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Chester Vacation Rentals

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    All 34 Rentals in Chester
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    The following rentals are within 15 miles of Chester.
    Writer's Room at Chestnut Lodge1 / 8
    (1)Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Escape to the Berkshires!1 / 20
    (4)Excellent
    Becket
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Lee
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The Gatehouse on Golden Hill1 / 13
    (1)Excellent
    Lee
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Secure Parking
    • Private Yard
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 15, 2017
    Stayed for 4 nights. Very spacious and well maintained. Greeted by Peter with prosecco, cheese, crackers,tomatoes, mint from the garden, and donuts. He gave us an orientation...
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    About this property
    We are located in the heart of America's cultural epicenter known as the Berkshires. Known as the 'Gatehouse' to upscale Erskine Park, this truly one of a kind Craftsmen inspired home is filled with unique features and materials seldom found including eucalyptus and Brazilian Cherry flooring,...
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    Lee, Berkshires 01238
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    Lee
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    sleeps 4 can combine with writer's room for large suite, private entrance. fireplace or windowed woodstove, ceiling fans cathedral ceiling, terrace with seating, pasture and forest views. windows line both sides of room and feels like a treehouse. beautiful wood floors and soft carpets make you...
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    Lee, Berkshires 01238
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Lee
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • Mountain Views
    • Patio
    • Grill
    • Parking
    • Wi-Fi
    • Shared Yard
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is the second floor of the barn. this is very rustic, literally a barn! Open cathedral ceiling. Wooden interior with open floor plan. Big queen sized bed with canopy . 2 twin beds. Great for traveling with family or friends. Kitchen area has microwave, mini fridge, induction cooktop, hot...
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    Lee, Berkshires 01238
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    chestnut lodge Queens Room1 / 2
    (1)Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    Reviewed August 16, 2015
    I had the pleasure of staying at the Chestnut Lodge in the Queen's room. From the moment you step into the foyer you are taken back to a simpler time in this historic lodge. The...
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    About this property
    Sunny, light , bright and wide! the queens room is one of the biggest rooms and has private ensuite bathroom with tub/shower. 2 big closets, large writing desk, comfy conversation area, 2 dressers full sized bed. a section of the room has original ceilings so persons taller than 6'2' would be...
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    Lee, Berkshires 01238
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Berkshires House, 40 wooded acres, Lake Frontage1 / 16
    (20)Very good
    Monterey
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Air Conditioning
    • Grill
    • Washer
    • Waterfront
    • Mountain Views
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 20, 2017
    Karl and his place are supremely magical. The cottage is nestled in the woods on activated lands with a beautiful comforting peaceful lake, nature trails, less than an hour from...
    Reviewed September 21, 2017
    We rented Karl's house for a 10-day time frame, to enjoy some family vacation time with our children and grandchildren. I have really struggled with what to say about this...
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    About this property
    Charming house with the feeling of a cottage, set on a knoll with adjacent cathedral-like pine forest. **The house has a Jacuzzi and ROKU access to online (cable) TV. ** Stone fireplace, woodstove, beautiful kitchen with modern appliances (gas stove, microwave, refrigerator with water/ice...
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    Monterey, Berkshires 01245 0933
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Lakefront Summer Vacation Cottages1 / 16
    (3)Excellent
    Goshen
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Parking
    • Wi-Fi
    • DVD Player
    • Housekeeping Included
    • Waterfront
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 20, 2018
    This review is a little late but we lived here last August through October while I was working in the area. We loved it. The Lake and the views were from late summer through...
    Reviewed August 12, 2017
    A perfect start to our 3 week stay in Mass. Fantastic, quiet, lakeside location with warm water - so different from the UK! Full use of kayaks, canoe, paddleboard and raft...
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    About this property
    We have shared the beauty of our lakefront property for many summers. We live on the property year round and rent three cottages from late June through September.We love our guests and honor their privacy. We are a family and pet (dog) friendly vacation spot,unique and enjoyable! The property is...
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    Goshen, Hampshire County 01032
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Quiet Comfortable Cabin 5 Min. Walk to Lake1 / 13
    (13)Very good
    Becket
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Parking
    • Grill
    • Porch
    • Washer
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 19, 2017
    The location was easy to get to (even in the dead of winter).The place was clean, spacious and exactly as described. The wood stove was a great heat source as it was really cold...
    Reviewed October 25, 2016
    A charming cozy cottage in a quiet setting with all you need for comfort included. We hiked, canoed and visited farms and museums close by. It was a lovely fall getaway!
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    About this property
    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,...
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    Becket, Berkshires 01223
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Monterey
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Washer
    • Grill
    • Wi-Fi
    • Patio
    • Air Conditioning
    • DVD Player
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The lakeside house is built on a 1.1 acre lot with view of Lake Garfield. It is only three minute walk to the public beach with life guards on site. In the summer, Jacob’s Pillow Dance Center and Tanglewood Music Center are about 25 to 30 minutes away. In the winter, Ski Butternut resort is about...
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    Monterey, Berkshires 01245
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    East Otis
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Balcony
    • Hot Tub
    • Parking
    • Wi-Fi
    • Grill
    • Terrace
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the beautiful Berkshires. Watch the horses roam. Have a guided trail ride (additional fee) or have a camp fire only feet away from the horses. Within steps from your accommodations, enjoy the largest recreational lake in Massachusetts. Bring your boat or jetski. Or use our row boat. Go...
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    East Otis, Berkshires 01029
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Hinsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • DVD Player
    • Washer
    • Balcony
    • Wi-Fi
    • Parking
    • Outdoor Dining Area
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on 19 acres of forest and a creek, mixing modern and traditional with a charming two story wall of windows overlooking a back deck. This comfortable furnished home has two bedrooms with an additional open loft area for a third bedroom, two baths, all hardwood floors, and contains a large...
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    Hinsdale, Berkshires 01235
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Monterey
    5 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Waterfront
    • Mountain Views
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get away from it all at our beautiful Berkshire lakefront wooded retreat. Swim, canoe, kayak, sunbathe, play tennis during the day, then enjoy the evening a short drive away at Tanglewood, Jacobs Pillow, or perhaps go to the movies in Great Barrington. Have dinner at the Red Lion Inn, or one of the...
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    Monterey, Berkshires 01245
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 6
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    Romantic Berkshire Cottage on Storybook Estate1 / 10
    (1)Excellent
    Tyringham
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Terrace
    • Cable/satellite TV
    • Outdoor Dining Area
    • Internet Access
    • DVD Player
    • Parking
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 19, 2017
    What a wonderful, magical place, heaven on earth! From the moment we were greeted warmly by Denise and entered our Tiny House, we knew this was such a special place.The sound of...
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    About this property
    Charming, One Bedroom Cottage, former sculpting studio on the Santarella Estate in Tyringham, MA. Known as the 'Silo Studio', there is a bedroom with queen bed upstairs, sitting room, wet bar with Micro/Fridge and bath downstairs. Fall asleep to sounds of babbling brook and views to pond and forest...
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    Tyringham, Berkshires 01264
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Berkshires Spacious Comfortable Charming Farmhouse1 / 24
    (2)Very good
    Lee
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 17, 2013
    This property was a great home base for our brief visit to the Berkshires. Plenty of space and well equipped. We especially enjoyed the beautiful property, whether sitting on...
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    About this property
    Experience a little of old New England. Our vacation rental is a charming historic family farmhouse apartment with lots of room and comfort,2100Sq.ft., situated on 22 acres. Built in 1782, our farm was famous for breeding Plymouth Barred Rock chickens. In the 1800's, one of these barred rock...
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    Lee, Berkshires 01238
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Lee
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    --Brand new 3400 sq ft Lee home in a private lake community, Berkshires --Situated on 4 wooded acres on a quiet country road --Pristine home features two master bedroom suites plus 3 additional bedrooms, 5 bathrooms --Spacious living room with vaulted ceiling & skylights --Fully equipped kitchen,...
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    Lee, Berkshires 01238
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Charming and Spacious Colonial Farmhouse on 4 Acre Estate1 / 15
    (1)Average
    Tyringham
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Washer
    • Mountain Views
    • Central Heating
    • Balcony
    • Wi-Fi
    • DVD Player
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 9, 2017
    The grounds are beautiful with lovely gardens. Denise is very friendly and accommodating (like when my son-in-law landed his drone in a tree). The kitchen is well equipped. We...
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    About this property
    Located on the Santarella Estate, an historic site located in the the Massachussetts' Berkshires. The colonial home is the former residence of sculptor Sir Henry Hudson Kitson. The estate includes the landmark, iconic storybook style 'Gingerbread House,' designed by Kitson to look like an English...
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    Tyringham, Berkshires 01264
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Lake House1 / 18
    (4)Excellent
    Lee
    5 Bedrooms, 6 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Wi-Fi
    • DVD Player
    • Sauna
    • Air Conditioning
    • Grill
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 2, 2016
    My family and I traveled to the Berkshires from Boston and stayed in this gorgeous lake house. We had booked vacation rentals in the past and had a whole range of experiences...
    Reviewed September 1, 2016
    We stayed at the Lake House on beautiful Laurel Lake with my family of 5 (two daughters, son, and my wife). We had an awesome time. The owners Marjorie and Frank were wonderful...
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    About this property
    Custom designed Furnished Lake House in The Berkshires in Massachusetts on the Lee/Lenox line. Gorgeous western sunsets ! The home has 4/5 bedrooms and one is equipped as a nanny suite or teen haven. It is close to skiing, golf, outdoor sports, shopping, and all cultural venues. It is located...
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    Lee, Berkshires 01238
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 9
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    Berkshire House Share-The Blue Room1 / 10
    (1)Excellent
    Lee
    3 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Share a beautifully renovated home in the Berkshire Mountains of Western MA. I would prefer a long-term housemate, but will be glad to do weekend or short term stays. Long-term pricing can be negotiable. Cable TV (in your room), internet, washer and dryer, big eat-in kitchen, well-lit living room....
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    Lee, Berkshires 01238
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 2
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    Lee
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    (Interior photos coming soon!) All New, renovated 400 sq. ft. cottage is located centrally in South Lee, / Stockbridge line. Only 1 mile from Stockbridge main street, nightly entertainment at the Red Lion's Den, close to everything, boutique shops, grocery stores, restaurants, and all Berkshire...
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    Lee, Berkshires 01260
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Becket
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Central Heating
    • Terrace
    • Balcony
    • Private Yard
    • Grill
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large home in wooded area of the Berkshires. Ideal for all the summer events such as visiting Great Barrington, Lenox, Lee, Stockbridge. Many mountain areas for picnics, biking, hiking in the summer and winter events such as skiing and snowboarding. Near Center pond where there are many boating...
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    Becket, Berkshires 01223
    Rental Home - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    Tyringham
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Terrace
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A bright, lovely and comfortable room with queen bed in a charming country farmhouse with adjoining private bath. Located in Tyringham, a bucolic, rural village on a scenic country road the beautiful and magical 'Hop Brook' valley. The house is surrounded by farmland surrounding it on all sides. A...
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    Tyringham, Berkshires 01264
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Tyringham
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Santarella Estate and Gardens in Tyringham, MA is a magical destination in the heart of one of the Berkshires' most beautiful valleys, located 3 miles from Interstate 90 and 15 minutes from most of the principal attractions (Tanglewood, Jacob's Pillow, Norman Rockwell museum, etc.) Pictures are...
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    Tyringham, Berkshires 01264
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Otis
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THIS IS A FULLY FURNISHED LARGE RETREAT IN THE HEART OF THE BERKSHIRES...SKIIING, LAKES, ANTIQUES, CRAFT SHOWS, ARTS, THEATRE ALL NEAR BY.....HOME IS IN A PRIVATE COMMUNITY WITH ITS OWN LAKE, POOLS, STATE OF THE ART FITNESS CENTER, CLUBHOUSE, HIKING TRAILS, TENNIS AND MORE! ONLY 2 1/2 HRS FROM NY...
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    Otis, Berkshires 01255
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    Becket
    2 Bedrooms, 2 Bathrooms, Sleeps 2 Quick View
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    • Waterfront
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Private Yard
    • DVD Player
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Becket, Berkshires 01223
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 2
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    Monterey
    Studio, 2 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    You'll love our hand-hewn post & beam beauty on 13 acres in the Berkshire Mountains of Western Mass located near the Monterey/Great Barrington line, close to everything. Great for summer and winter ski season. Rich in both outdoor and cultural attractions, shopping and antiquing. Located adjacent...
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    Monterey, Berkshires 01245
    Rental Home - 2 Bathrooms, Sleeps 7
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    Lee
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    • Patio
    • Cable/satellite TV
    • Central Heating
    • Porch
    • Wi-Fi
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Share a beautifully renovated Victorian home, in downtown Lee, Ma, right in the heart of the Berkshires. Walking distance to town, and on the bus line. Wifi, cable TV, off street parking. Shared kitchen and bath. I have two cats and one other housemate. I am a gospel and blues musician. This is a...
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    Lee, Berkshires 01238
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 1
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    Lee
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 1400 square foot, three bedroom home has all amenities including washer and dryer in basement. Electric heat and oven. Front porch and back deck. First floor is open floor plan with kitchen, dining area and living room flowing from one to the other. Skylights in the living/dining area and...
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    Lee, Berkshires 01240
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lee
    1 Bedroom, 2 Bathrooms, Sleeps 10 Quick View
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    • Central Heating
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    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note that homeowner lives in a separate building on the property and may be present during your stay* Gather your loved ones for a revitalizing Lee retreat when you book this lovely 3-bedroom, 2-bathroom vacation rental house that comfortably sleeps 10! With new furnishings, a private...
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    Lee, Berkshires 01238
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 10
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    Huntington
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • DVD Player
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You and your travel companions will be stricken by colonial beauty as you cross the threshold into this Huntington vacation rental home. The 3-bedroom, 2-bathroom house was constructed in 1789 and still boasts many of the original furnishings, but now features all of the modern amenities you'd...
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    Huntington, Hampshire County 01050
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Monterey
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Air Conditioning
    • Mountain Views
    • Cable/satellite TV
    • Washer
    • Patio
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Smiling Dog Meadow' is truly the ideal vacation rental house in scenic Monterey, Massachusetts! Nestled on 5 acres of land, this newly renovated home for up to 12 guests features a waterfront location with access to a private dock and several boats. Create unforgettable memories at Lake Garfield,...
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    Location Information
    Monterey, Berkshires 01245
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Otis
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in the woods of East Otis, you’ll have a peaceful stay in the Berkshires at this cozy 2-bedroom, 1-bathroom vacation rental cabin. Comfortably accommodating up to 5 guests, this retreat is perfect for a memorable family vacation. With miles of hiking trails to explore and the Otis Reservoir...
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    Location Information
    Otis, Berkshires 01029
    Cabin - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Goshen
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the New England woodlands and reconnect with the outdoors when you stay at this 2-bedroom, 1-bathroom Goshen vacation rental cabin that sleeps 8. This quiet, 725-square-foot cabin offers peace and comfort, with an open-concept living space, a large deck with a patio set and grill, a...
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    Location Information
    Goshen, Hampshire County 01032
    Cabin - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Chester Flight and Weather Info
    Airports nearby (1)
    Plan your day of travel
    BDL
    Bradley Intl Airport
    27.7 miles from Chester
    Low airfares recently found by TripAdvisor travelers
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    Local Weather
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    July
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    August
    69° 46°
    September

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