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Vacation Rentals in West Stockbridge, MA and nearby

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    1 / 20
    5 of 5 stars (25) Excellent
    West Stockbridge
    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    1 / 10
    West Stockbridge
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    1 / 8
    5 of 5 stars (2) Excellent
    West Stockbridge
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 6
    West Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Mountain Views
    • Parking
    • Wi-Fi
    • Terrace
    • Central Heating
    • Outdoor Dining Area
    • Balcony
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • x
    About this property
    Architect-designed, one bedroom studio cottage in peaceful setting on quiet road with a 5 acre view! What more could you ask! Perfect haven for artist or writer or anyone wanting to get away! Only 15 minutes to Tanglewood or Kripalu This little gem has just been renovated, with built in couches,... View all property information
    Location Information
    West Stockbridge, Berkshires 12029
    1 / 14
    5 of 5 stars (6) Excellent
    West Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Mountain Views
    • Wi-Fi
    • Balcony
    • Patio
    • Grill
    • Washer
    • Porch
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Located in West Stockbridge minutes from everything . Nestled in the Berkshire Mountains. Convenient yet Private. Visit our web-site aberkshirehome. The Berkshires is a world unto itself. It is scenic beauty married to cultural bounty. It is urban sophistication in an idyllic, rural setting. It is... View all property information
    Location Information
    West Stockbridge, Berkshires 01266
    5 of 5 stars Reviewed 3 days ago
    We had a wonderful stay in this large, lovely house that contained everything we needed for comfort and convenience. We were impressed with the degree to which details were...
    5 of 5 stars Reviewed November 2, 2014
    Had an outstanding couple of weeks staying here; place was quiet, peaceful and not too far from civilization. All the amenities and space you could wish for and Cassandra and her...
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    1 / 15
    West Stockbridge
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
    • Air Conditioning
    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    About this property
    2 story 1850's farmhouse in the Berkshires with original ceiling beams and 16" floor boards in much of the house. Fully furnished with 5 bedrooms, 2 full baths and a gorgeous screened- in porch overlooking 4 acres of gardens, stream and wooded mountains. Country kitchen with dish washer,... View all property information
    Location Information
    West Stockbridge, Berkshires 01266

    The following rentals are within 5 miles of West Stockbridge, Massachusetts.

    1 / 12
    4 of 5 stars (1) Very good
    Lenox
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
    • Balcony
    • DVD Player
    • Grill
    • Washer
    • Central Heating
    • Porch
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Charming, spacious and comfortable 1860's farmhouse adjacent to wildlife sanctuary. Cozy country decor with original wide plank floors, lovely views and outdoor dining or lounging on porch or deck. Walking distance to hiking trails in Pleasant Valley Wildlife Preserve or Kennedy Park. Quiet and... View all property information
    Location Information
    Lenox, Berkshires 01240
    4 of 5 stars Reviewed July 8, 2015
    Lovely farmhouse, convenient to Tanglewood and shops in Lenox as well as other nearby towns and sights. We were a family of 7, including a 2 year old, and the swing set in the...
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    1 / 16
    5 of 5 stars (5) Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Satellite TV
    • Porch
    • Parking
    • Washer
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Located a short walk to the town beach on the Stockbridge Bowl, and 1.5 miles from Tanglewood's Hawthorn entrance, this casual summer cottage is a great get away for the whole family. The master bedroom is equipped with a queen bed; two twins in the 2nd bedroom, and a full-size bed in the 3rd... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 stars Reviewed July 31, 2015
    This was a wonderful place to spend a family vacation. The house is immaculate, functional and well furnished. The proximity to all of the many venues and activities the area...
    4 of 5 stars Reviewed October 24, 2013
    Some friends and I wanted to have a reunion as we are spread out along the east coast, and we were debating between camping or renting. I heard no end of the gratitude from my...
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    1 / 4
    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Private Yard
    • Parking
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This farmhouse has 3 bedrooms available so guests may bring their family, several friends, or overlap with new ones. The Iris Room is bright and airy with 4 windows; the Nasturtium Room has a Full bed with a half bath and the Horse room has a full and single bed across from the community... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    1 / 26
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • Patio
    • Grill
    • Parking
    • Satellite TV
    • Air Conditioning
    • Washer
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Newly renovated contemporary house on 2 acres in Stockbridge. Great space surrounding house for outdoor sports and sitting around the fire at night. 3 bedrooms, 3 bathrooms, indoor fireplace, wood floors, many windows and closets. Large kitchen. WiFi. Master bedroom has king bed and master... View all property information
    Location Information
    Stockbridge, Berkshires 01238
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    1 / 29
    Lenox
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    • Wi-Fi
    • Private Yard
    • Patio
    • Parking
    • Air Conditioning
    • Satellite TV
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    AS YOU OPEN THE GATE FROM THE DRIVE YOU WALK ONTO YR FRONT DECK LEADING TO THE ENTRY , MUD ROOM WHICH HOLDS YR SUMMER NEEDS, SKIS AND BOOTS. THIS LEADS TO THE COTTAGE APT. [attached to the owner`s quarters} LIVING RM- HAS A SOFA SLEEPER TO ACCOMMODATE 2 MORE GUESTS. KITCHENETTE W/ LG CEILING... View all property information
    Location Information
    Lenox, Berkshires 01240
    1 / 4
    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Private Yard
    • Internet Access
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    This 1762 farmhouse features wide board floors, kitchen, dining and living room areas along with a spacious front porch. Agritour gardens, horseback riding, and close proximity to Tanglewood and the Norman Rockwell Museum make for an adventure filled visit. Larry prepares a great fresh egg... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    1 / 4
    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Internet Access
    • Private Yard
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    The 1762 farmhouse has 3 bedrooms available to bring your family and friends enjoy the close proximity to Tanglewood, Norman Rockwell Museum, and several lakes, many hiking areas, great restaurants. Larry makes a fresh egg breakfast which is included in your stay. You can join us for horseback... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    1 / 25
    Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Parking
    • Patio
    • Grill
    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This 1600 sq. ft. cottage boasts everything you would need for your visit to the Berkshires whether it be for a full summer / winter season to explore this beautiful area or a quick getaway to Tanglewood, The recently added master suite features a queen size bed, en-suite bathroom and a bonus... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    1 / 10
    4.5 of 5 stars (6) Very good
    Richmond
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Parking
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    • Air Conditioning
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    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    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... View all property information
    Location Information
    Richmond, Berkshires 01254
    3 of 5 stars Reviewed October 26, 2015
    Better directions to the house would have been helpful. For two nights my daughter and two granddaughters joined us and found the yard and swingset fun. The weather was quite...
    5 of 5 stars Reviewed September 7, 2015
    This house was very comfortable and quiet. We had everything that we needed in the house. The house was clean. The beds were comfortable and cozy. The neighborhood was also quiet...
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    1 / 8
    Lenox
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Parking
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    • Private Yard
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Great little house in a very convenient location. Set nicely back from the street with a spacious back and side yard. 8 minutes drive to tanglewood. All rooms are furnished. Living room with bay window and fireplace, hardwood floors throughout. Almost an acre of land with large trees and garden.... View all property information
    Location Information
    Lenox, Berkshires 01240
    1 / 32
    5 of 5 stars (2) Excellent
    Stockbridge
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Mountain Views
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Patio
    • Sauna
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    We call this house ‘South Sedgwick’ because of its location on a piece of land formerly used by the Sedgwick family for picnicking–an ideal spot for relaxation with stunning views of Monument Mountain and Ice Glen. The house is newly constructed with ash hardwood floors, custom white pine trim and... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 stars Reviewed December 3, 2014
    What a great place! Teva was wonderful to work with, communication was incredible, and he is very welcoming. The house was spacious, very comfortable with 9 people! Teva came by...
    5 of 5 stars Reviewed July 18, 2014
    Our family of 5 rented this home over July 4th weekend and we couldn't have been more pleased. The home has just been newly renovated, is very tastefully appointed and looks and...
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    1 / 11
    3.5 of 5 stars (4) Average
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
    • Central Heating
    • Internet Access
    • Washer
    • Satellite TV
    • Mountain Views
    • Waterfront
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    3-bedroom home on lake, near Tanglewood. 2 baths, den, screened porch, large yard. View all property information
    Location Information
    Stockbridge, Berkshires 01262
    4 of 5 stars Reviewed July 21, 2016
    The Stockbridge House was exactly what we expected from the description and pictures. The home is rustic and cozy, like a cabin in the woods. Having water access to the bowl was...
    4 of 5 stars Reviewed July 14, 2015
    Those who used the cottage this week ranged from me alone to one night with eight people for one night. Sleeping was not a problem. The house is ideally located between Lenox...
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    1 / 17
    Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Mountain Views
    • Patio
    • Air Conditioning
    • Internet Access
    • Grill
    • Washer
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Explore the culture and natural beauty of the Berkshires while vacationing in a completely restored colonial home with modern amenities. You will be central to all the wonderful cultural attractions and outdoor activities in the area. Walk to the quaint town of Stockbridge and the Norman Rockwell... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    1 / 22
    Lenox
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • Internet Access
    • Satellite TV
    • DVD Player
    • Grill
    • Air Conditioning
    • Mountain Views
    • Washer
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Just steps to Tanglewood Main Gate and Kripalu from this dramatic three-story shingle style contemporary with five bedrooms and five and a half baths. The six hundred square foot great room has a soaring ceiling, fireplace, interior balcony, and multiple French doors and windows to overlook the... View all property information
    Location Information
    Lenox, Berkshires 01240
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    1 / 24
    Lenox
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Sauna
    • Mountain Views
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • Shared Indoor Pool
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    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, large deck with 8 person hot tub and super seating... View all property information
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    Lenox, Berkshires 01240
    1 / 14
    Lenox
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    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 beautiful backyard for grilling. There is also an amazing dining room surrounded by windows... View all property information
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    Lenox, Berkshires 01240
    1 / 20
    Richmond
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Porch
    • Internet Access
    • Washer
    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool...
    • Grill
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Newly furnished 3 bedroom (with AC) & 2 1/2 bath single family home with stunning deck and in ground pool nestled in the quiet countryside opposite a horse farm. Situated minutes from West Stockbridge convenience stores and restaurants. Property is on 2 quiet tree lined acres with an enclosed... View all property information
    Location Information
    Richmond, Berkshires 01254
    1 / 23
    5 of 5 stars (1) Excellent
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • Mountain Views
    • Waterfront
    • Satellite TV
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    PRIVACY-QUIET- HIKE-SKI-RELAX FYI in the winter, a huge hill behind the house on our property is fantastic for sledding . Animals you might see- Turkeys, Ducks, Bobcat, Bear, Deer, Otter, Muskrat, Heron depending on the season. A 1/4 mile driveway thru the woods takes you to 38 acres, and this... View all property information
    Location Information
    Stockbridge, Berkshires 01260
    1 / 20
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Internet Access
    • Patio
    • Waterfront
    • Central Heating
    • Satellite TV
    • Porch
    • Parking
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Blue House on the Bend Newly renovated historic eyebrow colonial located on an idyllic bend of the Housatonic river comfortably accommodates 5 or 6 people. Built around 1820, the Blue House on the Bend has been updated and outfitted for modern day convenience but retains its charm and unique... View all property information
    Location Information
    Stockbridge, Berkshires
    1 / 30
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Elevate your Stockbridge experience by staying at this 3-bedroom, 1.5-bath vacation rental house, which sleeps 6. Nestled within the serene forests of the Berkshires, ‘The Redway House’ is the quintessential setting for your next Massachusetts retreat. Welcome to ‘The Redway House’! You’ll... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    1 / 21
    5 of 5 stars (21) Excellent
    Lenox
    4 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • Porch
    • Washer
    • Parking
    • Internet Access
    • Central Heating
    • Grill
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Located on a quiet side street in the charming Berkshire town of Lenox, Gartner House is a great place to call home while exploring this scenic, historical, and culturally rich area of Western Massachusetts. Walk to breakfast, lunch or dinner at one of the town's many charming restaurants, explore... View all property information
    Location Information
    Lenox, Berkshires 01240
    5 of 5 stars Reviewed January 20, 2016
    My friends and I loved the Gartner home. It was conveniently located to downtown Lenox, cozily furnished and spotlessly clean. The eat in kitchen was well stocked with everything...
    4 of 5 stars Reviewed October 16, 2015
    We were here during the 2015 foliage season. Absolutely beautiful. The house was very roomy and very comfortable. Has all the amenities you need in kitchen and other rooms...
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    1 / 22
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Completely renovated vacation home with state of the art kitchen and marble baths, centrally located in the Berkshires 3 miles from Tanglewood, on 10 acres on a quiet country road. New in-ground pool surrounded by patio and expansive deck and pool house nestled in the woods. Central air... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    1 / 10
    5 of 5 stars (1) Excellent
    Richmond
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • DVD Player
    • Washer
    • Private Yard
    • Satellite TV
    • Grill
    • Secure Parking
    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful two bedroom house sits just steps from Richmond Pond. Enjoy a day on the water swimming and fishing followed by an evening enjoying the symphony at Tanglewood (ten scenic minutes away). Yoga enthusiasts will love the proximity to Kripalu (again, ten minutes away). Leaf peepers and skiers... View all property information
    Location Information
    Richmond, Berkshires 01254
    5 of 5 stars Reviewed June 14, 2016
    My wife and I stayed here for a week in June. The hosts/owners are new to the rental business, but were eager to make sure everything was in order for us. The house is very well...
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    1 / 9
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Beautifully appointed farm house situated on 200 acres of this pristine estate located in the heart of the Berkshires. This home offers three bedrooms, three bathrooms, fully equipped kitchen, laundry room, deck and porch. Perfectly located to all The Berkshires attractions, This home is within 4... View all property information
    Location Information
    Stockbridge, Berkshires