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300+ Rentals · Chester
300+ Rentals · Chester
North Bedroom in charming old home just outside Chester Village. House recently restored and renovated. Feel free to use the entire house, country kitchen and dinette. Spacious yard to play. Learn More
North Bedroom in charming old house just outside Chester Village. Recently restored and renovated. Engish-American cottage decor. Feel free to use the entire house, country kitchen and dinette. Spacious yard to play with gardens and trails leading up Pine Hill. Mid 19th century house, kindly restored and updated in 2014 - retaining many old house features like plaster walls and windows, with new bathrooms for convenience. Located on the second floor, the North Room has a double bed. Share...
Super quiet area right on westfield river. Private room with a private entrance if needed. Room is very plain in décor. Shared bathroom. The room does have a small fridge and desk. Learn More
Deck and side yard. I do live here full time so there is a bit of interactions with the guest. I can also offer a recommendations for guest if they are looking for things to do in the area. I am located 30 mins to Lee & Lenox Ma 35 mins to Northampton Ma 40 mins to Pittsfield Ma 20 mins to Westfield Ma I do have a 3 year old Vizsla pup. He is very friendly but excites easily. Has a tendency to jump when upon first meeting but then will become your best friend.
The bed is a latex full size bed. We live within walking distance of the center of town and a short drive, 2 1/4 mile walk or bike ride from Kripalu & Tanglewood. Our home is lovely, quiet, and comfortable. Learn More
Our rooms are comfortable and well decorated. WiFi is high speed. Guests have access to the living room, back deck, garden and kitchen. They may cook if they want. Just clean up afterwards and remove all items from the refrigerator before checking out. We tend to be very busy so we generally do not interact much with guests. Probably the most interaction in general occurs in the kitchen or outside on the deck. Although we have 7 bedrooms, we only offer two for long term rentals and...
This cute little apartment is perfectly situated minutes to Tanglewood, Kripalu, laurel lake and downtown Lenox. 20 minutes to Stockbridge in summer traffic and 30 minutes to Great Barrington. Located in a small residential neighborhood, enjoy a little Pied a terre for the price of a highway motel. Learn More
The Apartment is The basement level of my 1954 Cape style home, though the entrance is ground level and direct from the driveway. The bedroom has a Ac unit in the window and It is quite comfortable. You have a private patio with dining table and gas grill.The kitchen is fully equipped. TV had Roku Streaming with Netflix and Hulu Plus. The Apartment is fully contained, Parking for two cars.My neighborhood is a small dead end street with 6 homes in a residential hamlet of Lenox lovingly cal...
Comfortable home on beautiful property walking distance to two parks with hiking trails, close to skiing, Lenox Town, many famous cultural institutions, theater, dance, Tanglewood, Kirpalu, Clark Museum, Mass Moca, Norman Rockwell museum, dining. Learn More
Living room, den, three generous-sized bedrooms- one with a king bed, one with two double beds and a charming loft room with a double, mud room with washer and dryer. Eat-in fully equipped kitchen with dishwasher, cookware, separate dining area, three large bedrooms and one full bathroom upstairs and one full bath downstairs, master bedroom with king bed, second bedroom with two doubles, loft bedroom with double. There is a large grass yard, swing set, pingpong table, kayaks, charcoal gri...
November to May enjoy this home away from home, each bedroom has its own bath, King room first floor, two queen rooms, one room two twin beds, TV each bedroom, frig in each queen room, guest parlor has frig micro, toaster, kurig coffee, kitchen use Learn More
This master bedroom has a queen bed. Bathroom located right outside of the bedroom. Lovely, convenient Lenox location. Learn More
We are walk into town, and also walking distance to Tanglewood and Kripalu. A lovely neighborhood.
Beauty is inside and outside here. Nestled in pine trees, this B&B is a quiet retreat 2 miles from town, comfortable and clean. Shared bath. A/C. WiFi. 4 miles to Tanglewood & Kripalu. Smoke/free. Pet/free. Breakfast included. Learn More
Centrally close to all activities in the Berkshires. Guests have access to living room with DVD/VCR player, stereo, and a piano. There is also access to a small space in the refrigerator. Conversations are always nice with guests, and at the same time, their privacy is always respected. I am always here at home. Spacious land and woods in neighborhood, with flowers, either cultivated or wild. Nature surrounds, with wildlife. Very, very peaceful and quiet. There are taxis available, ...
Come, enjoy Tanglewood! A recently renovated cottage in a walk-to-town location, will allow you to explore the best of Lenox and the Berkshires. Walk to Tanglewood, Shakespeare and Company, Canyon Ranch or one of the amazing, Lenox restaurants! Learn More
This summer cottage built in the 1950's has recently been completely renovated from stem to stern to bring it up to date with the most current design standards. It is a 2-bedroom, 1-bathroom space with a large front yard and beautiful backyard for grilling. Features include a beautiful dining room surrounded by windows and backyard patio access to enjoy the lush forests adjacent to the space. Breathe in the fresh mountain air and appreciate the beautiful greenery in the spring, summer a...
Bedroom in mid 19th century home. This room has two twin beds. Adjacent to the back stair and sitting room, it's rather private. Two other bedrooms and additional bath available in home. Whole house rate available. Learn More
Recently restored, this c1853 home retains old plaster walls, hemlock flooring, original windows. It has updated bathrooms. Please feel free to use the whole house, kitchen and dinette. Lovely yard with gardens. Watch the motorists from the porch while enjoying your morning coffee. Your hosts will likely greet you on arrival. We are just 3 miles up the road. We'd be happy to direct you to local spots or assist you with anything to make your stay pleasant. Chester village is less than a m...
On the grounds you will find outdoor tennis courts, a putting green, shuffleboard and bocce courts, basketball courts, a playground, rowboats and canoes for use on site, 200 acres to walk, hike, bike or cross country ski, and gas barbecue grills! Learn More
Great little house in a very convenient location. Set nicely back from the street with a 1 ac. spacious back and side yard. 8 minutes drive to Tanglewood. All rooms are furnished. Living room with bay window and fireplace, hardwood floors throughout. Learn More
2 Bedrooms 1 bathroom House Full access. I can be contact by phone and email.
220+ Acres W\ Tennis Cts, Indoor / Outdoor Pool, Canoe, Fishing Boat, Hot Tub.New first time rental of 4 BR, 2BA, Cape Cod style, sleeps 10-12. New fully equipped kitchen w/ center island, indoor and outdoor barbecues, wine cooler, 2 fireplaces. Learn More
New first time rental of 4 BR, 2BA, Cape Cod style, sleeps 10-12. New fully equipped kitchen w/ center island, indoor and outdoor barbecues, wine cooler, 2 fireplaces, large deck with 7 person hot tub and super seating for beautiful sunsets, Dacquiris and Bloody Mary's ( ingredients included). Fabulous great room with pool table, 65' Smart TV and 40' HD TV for you sports fans. Great indoor / outdoor sound system and don't worry about the neighbors. Summer weeks include 2 rounds of golf at n...
This is a smaller bedroom with a twin size bed (1 year old) overlooking front of house with plantings and woods. House is across from Cranwell and this is one of the best deals in the Berkshires but the room is only for 1 person. Learn More
This is a nice size room. It is opposite the main bathroom and next to the kitchen. With woods in the front of the house it is private. Cranwell is across the street which has a spa, 3 restaurants and lovely walkways for summer or snowshoeing/cross country skiing in the winter. October Mountain is just down the road for great hiking trails and less than 2 miles away is the village of Lenox, Shakespeare Theater, Tanglewood and Kripalu. You will have access to the fist floor. This ...
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This space is a private single with its own full bath. The bedroom is adjacent to another room which is your TV/exercise space. The whole area is about 640 sq ft....or half the downstairs area of our large raised ranch with off street parking. Guest also have wiifi and use of the deck, grill and backyard. Our home is located on the eastern side of Lenox less than a mile from the center of Town. It's another half mile to Tanglewood. Learn More
Cottage is a stand-alone building on our 2-acre property overlooking beautiful October Mountain, part of the Appalachian Trail. It is attached to an unused horse barn, which still has two horse stalls and a tack room. The location is close to downtown Lenox but very quiet and private. Learn More
The cottage's porch leads to a large, open "great room" that feels very much like a ski lodge or cabin, with wide-plank wood floors and exposed beams. The great room has a dining table with 4 chairs, a bar with 3 stools, a cool mid-century orange sofa and 2 matching chairs and an entertainment unit with a TV and DVD player. There is also a ceiling fan for air circulation and a skylight that can be opened to allow air in and out (plus, it has an automatic shade, should you want to block th...
Modern, comfortable, and cozy townhouse 3 BR & 3 1/2 BA Airy and nice flow and high ceilings Bamboo floors Screened-in large porch with logia and dining Sleeps 6 people Learn More
Very spacious and airy, high ceilings Bamboo hardwood floor 3,000 sq. ft. Attached garage and guest parking space. 3 bedrooms: 1 king size bed, 2 twins beds together making another king size bed, 1 queen size bed. 3 1/2 bathrooms, eat in kitchen (8 people), dining room for 10, screened in porch dining for 8, loggia sitting area for 8/9, outside seating for 8 or more. On golf course. Convenience of Location for the cultural activities of the Berkshires and sports activities of the Cran...
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Our heated two bedroom cottage is just a few steps from beautiful Laurel Lake. The sun deck is a great place to enjoy morning coffee. Each cozy bedroom has a large window overlooking the picturesque lake. The eclectic kitchen is fully equipped for cooking meals or baking treats. Learn More
The location is especially beautiful. The cottage is delightfully livable, though not updated, with comfy couches and chairs, a well-equipped kitchen, a washer and dryer, bathroom with tub-shower combo and two full beds with reading lights. There is a third room for TV watching. We have AC in the main living space and a propane furnace. There is also a wood burning stove which can be used as a fireplace. You will have access to everything in the house and yard. I will not be here, so ...
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