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

A spacious kitchen features wooden cabinetry and modern stainless steel appliances. A large island with a dark countertop is surrounded by rustic stools. Beneath warm lighting, decorative elements include wooden accents and an ornamental bear figure positioned above the cabinets.

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

A wooden deck overlooks a calm lake, framed by lush trees and distant mountains. Two reclining chairs are positioned on the deck, with one chair facing the water and a flag nearby, highlighting the serene atmosphere during sunset.

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

An open door leads to a private balcony, where a serene tree offers shade. A large, relaxed dog rests on the balcony floor. Bright greenery is visible, enhancing the tranquil outdoor atmosphere.

Apartment in Wilmington

Globetrotter Retreat too - Minutes to the Mountain

XianlongRating, 5 stars4 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.

5 out of 5 average rating, 39 reviews

Cabin in Lake George

Great location. Walk to Village attractions/beach!

MarinaRating, 5 stars3 months ago

Katrina was a wonderful host! She was responsive and thoughtful with her recommendations. The home was incredibly clean and had everything you could need for your stay and more. We felt very comfortable in the space and were so impressed with how well the space was maintained and that no detail was overlooked to make guests feel at home. The location was great and the lake views were beautiful at night with the holiday lights! Highly recommend Katrina and the cabin!

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.

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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, 233 reviews

The exterior of the home is illuminated by string lights, enhancing the cozy ambiance at night. A fire pit is surrounded by comfortable seating, inviting gatherings under the stars. The home's two-story structure features large glass doors, contributing to a welcoming atmosphere.

Home in Warrensburg

INCREDIBLE Adirondack Home (Lake George/Gore Mtn.)

MrRating, 5 stars1 month ago

Everything as described. Easy to find. Easy parking. Private and well equipped. Host quick to respond.

5 out of 5 average rating, 10 reviews

A calm lake captures the reflection of surrounding trees and hills, under a clear blue sky. The sandy shore gently lines the water's edge, and small boats can be seen anchored in the distance. A serene atmosphere is created by the tranquil waters.

Home in Chestertown

Secluded and Cozy Townhome near Tripp Lake

NicoleRating, 5 stars9 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

An aerial view captures the expansive Wilburton resort, surrounded by lush greenery and mountains. The scenic landscape features a serene outdoor pool, with inviting lounge chairs arranged around it. The main house displays elegant architecture, harmonizing with the beautiful natural surroundings.

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

A serene forest scene is captured, featuring a gentle stream flowing over smooth, moss-covered stones. Tall trees frame the sides, with sunlight filtering through the leaves, creating dappled light patterns on the rocky ground.

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

A log cabin is showcased surrounded by pine trees, displaying a welcoming exterior with a green roof and a large American flag positioned at the front. A gravel driveway leads up to the porch, which features a railing and ample space for relaxation.

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

A spacious kitchen and dining area is seen, featuring a large granite island with bar seating. Open shelving and modern appliances are present. A staircase with wooden steps and metal railings leads to the upper level, while large windows invite natural light into the room.

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!

4.98 out of 5 average rating, 104 reviews

A tranquil view of a sandy beach leads to a calm lake, reflecting the colorful foliage of trees surrounding the water. The gentle hills in the background are dotted with a mix of greens and autumn hues, creating a serene natural landscape.

Cottage in Minerva

Camp Knotty and Nice at Minerva Lake. In the Adk

LoriRating, 5 stars6 months ago

This was my first time staying at Ken’s beautiful home on Minerva Lake. When I walked inside I was in awe. The interior home is stunning. A large dining room table was off to the side of the living room and we loved gathering around the table to do watercolor paintings. The bedrooms are comfy and cute. Little details around the house like nightlights and paintings are so sweet. Everything we needed was there for us. The kitchen was cute and we enjoyed cooking our meals and making salads. The fire pit outside was also lots of fun. We made s’mores and we were hoping to see the Northern Lights but unfortunately they didn’t come down south far enough, but we still had fun. The house is extremely comfortable and inviting. We loved our stay and look forward to coming back. Thanks Ken for everything. Lori.