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Compare 350 Vacation Homes in Rupert with updated reviews, rates, and availability.

Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

8.6 out of 10, Excellent, (4)
"Our group had a great time enjoying this bright open space. Such a pretty place. Michael was very responsive and communications were timely and simple. Nice place for gathering."
Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle

10.0 out of 10, Exceptional, (39)
"This property couldn’t be better situated or more accommodating in regards to size, layout and comfort. With 3 master suites and additional rooms for children our large family had plenty of space to spread out. The shuttle to and from the mountain are an added bonus to avoid the parking scene at the base of the mountain. We couldn’t have enjoyed our stay more, and will be back again! "
Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle

Secluded home with game room, private hot tub, golf, river & mtn views, firepit

9.8 out of 10, Exceptional, (6)
"Very nice. Could use curtains or blinds in more rooms."
Secluded home with game room, private hot tub, golf, river & mtn views, firepit

Bear Pass - Mountain View by RedAwning

10.0 out of 10, Exceptional, (1)
"Great house. 35 minutes from Stratton mountain. House had everything needed, plenty of supplies, towels, blankets, etc. highly recommended. Ad was exactly what you got"
The price is AED 871
AED 2,285 total
includes taxes & fees
11 Mar - 12 Mar
Bear Pass - Mountain View by RedAwning

7200 sf Villa & Barn on 4 Acre Manchester Estate

9.6 out of 10, Exceptional, (8)
"We were absolutely delighted with our stay at the villa. The house is big, spacious, and most importantly, clean. The house has everything you need for a comfortable stay. Everything is thought out to the smallest detail. We had both kids and teenagers with us - everyone felt comfortable. Lots of space, a large table for a large company. The location is literally 3 minutes from the city center, where there are many shops and restaurants. 30 minutes from the ski resort. There were no problems...
7200 sf Villa & Barn on 4 Acre Manchester Estate

Dog-friendly house with picturesque mountain view & near skiing - close to Okemo

9.8 out of 10, Exceptional, (50)
"Fantastic Vermont farm house in a great setting close to Okemo and Killington. Very accommodating, clean, warm and comfortable. After skiing we enjoyed just sitting around the fireplace and talking. We plan on returning next year."
Dog-friendly house with picturesque mountain view & near skiing - close to Okemo

Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Hike, Indoor Pool, Relax!

10.0 out of 10, Exceptional, (1)
"We had such a lovely time in this well loved cabin. Super quiet location and well stocked with everything we needed for our end of year ski trip in Stratton. The owner was very friendly and helpful. We hope we will be back soon!"
Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Hike, Indoor Pool, Relax!

Peaceful Stay at Birds of a Feather Farm & Spa

9.6 out of 10, Exceptional, (16)
"The place was just as described and perfect for my stay while doing a workshop nearby. Host was easy to communicate with and helped me out as I forgot an item! "
The price is AED 404
AED 950 total
includes taxes & fees
1 Apr - 2 Apr
Peaceful Stay at Birds of a Feather Farm & Spa

Your own Private Lake - Breathtaking Views - Gym - Sauna - Hot Tub

10.0 out of 10, Exceptional, (25)
"We rented this property as a way to spend time with family right before the busy holiday season. We couldn’t have picked a better place to stay. The house was very cozy, clean, and had everything we needed and more! Check-in was super easy, and the host responded very quickly. The hot tub and sauna were great additions, but the view of the lake and mountains every morning was just what we wanted. We will definitely be recommending to friends and family!! "
Your own Private Lake - Breathtaking Views - Gym - Sauna - Hot Tub

By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.

9.8 out of 10, Exceptional, (63)
"Rented this lodge based on other positive reviews - and they were spot on! Greeted by snowy landscape and cozy, warm, lodge wonderfully appointed More you looked, more you saw! Comfy beds, good showers, full service kitchen, spotless. Our family of 5 adults , 13 yr old twin granddaughters greed we felt like we were in a welcoming home. Brad, part owner/prop. manager immediately responded to call or text. We are looking forward to Dec 2025 to do it all again. Don’t miss Zoe’s grill in Manchester "
By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

7.8 out of 10, Good, (45)
"Cleanliness was fine, but keys were missing when we checked in. Kitchen pots/pans we're good quality and fine for small meals but missing basics like a spatula and knivesBathroom had insufficient towels, no shampoo and only 1 small soap. Property manager did not bring replacements when called. Vacasa was the manager "
The price is AED 342
AED 1,140 total
includes taxes & fees
25 Mar - 26 Mar
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Vermont Lakefront Getaway “The Wild Loon” Waterfront Home with phenomenal Views!

9.8 out of 10, Exceptional, (34)
"Super quiet , place was clean and easy to check in, hosts were great to communicate with"
Vermont Lakefront Getaway “The Wild Loon” Waterfront Home with phenomenal Views!

UNBELIEVABLE MOUNTAIN VIEWS! Convenient to Manchester,skiing,outlets

4.0 star property
10.0 out of 10, Exceptional, (15)
"We had a wonderful time! Alex was extremely accessible and made the whole process very easy. He was quick to replying to questions and recommendations. The house was very clean and cozy and perfect for two families of 5. We would return for sure!"
UNBELIEVABLE MOUNTAIN VIEWS! Convenient to Manchester,skiing,outlets

Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

10.0 out of 10, Exceptional, (21)
"My family stayed at this property for a Stratton ski trip. Everything about the house was wonderful. The house was incredibly clean cozy and inviting. The owners go above and beyond to ensure that every little detail is met to ensure a visit that truly makes you feel like your home away from home. "
Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

10.0 out of 10, Exceptional, (116)
"Exactly as described. Really nice home with excellent property communications. We loved the hot tub on the deck and the amazing views. Nice kitchen that was well equipped with all appliances needed. Bring your own sharp knives :-). "
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

10.0 out of 10, Exceptional, (163)
"Long weekend with friends and our beloved old dog. We were anxious to get back to Vermont and this home was just what we needed. Close to the activities we like, cross country skiing, great book store, cute shops. Accommodations were above what we expected. Dan could not be a better host. We will be back!"
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Sunny Stratton Townhome ~ 1 Mi to Skiing!

9.8 out of 10, Exceptional, (7)
"The townhouse was roomy, perfect for my group."
Sunny Stratton Townhome ~ 1 Mi to Skiing!

Manchester Center Home w/ Green Mtn Views!

9.6 out of 10, Exceptional, (33)
"The hosts of this lovely home truly created an atmosphere that was warm and inviting. We loved the location as we skied, dined, shopped nearby and were able to spend time with our dog at the Dana Thompson Park. "
Manchester Center Home w/ Green Mtn Views!

Charming Dorset Cottage Retreat.

2.0 star property
10.0 out of 10, Exceptional, (7)
"We had a wonderful stay at this beautiful, cozy cottage in Dorset. It’s close to multiple ski mountains and the charming town of Manchester, and the hosts were super friendly and helpful. Check-in and check-out were easy, and the place was just as advertised."
Charming Dorset Cottage Retreat.

Room for the whole family 8 minutes to Manchester

10.0 out of 10, Exceptional, (1)
"Very priceable and great house with 5 bedrooms - each rooms are big and clean! Love it! Will come back again for next ski plan"
Room for the whole family 8 minutes to Manchester
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 Rupert

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very Good, (73)
"Condo was great, cozy, and clean. Has access to the pool and hot tubs from back porch and has great Mountain View’s. The village had plenty of food, little expensive, but pretty good. Overall great place to stay and enjoy the mountain. "
The price is AED 1,341
AED 1,666 total
includes taxes & fees
1 Apr - 2 Apr
Long Trail House at Stratton Mountain Resort

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (209)
"The cabin was everything we thought it was going to be! Cozy and enjoyed the fireplace."
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Secluded home with game room, private hot tub, golf, river & mtn views, firepit

9.8 out of 10, Exceptional, (6)
"Very nice. Could use curtains or blinds in more rooms."
Secluded home with game room, private hot tub, golf, river & mtn views, firepit
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.