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

Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
10.0 out of 10, Exceptional, (8)
"The photos are accurate, but the place seemed even better than I anticipated. It was perfect for our family of 4 (two teen boys) and dog. The weather was rainy and cold for a couple of days, but the house was cozy. The hot tub was great. And also the access the Manchester was a complete surprise to us. We didn't really know where we were going and we were pleasantly surprised to find a quaint town with shops and restaurants. The book store in town was amazing. We did lots of hiking and...
The price is SAR 777
SAR 2,365 total
includes taxes & fees
1 Oct - 2 Oct
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Idyllic Wallingford Retreat - Near Skiing & Hiking
Wallingford Vacation Rental | 1BR | 1BA | 600 Sq Ft | Stairs Required for Access
Idyllic Wallingford Retreat - Near Skiing & Hiking
9.8 out of 10, Exceptional, (14)
"Nice loft. Had everything we needed. It had lots of little extras. Everything was very clean with only an exception of a pan that the previous guest had not washed completely. Overall it was very nice."
Idyllic Wallingford Retreat - Near Skiing & Hiking
Adirondack Lake home w private dock
Tupper firepit 2
Adirondack Lake home w private dock
10.0 out of 10, Exceptional, (13)
"Our group had a lovely week on Tupper Lane! The best part was that we were able to bring our dogs with us. We’ve never seen them so happy! The house was beautiful and clean. And we really enjoyed the fire pit and screened in porch. Karen was so easy to communicate with. I would definitely recommend this place!"
Adirondack Lake home w private dock
Vermont house in stunning private country setting and 360 degree panoramic views
Vermont house in stunning private country setting and 360 degree panoramic views
10.0 out of 10, Exceptional, (6)
"Fantastic place to get away from it all. Romantic and serene with everything you need to enjoy the stunning area. We will absolutely come back "
Vermont house in stunning private country setting and 360 degree panoramic views
Family-Friendly Stratton Gem Close to Slopes!
Stratton Vacation Rental | 4BR | 3.5BA | Stairs Required | 1,900 Sq Ft
Family-Friendly Stratton Gem Close to Slopes!
10.0 out of 10, Exceptional, (7)
"Super comfortable, clean, and close to the slopes. Second time here and will definitely stay again"
Family-Friendly Stratton Gem Close to Slopes!
Vermont Lake House
Property grounds
Vermont Lake House
10.0 out of 10, Exceptional, (12)
"We had a fantastic long weekend stay. House was very well equipped for two different families to stay. Plenty of space for kids and adults to empty different activities. Water access is great and we all loved the boats. Hosts were very communicative and kind. "
Vermont Lake House
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Your Barn!
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
10.0 out of 10, Exceptional, (194)
"The place was beautiful and immaculate "
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Plenty of Room For Everyone! - 5 Minutes to Stratton
Fire Pit - Front Yard
Plenty of Room For Everyone! - 5 Minutes to Stratton
10.0 out of 10, Exceptional, (8)
"Property was fabulous! Very clean and well stocked. The set up was great for groups and with 14 people, we never felt on top of each other. Casey was very responsive to any questions we had. Highly recommend and will book again!"
The price is SAR 902
SAR 3,358 total
includes taxes & fees
7 Oct - 8 Oct
Plenty of Room For Everyone! - 5 Minutes to Stratton
Shuttle or walk to village and lifts! The Powder Haus Chalet!
Exterior
Shuttle or walk to village and lifts! The Powder Haus Chalet!
10.0 out of 10, Exceptional, (31)
"Our group of 8 found the property to be a perfect accomodation while staying in town for a wedding. Check in was very convenient and communication with the host was excellent. The home was very spacious, the living area was a great space to hang out and spend time together. We had all the amenities we needed for an easy weekend while attending a friend's wedding. The location is excellent and was very convenient to the mountain. We are especially grateful for the host allowing our furry friends...
Shuttle or walk to village and lifts! The Powder Haus Chalet!
Dog-friendly cabin in the woods with firepit - ski & golf at nearby mountains
Dog-friendly cabin in the woods with firepit - ski & golf at nearby mountains
9.0 out of 10, Wonderful, (65)
"We loved it and plan to return some day."
Dog-friendly cabin in the woods with firepit - ski & golf at nearby mountains
Perfect Reunion House w/fireplace & piano. Dogs welcome. Discounted ski tix at Bromley. Add private indoor pool on request.
Firepit and big lawn at The Reunion House
Perfect Reunion House w/fireplace & piano. Dogs welcome. Discounted ski tix at Bromley. Add private indoor pool on request.
9.8 out of 10, Exceptional, (22)
"Friendly host, ans check in process was very simple. House was big enough for 8 adults and 6 children. Location is 30-40 mins away from stratton, which we decided to go fo skiing. It felt a little further away due to traffic and busy long weekend."
Perfect Reunion House w/fireplace & piano. Dogs welcome. Discounted ski tix at Bromley. Add private indoor pool on request.
Winhall Home w/ Sauna < 1 Mi to Stratton Mountain!
Winhall Vacation Rental | 4BR | 2BA | 1,800 Sq Ft | Stairs Required
Winhall Home w/ Sauna < 1 Mi to Stratton Mountain!
9.6 out of 10, Exceptional, (34)
"Initially, I was concerned when we got there, the front door Was a challenge to get into, and there were a few large gaps in the railing of the stairs making it dangerous for small children. After I blocked that off, things were pretty good. Nice accommodations, well stocked kitchen, toys etc. any issues I had initially contacting management were from the evolve company, not the owners."
Winhall Home w/ Sauna < 1 Mi to Stratton Mountain!
Beautiful ski home with Stratton mountain views and hot tub!
Summertime view of Stratton from deck and living room
Beautiful ski home with Stratton mountain views and hot tub!
10.0 out of 10, Exceptional, (82)
"This is our second year in a row staying at the house. Always well appointed, clean, and plenty of room for three families with kids. Great views of the mountain, hot tub , fireplace. We will definitely be back!"
Beautiful ski home with Stratton mountain views and hot tub!
Luxury Post and Beam Barn Set On 10 Acres
Exterior
Luxury Post and Beam Barn Set On 10 Acres
10.0 out of 10, Exceptional, (81)
"Amazing property and host. Would love to stay again next time in the area. "
Luxury Post and Beam Barn Set On 10 Acres
Three Bedroom home with loft
Three Bedroom home with loft
Three Bedroom home with loft
Spacious Family getaway near Magic Mountain, VT
Living area
Spacious Family getaway near Magic Mountain, VT
9.4 out of 10, Exceptional, (3)
"Perfect house for family with kids ! Plenty of room for three families !"
Spacious Family getaway near Magic Mountain, VT
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
7.6 out of 10, Good, (40)
"Can't beat the location. We had a great stay."
The price is SAR 278
SAR 1,096 total
includes taxes & fees
24 Sep - 25 Sep
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
hot tub with incredible views...this is why we come to VT!
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
10.0 out of 10, Exceptional, (108)
"My friends and I had a wonderful stay at Mountain Nest. The house is lovely and nestled into the Green Mountains with close proximity to Arlington, Manchester, and surrounding hikes and activities. We will definitely be returning in the future!"
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
Countryside 6-bedroom house centrally located
Private kitchen
Countryside 6-bedroom house centrally located
9.0 out of 10, Wonderful, (4)
"Nice neighborhood, Big property, big yard.. House needs some updates. Thanks "
Countryside 6-bedroom house centrally located
Private home with fireplace, grill, games, AC & great Manchester location
Private home with fireplace, grill, games, AC & great Manchester location
9.2 out of 10, Wonderful, (9)
"We really enjoyed our time, and this property had it all. The perfect mix of “old Vermont” and new clean modern living. The wow factor is real!! From the moment we arrived, and the moment we reluctantly checked out…it was perfect. Lots of room for our family of 5, and close to everything. Morning walks….evening fire, but 2 minutes to the grocery store and the centre of town. The perfect spot. We’ll be back!"
Private home with fireplace, grill, games, AC & great Manchester location
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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

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
Exterior
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
10.0 out of 10, Exceptional, (156)
"Came for four day stay because of my daughter and her new husband‘s wedding… At the old Gray barn… My brother and nephew and I shared the Creekside cabin… Beautiful rustic cabin with all the amenities one could want… I can see now why they picked the spot to get Married… It is a beautiful location in Dorset… Finding the Creekside cabin was a great find my brother said he owes me for years to come now lol dan’s place is spectacular"
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
Long Trail House at Stratton Mountain Resort
Living room
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very Good, (71)
"The unit was perfect for our ski race weekend. Very accessible, underground parking included (ski boxes on top of SUVs will not fit - thankfully we left ours at home), really nice place with everything we needed!"
Long Trail House at Stratton Mountain Resort
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
Active Tinmouth cabin in the eve!
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
10.0 out of 10, Exceptional, (156)
"We had a wonderful trip and stay at the cabin. The owners were so helpful and great communication. They went above and beyond to make sure our stay was great!"
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
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.