Vacation rentals in Rupert

5 out of 5 average rating, 10 reviews

Home in Wilmington

Lake & Mountain View Cabin - Sauna, Hot Tub, Hikes

VanessaRating, 5 stars1 month ago

There is not a shortage of things to do at Anthony's place. The game tables, sauna and hot tub made the weekend really fun, especially for the non skiers of the group. The view from the house is also spectacular! We would definitely rent this place again.

4.81 out of 5 average rating, 133 reviews

Home in Tinmouth

Vermont Lakefront Getaway "The Wild Loon"

WilliamRating, 5 stars2 months ago

The place was perfect for our winter family vacation. The home was as described in a beautiful setting with a great view. If staying in the winter months having a vehicle with at least all wheel drive is helpful, as this is Vermont. The home is out of the way, but easy driving distance to ski and explore the nearby towns.

4.86 out of 5 average rating, 126 reviews

Cabin in Lake George

Spacious Lake George Lodge -Near West & Gore Mnt

LisaRating, 5 stars2 months ago

We had a wonderful time staying at Nathan’s cabin for my birthday weekend. We were so close to the town of Lake George but also had some privacy. Despite being on a small one-lane highway, it still felt like a lovely woodsy retreat and it turned out to be in our benefit because when it snowed, the road was cleared very quickly. The house is cozy and the beds are comfy! We would def recommend staying here!

4.98 out of 5 average rating, 128 reviews

Home in Lake Luzerne

River Cottage

JensyRating, 5 stars5 months ago

Brianna is a wonderful host, very friendly, always available and ready to help in anything we may need. The house is like a Dream House. Lovely living room with a fireplace, TV and a big and comfy sofa. Every room in the house was excellently decorated with a high test and good sense of space making you feel warm and welcome, like your own home. The surroundings are so beautiful that you even have a river running in the backyard. Like fairytale stories. The most amazing thing is the Kitchen fully equipped with seasonings, coffee, tea and beautiful crockery and pot sets. Everything you may need for a memorable vacation is here! We loved this place and definitely we're going to come back. Thank you very much Brianna, you're amazing!

5 out of 5 average rating, 51 reviews

Home in Hadley

The Summit on The Sacandaga is sure to Satisfy.

DebraRating, 5 stars1 week ago

great house with everything needed to enjoy the beautiful surroundings for a family vacation- pups included. the summit at sacandaga was everything we hoped for: beautiful lake views surrounded by mountains in a very private setting. the entire house was very clean and well appointed especially in bedrooms, kitchen and bathrooms. we loved our stay. heather was very responsive and helpful and we had no issues from start to finish- only a positive experience. we would definitely stay there again and highly recommend this beautiful spot on the lake.

4.91 out of 5 average rating, 134 reviews

Apartment in Wilmington

Globetrotter Retreat too - Minutes to the Mountain

XianlongRating, 5 stars3 weeks ago

Thanks for the host making this place like home. Furnitures are well organized. My partner and I love the sofa in the living room. There is a big sofa and single arm chair sofa. It’s good for staying with partner to kiss cuddle and more. We love the well organized kitchen. Very well-equipped. They even have some stock of food, coffee and tea bags just in case if you are hungry in mid night. We came here for skiing trip. It’s just 15 min to Mt Snow, 1.5h to Okemo. Stratton is also around this area. Great location for mountain staycation.

4.91 out of 5 average rating, 100 reviews

Cabin in Bridgewater

100 Acres Views & Creek near Woodstock/Killington

ChristopherRating, 5 stars1 month ago

Had a great stay with friends at Laura’s place. Laura was friendly flexible and reached out to make sure we didn’t have any issues checking in. Very nice place with a nice Vermont feel. 10-15 minutes from skyeship base. Had a great weekend. Would stay again.

4.93 out of 5 average rating, 71 reviews

Apartment in North Creek

The Rail house

KristaRating, 5 stars1 month ago

A friend and I stayed at The Railhouse for 5 nights over the course is US Alpine Masters Nationals. The house is cute, cozy and clean. Rebecca has clearly taken great care to have everything her guests might need, and to make the place comfortable and fun for an extended stay in the area. Rebecca was friendly and very helpful and responsive; an amazing host. Location is amazing - 5 minutes from Gore, RIGHT in town, but private, walkable to the shops and a great coffee shop (shout out to Sarah’s). Look forward to staying again

Vacation rentals for every style

Get the amount of space that is right for you.

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Rupert vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Rupert

4.85 out of 5 average rating, 232 reviews

Home in Warrensburg

INCREDIBLE Adirondack Home (Lake George/Gore Mtn.)

RachelRating, 5 stars1 month 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!

5 out of 5 average rating, 10 reviews

Home in Chestertown

Secluded 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.

4.86 out of 5 average rating, 35 reviews

Home in Manchester

Your VT Dream House: Fireplace, Pool, Dogs

AtulRating, 5 stars8 months ago

Beautiful area great amenity. Wish there was 1/2 bath downstairs. That was the only inconvenience.

4.91 out of 5 average rating, 11 reviews

Home in Dover

Amazing Family getaway!

KerriRating, 5 stars1 month ago

This house was a great spot to stay in between days of skiing. Everything was clean and comfortable.

4.98 out of 5 average rating, 177 reviews

Cabin in North Creek

Gore Mountain Log Cabin Getaway

DennisRating, 5 stars1 month 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.

5 out of 5 average rating, 16 reviews

Home in Plymouth

Luxury Modern Cabin near Okemo & Killington

TariQRating, 5 stars1 month 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!

4.94 out of 5 average rating, 69 reviews

Villa in Pownal

Vermont Vacation Villa—Grapevine Getaway

CindyRating, 5 stars2 months ago

lovely stay for my group’s annual ski trip! beautiful home - would love to stay here again :)