
Holiday houses in Stratton
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Top-rated holiday rentals in Stratton
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Stratton
Top Guest favourite

Apartment in Winhall
5 out of 5 average rating, 34 reviewsPrivate & Quiet Apartment near Stratton Access Rd
NicoletteRating, 5 stars2 months ago
Margaret's place was very cozy and the perfect stay for going skiing at Stratton Mountain. The location was ideal and perfect. This place was very clean and looks exactly as the images portrayed them. There were books, board games, and an organized binder of local shops and entertainment provided. The communication feedback was quick and friendly. The next time I come visit Vermont, I would love to come back to this Airbnb.
Guest favourite

Cabin in Cambridge
4.97 out of 5 average rating, 31 reviewsPond View Cabin. Off-Grid, Rustic & Dog Friendly.
EmilyRating, 5 stars1 week ago
Highly recommend Brian’s off grid cabin! His directions were very helpful and made navigating the generator, camp shower, and other on-site details super easy to understand and execute. His property is beautiful and peaceful. We’re already looking at our calendars for another time to visit. Our dog, Stumpy, very much enjoyed the outdoor access and pond. He didn’t want to leave!
Guest favourite

Cabin in Wardsboro
4.93 out of 5 average rating, 42 reviewsMt Snow Château
AndrewRating, 5 stars3 months ago
What a great stay! Srini was very accommodating prior to our arrival and was always quick to respond. This home is a perfect in between to Stratton and Mt Snow which served our group well. Cozy doesn’t begin to describe the living areas and the garage was a great addition at night. We would absolutely recommend this property to anyone considering it. Can’t wait to visit again!
Superhost

Home in Dover
4.91 out of 5 average rating, 82 reviewsFULLY renovated 1 bed/1 bath ski in-out condo!
AnastasiaRating, 5 stars2 months ago
My husband and I spent a long last winter weekend here. The condo was perfect for ski on/off and we enjoyed a day on the mountain. Though the weather wasn’t great the whole time, Brittany & Jen were quick to send recommendations for things to do, trails to hike and their favorite restaurants. So close to lots of great spots in this little mountain town. We would absolutely stay here again
Top Guest favourite

Cabin in Stratton
5 out of 5 average rating, 38 reviewsModern Cabin in Stratton
LeonRating, 5 stars2 weeks ago
We had an absolutely wonderful stay at Jana’s place. She was incredibly kind and accommodating, allowing us to check in early and check out late at our convenience — which made our trip all the more relaxing. Communication with her was smooth, clear, and effortless from start to finish. The home itself is one of the cleanest, most comfortable, and most thoughtfully designed places we’ve ever stayed. Everything felt fresh and sophisticated — from the brand-new appliances to the high-quality bedsheets and spotless, carpet-free floors. The mattress was exceptionally comfortable — one of the best we’ve ever slept on — and Jana even provided backup toiletries, which was such a thoughtful touch. The location is peaceful and quiet, surrounded by greenery and nature — a perfect retreat. We left feeling deeply rested and extraordinarily happy. Thank you, Jana, for creating such a beautiful and welcoming space!
Guest favourite

Cabin in Jamaica
4.93 out of 5 average rating, 60 reviewsThe Woodland A-Frame
JannaRating, 5 stars1 week ago
This was a beautiful stay! My boyfriend, and his dog, really enjoyed our time here. I would highly recommend anyone to stay here! 10/10 would stay there again! ❤️
Top Guest favourite

Chalet in Winhall
5 out of 5 average rating, 50 reviewsSummer Fun in Winhall! Family Game Room & Deck!
BryanRating, 5 stars3 weeks ago
This was an enjoyable stay. Slept 6 comfortably. We also had such a great time in the game room playing pool, watching tv, and utilizing the arcade games. Totally recommend!
Top Guest favourite

Chalet in Wardsboro
5 out of 5 average rating, 17 reviewsThe Mont Haus- WOOD FIRED SAUNA!
MarlynRating, 5 stars2 days ago
We had a wonderful stay at this cozy cabin. We could tell a lot of attention went into the little details— everything was thoughtfully decorated and incredibly inviting. The space was clean and had all the amenities we needed for a comfortable stay. We appreciated how dog-friendly it was with the dog toys and bed. Highly recommend for anyone traveling with pets or just looking for a peaceful getaway!
Quick stats about holiday rentals in Stratton
Total rentals
180 properties
Nightly prices starting at
$100 NZD before taxes and fees
Total number of reviews
4.9K reviews
Family-friendly rentals
150 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
50 properties have a pool
Destinations to explore
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Six Flags Great Escape Lodge & Indoor Water park
- Jiminy Peak Mountain Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- West Mountain Ski Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Saratoga Spa State Park
- Mount Greylock Ski Club
- Berkshire East Mountain Resort
- Lake George Expedition Park
- Dorset Field Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area
- Hildene, The Lincoln Family Home
- The Shattuck Golf Club
- Bromley Mountain Ski Resort
- Fox Run Golf Club
- Pineridge Cross Country Ski Area