Stephentown Vacation Rentals

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Browse Select Stephentown Vacation Homes

Spacious 5-bedroom house in charming Lee with WiFi

The price is CA $496
CA $985 total
includes taxes & fees
Aug 13 - Aug 14
Spacious 5-bedroom house in charming Lee with WiFi

Contemporary Berkshire Home with Views of Taconic Golf Course

10.0 out of 10, Exceptional, (5)
Contemporary Berkshire Home with Views of Taconic Golf Course

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (45)
"We went as a family to get away from the city life for the weekend. We have no complaints except that it could’ve been a bit cleaner in the sense that there were many cobwebs. Nonetheless we rlly enjoyed our weekend in Great Barrington "
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Charming Berkshires Retreat – Minutes to Williamstown

6.0 out of 10, (2)
"This was the perfect little spot for our family to stop and stay on our way to dropping our daughter at camp and enjoy Williamstown. Our hike at the Clark Institute was a highlight along with the proximity to downtown’s great restaurants.We were talking about how gorgeous it must be in the fall… when it must be even more scenic and amazing."
Charming Berkshires Retreat – Minutes to Williamstown

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

10.0 out of 10, Exceptional, (52)
"Great spot on the lake. Super quiet and relaxing."
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (14)
"Very friendly hosts, great location. "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Charming 3-bedroom house in Troy, near RPI, Albany, & Saratoga

8.0 out of 10, Very good, (1)
"The unit itself is very nice and has many modern touches. We loved the gaming setup and enjoyed all the modern touches. The kitchen and bathroom are really well done and made our stay enjoyable. The surrounding area/neighbors are not the best. The parking is in an adjacent medical center lot and you have to walk by neighbors who threw things at us and generally spent the entire time outside. This is also along a main road and the building shakes often from the trucks driving by,."
Charming 3-bedroom house in Troy, near RPI, Albany, & Saratoga

19th c. Barn in the Berkshires

9.6 out of 10, Exceptional, (90)
"We planned to stay at this property in order to ski at Jiminy peak, and it was perfect, not a long drive at all. The barn stays very warm with the individual heaters as well as the wood stove in the middle of the main room. The kitchen was equipped with everything you need, they even had coffee and sugar! .. Communication with the hosts was seamless. We lost power due to a winter storm, the entire area did, and that wood stove worked its magic. The property owners made sure we were alright...
19th c. Barn in the Berkshires

Art House! Spacious Getaway By Mass Moca

10.0 out of 10, Exceptional, (11)
"We had a great girls weekend e joying local trails, MassMOCA, local restaurants and this very clean, spacious house! Location is walkable to the museum and down town and we enjoyed a soak in the tub after a day of hiking in local conservation areas! "
Art House! Spacious Getaway By Mass Moca

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

8.8 out of 10, Excellent, (30)
"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "
The price is CA $169
CA $414 total
includes taxes & fees
Aug 7 - Aug 8
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (9)
"Elise was an excellent host and super easy to work with. The property was even bigger, nicer, and cleaner than we expected. Plenty of room for a family getaway. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Star Gazer Farm

10.0 out of 10, Exceptional, (15)
"Thank you for the lovely get away! The property was lovely. "
Star Gazer Farm

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.4 out of 10, Exceptional, (44)
"The home is very nice and cozy. It really felt like a comfy home."
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

North Getaway Cottage

9.6 out of 10, Exceptional, (20)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
The price is CA $279
CA $615 total
includes taxes & fees
Aug 7 - Aug 8
North Getaway Cottage

Spacious Home w/ Yard & Patio, 2 Mi to Dtwn Troy

10.0 out of 10, Exceptional, (1)
"We had everything we needed to have a wonderful weekend celebrating my husband's graduation! Surprisingly, the single shower was able to accommodate the full house (never rand out of hot water) and there was plenty to do with the outdoor games and card/board games indoors! Thank you for sharing this beautiful home with us!"
Spacious Home w/ Yard & Patio, 2 Mi to Dtwn Troy

Secluded Family Home in Serene Stockbridge Woods

10.0 out of 10, Exceptional, (21)
"We spent a short weekend here in Stockbridge to attend the Naumkeag Pumpkin Show. The kids (2 + 4) were in amazement the entire time. The house was a fantastically creative environment with books, games, toys, and a massive yard with swings. A+ would stay again."
Secluded Family Home in Serene Stockbridge Woods

Charming 3-bedroom farmhouse in Lenox

10.0 out of 10, Exceptional, (1)
"House is comfortable and spacious, with a well-supplied kitchen. Hosts had thought of everything we might need. A/C was very helpful in the heat! Perfect location for exploring the Berkshires, and a fairly easy walk into town."
Charming 3-bedroom farmhouse in Lenox

Country Living just minutes from Everything!

10.0 out of 10, Exceptional, (28)
"Jandie's was the absolute best rental house we have ever stayed at. The house was clean and well kept, everything felt brand new. The set up was great, open kitchen, dining room and living room and made entertaining very easy. The kids had their own room and enjoyed spending time together in their own space. Julie was a pleasure to work with and accommodated us in anyway she could, from beginning to end. She even made us homemade delicious treats. We would highly recommend Jandie's and we...
Country Living just minutes from Everything!

Sophisticated Lenox Retreat by Evergreen Home

9.8 out of 10, Exceptional, (9)
"Very quaint location, clean property, and great place to stay"
Sophisticated Lenox Retreat by Evergreen Home

2 bedroom town house with game room

5.8 out of 10, (16)
"Property was easy to get to. Located right off the thruway. House was clean and located close to plenty of shopping options. There was also fast food restaurants located within walking distance. "
2 bedroom town house with game room
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Stephentown Hotel Reviews