Holiday houses in Rupert

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Top-rated holiday rentals in Rupert

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Home in Wilmington

5 out of 5 average rating, 8 reviews

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

DevonRating, 5 stars3 months ago
Our family has been going to VT in the fall for 25+ years. The usual house we stay in was unavailable and lead us to find this home. Upon arrival we were stunned at the view, it is incredible in person! We had 5 adults and two children o this trip and this home offered us so much space and activities. My father even noted how everyone had their own space to dow whatever they wanted at any point in the day. We utilized the amenities every day and my kids were thrilled to have all the games to play inside as well as a beautiful lawn to run around and play on. Just a short drive down the driveway you reach the water which we also utilized mulitple times a day. Overall it was very peaceful and felt like a retreat and now my kids prefer this house over the old one! Definitely hoping to come back soon! Also, the hosts were very communicative and responsive before and during our stay, we very much enjoyed our time.
Superhost

Cabin in Lake George

4.85 out of 5 average rating, 124 reviews

Spacious Lake George Lodge -Near West & Gore Mnt

CarolRating, 5 stars1 month ago
It was the perfect family Christmas gathering place. Even though it was on the main road when you walk into the cabin you feel like you’re in the woods. Any road noise was worth it just to have everyone in one spot for a change!
Guest favourite

Home in Lake Luzerne

4.98 out of 5 average rating, 128 reviews

River Cottage

JensyRating, 5 stars2 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!
Guest favourite

Home in Hadley

5 out of 5 average rating, 50 reviews

The Summit on The Sacandaga is sure to Satisfy.

CarolineRating, 5 stars2 months ago
This home and host were such an incredible find! Of all the locations you can choose for a weekend getaway with a waterfront view, I would 1000% recommend this place. The hosts went above and beyond for me, they were so accommodating and responded quickly! This home is even better in person, from decor to the views you get from the living room and bedroom. They did a beautiful job making it feel cozy and thought of everything you might need during your stay. What I especially loved is that it’s very private. Perfect for a relaxing family trip.
Guest favourite

Apartment in Wilmington

4.91 out of 5 average rating, 129 reviews

Globetrotter Retreat too - Minutes to the Mountain

RichardRating, 5 stars2 days ago
This is our second stay at this location (different apartment in same building) and it was very centrally located and close to Mount Snow. This is a great place to stay in Wilmington.
Guest favourite

Home in Chestertown

5 out of 5 average rating, 14 reviews

Adirondack Home 15 minutes from Gore

LouRating, 5 stars2 weeks ago
Amber the host was extremely helpful and responsive. Her place was amazing, great inside and out! Plenty of space, very cozy, clean, well stocked with all we needed and welcoming. We had 11 people and a dog and it was perfect for our long weekend away. The outside space was amazing too. The porch, hot tub , fire pit by the gazebo and pond were fantastic. We hiked locally behind the pond into the hills during a light snow and it was great. We also hiked to Stewart Mountain where the trail begins about a 1/4 mile down the road. It is easy to get to and a moderate hike with great views of Loon lake at the top. Highly recommend Ambers place!
Guest favourite

Cabin in Lake George

5 out of 5 average rating, 39 reviews

Great location. Walk to Village attractions/beach!

MarinaRating, 5 stars1 month 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!
Guest favourite

Apartment in North Creek

4.92 out of 5 average rating, 61 reviews

The Rail house

NatRating, 5 stars1 week ago
It’s a very nice cozy place in the village and just minutes from Gore if you’re a skier. The place is just as advertised, was easy to find, and checkin was easy too. No surprises. Rebecca is very responsive and very pleasant. We left one item in the unit and Rebecca called me to let me know she has it. She will make arrangements with the owner to get it returned. Thought that was very thoughtful of her.
Guest favourite

Apartment in Pittsford

4.97 out of 5 average rating, 30 reviews

Norm's Place

MarissaRating, 5 stars1 week ago
The home was quaint, quiet, and very clean! Very happy with my stay at this home, and hope to return again in the future.
Guest favourite

Guest suite in Lake George

4.95 out of 5 average rating, 74 reviews

Lake George Perfect Location

ZachRating, 5 stars3 months ago
We greatly enjoyed our stay at Peter's home! The house was exceptionally clean and everything was as pictured and described. Peter was very friendly and checked in with us occasionally in case we needed anything or had any questions. We would highly recommend Peter's place.
Superhost

Cottage in Lake George

4.75 out of 5 average rating, 84 reviews

Renovated Cottage in Lake George

DwayneRating, 5 stars5 months ago
the cottage was great. perfect for our needs and dog friendly. we even decided to stay an extra day. the host was extremely responsive. would definitely recommend
Guest favourite

Home in Cavendish

4.96 out of 5 average rating, 23 reviews

Charming New England Cape- 10 Minutes from Okemo!

MatthewRating, 5 stars5 days ago
Megan was great! We needed a little bit of extra time to get another ski day in Sunday and she kindly accommodated us. Great communicator and quick to respond! Minutes from restaurants and Okemo mountain. Beautiful home with rustic Vermont charm.

Popular amenities for Rupert holiday rentals

Other great holiday rentals in Rupert

Superhost

Home in Warrensburg

4.84 out of 5 average rating, 224 reviews

INCREDIBLE Adirondack Home (Lake George/Gore Mtn.)

ChristianRating, 5 stars3 weeks ago
Booked for a 3 day ski trip during January 2025. Perfect place for a larger group to relax, enjoy movies, take in the amazing back porch view and get to the mountain in under 20 minutes. Hot showers were amazing post skiing and Warrensburg had plenty to offer in terms of food and activities! Cannot wait to return again!!
Guest favourite

Home in Woodstock

4.92 out of 5 average rating, 24 reviews

Great Maples

MeganRating, 5 stars4 weeks ago
We can’t say enough good things about this house. It was PERFECTION; it was EXACTLY what we were looking for. We traveled with 10 people (6 adults and 4 kids) and everyone fit in the house comfortably. The kids space to play was so great for the kids. The fireplace room was big enough for all of us to sit by a cozy fire and watch tv after a day of skiing or playing in the snow. The kitchen was stocked with everything we needed to cook meals. And we were all able to sit at the dining room table for dinners. The land was absolutely incredible. We could skate on the lake, we had snowball fights, built snowmen, we explored the property to take pictures, and the kids were able to play on the play ground. We truly cannot say one negative thing about this house. We wish we could take this house on each vacation we go on!
Guest favourite

Home in Chestertown

5 out of 5 average rating, 10 reviews

Secluded and Cozy Townhome near Tripp Lake

NicoleRating, 5 stars6 months ago
We really enjoyed staying at the condo in Green Mansions. It was very spacious and Bryce was extremely communicative.
Superhost

Home in Manchester

4.85 out of 5 average rating, 34 reviews

Your VT Ski House: Fireplace, Indoor Pool, Dogs

KaylaRating, 5 stars11 months ago
melissa was very responsive and even sent help when we needed heater :) nice house for a family gathering, our group had a great time!!
Superhost

Townhouse in Wilmington

4.87 out of 5 average rating, 15 reviews

VT Ski House - Great for Families and Groups!!!

MitchellRating, 5 stars35 months ago
Beautiful home right off the mountain. But Gregg responded Immediately to any hiccups and Concerns And made sure that everything was taken care of immediately… Thank you so much
Guest favourite

Home in Plymouth

5 out of 5 average rating, 12 reviews

Luxury Modern Cabin near Okemo & Killington

DenizRating, 5 stars5 days ago
The house is beautiful exactly like in the pictures, specious open concept, modern nicely decorated. It was a out 25 min drive to killington k1 lodge, very convenient for who is looking to stay for ski trip with a family.
Guest favourite

Home in Saratoga Springs

4.95 out of 5 average rating, 39 reviews

Great Saratoga House with Pool Walk to Everything!

CaitrinRating, 5 stars1 month ago
Loved staying here! It was super cozy and a lovely home away from home for the holidays. House is as described and very spacious. Fireplace makes it extra cozy when the weather got cold. Host was very proactive and responded to any question or issue almost immediately. We will definitely be staying here again!
Guest favourite

Tiny home in Fort Edward

4.86 out of 5 average rating, 58 reviews

Tiny Home In Paradise “The Big Dipper”

AlannaRating, 5 stars7 months ago
If you’re looking for a quiet place to get away for the weekend, look no further!! Pete was so nice and incredibly responsive. My fiancée and I will definitely be staying here again!

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Bennington County
  5. Rupert