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Chester Vacation Rentals

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    All 38 Rentals in Chester
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    The following rentals are within 15 miles of Chester.
    Escape to the Berkshires!1 / 20
    (4)Excellent
    Becket
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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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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    Lake House1 / 18
    (4)Excellent
    Lee
    5 Bedrooms, 6 Bathrooms, Sleeps 9 Quick View
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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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    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
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Sauna
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Shared Indoor Pool
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I have a corner unit first floor 2-bed resort presidential suite in beautiful Berkshires! Just 2 hours drive down the Mass Pike from Boston. It's July 4th week and James Taylor will be playing at Tanglewood. This is one of the most sought after concerts every year and you wouldn't want to miss it!...
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    Lee, Berkshires 01238
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Berkshires Spacious Comfortable Charming Farmhouse1 / 12
    (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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    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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    Lakefront Summer Vacation Cottages1 / 16
    (4)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 September 5, 2018
    Wonderful Labor Day weekend trip with our grandchildren, ages 5 and 8, and out 2 year old Great Pyrenees. Clean and comfortable cottage, appropriately stocked kitchen, and the...
    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...
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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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    Enjoy horses and the largest recreational lake in Massachusetts1 / 20
    (1)Excellent
    East Otis
    1 Bedroom, 1 Bathroom, Sleeps 4 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
    Reviewed November 7, 2018
    I stayed here with a few friends looking to escape the city for a cozy weekend away. Wendy ad Kevin were amazing and went above and beyond their responsibilities as hosts. Wendy...
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    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 4
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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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    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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    Writer's Room at Chestnut Lodge1 / 8
    (1)Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Outdoor Dining Area
    • Mountain Views
    • Air Conditioning
    • Hot Tub
    • Balcony
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 17, 2014
    We have taken the Writer's Room each Summer for about three years now. We find the Lodge to be authentic New England... our natural wood room to the rest of the house. It is...
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    About this property
    The Writer's Room is at the top of the stairs on the right. This handsome room is made completely of wood. Ceilings are higher and there's a sitting area in the big dormer. dormer faces east and get the morning sun! The floors are wide plank cherry milled from the property. the walls are pine....
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    Lee, Berkshires 01238
    Private Room - 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
    Kid friendly
    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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    Serene Lakefront Cottage1 / 17
    (13)Excellent
    Becket
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 21, 2018
    My husband and I rented this lovely house for the first week in September, including Day weekend. What we wanted was a week long retreat from the world and all of its noise...
    Reviewed July 16, 2016
    We stayed for a week with two teenaged boys and two dogs. We had a wonderful time. The lake was fully accessible and the boats and life vests well cared for. The photos are...
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    About this property
    Pretty cottage in the woods on a beautiful clean 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 (both supplied with life vests) or...
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    Becket, Berkshires 01223
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    chestnut lodge Queens Room1 / 2
    (1)Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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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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    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Grill
    • Mountain Views
    • Outdoor Dining Area
    • Balcony
    • Patio
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Lee, Berkshires 01238
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Monterey
    Studio, 2 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
    Kid friendly
    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
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
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    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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    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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    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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    BSO Tanglewood + Jacob's Pillow. Lenox-Stockbridge. 5bdr/6bth. sleeps 24+1 / 22
    (2)Excellent
    Lee
    5 Bedrooms, 6 Bathrooms, Sleeps 30 Quick View
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    • Wi-Fi
    • Porch
    • Air Conditioning
    • Balcony
    • Washer
    • Mountain Views
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 27, 2017
    Excellent location to enjoy the best of the Berkshires, and a comfortable, spacious house full of historic character. 3 wood burning fireplaces and a screened porch make this...
    Reviewed May 29, 2016
    My family loved this house - parents and kids, all found it comfortable, spacious, and welcoming. Host is accommodative on last-minute changes or special requests. Easy...
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    About this property
    In the heart of the Berkshires: near Tanglewood, Jacob's Pillow, Jiminy Peak, Ski Butternut, Lenox MA, Stockbridge MA. Completely restored historic house with fully equipped kitchen, 5 bedrooms (each with a private bathroom), 3 spacious common rooms. A comfortable place for a family reunion,...
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    Lee, Berkshires 01238
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 30
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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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    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Air Conditioning
    • Wi-Fi
    • Patio
    • Grill
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    All New, renovated 400 sq. ft. cottage is located centrally in South Lee, / Stockbridge line. Only 1 mile from Stockbridge main street, Marion Father's, nightly entertainment at the Red Lion's Den, close to everything, boutique shops, grocery stores, restaurants, and all Berkshire cultural...
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    Lee, Berkshires 01260
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Lee
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fully furnished, 3 bedroom, 2 full bath condo in private, quiet, secluded community, adjacent to October Mt. State Forest. Assigned parking, heated swimming pool, tennis courts and lending library within one block of condo. Open concept living room, dining room and kitchen on first floor. Bedroom...
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    Lee, Berkshires 01238
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    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' offers the ideal escape to Massachusetts's scenic Berkshires region! Nestled on 5 acres, this newly renovated home for up to 12 guests features 4 bedrooms, 2.5 baths, and a waterfront location with access to a private dock and several boats. Create unforgettable memories at...
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    Monterey, Berkshires 01245
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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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
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Central Heating
    • Wi-Fi
    • Washer
    • 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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    Location Information
    Lee, Berkshires 01238
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Lee
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    Amenities & Details
    • 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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    Location Information
    Lee, Berkshires 01238
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 1
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    Huntington
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Washer
    • Patio
    Suitability
    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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    Location Information
    Huntington, Hampshire County 01050
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Otis
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • 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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    Becket
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Central Heating
    • Patio
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    • Grill
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A beautiful retreat awaits you at this 3-bedroom, 3-bathroom vacation rental house in Beckett! Up to 8 guests can share this peaceful home, situated on 11 private acres of wooded land with a swimming pond. Venture out to explore the Berkshires where you'll find 9 lakes, watersports, renowned spas,...
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    Location Information
    Becket, Berkshires 10021
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    Monterey
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Waterfront
    • Terrace
    • Patio
    • Wi-Fi
    • Grill
    • Balcony
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With 150 feet of gorgeous lakefront property on Lake Buel - a pristine 192-acre mountain lake - this lovely 3-bedroom, 2.5-bath home is sure to be the perfect 3-season getaway for 10! Enjoy sitting out on the deck to take in the water views, gathering around the fire pit to roast s’mores, or...
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    Location Information
    Monterey, Berkshires 01230
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Monterey
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Washer
    • Central Heating
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay a 5-minute walk from the Lake Garfield Beach and explore the area's historic attractions, outdoor recreation, and more at this 3-bedroom, 2.5-bath vacation rental! Up to 7 guests can enjoy a classic getaway at this country home, featuring a stone patio, gas grill, screened porch, and all the...
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    Location Information
    Monterey, Berkshires 01245
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Chester Flight and Weather Info
    Airports nearby (1)
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    BDL
    Bradley Intl Airport
    27.7 miles from Chester
    Low airfares recently found by TripAdvisor travelers
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