Search Vacation Homes in Stephentown

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

In two weeks

In one month

In two months

In three months

Vacation Homes in Stephentown

Our top choices for Stephentown vacation homes

"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "

"Great location for access to both Tanglewood and Lenox center. "

"Fantastic home! Clean, well stocked and very comfortable. We had a great time and will be back. The owner was kind, considerate and appreciative of our stay. Thanks again! "

"Kind and responsive host."

￥71,217 total

includes taxes & fees

Aug 26 - Aug 27

"We had an awesome stay at Nate’s place! The stone architecture and wood oven fireplace gave a truly unique experience, and the house was very spacious. The fully equipped kitchen made for anxenjoyable cooking experience. Nate was also flexible and responsive. Definitely recommend this for your weekend getaway home!"

"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 "

"Perfect for a family vacation with a baby and dog. Particularly enjoyed having drinks and dinner on the deck, overlooking the water. Felt like a private retreat. "

"Was as nice as the pictures. A plus for a very comfortable king sized bed! Right in town for walking to shops and restaurants. Thank you!"

"Very cozy and comfy place!"

"This place truly has everything you could want in a vacation rental. It was exceptionally clean, spacious, and accommodating. From the moment we arrived, it felt like a home away from home. The host clearly puts a lot of care into maintaining the property and ensuring guests are comfortable. We had everything we needed for an enjoyable stay. Highly recommend and would definitely book again!"

"Great spot on the lake. Super quiet and relaxing."

"We had a wonderful time in this home. It accommodated our family of 4 easily. Several of us had to work the first day there and there were ample quiet spots and quality wifi for us. So easy to walk to town to restaurants etc"

"Great location and convenient walking distance to downtown Lenox. "

"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."

"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."

"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...