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Compare 537 Vacation Homes in Stockbridge with updated reviews, rates, and availability.

Beautifully renovated with fireplace and coffee bar
10.0 out of 10, Exceptional, (74)
"We stayed at this cute and well appointed cottage when dropping our son off to Dartmouth. The cottage was clean and very comfortable. The beds were comfortable and the kitchen was very well appointed. It was a breeze to get laundry done in a laundromat right next door. You have to download an app for the laundry to work, but it was straightforward and the same app works at the Dartmouth dorms. Thanks for a wonderful stay. Would recommend to anyone who's looking for a comfortable and...
Beautifully renovated with fireplace and coffee bar
Historic Schoolhouse in Rural Vermont Beauty Spot
10.0 out of 10, Exceptional, (24)
"The schoolhouse was just what we were looking for- a quiet country location with good walking, hiking, exploring, and close to Randolph. We appreciated the ephemera- books, maps, newspapers. Looking through the shelves and cabinets was an adventure unto itself. We spend time outdoors so one plus would have been more comfortable outdoor furniture. Thank you, Terrie, we have a terrific time!"
Historic Schoolhouse in Rural Vermont Beauty Spot
4 Season Secluded Lakefront Home near Ski Mountains
9.4 out of 10, Exceptional, (61)
"This is now on our top 10 vacation lists. It is an outstanding location. The water quality is great, and there's a perfect little beach for the very little people. The house is rustic but has everything one might need. The variety of boats allowed us to see around the lake. We hated to leave."
4 Season Secluded Lakefront Home near Ski Mountains
Family Getaway Cozy 4BDR Home
9.0 out of 10, Wonderful, (2)
"Everything was good, except road noise was a bit of an issue. We closed the windows in the front of the house and that solved the problem."
Family Getaway Cozy 4BDR Home
Idyllic Lakefront House Suited Two Families
9.8 out of 10, Exceptional, (150)
"Beautiful lake, kayaking, backyard firepit, hiking , such a fun area with a lot to explore.nearby, "
Idyllic Lakefront House Suited Two Families
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
10.0 out of 10, Exceptional, (15)
"Gorgeous property with everything that we needed! It was relaxing and comfortable for everyone. The kids had a blast! The property management team was great with communication and offered early check in and late check out. Would absolutely stay here again!"
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail
9.2 out of 10, Wonderful, (62)
"we enjoyed staying there it was Ow same "
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail
Blueberry Hill Escape Pet Friendly HotTub Fire pit
9.8 out of 10, Exceptional, (12)
"On arrival I loved the breathtaking views of the mountains ! The house was so spacious. Each kid had their own room and my husband and I loved having a master suite ! Our dog was so comfortable there as well ! I am really big on cleanliness and this house was immaculate !! We loved the hot tub! So relaxing ! I walked the dog around the house every morning and had noticed fruit trees ! The peaches were delicious ! Got Home from dinner one night amd we were getting of the car and a black bear...
The price is AED 742
AED 2,074 total
includes taxes & fees
30 Sep - 1 Oct
Blueberry Hill Escape Pet Friendly HotTub Fire pit
HappyCub! Hot tub, game room, fire pit!
10.0 out of 10, Exceptional, (12)
"My husband, son and our friends enjoyed staying at this home. We all slept comfortably and had all of the necessary amenities. Hosts were very proactive and responsive. Appreciated the added touch they provided with the Vermont Maple syrup for our pancakes (I had actually forgot to bring syrup) and coffee. The group was able to enjoy the hot tub each night after a long day of skiing! Will definitely look to stay here again!"
The price is AED 710
AED 2,086 total
includes taxes & fees
9 Oct - 10 Oct
HappyCub! Hot tub, game room, fire pit!
Cozy private country setting - 15 miles from Woodstock
10.0 out of 10, Exceptional, (20)
"A lovely spot to stay! Great communication with the host!"
Cozy private country setting - 15 miles from Woodstock
Log manor on 65 private acres of land with entertaining amenities & hot tub
9.8 out of 10, Exceptional, (6)
"Great property and beautiful views. Not too far from Killington. A wonderful trip to remember. Would definitely stay here again."
Log manor on 65 private acres of land with entertaining amenities & hot tub
Mountainside 5-BR Ski-In/Out Okemo Villa
2.0 star property
10.0 out of 10, Exceptional, (1)
"We had a family holiday here, and loved the region, the house location and the house's structure for a large group. The game room was a true hit in the evenings, and the kitchen, living and dining room were so well structured for our group. All appliances worked well, all aspects of the home were clean and well cared for. "
Mountainside 5-BR Ski-In/Out Okemo Villa
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
9.8 out of 10, Exceptional, (198)
"We had a great and restful stay. The house was exactly as listed. Views were great with ducks, beaver and a family of deer. Good fishing from the dock. This is in my top 3 of all places at which we have stayed! Definitely recommended!!!"
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Lovely wooded home with deck, enclosed porch - dog-friendly
7.8 out of 10, Good, (18)
"We enjoyed our stay. It is a beautiful property. The only complaint I have is the TV did not have any good channels. No news channels not cable etc.."
Lovely wooded home with deck, enclosed porch - dog-friendly
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
9.8 out of 10, Exceptional, (52)
"This is our second stay at Joel’s condo. His improvements to the lower floor are very nice and made a lot of sense. We enjoyed the location and condo once again. Joel continues to be very thoughtful and helpful. A great place to get away, relax, and have fun. We also got some late season skiing in for those of us who enjoy the slopes."
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
Spacious 3-story home near ski area with private hot tub, Ping-Pong
6.8 out of 10, (13)
"Enjoyed our stay. The home was cozy with lots of amenities. "
Spacious 3-story home near ski area with private hot tub, Ping-Pong
☆ SKI ON & OFF ☆ Spruce Glen C on Great Eastern Trail w/AC, Sauna, Fireplace
9.6 out of 10, Exceptional, (60)
"Very comfortable stay. Convenient to Killington, Woodward reservoir, and Woodstock not far away. Great communication. "
☆ SKI ON & OFF ☆ Spruce Glen C on Great Eastern Trail w/AC, Sauna, Fireplace
Spectacular 4 Bed Killington Home
9.8 out of 10, Exceptional, (104)
"Beautiful area with lots to do nearby. Perfect getaway my family and I needed!"
Spectacular 4 Bed Killington Home
Ski house 8 min from the mountain
9.8 out of 10, Exceptional, (14)
"Great time at this place gorgeous view and host was a pleasure to deal with. 👍👍"
Ski house 8 min from the mountain
The Brandon Inn - Fourth Floor Queen Room
9.4 out of 10, Exceptional, (3)
"This is a great spot. Was in town w Gus my field spaniel and we had a nice time at the Inn. The room was a bit antiquated but that’s part of the charm. We hiked the green mountains/silver lake trail and this place was perfect to rest weary bones. The rates are very reasonable and the property is quite beautiful. Will be back! "
The price is AED 533
AED 679 total
includes taxes & fees
20 Oct - 21 Oct
The Brandon Inn - Fourth Floor Queen Room
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Other property types in Stockbridge

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (462)
"If you’re looking for rest and relaxation this is it. You are one with nature at this cabin which has everything you need. Host was very nice and accommodating. Plenty of yard games for the family and trails to explore. Hope to be back in the future. "
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (38)
"Absolutely perfect! Very nice location. Quiet and cozy little townhome. Short drive to Bear Mountain and Killington Ski Resort. Amazing area with plenty of awesome views."
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, (209)
"We had a wonderful time .. accommodations could not have been more romantic 💝 "
Cozy Loft for two with Hot Tub
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.