
Vacation rentals in Rupert
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Top-rated vacation rentals in Rupert
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Superhost

Home in Warrensburg
4.85 out of 5 average rating, 232 reviewsINCREDIBLE Adirondack Home (Lake George/Gore Mtn.)
RachelRating, 5 stars2 weeks ago
We loved our stay, the house was perfect for what we needed. Beautiful view from the back porch, clean, cute decor, lots of space and the kitchen had all we needed. Easy drive to Gore mountain. Easy entry and contact with owners. We will definitely rent again!
Top guest favorite

Home in Peru
5 out of 5 average rating, 10 reviewsHighland Haus: stunning ski getaway with hot tub
ChristopherRating, 5 stars3 weeks ago
Beautiful home that is about 15min from Manchester, which is wonderful to walk around (shops, restaurants). The home is secluded on a nice piece of property in the woods. It was a charming getaway with a wood-burning fireplace and great amenities (games, dart board, hot tub, etc). Highly recommend!
Guest favorite

Home in Chestertown
5 out of 5 average rating, 10 reviewsSecluded and Cozy Townhome near Tripp Lake
NicoleRating, 5 stars8 months ago
We really enjoyed staying at the condo in Green Mansions. It was very spacious and Bryce was extremely communicative.
Guest favorite

Home in Bellows falls
5 out of 5 average rating, 8 reviewsAmazing Views, Skiing Nearby and Amenities Galore!
GillianRating, 5 stars2 months ago
We absolutely loved our stay at Barbara’s home! It was spacious enough to accommodate 6 adults and 1 child with no issue. The kitchen is well appointed, allowing us to cook meals throughout our stay. We had a small storm roll through, which dropped 5” of snow overnight (great for our next day on the mountain!), and we were thrilled to see that the driveway and walkway had been cleared prior to 7am. The bedrooms were comfortable and the view from the great room is truly stunning. Would love to stay here again! Thank you, Barbara!
Superhost

Home in Manchester
4.86 out of 5 average rating, 35 reviewsYour VT Dream House: Fireplace, Pool, Dogs
AtulRating, 5 stars7 months ago
Beautiful area great amenity. Wish there was 1/2 bath downstairs. That was the only inconvenience.
Top guest favorite

Home in Chittenden
5 out of 5 average rating, 8 reviewsModern Retreat next to Mountain Top Inn,Killington
MaddyRating, 5 stars1 month ago
I couldn't recommend this place more! My cousins and I had a great time and Uli is super attentive. The hot tub has a great view of the lake, it was also salt water which I love. The space was extremely cozy and exactly what we needed. We snowboarded pico and killington and it was about a 25-30 minute ride. We will for sure be back! Thank you guys so much!
Top guest favorite

Cabin in North Creek
4.98 out of 5 average rating, 177 reviewsGore Mountain Log Cabin Getaway
DennisRating, 5 stars1 week ago
Words cannot express how beautiful the cabin and property are. Everything is perfect. It’s the perfect location for a ski/board trip to Gore. The cabin is nestled on a hill, totally secluded. Very private location. The property has a trail which has a stream trickling by. Everything in the cabin works. You’ll need food, that’s about it. If your lucky to find this place open to rent, well then your lucky.
Top guest favorite

Home in Plymouth
5 out of 5 average rating, 16 reviewsLuxury Modern Cabin near Okemo & Killington
TariQRating, 5 stars3 weeks ago
Stephanie was an Incredible host! The listing matched her description and the property looked even better upon checking in. Stephanie maintains this property really well and I couldn’t have felt any more at home. The home was clean and had a perfect cozy feeling to it. In addition, this was really close to the mountain, which made the getaway even better. I enjoyed the privacy and waking up to a nice snow dusting before my trip to the mountain. I highly suggested staying at Stephanie’s property if you’re looking for a quick getaway. I certainly will be looking to book again soon. Thank you Stephanie!
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- Okemo Mountain Resort
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Gore Mountain
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Berkshire East Mountain Resort
- Albany Center Gallery
- Saratoga Spa State Park
- West Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Saratoga Race Course
- Mount Snow Ski Resort
- Mount Greylock Ski Club
- Clarksburg State Park
- Huck Finn’s Playland, Albany
- Pineridge Cross Country Ski Area
- Peebles Island State Park
- Gooney Golf
- Lake George Expedition Park
- Ekwanok Country Club
- National Museum of Racing and Hall of Fame
- Willard Mountain
- Dorset Field Club