New England...home and hearth, the nearby arts and surrounding countryside

Left on Jun 17, 2014 for a stay in June 2013

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 rustic 18th century all the way.

We either make our own meals or join in with others...cooking indoors and eating at the big banquet table, or outside at the BBQ.

We love the arts...Jacob's Pillow for dance, …

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$450

1 BR / 1 BA / Sleeps 2

1 Reviews

$450

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rustic Chestnut Lodge! vintage Berkshires home !

Lee B&B
1 BR / 1 BA / Sleeps 2 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

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 of the Lincoln …
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Washing Machine
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Beautiful, historic, atmospheric, peaceful, getaway lodge.

Left on Jun 12, 2014 for a stay in August 2013

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, dance, theater, Shakespeare, art, homes of historical writers and sculptors. Or just relaxing and reading and often game nights. Smoke free. I look forward to my return.

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$200

2 BR / 1 BA / Sleeps 4

1 / 6

$200

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Retreat in the Woods

Savoy house
2 BR / 1 BA / Sleeps 4 | Quick view

Details

Located in a quiet corner of the northern Berkshires, this lovely two-bedroom home has a combined living room/kitchen with cathedral ceilings and a spacious bathroom complete with a 2-person jacuzzi tub. The house is located about a mile from beautiful Tannery Falls in the Savoy State Forest and other hiking trails …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Porch
  • Parking
  • Suitable for children - over five
  • Suitable for the elderly - ask

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$500

4 BR / 3 BA / Sleeps 8

1 / 18

$500

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BEAUTIFUL LINDAL CEDAR HOME WITH GREAT LAKE VIEW

Hinsdale house
4 BR / 3 BA / Sleeps 8 | Quick view

Details

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 lake, is open to the …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

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$400

4 BR / 2 BA / Sleeps 10

1 / 18

$400

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LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

Lenox house
4 BR / 2 BA / Sleeps 10 | Quick view

Details

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 for beautiful sunsets…
  • Ocean or water views
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

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$350

4 BR / 2 BA / Sleeps 9

1 Reviews

$350

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Field View Cottage , Convenient to All Berkshire

Great Barrington house
4 BR / 2 BA / Sleeps 9 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

The perfect house for friends and family to share! Bright,uncluttered, and inviting, with privacy and views just minutes to town. There are two fireplaces,a sunken living room, dining room with seating for 10, 4 bedrooms, 2 full bathrooms, and a cozy hang out area in the basement. There is a washer and dryer, …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Best Memorable Thanksgiving Ever

Left on Feb 05, 2015 for a stay in November 2014

This was the first time we had a rental cottage, but it surpassed all of our expectations. The cottage was clean and well arranged. Kitchen was spacious enough for more than a few people cook together. Fireplace was lovely and so fun! The neighborhood was so quiet and calm. It snowed right before Thanksgiving, and the view was priceless! We would like to come back again!

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$189

2 BR / 2 BA / Sleeps 6

1 Reviews

$189

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Berkshires Vacation Rental - Bentley Brook Resort Suite

Hancock condo
2 BR / 2 BA / Sleeps 6 | Quick view
Very Good1 Reviews

Details

Reviews

(1)

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 vacation. Free parking and…
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(1)

Beautiful area in the fall

Left on Oct 25, 2014 for a stay in October 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 children above us. They enjoyed running and moving furniture. Oh well. Still had a nice stay despite that and a couple of days of rain.

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$100

1 BR / 1 BA / Sleeps 5

1 Reviews

$100

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Yankee Suites Extended Stays

Pittsfield condo
1 BR / 1 BA / Sleeps 5 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

A Fully-Furnished Extended Stay property in the Berkshires. Located across the street from the Colonial Theatre and within minutes of most Berkshire County attractions. Each spacious, efficiency (condo-style) single bedroom apartment includes living room, kitchen with full size appliances, bathroom, and deck. Enjoy …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Excellent Rooms Plus Exceptional Service

Left on Jul 03, 2013 for a stay in January 2013

WOW, this place was very nice! What you get is a place with a five minute walk from downtown, well kept buidlings and grounds, excellent floor plans, new furniture, modern kitchen, large closets, a lot of storage space, outside deck, deckbawasher and dryer in the basement, latest technology i.e. cable TV, internet, maid service twice a week.

Plus a friendly staff on-site seven days a week …

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$225

4 BR / 2 BA / Sleeps 10

3 Reviews

$225

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2200sf Country House on 16 Acres-2 Miles to Jiminy

Hancock house
4 BR / 2 BA / Sleeps 10 | Quick view
Excellent3 Reviews

Details

Reviews

(3)

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 feel. Each one of the 3…
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(3)

Had a great time!

Left on Oct 07, 2010 for a stay in August 2010

The house was very clean and well supplied. The location is very convenient to fun family activities.

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$375

4 BR / 3 BA / Sleeps 8

16 Reviews

$375

Inquire

Beautiful Berkshire House w/ Tennis

Sheffield house
4 BR / 3 BA / Sleeps 8 | Quick view
Excellent16 Reviews

Details

Reviews

(16)

Enjoy your vacation in a beautiful historic house located in the heart of the Berkshires. Located two and a quarter hours north of New York City, this circa-1770s center chimney colonial will charm and delight your family and guests. 88 acres of land with views of Mt. Washington and Mount Everett promises privacy, …
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(16)

home on the range

Left on Jul 08, 2010 for a stay in May 2003

my wife and i stayed at this lovely home for the entire summer, may through october, and we returned during the new year holiday the following winter. the setting is extremely private and sits on a gorgeous field surrounded on one side by the mountains and the other side of woods and cleared fields with an infinite skyscape, especially interesting on a starry night for heaven seekers.
the home …

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$100

4 BR / 3 BA / Sleeps 15

8 Reviews

$100

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Race Mountain House

Sheffield house
4 BR / 3 BA / Sleeps 15 | Quick view
Excellent8 Reviews

Details

Reviews

(8)

The Race Mountain House is set high on the slopes of the Taconic Mountains in Southern Berkshire County. Large, east-facing windows look out over a sweeping view of the Housatonic River Valley. In the early hours, the house floods with warm morning light and sunrises are spectacular. The inviting, creative design …
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(8)

Perfect weekend getaway!

Left on Feb 12, 2014 for a stay in December 2013

A truly beautiful house in such a magical place! I spent a lovely weekend here with a group of friends from NYC, and we all had our own space to relax, and enjoyed coming together to cook and unwind in the spacious kitchen and living room (the fire place is awesome!). The perfect spot for a peaceful weekend in the woods, plus it's only a short walk to Race Brook Lodge to enjoy some food and …

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$125

1 BR / 1 BA / Sleeps 2

1 / 10

$125

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ground floor garden room

Lee B&B
1 BR / 1 BA / Sleeps 2 | Quick view

Details

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 is ceramic tiled. …
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Outdoor Dining Area
  • Balcony or terrace
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$500

3 BR / 3 BA / Sleeps 8

1 Reviews

$500

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Fall/ Winter- Spectacular Setting-Family- Ski Sled Hike Fish Relax

Stockbridge house
3 BR / 3 BA / Sleeps 8 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

A home for the family: SKIING, SNOWSHOEING, AND SLEDDING. Fall and Winter availability. Behind the house, on the property is a HUGE hill that is great for sledding. 12 mins to Butternut. 25 mins to Jiminy. Across the road is a park that is great fun to hike, snowshoe, CC ski, and explore. A 1/4 mile driveway …
  • Waterfront
  • Ocean or water views
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Pet friendly
  • Suitable for the elderly

Details

Reviews

(1)

A little piece of paradise!

Left on May 18, 2010 for a stay in July 2009

This house had it all... my wife and I loved our time there. During the day we would either sit on the deck and read or go swimming in our own private lake that was very, very clean. It was close to town for us to go shopping and there were lot's of places to take walks and things to see and do. At night we would make a fire outside in the fire pit and we would soak in the hot tub. The house was …

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$600

2 BR / 2 BA / Sleeps 5

3 Reviews

$600

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July 26 to August 2 Berkshire Oak & Spruce resort

Lee condo
2 BR / 2 BA / Sleeps 5 | Quick view
Very Good3 Reviews

Details

Reviews

(3)

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.
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Housekeeping Optional
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Peaceful, Quiet, and Scenic

Left on Jun 25, 2014 for a stay in June 2014

I was planning to spend the week traveling around the upper Northeast of the US (Conn, Rhode Island, New Hampsire, Vermont, Maine, and New York.) I chose this resort based on its central location and that it had two bedroom/two bath untis available.

Other than checking in late at night (quite efficient and pleasent by the way), the only other contact I had with resort staff was the minor …

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$375

2 BR / 2 BA / Sleeps 6

1 / 5

$375

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July4th Berkshires/James Taylor/2Bed Presidential

Lee condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

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! Tanglewood/Lenox is …
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

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$240

2 BR / 2 BA / Sleeps 8

1 / 4

$240

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Wyndham Bentley Brook (Jiminy Peak mountain)

Hancock resort
2 BR / 2 BA / Sleeps 8 | Quick view

Details

Exclusive Deal for Christmas week, the most wanted week of the year! Ski-In/Ski-Out Plus Year-Round Mountainside Fun! Wyndham Bentley Brook is situated right at the base of Jiminy Peak ski mountain, making this resort an exceptional choice for mountainside play. During the winter, ski out your door and onto the lifts…
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Sauna
  • Wireless Internet
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible - ask

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$357

6 BR / 5 BA / Sleeps 12

1 / 23

$357

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Elegant 6000+Sf Luxury Estate on 13+ Park

Great Barrington house
6 BR / 5 BA / Sleeps 12 | Quick view

Details

This Elegant Luxury Estate offers 6000+ SF of Living Space on 13+ park-like, sunny acres located within only minutes from the downtown Great Barrington. This fantastic home offers 5 Bedrooms, 4.5 bathrooms, sweeping dual staircase ending with the magnificent open gallery, the kitchen offers the magnificent, high end …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$249

2 BR / 2 BA / Sleeps 8

1 / 19

$249

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Wyndham Bentley Brook

Hancock condo
2 BR / 2 BA / Sleeps 8 | Quick view

Details

Ski-In/Ski-Out Plus Year-Round Mountainside Fun. Wyndham Bentley Brook is situated right at the base of Jiminy Peak ski mountain, making this resort an exceptional choice for mountainside play. In winter, ski out your door and onto the lifts; in spring, summer and fall, enjoy hiking and horseback riding, Tanglewood …
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Sauna
  • Fireplace
  • Suitable for children

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