Stephentown Center Vacation Rentals

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Browse Select Stephentown Center Vacation Homes

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (243)
"What a great spot to stay for the few days we were there Can’t wait to come back! "
The price is CA $207
CA $317 total
includes taxes & fees
May 3 - May 4
Berkshire Village Carriage House - Super Private!!

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Very kinda hosts, and wonderful house."
The price is CA $759
CA $1,431 total
includes taxes & fees
May 5 - May 6
Hancock Village Inn at Jiminy Peak

Romantic Villa

10.0 out of 10, Exceptional, (21)
"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. "
Romantic Villa

Secluded Lux Mansion Pool Home with Amazing Views

10.0 out of 10, Exceptional, (1)
"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. "
Secluded Lux Mansion Pool Home with Amazing Views

Heart of Lenox Walk to Town Cozy Cottage!

10.0 out of 10, Exceptional, (70)
"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. "
Heart of Lenox Walk to Town Cozy Cottage!

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

10.0 out of 10, Exceptional, (4)
"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!

Mountain Blossom Retreat by Evergreen Home

10.0 out of 10, Exceptional, (5)
"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!"
Mountain Blossom Retreat by Evergreen Home

4 Bdrm Modern Victorian with Tree House and playground

9.8 out of 10, Exceptional, (110)
"Large kitchen and living space, great outdoor deck."
4 Bdrm Modern Victorian with Tree House and playground

Near Tanglewood: Historic Summer Retreat

9.4 out of 10, Exceptional, (20)
"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. "
Near Tanglewood: Historic Summer Retreat

Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring

10.0 out of 10, Exceptional, (10)
"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."
Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (121)
"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. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.6 out of 10, Exceptional, (42)
"Absolutely no complaints. Great place to stay, great host! Happy 2025 wishes from our family to everyone reading this post! "
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

6 Mi to Skiing: Pet-Friendly Home in Pittsfield!

10.0 out of 10, Exceptional, (4)
"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."
6 Mi to Skiing: Pet-Friendly Home in Pittsfield!

Dancing Horse Lodge

9.6 out of 10, Exceptional, (41)
"Very cozy property in a nice secluded location. "
Dancing Horse Lodge

Spacious 5-bed house centralized within hour of skiing, Race track & Lake George

10.0 out of 10, Exceptional, (1)
"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."
Spacious 5-bed house centralized within hour of skiing, Race track & Lake George

Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond

10.0 out of 10, Exceptional, (34)
"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! "
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond

Cozy Cape Close to Everything: Family, hiking, shopping and restaurants!

10.0 out of 10, Exceptional, (48)
"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!"
Cozy Cape Close to Everything: Family, hiking, shopping and restaurants!

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

Country Living just minutes from Everything!

10.0 out of 10, Exceptional, (28)
"Very nice, very clean property. Everything you need. Communication with owner is excellent. My family and I were extremely comfortable here!"
Country Living just minutes from Everything!

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (139)
"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! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
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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Other property types in Stephentown Center

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1800)
"Great property"
The price is CA $152
CA $182 total
includes taxes & fees
May 5 - May 6
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (928)
"Staff was exceptionally helpful and friendly."
The price is CA $185
CA $207 total
includes taxes & fees
May 4 - May 5
Jiminy Peak Mountain Resort

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is CA $310
CA $346 total
includes taxes & fees
May 9 - May 10
The Ponds at Foxhollow
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.