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$300

4 BR / 2 BA / Sleeps 8

Colesbrook Manor - Cheshire vacation rentals
1 / 12

$300

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Colesbrook Manor

4 BR / 2 BA / Sleeps 8 | Quick view

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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.
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

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$200

4 BR / 3 BA / Sleeps 10

Flower Hill Farm Retreat Apartment/ Entire Retreat - Cheshire vacation rentals
1 / 27

$200

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Flower Hill Farm Retreat Apartment/ Entire Retreat

4 BR / 3 BA / Sleeps 10 | Quick view

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Flower Hill Farm Retreat is housed within a 1790 farmhouse and studio situated on an east facing hillside fifteen minutes west of Northampton, Massachusetts. You can rent the entire retreat or separate apartments. See Rates below in this write up. Rambling organic gardens, fields and forest surround the Retreat …
  • Mountain Views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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$135

3 BR / 2 BA / Sleeps 8

5 Reviews

$135

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Flight's End-A Country Home with Babbling Brook

3 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 5 Reviews

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Reviews

(5)

3 Bedroom house, know as Flight's End, is for rent by day, weekend, week or month. Great for romantic get away or a family outdoor vacation. Not a party house. Fifteen minutes to Charlemont, Ashfield and Shelburne Falls. House is located on a brook and across the road from a private pond (not suitable for …
  • Ocean or water views
  • Mountain Views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(5)

lovely bucolic setting in the berkshires

Left on Jun 07, 2014 for a stay in May 2014

Such a sweet little home. Tucked away but easy drive to so many sights and activities. We loved the decor, the gardens around the home, the pond across the street.

Great getaway.

Thanks,

Caleb and Anu

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$72

2 BR / 2 BA / Sleeps 8

2 Reviews

$72

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Wyndham Bentley Brook - 2 Bedroom 2 Bath

2 BR / 2 BA / Sleeps 8 | Quick view
“ Very Good ” 2 Reviews

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Reviews

(2)

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 Wyndham Bentley …
  • Sauna
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Nice place to gather with friends

Left on Aug 19, 2014 for a stay in August 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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$250

3 BR / 3 BA / Sleeps 7

5 Reviews

$250

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MARCH MADNESS Weekend Special Rate Spring Skiing

3 BR / 3 BA / Sleeps 7 | Quick view
“ Excellent ” 5 Reviews

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Reviews

(5)

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. It is a destination…
  • Mountain Views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(5)

A memorable weekend getaway includes the most perfect house..

Left on Apr 17, 2013 for a stay in July 2012

My husband and I had the pleasure to rent out this house last summer with another married couple and their son. Although our daughter and their son truly enjoyed Tanglewood and our visits into Town (which are both extremely close), I can't help but think that my favorite part of our vacation was the house we were staying in! The space felt both warm and welcoming and fit our group size perfectly…

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$250

3 BR / 2 BA / Sleeps 8

2 Reviews

$250

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Berkshires Spacious Comfortable Charming Farmhouse

3 BR / 2 BA / Sleeps 8 | Quick view
“ Very Good ” 2 Reviews

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Reviews

(2)

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 roosters won the grand …
  • Mountain Views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(2)

lovely stay

Left on Sep 24, 2010 for a stay in August 2010

The house is comfortable, clean, and convenient to Lenox, Stockbridge, and the rest of the Berkshires. Traffic from the street can be a bit loud at times, but it quiets down at night.

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$135

3 BR / 1 BA / Sleeps 6

4 Reviews

$135

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Lakeview home with swingset & firepit!

3 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 4 Reviews

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Reviews

(4)

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 and very private …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(4)

Best little hidden treasure

Left on Jul 07, 2010 for a stay in June 2010

We contacted the owners on a referal from a friend and had all our questions answered and more in regards to the propery and its amenities . Upon our arrival we got out of the car and was immediately greeted with a spectacular view of the lake. The house , was immaculate , clean , organized and big enough for me and my family to feel at home. We had a fantastic vacation and I would highly …

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$212

3 BR / 2 BA / Sleeps 10

16 Reviews

$212

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Berkshire house w/ fireplace, A/C, WiFi & laundry

3 BR / 2 BA / Sleeps 10 | Quick view
“ Excellent ” 16 Reviews

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Reviews

(16)

Experience a Berkshire get-away in this huge secluded luxury modern house. It's the only house that is surrounded by 10,000 Acres of protected Hawley State forest. Escape from headaches and the rat race. No cell phone reception here! But we have WiFi and a house phone. We like to define our country home as a place to …
  • Ocean or water views
  • Mountain Views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(16)

Majestic peaceful location

Left on Mar 25, 2013 for a stay in July 2012

The house is large and roomy with a nice open porch. The backyard opens onto a beautiful lake which is fun to hike around, explore the old water mill ruins and fish. Had great time tubing down the river and visiting the locale historic sites. Great place to stay

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$360

5 BR / 3 BA / Sleeps 11

8 Reviews

$360

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Bird Watchers Delight! Country Get-Away w/Pond!

5 BR / 3 BA / Sleeps 11 | Quick view
“ Very Good ” 8 Reviews

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Reviews

(8)

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 electric and plumbing in …
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Central heating

Details

Reviews

(8)

Great Girlfriends' Getaway!

Left on Jan 31, 2012 for a stay in January 2012

We decided on fairly short notice to get away with a group of girlfriends to the Berkshires. Robin was so gracious to accommodate us on short notice. We arrived on a frigid day to find a clean and comfortable house, with a fire laid and ready for us. The kitchen had everything we needed for preparing our meals. We especially love the oversized coffee mugs! It's the little things that make a …

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$175

2 BR / 1 BA / Sleeps 4

12 Reviews

$175

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Stone School Cottage

2 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 12 Reviews

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Reviews

(12)

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 adventures. We are …
  • Mountain Views
  • Internet Access
  • Housekeeping Optional
  • Outdoor Dining Area
  • Central heating
  • Suitable for children

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Reviews

(12)

Great location, with wonderful scenic spots very close by

Left on Oct 17, 2011 for a stay in October 2011

The best thing about this place was the location. We came here to see the foliage, and we didn't have to go anywhere else driving around looking for it. This is right on the road to Mt Greylock which has so many hiking trails and scenic overlooks.

The Old Stone School cottage is a quaint setup, and the classroom doubles as a bedroom. This is not much of a bedroom, but just a big room with 2 …

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$250

5 BR / 2 BA / Sleeps 12

12 Reviews

$250

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Berkshire Farmhouse Vacation

5 BR / 2 BA / Sleeps 12 | Quick view
“ Excellent ” 12 Reviews

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Reviews

(12)

Quaint, , 2 story 1850's farmhouse in the Berkshires with original ceiling beams and 16" floor boards in much of the house. Fully furnished with 5 bedrooms, 2 full baths and a gorgeous screened-in porch overlooking 4 acres of gardens, stream and wooded mountains. Country kitchen with dish washer, microwave, toaster …
  • Mountain Views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(12)

Fantastic place to stay in the Berkshires

Left on Jan 08, 2014 for a stay in December 2013

Elaine was a very gracious host, and the...accommodations were lovely
and in a great location. The historic house has a lot of charm and many
nice updates, especially the clean, updated bathrooms and the huge
screened-in porch. ... We had room to spare, and everyone had a room to
themselves. The kitchen was well stocked, and the living room very cozy...
This would be a great place for skiers. …

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$265

3 BR / 2 BA / Sleeps 8

3 Reviews

$265

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Rose & Goat Retreat- Mountain Top Lodge

3 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 3 Reviews

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Reviews

(3)

Spectacular views are yours from this 2000 square foot Chalet Lodge located on the 50 acre Rose and Goat Retreat on the top of beautiful Florida Mountain in the Berkshires in Western Massachusetts. Enjoy cozy evenings in front of the massive stone fireplace after a day of enjoying all that the the Berkshires has to …
  • Mountain Views
  • Fireplace
  • Outdoor Dining Area
  • Central heating
  • Deck
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - adapted

Details

Reviews

(3)

"Can we stay here for every vacation!"

Left on Feb 01, 2014 for a stay in January 2014

Those are the words of my 15 year old son, who loved every minute at the Rose and Goat Retreat Chalet Lodge!! My husband and I returned to the Rose and Goat after a lovely weekend in October at the Romantic Rose and Goat Retreat, but in the cozy apartment below the Chalet Lodge. This time we were accompanied by 5 teenagers, boys and girls, and they wanted to move right in! We had a beautiful …

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$195

4 BR / 3 BA / Sleeps 7

15 Reviews

$195

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Berkshire Gorge House

4 BR / 3 BA / Sleeps 7 | Quick view
“ Excellent ” 15 Reviews

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Reviews

(15)

The Berkshire Gorge House sits beside the Green River above a turbulent set of cascades, on the western slopes of Mt. Greylock. This 5-bedroom house was built in 1910 by New England’s finest craftsmen. It has been recently remodeled and is offered for rent. The house offers a new kitchen with gas range, new washer/…
  • Ocean or water views
  • Mountain Views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(15)

A peaceful setting minutes away from action and activities

Left on Apr 16, 2012 for a stay in March 2012

A fantastic, rustic house on a wonderful piece of property with easy access to skiing and other activities at Jiminy Peak, historic Williamstown, and the rest of the Berkshires. The house has a ton of character - we especially appreciated its an abundance of rooms and space for us to host friends and family for overnight visits; the new kitchen (including new appliances) was perfect for a ski …

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$130

3 BR / 2 BA / Sleeps 7

1 / 8

$130

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New Timberframe House Rental in the Berkshire Mountains, Masschusetts

3 BR / 2 BA / Sleeps 7 | Quick view

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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 kitchen with all new …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Central heating
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

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$250

2 BR / 2 BA / Sleeps 6

1 / 6

$250

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Jiminy Peak Ski Resort-Country Village's Best Unit

2 BR / 2 BA / Sleeps 6 | Quick view

Details

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.
  • Fireplace
  • Housekeeping Optional
  • Central heating
  • Linens Provided
  • Towels Provided
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$300

6 BR / 3 BA / Sleeps 11

1 / 9

$300

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Beautiful Colonial in Secluded Berkshires

6 BR / 3 BA / Sleeps 11 | Quick view

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Enjoy the Fall in our New England farmhouse! Cross country ski at Canterbury Farms, only 5 minutes away! Beautifully restored Colonial historical farmhouse (1790) with almost 2 acres of lawn for playing croquet and hanging out in the sun. There is a small pond (unfenced) for frogs and birds. Large screened in …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Central heating
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$300

2 BR / 2 BA / Sleeps 1

1 Reviews

$300

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Vac Rent Hancock Ma Ski-In Ski Out @ Jiminy Peak

2 BR / 2 BA / Sleeps 1 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

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 Stage Company in …
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible - ask

Details

Reviews

(1)

Great, but

Left on Jul 21, 2014 for a stay in July 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 the pool is in a different building (basically need to walk outside and down two sets of steps, not such a big deal.) My one issue is that the price $175 a night was posted, yet I ended up being charged $200 per night …

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$150

1 BR / 1 BA / Sleeps 5

2 Reviews

$150

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Rose and Goat Retreat - Mountain View Apartment

1 BR / 1 BA / Sleeps 5 | Quick view
“ Excellent ” 2 Reviews

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Reviews

(2)

50 acre mountain top property in the Berkshires located between North Adams and Charlemont, Massachusetts with mountain views and within close proximity to all kinds of outdoor recreational opportunities including beaches, swimming, whitewater rafting and kayaking, hunting and fishing, hiking and biking, skiing (…
  • Mountain Views
  • Internet Access
  • Housekeeping Optional
  • Outdoor Dining Area
  • Central heating
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(2)

Should have stayed here for my honeymoon!

Left on Nov 01, 2013 for a stay in October 2013

What could be better than a private apartment on top of a mountain in the fall in western Massachusetts with french doors open to the sunrise? Margot is a most gracious and attentive owner. Very engaging and thinking of every last detail. From the breakfast basket, bottle of wine chosen for me and sparkling water for my husband, to the full-size selection of bath products, lovely white fluffy …

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$200

3 BR / 2 BA / Sleeps 8

1 Reviews

$200

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Stockbridge Bowl house

3 BR / 2 BA / Sleeps 8 | Quick view
“ Average ” 1 Reviews

Details

Reviews

(1)

3-bedroom home on lake, near Tanglewood. 2 baths, den, screened porch, large yard.
  • Waterfront
  • Ocean or water views
  • Mountain Views
  • Internet Access
  • Fireplace
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(1)

Great location, tired house

Left on Jul 30, 2014 for a stay in July 2014

Nice house but tired bathrooms and kitchen. One great bedroom, two so so. Hot one nite and needed non existing a/c. Great screened porch with view of water. Canoe was a plus. With a little updating and a good cleaning,it could be fantastic.

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$200

2 BR / 1 BA / Sleeps 4

1 / 6

$200

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Retreat in the Woods

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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$70

1 BR / 1 BA / Sleeps 2

1 / 6

$70

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ROOM walking distance to Mass MoCa

1 BR / 1 BA / Sleeps 2 | Quick view

Details

I have a two bedroom apartment and I am renting out the spare bedroom. It is at the end of a dead end street with a huge wooded backyard that includes a grill, picnic table and two fire pits. It is walking distance to Mass MoCA and minutes from downtown Williamstown and/or downtown North Adams. The spare bedroom …
  • Mountain Views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children

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$175

2 BR / 1 BA / Sleeps 6

1 / 12

$175

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Berkshire Cottage

2 BR / 1 BA / Sleeps 6 | Quick view

Details

Peaceful, mountain hideaway. Rural, yet easily accessible to all major Berkshire County and Pioneer Valley attractions. Recently renovated, this charming 2-bedroom cottage can comfortably accommodate 4-6 people or could be a romantic retreat for two. Full kitchen with all appliances gives you the option of cooking …
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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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

4 BR / 3 BA / Sleeps 8 | Quick view

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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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$125

2 BR / 1 BA / Sleeps 6

2 Reviews

$125

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Cozy & Modern Home -mins from Tanglewood & Kripalu

2 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

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 room, fall foliage and…
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Great home, great location

Left on Nov 26, 2013 for a stay in November 2013

Beautiful, modern and cosy home which proved to be a great base for the trip! The fire was an added treat at the end of the day! Location wise the cottage was perfect - close to some wonderful hikes, gorgeous villages and towns and some wonderful food options and restaurants. Already looking forward to the next visit!

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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

2 BR / 2 BA / Sleeps 6 | Quick view
“ Very Good ” 1 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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$225

3 BR / 2 BA / Sleeps 7

4 Reviews

$225

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Family-friendly Cottage Near Lake, Tanglewood

3 BR / 2 BA / Sleeps 7 | Quick view
“ Excellent ” 4 Reviews

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Reviews

(4)

Located a short walk to the town beach on the Stockbridge Bowl, and 1.5 miles from Tanglewood's Hawthorn entrance, this casual summer cottage is a great get away for the whole family. The master bedroom is equipped with a queen bed; two twins in the 2nd bedroom, and a full-size bed in the 3rd bedroom. A sofa in the …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(4)

Hidden Gem

Left on Jul 18, 2013 for a stay in July 2013

I would like to tell you not to go here. I would like to say stay away, that way it will be availible whenever we want to go back. It is the perfect place to use as a centre to see the area, or sit and do nothing. It was my wife, kids and grand mothers. We did hike, we did spend a day on the beach right by the house, but we also felt at ease to just sit on the screened porch and play cards or …

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$157

2 BR / 2 BA / Sleeps 1

1 / 9

$157

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Rent Hancock Ma.2 Bedroom Vac Village Ski Condo

2 BR / 2 BA / Sleeps 1 | Quick view

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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.. Just one half mile …
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Central heating
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

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$229

2 BR / 2 BA / Sleeps 4

1 Reviews

$229

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Golden Triangle in the Berkshires

2 BR / 2 BA / Sleeps 4 | Quick view
“ Very Good ” 1 Reviews

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Reviews

(1)

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 TV to unwind after a…
  • Mountain Views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Spacious, adequate, nice views!

Left on Aug 11, 2013 for a stay in August 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 waiting for us on our arrival, we had a very nice stay. Nice mountain view from the deck, mostly clean house, and the three of us and our cat were very comfortable!

Good selection of movies for rainy days, great grill on …

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$432

5 BR / 3 BA / Sleeps 14

1 / 8

$432

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Hawk Mountain Lodge at Zoar Outdoor

5 BR / 3 BA / Sleeps 14 | Quick view

Details

Hawk Mountain Lodge offers a year-round New England vacation experience! Enjoy comfortable accommodations conveniently located in Charlemont in the northern Berkshires, just 2.5 hours from Boston and 3.5 to 4 hours from New York City. Overlooking the Deerfield River Valley and Berkshire East Ski Resort, our …
  • Ocean or water views
  • Mountain Views
  • Internet Access
  • Housekeeping Optional
  • Central heating
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

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$100

1 BR / 1 BA / Sleeps 5

1 Reviews

$100

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Yankee Suites Extended Stays

1 BR / 1 BA / Sleeps 5 | Quick view
“ Excellent ” 1 Reviews

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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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$325

4 BR / 3 BA / Sleeps 8

1 / 21

$325

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Historic South Lee Schoolhouse near Stockbridge

4 BR / 3 BA / Sleeps 8 | Quick view

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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 schoolhouse has been …
  • Mountain Views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

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$134

3 BR / 2 BA / Sleeps 6

1 / 13

$134

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Berkshires- 2015 Summer Rental July And August

3 BR / 2 BA / Sleeps 6 | Quick view

Details

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.
  • Mountain Views
  • Sauna
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Suitable for children
  • Suitable for the elderly

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$450

3 BR / 3 BA / Sleeps 6

1 / 20

$450

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New Pristine Berkshire Vacation Rental with Pool (5 miles Tanglewood)

3 BR / 3 BA / Sleeps 6 | Quick view

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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 idyllic swimming pool …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

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$150

4 BR / 1 BA / Sleeps 7

19 Reviews

$150

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Gartner House, a charming home in Lenox

4 BR / 1 BA / Sleeps 7 | Quick view
“ Excellent ” 19 Reviews

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Reviews

(19)

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 quirky little shops …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Central heating
  • Pet friendly - ask
  • Suitable for children - ask

Details

Reviews

(19)

Quaint & Cozy Condo!

Left on Jan 10, 2012 for a stay in December 2011

Having stayed at Gartner House a few times, I would recommend it to anyone looking for a comfortable getaway. It is a convenient, short walk to the center of Lenox allowing easy access to all of the wonderful little shops and some great places to eat.
The condo offers all the comforts of home including full kitchen, land line phone, microwave, washer/dryer and a small side yard. Its spacious …

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$250

3 BR / 2 BA / Sleeps 8

1 Reviews

$250

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N. Adams/Williamstown Exclusive Lakeside Home

3 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

Windsor Cottage is a beautiful, newly renovated lakeside retreat located on Windsor Lake in North Adams, MA. where you can enjoy your own private water access from your front lawn. You will feel like you are in the middle of the forest, yet you are in walking distance to the town, Mass MoCA and Massachusetts …
  • Waterfront
  • Ocean or water views
  • Mountain Views
  • Fireplace
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Charming, serene and immaculate cottage on Windsor Lake

Left on Aug 16, 2014 for a stay in August 2014

The cottage is well located, seemingly remote, but with nearby access to local attractions and restaurants. I enjoyed sitting on the deck, looking out over the water in the morning - very peaceful. The charming furnishings and immaculately maintained rooms made for a very pleasant stay. I would highly recommend this property.

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$200

1 BR / 1 BA / Sleeps 4

1 / 11

$200

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little blue cottage lots of cute! 1 mile to stockbridge center . pet friendly!

1 BR / 1 BA / Sleeps 4 | Quick view

Details

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 kitchen with peninsula…
  • Mountain Views
  • Internet Access
  • Fireplace
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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$500

3 BR / 2 BA / Sleeps 6

1 / 11

$500

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Vacation Home on 10 Acres with Pool and Spa

3 BR / 2 BA / Sleeps 6 | Quick view

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Vacation home centrally located in the Berkshires, 1 mile from Norman Rockwell and 3 miles from Tanglewood, on a quiet country road. Spacious grounds with large 2-level deck overlooking gardens and woods, private in-ground pool with pool house and deck, hot tub. House includes 3 bedrooms, 2 newly renovated baths, …
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

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$250

3 BR / 2 BA / Sleeps 8

1 / 10

$250

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Josiah Loomis Homestead

3 BR / 2 BA / Sleeps 8 | Quick view

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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 later. His 3 room …
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

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$225

2 BR / 2 BA / Sleeps 8

1 / 16

$225

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Wyndham Bentley Brook Jiminy Peak ski in/out

2 BR / 2 BA / Sleeps 8 | Quick view

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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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$575

3 BR / 3 BA / Sleeps 5

1 / 5

$575

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Artist designed luxury in Stockbridge

3 BR / 3 BA / Sleeps 5 | Quick view

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Private setting on over three acres, this artist designed and newly renovated home has cathedral ceilings in all rooms. It features a luxurious and spacious master bedroom suite with jacuzzi tub & outdoor shower Skylights are everywhere and designed to let in the light and mountain views from every room. Relax in …
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly
  • Wheelchair accessible

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$445

5 BR / 5 BA / Sleeps 16

1 / 17

$445

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House On Main Street

5 BR / 5 BA / Sleeps 16 | Quick view

Details

Lots of space, great yard, plus you can walk to everything: restaurants, museums, Williams College, theater, night life, etc. This beautifully maintained historic House On Main Street was known as the Victorian Tourist & Antique House in a by-gone era. It was originally constructed in the mid 1700's and was …
  • Wireless Internet
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly - ask
  • Suitable for children
  • Wheelchair accessible - ask

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$200

1 BR / 1 BA / Sleeps 6

1 / 7

$200

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the BIG room at chestnut lodge

1 BR / 1 BA / Sleeps 6 | Quick view

Details

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 feel right at home, …
  • Pet friendly
  • Suitable for children - ask

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$300

2 BR / 2 BA / Sleeps 6

8 Reviews

$300

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Wyndham Bentley Brook at Jiminy Peak

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 8 Reviews

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Reviews

(8)

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

(8)

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

2 BR / 2 BA / Sleeps 6

1 / 4

$175

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Berkshires Rental 15 minutes to Tanglewood

2 BR / 2 BA / Sleeps 6 | Quick view

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Two Bedroom two bathroom condo located on beautiful resort in the Berkshires. Oak and Spruce Resort located 15 minutes to Tanglewood is the summer home in the Berkshires of the Boston Symphony Orchestra. Condominium sleeps 6 with an eat in kitchen and living area. Recreational activities, ample parking located in …
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

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$140

3 BR / 1 BA / Sleeps 7

1 Reviews

$140

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Lakeside 2Bedroom Home in the Beautiful Berkshires

3 BR / 1 BA / Sleeps 7 | Quick view
“ Poor ” 1 Reviews

Details

Reviews

(1)

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 hiking, swimming, …
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Balcony or terrace
  • Parking
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(1)

Major Let Down

Left on Sep 10, 2014 for a stay in August 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 owners require that you pay a $75 cleaning fee, but the house was clearly not cleaned before we arrived. The owners also mailed the wrong keys, so we were locked out of the house after Tanglewood until about midnight when …

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$300

3 BR / 4 BA / Sleeps 6

1 / 16

$300

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Charming Home Nestled in the Berkshires

3 BR / 4 BA / Sleeps 6 | Quick view

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Charming 3 bedroom home nestled on 5 acres of secluded woods in the beautiful Berkshire Mountains. Located in the lovely town of Becket on a private road. Completely updated home with a large, open floor plan. Master bedroom with attached private full bathroom on first floor, two additional bedrooms on second …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly

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$250

2 BR / 1 BA / Sleeps 5

1 / 14

$250

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Lenox Walk to Town / Tanglewood

2 BR / 1 BA / Sleeps 5 | Quick view

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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 and the lush forest …
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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$150

3 BR / 2 BA / Sleeps 8

1 Reviews

$150

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Berkshire's Getaway ---Peace & Tranquility

3 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

House is very private and located on 4 acres of Land. Back yard is peaceful and overlooks ponds. The backyard has a patio/picnic area with gas grill and firepit. One of the ponds has a spurting and lighted fountain that is relaxing ...so have a campfire at night and watch the lighted fountain for a relaxing evening. …
  • Waterfront
  • Mountain Views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(1)

Quaint home on its own lake--don't miss this!

Left on Nov 29, 2014 for a stay in November 2014

The photos speak for themselves. Overall, the home was a great escape from city life, and included its own scenery and lake. My only complaint is that our stay was so short-lived. From our email communication with the owners, they seemed just as charming. We'll be back again.

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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

3 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 1 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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$150

3 BR / 1 BA / Sleeps 5

1 / 9

$150

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Hillside Hideaway with Trout Stream

3 BR / 1 BA / Sleeps 5 | Quick view

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You can 'have it all' in the Berkshires! Our cozy contemporary home is less than 30 minutes from all Berkshire cultural and historical attractions, but tucked away in woodsy peace and privacy. Our four acres look out over a large lawn, lovely flower and herb garden, old apple orchard, and trout stream to a facing …
  • Suitable for children
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