Search Vacation Homes in Rupert

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 344 Vacation Homes in Rupert with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (37)
"This was a fantastic home for our family of 8 plus a toddler. The house is spacious and yet cozy, with everything one would need. The beds were very comfortable as were the sectionals on each floor. Playing games with a warm fire and expansive views…. A really special treat to stay here. And Beth is responsive and super accommodating. "
Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

10.0 out of 10, Exceptional, (14)
"This place was absolutely perfect and wonderful. It offered a cozy family getaway to enjoy the southern Vermont scene that we have grown to love so very much. The house and owner are absolutely amazing and we hope to stay here again for our trips back to this area. Highly recommend! "
The price is SAR 1,853
SAR 3,841 total
includes taxes & fees
23 Feb - 24 Feb
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Vermont's Mountain Villa: Hot tub, Ski views, Pet+

10.0 out of 10, Exceptional, (8)
"I love Winter and love to be in the snow and crisp air. The week was perfect for outside adventures and this home was perfect to warm us and nourish our hearts, bellies and spirits. The views at sunrise and sunset are extrodinary. "
Vermont's Mountain Villa: Hot tub, Ski views, Pet+

Historic 6-BR Across From Equinox Resort

9.0 out of 10, Wonderful, (8)
"Really enjoyed our stay"
Historic 6-BR Across From Equinox Resort

Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen

10.0 out of 10, Exceptional, (1)
"Beautiful house well stocked with spices and everything you need. The only thing they are missing is there’s no hairdryer and I called a few times to the property manager for a blanket because the master upstairs has no blanket and I never received one."
Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen

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

9.8 out of 10, Exceptional, (49)
"This is a lovely home -- spacious, beautifully furnished, and well-located, about 15 minutes from Okemo & downtown Ludlow. 4wd recommended for winter visitors: the house is up a steep hill, and in January the road surface was packed-down snow, so it was slippery for cars without all-wheel-drive."
Dog-friendly house with picturesque mountain view & near skiing - close to Okemo

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

Beechwood Bear - NEW ! Stratton Mt Resort House - < 2 Mi from Lifts-Village

Beechwood Bear - NEW ! Stratton Mt Resort House - < 2 Mi from Lifts-Village

7200 sf Villa & Barn on 4 Acre Manchester Estate

9.6 out of 10, Exceptional, (7)
"This rental was stunning! Such a cool property with so many different spaces for a large group to spend time. Everything was labeled for ease of access (very grateful for this!), we enjoyed many of the amenities, and communication with the host was fast! Wonderful stay with no issues!H"
7200 sf Villa & Barn on 4 Acre Manchester Estate

Cozy Manchester Getaway with Amazing Views!!!

9.8 out of 10, Exceptional, (24)
"Great house for two families. Perfect location close to Bromley and Stratton and also close to Manchester. Will definitely book again. "
Cozy Manchester Getaway with Amazing Views!!!

Historic Rideout 16m to Okemo Walk to Town

10.0 out of 10, Exceptional, (21)
"We were a large group of adults, teens and tweens and this house was perfect for our vacation! There are so many private nooks to have some alone time along with a great open family room and kitchen area to come together. We loved its charm, its coziness and variety of spaces. David was great to work with and very accommodating. Would definitely recommend and book again."
Historic Rideout 16m to Okemo Walk to Town

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!

Stunning 4 bed Timber Frame Ski Retreat on 6 acres

10.0 out of 10, Exceptional, (2)
"Great property for a ski trip up to the mountains!"
Stunning 4 bed Timber Frame Ski Retreat on 6 acres

Brazer's Way Minutes to Sun Bowl & Stratton Base Lodge

2.0 star property
10.0 out of 10, Exceptional, (3)
"The property was well marked and easy to get to. We had a great time and everything was as described in the listing. Just a few minutes to skiing at Stratton which was perfect for accommodating the skiers and non-skiers in our group. Mt Snow was also close and pretty easy to get to. Lots to do near by and perfect for our family vacation! "
Brazer's Way Minutes to Sun Bowl & Stratton Base Lodge

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 SAR 476
SAR 1,346 total
includes taxes & fees
3 Mar - 4 Mar
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

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

9.6 out of 10, Exceptional, (5)
"Very nice. Could use curtains or blinds in more rooms."
Secluded home with game room, private hot tub, golf, river & mtn views, firepit

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

Beautiful dog-friendly house w/ fireplace, firepit, bbq, deck, patio, w/d, wifi

10.0 out of 10, Exceptional, (2)
"We had an amazing three days of skiing with family and friends. The house was perfect for the twelve of us. The only thing missing was a large pasta pot but luckily we had one person who left home late and was able to bring one. The house was very spacious, clean, beds were comfortable and there was parking for the four cars we had. We are definitely coming back. "
Beautiful dog-friendly house w/ fireplace, firepit, bbq, deck, patio, w/d, wifi

5BR, 6 min from Stratton, pet friendly, private, jacuzzi tub, wrap around deck!

10.0 out of 10, Exceptional, (3)
"Home was spacious, clean and family friendly. We had a group of 12 including an infant and all had a wonderful time. There was ample kitchenware, linens and space for all to spread out, play games, sit around the fireplace and enjoy the snowscape. The area is centrally located close to Stratton Village and easily navigated. We had some minor heat problems but the property managers were super responsive and were at the house in under 10 minutes. Would definitely go back!"
5BR, 6 min from Stratton, pet friendly, private, jacuzzi tub, wrap around deck!

Spacious Riverfront Home 7 Minutes to Stratton!

10.0 out of 10, Exceptional, (27)
"We loved our stay! We had a big group: two families with several college-aged kids and a couple of their friends. There was plenty of room for everyone, a big kitchen for food prep, stocked with plenty of dishware, and a large dining room table. And there was lots of spaces for people to sit and read, or puzzle, or play pool when not out on the slopes. And for runners, we really enjoyed the challenge of running "uphill", including some beautiful views near the top where the road flattened out a...
Spacious Riverfront Home 7 Minutes to Stratton!
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.
Don't see what you're looking for?
See all available properties in Rupert
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Rupert

Gorgeous Victorian-Style House w/ Hilltop Pool!

8.8 out of 10, Excellent, (29)
"The house was a perfect weekend getaway for a group of friends from the city. It was absolutely gorgeous and had everything we could need. We even got two feet of snow, so it was a magical Vermont experience! We would definitely go back and thank you!"
Gorgeous Victorian-Style House w/ Hilltop Pool!

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very Good, (72)
"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 SAR 1,556
SAR 1,934 total
includes taxes & fees
3 Mar - 4 Mar
Long Trail House at Stratton Mountain Resort

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

9.6 out of 10, Exceptional, (206)
"Perfect get away. "
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
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.