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Compare 346 Vacation Homes in Rupert with updated reviews, rates, and availability.

Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton

9.8 out of 10, Exceptional, (30)
"One of the best experiences I’ve had. Communication before we arrived was as expected, and everything was better than the pictures reviews and descriptions."
The price is AED 2,016
AED 4,864 total
includes taxes & fees
2 Feb - 3 Feb
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

10.0 out of 10, Exceptional, (11)
"My family enjoyed our stay at this house. It had plenty of room for all of us and the 5 bathrooms were great to have. Extremely clean. We didnt use the hot tub because it was too cold but that is definitely a plus to have. It is only a few minutes from Manchester Center and close to a lot of other restaurants and shops. The ownwr reached out days in advance and was available if needed, which we didnt. We will definitely be looking to book this house in the future! A++++"
The price is AED 1,509
AED 3,273 total
includes taxes & fees
6 Jan - 7 Jan
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

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

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

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

10.0 out of 10, Exceptional, (160)
"This was our second Thanksgiving at Creekside Camp. Once again, we had a wonderful stay. Not enough can be said about this charming and cozy cabin. Dan and Kellie do a phenomenal job as hosts and managing the property. We highly recommend a stay in this rustic, yet highly appointed property!"
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

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

10.0 out of 10, Exceptional, (18)
"Everything about this house was great! We will definitely be back!"
Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

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

10.0 out of 10, Exceptional, (34)
"This beautiful, charming and spacious house served our family's needs beautifully for a one week fall getaway. The photos don't do it justice. The linens and beds were very comfortable. The ease of a gas fireplace in the breakfast/dining area was very welcome on chilly mornings. The location was great. Beth was very accommodating. If we come back to the area we will definitely try to stay here again."
Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle

Miner Cottage-Historic Antique Home just steps from the Equinox Resort

10.0 out of 10, Exceptional, (22)
"GREAT TIME ! GREAT HOUSE"
Miner Cottage-Historic Antique Home just steps from the Equinox Resort

Cozy Cabin Between Stratton Resort & Mount Snow

10.0 out of 10, Exceptional, (1)
Cozy Cabin Between Stratton Resort & Mount Snow

The Green Mountain Chapel // Old Church repositioned into 3 BR

2.0 star property
10.0 out of 10, Exceptional, (12)
"I really loved this place and plan to return. Every thing about this chapel was gorgeous! The openness of the house was perfect and allows for being able to see the stunning stained glass from just about anywhere you are. The bathrooms were fantastic. This was the only place I've rented out that actually had the warm cozy home feel which we really loved. I also very much love that he had actual art around the chapel. I also greatly appreciate Tylers communication with the check-in process and...
The Green Mountain Chapel // Old Church repositioned into 3 BR

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

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

Gather Together – Stratton Mtn Luxury & Comfort with a View

10.0 out of 10, Exceptional, (1)
Gather Together – Stratton Mtn Luxury & Comfort with a View

Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

10.0 out of 10, Exceptional, (54)
"We rented the barn as an overflow space from the main house. The barn has everything you need and is a really cool spot to sit and view the entire property."
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

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

9.8 out of 10, Exceptional, (48)
"We went up in December to Ski Okemo. This is a great house and has all amenities including an awesome fireplace and large eating area. Great location for two of three families to go away together and enjoy VT!"
Dog-friendly house with picturesque mountain view & near skiing - close to Okemo

Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton

10.0 out of 10, Exceptional, (75)
"This is our third trip to this property and it never disappoints! Wonderful weekend away in VT."
Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton

Historic 6-BR Across From Equinox Resort

8.8 out of 10, Excellent, (5)
"Great house in a perfect location, we really enjoyed our stay for a family vacation!"
Historic 6-BR Across From Equinox Resort

Manchester Center Home w/ Green Mtn Views!

9.6 out of 10, Exceptional, (31)
"This home had a lot of character! It had a wonderful kitchen, and it was easy to cook there. It had a beautiful dining room! We were there for Christmas and the owners put up some beautiful decorations, and a nice tree for us. Both of the hosts are creative types, and you could tell by the decor in the house. There was beautiful artwork all over. The hosts were helpful as they salted and sanded the walkway from the car to the house. The very hospitable. The view from the house of the mountains...
Manchester Center Home w/ Green Mtn Views!

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!

Cozy Manchester Getaway with Amazing Views!!!

9.8 out of 10, Exceptional, (22)
"Totally enjoyed our stay. The house was comfortable & cozy. The views from the deck were beautiful. The house is located in the perfect spot. Somewhat secluded but close enough to the main road & town. Loved it!"
Cozy Manchester Getaway with Amazing Views!!!

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

10.0 out of 10, Exceptional, (6)
"Nice place, nice area, nice owners"
Vermont's Mountain Villa: Hot tub, Ski views, Pet+

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

10.0 out of 10, Exceptional, (1)
"House looks exactly as it does in the photos. No real yard, but the house itself is very comfortable. Plenty of space, comfortable beds and accommodating common areas. We struggled with the Internet through the duration of our stay, due to storms in the area. The property managers were in constant communication with us, but couldn't get the Internet service provider to resolve the issue. House is less than 10 minutes from Stratton Mountain, which is great. Unfortunately, it rained for the...
5BR, 6 min from Stratton, pet friendly, private, jacuzzi tub, wrap around deck!
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

10.0 out of 10, Exceptional, (160)
"This was our second Thanksgiving at Creekside Camp. Once again, we had a wonderful stay. Not enough can be said about this charming and cozy cabin. Dan and Kellie do a phenomenal job as hosts and managing the property. We highly recommend a stay in this rustic, yet highly appointed property!"
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

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 AED 1,275
AED 1,585 total
includes taxes & fees
15 Jan - 16 Jan
Long Trail House at Stratton Mountain Resort

Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.

10.0 out of 10, Exceptional, (162)
"Wonderful property, gracious hosts, zero complaints"
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.