Take advantage of this trend to stay in homes and condos rented out by the owner - so much more space and luxury for less $$.
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Woodland Cottage-NEW! Convenient, private, family friendly- see CLEANING DETAILS
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Woodland Cottage-NEW! Convenient, private, family friendly- see CLEANING DETAILS - 3BR/2BA, sleeps 8; min stay 3-7 nights, Avg $225/nt -
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 VRBO #1766751 - 3 Bedroom (Sleeps 8), 2 bath, luxury log cabin wth woodland trails, dog friendly
Lovely craftsman-built log home with modern amenities on 50 acres. Private 10 x 32' covered rear deck overlooking beautiful woodland views. Property has marked walking trails and the Appalachian Trail is within 1/2 mile. Local ski resorts (Otis Ridge, Butternut and Jiminy Peak) are close by and many arts and culture venues (Jacob's Pillow, Tanglewood, etc.) are within a short drive. The towns of Lenox, Lee, Great Barrington and Stockbridge provide great shopping and restaurants. This property is perfect for couples or families. It is an outdoor paradise perfect for hiking and snowshoeing. Dogs welcome!
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Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
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Rustic Berkshires Cottage at Lake Buel w/ Kayaks! - 1BR/1BA, sleeps 2; min stay 3-120 nights, Avg $183/nt -
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VRBO 4736901ha - 3 Bedroom (Sleeps 8), 2 bath, luxury log cabin wth Bring your loved one or best friend along on a Berkshires getaway in this 1-bedroom, 1-bath vacation rental in New Marlborough. Nestled just 30 yards from private right-of-way access to Lake Buel, this cabin offers unbeatable views of the lake and the Berkshire Mountains. Launch the 2 new kayaks, hike along the Appalachian Trail, or check out the local cultural scene! Whether you’re visiting for a romantic retreat, cultural indulgence, or an active outdoor getaway, this is the ideal home base.
-- THE PROPERTY --
Pets Welcome | Right-of-Way Lake Access | 2 10-Foot Kayaks | Fire Pit
This rustic cottage provides simple, economical, accommodations for those who want to enjoy a wonderful lake and experience all that the Berkshires has to offer without breaking the bank on lodging and restaurants! Read more |
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Peace And Quiet On The Lake
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Peace And Quiet On The Lake - 2BR/2BA, sleeps 6; min stay 2 nights, Avg $244/nt -
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VRBO #892478 - OPEN FOR ALL THE WONDERFUL SEASONS! You will love the peaceful and private lake and have plenty of other great things to do while in the Berkshires. Very close to Tanglewood, Jacobs Pillow, Lee Outlets, Theater, concerts, skiing, restaurants and much more. Or just hang out on kayaks enjoy mother nature and this rustic style home. The kids swimming at the beach. Sherwood Shoppe has everything you need for a camping feel and ice cream! The fall foliage doesn't get much better than this! Or enjoy this winter wonderland and all the Berkshires have to offer in winter. You will even enjoy watching mother nature come back to life right in front of your eyes in the spring,Read more |
Great Barrington Rental Home, Sleeps 4
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Cozy and clean in Gt Barrington - 2BR/2BA, sleeps 4; min stay 3 nights, Avg $130/nt - BOOK IT!
Trip Advisor #FKN3225390 -Great Barrington – Our home is located in Great Barrington, given the title of the #1 Best Small Town in America by Smithsonian Magazine. There are many great restaurants, shopping, the Mahaiwe theater, a cineplex, golf, natural foods Co-op, a State Forest, yoga studio, and more. There are about twelve (12!) hiking trails in Great Barrington alone. We have our own ski resort and there are 4 other ski resorts nearby. The Berkshires are a beautiful and interesting place to visit- the perfect blend of nature and culture.
Our well-kept and comfortable home is available for 1 week during the summer (you choose the week). Ideal for a romantic getaway or a peaceful retreat. Our house is eco-friendly: recycling, composting, clothesline, push mower, etc. The home is ½ of a duplex.
- 2-story home with 2 bedrooms (one room w/ king bed, one with double),
- romantic wood stove in the living room
- 1½ bathrooms (w/ Swedish toilets)
- an extra room w/ desk
- screened patio and deck- perfect for an outdoor meal
- 2 bicycles
- Wifi internet
- flat screen TV w/ DVD player Read more |
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Country Haven, Sleeps 4
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Unique People & Pet-Welcoming Country Haven - 1BR/1BA, sleeps 4; min stay 2 nights, Avg $70/nt - BOOK IT!
Trip Advisor #FKN3609336 -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. Nestled at the base of the Charlemont hills and located on a very quiet country road, Cavalier Cottage is spacious, bright and comfortable. The live-in area is simply but graciously appointed, featuring ceiling to floor windows, a queen size bed, private entrance and private deck. The fully equipped kitchen has an eat-in area with a full size stove and refrigerator (in case you want to cook-in), and a private bathroom. Relax on the private deck and enjoy the country view. For entertainment, you can access Netflix movies on your laptop, watch Direct TV with over 100 channels, or play classic board games. To stay in touch with the outside world, the cottage is equipped with Wifi. Park your car in an enclosed garage if you need to. Amenities also include a delicious Continental breakfast with Pat's English scones, a small but growing library, and a CD player with a collection of jazz and classical CD's. Read more |
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
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Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating - 2BR/1BA, sleeps 4; min stay 2 nights, Avg $142/nt -
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VRBO #182224ha 2 bedrooms, 1 bath, sleeps 2-4
Remember the simple pleasures of a country, lakeside vacation where you can spend the day swimming or boating, exploring the countryside, or just read the afternoon away on the screened-in porch? Get back to those simple pleasures in our cabin, located in a beautiful, quiet country setting in the heart of the Berkshire Mountains. The cabin is just a five minute walk to a lake where you can swim, fish, kayak or canoe (boats, paddles and life jackets provided). Or spend the day exploring the many surrounding towns with antiques, restaurants and shopping galore; take a drive down a country road looking for roadside farm stands; go for a long walk in the woods; or explore the nearby rock quarry. At night, have dinner at an outdoor restaurant, grill on the deck, relax with a glass of wine on the porch, roast marshmallows, do a puzzle, or enjoy your favorite streaming on our Roku TV with Netlifx, Hulu, Amazon Prime, and more. Even with many area cultural events and attractions closed for the summer, you're sure to find plenty to do here to relax and have fun at a safe distance from others.
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Berkshires Escape in Becket, Sleeps 8
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Escape to the Berkshires! - 4BR/3BA, sleeps 8; min stay 2 nights, Avg $340/nt - BOOK IT!
Trip Advisor #FKN2383071 -Becket-Come to the Berkshires and stay in one of the most beloved areas of Massachusetts.
We are located close to Lenox, Stockbridge, Lee, Great Barrington and more.
Our 3400 square foot ranch home is located in the heart of the Berkshires with Fall foliage, spring in bloom, and picturesque setting, and a local lake that is a beautiful respite and available for picnicking and swimming all day long. We also have a tennis court in town that is public.
A scenic drive away from the iconic Berkshires destinations including: Jacob's Pillow, Tanglewood, the Norman Rockwell Museum and historic Lenox, Stockbridge and Great Barrington where you will find dining, music, and culture. Near Williamstown where you can enjoy The Clark and Shakespeare Festivals. Read more |
8 Room Apartment in the Woods, Sleeps 8
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Apartment walking distance to Mass Museum of Contemporary Art!! - 2BR/1BA, sleeps 10; min stay 1 nights, Avg $192/nt - BOOK IT!
Trip Advisor #FKN4634898 -North Adams - 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 bed and the spare bedroom has a futon that pulls out to a double sized bed ( I also have an air mattress if that is needed).
There's a huge backyard with two fire pits, a picnic table and a grill.
If you have any questions please ask!! Read more |
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Beautiful Berkshire Home with Tennis Court
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Beautiful Berkshire Home W Tennis Court; Close to Skiing! - 4BR/3BA, sleeps 9; min stay 3 nights, Avg $443/nt
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VRBO #95599 - the Sheffield house is historic and located in the heart of the Berkshires, two and 15 min 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, peace and quiet. Search 'Berkshire Winter Rental' on Vimeo to see a winter video of the house.
With 3100 sq. ft of wood floors and elegant decor, this spacious house was renovated with two additions: sun room with master bedroom above, and the gourmet kitchen. The original portion of the house includes a den with fireplace and 42" plasma TV with satellite surround sound home theater system. Built-in bookshelves have loads of great reading and an eclectic DVD library that should have something for everyone. The Parlor is a wood-paneled room with wood-burning stove and door opening up to a small deck with Adirondack chairs for lounging. This is a great room for entertaining. Connecting to the parlor is the traditional dining room which has a table that can seat 10 and a fireplace. Read more |
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Beautiful Waterfront House Rental- Right on Lake Garfield
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Beautiful Waterfront House Rental- Right on Lake Garfield - 3BR/2BA, sleeps 6; min stay 7 nights, Avg $275/nt -
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VRBO #385685 - House, 3 Bedrooms, 2 Bath, (Sleeps 6) -Everyone says, 'WOW what a GREAT view' we have of the lake and we are only 40 feet from the water. Our home is well equipped and conducive to a comfortable stay. Enjoy our wrap around deck for relaxing or dining. The open airy living room/dining room combination with cathedral ceilings also features a full size wood fireplace for those cool summer evenings.
Stroll down to the lake to enjoy sunbathing or fishing from the large dock. Or canoe or kayak on the lake. The fishing is excellent and we have caught trout, large and small mouth bass, perch and many others .
The house is located on a quiet private road. It has a queen size bed in the master bedroom, a queen bed in the second guest room and twin over full bunk in the third guest room.
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Country Waterfront Lakehouse in The Berkshires
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Country Waterfront Lakehouse in The Berkshires- 3BR/1 1/2BA, sleeps 6; min stay 2 nights, Avg $185/nt -
BOOK IT - Instant Confirmation!
VRBO #4149878ha - Completely Remodeled 3 Bedroom , 1.5 Bath Home With Water Views , Decks & Porchs
Peaceful and private setting with a long driveway along the river and waterfall leads to this peninsula at the lake. Inside , the rooms are filled with light and windows, radiant heated marble tiles, and wood all around. Several decks and a large screened porch offer the outside at your leisure. One bedroom downstairs with a brand new comfortable queen bed and full downstairs large jacuzzi tub bathroom, a 20' x 20' kitchen---all new appliances...All new furniture...Giant 4hdtv screen , wifi internet . 2 bedrooms upstairs, one with a queen bed, the other with two identical twin sized, and a convenient half bath. Wildlife viewing---especially bird watching --- anywhere from the house and yard, fishing, boating , and a wonderful walking/running/biking trail an easy walk away. For bird watchers this is an incredibe sactuary to see various ducks, bald eagles, great blue herons, geese, songbirds, osprey, etc.
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New! wheelchair accessible, petfriendly, by owner rentals in the Berkshires.