Berkshires

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$120

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Unique People & Pet-Welcoming Country Haven

Charlemont condo
1 BR / 1 BA / Sleeps 4 | Quick view
Excellent112 Reviews

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Reviews

(112)

Discover Cavalier Cottage B&B;, a pet-friendly home away from your home and an attractive alternative to conventional hotels, motels and B&B;'s. We warmly welcome visitors who come to this beautiful and diverse area of Western Massachusetts with or without their companion animals. Since opening the cottage in …
  • Mountain Views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(112)

A wonderful place to stay with or without pets.

Left on Mar 15, 2012 for a stay in February 2012

The cottage is clean, full of light and simply decorated. I have stayed in frilly, cutesy, flowery places that felt downright claustrophobic. The full-size kitchen has new appliances and is stocked with everything one could want, from coffee and teas to hot cereal and a variety of fresh fruit. Pat, the proprietor, spoiled me with fresh baked English scones each morning of my stay.
It is …

$130

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Apartment walking distance to Mass MoCa!!

North Adams condo
2 BR / 1 BA / Sleeps 8 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

I have a 2 to 3 bedroom first floor apartment located in a dead end street. This spacious 8 room apartment is surrounded by woods and minutes from downtown North Adams or Williamstown!! It is also walking distance to Mass MoCa!!! Animals are welcome is needed. . The master bedroom has an extended queen sleep number…
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Friendly host ample space

Left on Jul 06, 2014 for a stay in July 2014

Stephanie was helpful and accommodating of us and our last minute request . Sheafs it easy to stay, come and go and we found the location convenient yet private and remote from noise.

ROOM walking distance to Mass MoCa - North Adams vacation rentals
1 / 6

$70

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ROOM walking distance to Mass MoCa

North Adams apartment
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
Berkshires Resort Apartment - South Lee 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

$125

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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
  • Internet Access

    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.

    $125

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    Cozy & Modern Home -mins from Tanglewood & Kripalu

    West Stockbridge condo
    2 BR / 1 BA / Sleeps 6 | Quick view
    Excellent2 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!

    $135

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    Lakeview home with swingset & firepit!

    Richmond house
    3 BR / 1 BA / Sleeps 6 | Quick view
    Excellent4 Reviews

    Details

    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 …

    $139

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    Serene Lakefront Cottage

    Becket house
    2 BR / 2 BA / Sleeps 4 | Quick view
    Excellent9 Reviews

    Details

    Reviews

    (9)

    Pretty cottage in the woods on a beautiful private lake with a stream running through the property's two acres of land. Newly constructed, spacious and sunny second floor with views of the lake. Hardwood floors throughout the house. Swim, kayak, canoe or fish from the back yard, or just lounge all day watching the …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Outdoor Dining Area
    • A/C or climate control
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly - ask

    Details

    Reviews

    (9)

    Idyllic retreat

    Left on Oct 08, 2012 for a stay in October 2012

    Quiet rural getaway in a beautiful setting. The backyard ends in the pond shown in the picture, which is surrounded by trees in full fall color. I spent a few hours perched at its edge and lost track of time for the first time in weeks. A complete absence of traffic noise means that the only outside sounds are of running water and rustling leaves, so you can hear yourself breathe. Not much by way…

    $119

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    Quiet Comfortable Cabin 5 Min. Walk to Lake

    Becket house
    2 BR / 1 BA / Sleeps 4 | Quick view
    Excellent8 Reviews

    Details

    Reviews

    (8)

    Remember the simple pleasures of a country, lakeside vacation where you can spend the day swimming or boating, exploring new towns and attractions, or just spending a lazy afternoon reading on the screened-in porch? Get back to those simple pleasures in our cabin, which is located in a beautiful, quiet country …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly - ask

    Details

    Reviews

    (8)

    Quaint,relaxing Berkshire getaway

    Left on May 20, 2013 for a stay in April 2013

    We really enjoyed our stay at your cottage---it was just what we were hoping for! You do a wonderful job of making sure everything's covered with the detailed instruction list, and all the amenities you advertise are just as you said. We loved being able to take the canoe out on the lake, and we used the firepit the first evening we arrived. The cottage itself is great,and we felt right at home…

    $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 …

    1 / 8

    $130

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    New Timberframe House Rental in the Berkshire Mountains, Masschusetts

    Hinsdale house
    3 BR / 2 BA / Sleeps 7 | Quick view

    Details

    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
    1 / 6

    $122

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    Berkshires on the Pond

    Becket house
    2 BR / 2 BA / Sleeps 4 | Quick view

    Details

    Lovely house on pond, Beautiful views of pond from every room, except one. Lounge on the deck with a glass of wine watch the Great Blue Heron has he stalks his fish, see the beavers swim lazily across the pond, flapping their tails to let you know they are there. Every room but one has a water view. Bedroom sleeps …
    • Waterfront
    • Ocean or water views
    • Wireless Internet
    • Washing Machine
    • Clothes Dryer
    • Suitable for the elderly - ask

    $100

    Book

    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

    Book

    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

    $100

    Book

    The House in Pumpkin Hollow B&B

    Conway house
    2 BR / 1 BA / Sleeps 4 | Quick view
    Excellent4 Reviews

    Details

    Reviews

    (4)

    The House in Pumpkin Hollow Bed and Breakfast is nestled in the foothills of the Berkshires in Conway, Masschusetts. It is surrounded by woods. fields, and other historic homes. Ideally situated 6 miles off Route 9, it is close to Northampton, Deerfield, Brattleboro, Amherst and Shelburne Falls. This spacious, 1860 …
    • Mountain Views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (4)

    Lovely Stay

    Left on Apr 03, 2014 for a stay in October 2013

    We so enjoyed our stay at The House in Pumpkin Hollow in the sweet town of Conway. We needed a getaway and it was perfect. Diane and her darling dogs greeted us, and she was available for any questions we had. She's a warm and engaging host. The house is stunning with beautiful decor, antiques, large windows and a curving staircase up to our rooms. It was quiet and very private. Nice restaurants …

    1 / 19

    $130

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    Solid Rock Farm

    Stockbridge farmhouse barn
    3 BR / 3 BA / Sleeps 8 | Quick view

    Details

    Our 1762 Farmhouse is lovingly being restored with gardens in the Berkshires. Mission statement: Educating members in life, farming, and creative art skills acknowledging God as our provider. One mile from the Norman Rockwell Museum and 5 miles from Tanglewood. Come join the farm "Agritourism" experience!
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Central heating
    • Parking
    • Pet friendly - ask
    • Suitable for children
    1 / 6

    $50

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    SKI HOUSE IN MONTEREY MASSACHUSETTS

    Monterey condo
    1 BR / 1 BA / Sleeps 1 | Quick view

    Details

    We rent our house for a full winter season from November through March. You can enjoy all holidays, school breaks, weekends during the winter in your own winter wonderland. Contact us for all details. Walk to charming 200 year old Monterey with library, playground, playing fields, ice skating rink.15 minutes to Great …
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask
    1 / 13

    $59

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    Glamping the best of the Berkshires

    Tyringham camper van
    1 BR / 1 BA / Sleeps 2 | Quick view

    Details

    Conversion Van with comfy and clean Full sized bed. Bohemian functional decor. Hose hold power for the space heater, lights, electric blanket, and for charging your phone. Coffee in adjacent barn. Private half bath. Ask for special offer to use house kitchen & shower Private off street location, awesome hideout! …
    • Central heating
    • Parking
    • Garden
    • Linens Provided
    • Towels Provided
      1 / 12

      $115

      Inquire

      Comsomore Cottage

      Charlemont cabin
      1 BR / 1 BA / Sleeps 6 | Quick view

      Details

      If you're looking for gorgeous mountain views in a peaceful setting, come stay in Comsomore Cottage - a mountainside log cabin located on the 50 acre mountain top estate, the Rose and Goat Retreat in the beautiful Berkshires, USA. Ideal for someone who wants to make this their home for a little while or longer, rental…
      • Mountain Views
      • Wireless Internet
      • Washing Machine
      • Clothes Dryer
      • Outdoor Dining Area
      • Suitable for children
      • Suitable for the elderly
      • Wheelchair accessible - adapted

      $72

      Book

      Vacation Village BerkshiresAug30-Sept6, Only$499WK

      Hancock apartment
      2 BR / 2 BA / Sleeps 8 | Quick view
      Excellent1 Reviews

      Details

      Reviews

      (1)

      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! 2 bedroom, 2 bath, sleeps 8 Fully furnished with cooking utensils, linens and towels for up to 6 people. August 30 to …
      • Mountain Views
      • Hot Tub/Jacuzzi
      • Wireless Internet
      • Washing Machine
      • Clothes Dryer
      • Suitable for children
      • Suitable for the elderly
      • Wheelchair accessible - adapted

      Details

      Reviews

      (1)

      Secluded spot, not overly commercialised

      Left on Feb 16, 2015 for a stay in September 2014

      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 the air is so fresh and pure that you want to bottle it. But in this corner of New England we found an environment that nearly matched the Caledonian air!

      But in it's favour it is much warmer and the outdoor pool and…


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