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Compare 335 Vacation Homes in Stephentown with updated reviews, rates, and availability.

"What a great spot to stay for the few days we were there Can’t wait to come back! "

AED 841 total

includes taxes & fees

3 May - 4 May

"Very kinda hosts, and wonderful house."

AED 3,801 total

includes taxes & fees

28 Apr - 29 Apr

"The property was lovely, quiet, and clean. The host will truly go out of her way to be very sure that your stay meets your needs. "

"Perfect location for a peaceful, scenic vacation."

"We had a great time staying in the house for the weekend as a group of 10. Kitchen and bathrooms are well-stocked. The living room couch is enormous. All of the bedrooms are bright and cozy. The views and property are absolutely stunning. Had we been fewer, we probably would have used the outdoor firepits. Barry and Alisha are lovely and helpful hosts -- they sent along a great list of food reccs ahead of time, responded quickly when I couldn't find a few things, etc. "

"Going to the Berkshires this is a great place to stay. It is within walking distance to over 8 restaurants in downtown Lenox. Great gas stove and comfortable bed. Owner makes sure your stay is great. Would stay here again. "

"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. "

"We spent a wonderful weekend at this truly stunning property! The house is incredible, so well equipped, every detail has been thought of and the interior is beautiful. The outdoor spaces are amazing, the pool, hot tub, fire pit, outdoor seating, beautiful gardens are stunning! The location of the house is perfect, so close to lots of farms and orchards. We so look forward to making a return visit I!"

"Large kitchen and living space, great outdoor deck."

"Lots of cozy relaxation by the fire and fun meals at the spacious dinning table. We had plenty of room to spread out and enjoy ourselves. "

"Beautiful house in a quiet location. Perfect for our trip to go see The Norman Rockwell museum , Stockbridge Christmas holiday lights only about 25 minutes away. "

"The location is absolutely beautiful, the pool was great, and there was plenty of room for everyone. This was our second time staying at this house and we will be back."

"Property as described. Great location to towns. Larger interior space than anticipated. Great Kitchen for a group of 5 to cook, chat and enjoy! Overall a warm and spacious home for old college friends to reunite. "

"Absolutely no complaints. Great place to stay, great host! Happy 2025 wishes from our family to everyone reading this post! "

"We had a great weekend stay here with our dog. He loved the backyard and felt right at home. Everything was clean and great location."

"We had a great stay with our family. Clean and close to where my daughter lives."

5 bedrooms, iron/ironing board, travel crib, WiFi

"Spacious home for my family to gather during a death in our family. Great communication with host, house was very well equipped with everything you could need. Thank you."

"We had a wonderful time at this property! It was perfect for what we wanted- a place to ourselves in nature with beautiful views. Host was great! Would definitely recommend! "

"Perfect location, warm and comfortable house. Our family really enjoyed staying there with our 2 dogs!"

"We were very happy with our stay. The house was as described and pictured in the listing. Well stocked for our needs, spare toothbrush, coffee, etc. Would definitely stay again!"