Rupert Holiday Rentals

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Holiday Rentals in Rupert

Gorgeous Victorian-Style House w/ Hilltop Pool!

8.8 out of 10, Excellent, (29)
"The house was a perfect weekend getaway for a group of friends from the city. It was absolutely gorgeous and had everything we could need. We even got two feet of snow, so it was a magical Vermont experience! We would definitely go back and thank you!"
Gorgeous Victorian-Style House w/ Hilltop Pool!

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 AU$774
includes taxes & fees
24 Mar - 25 Mar
Long Trail House at Stratton Mountain Resort

Lovely ski-in/out condo steps from ski lift with trails and amazing views

8.8 out of 10, Excellent, (22)
"Unit is very close to ski lift. Ski in / ski out was great!!!"
The price is AU$467
includes taxes & fees
24 Feb - 25 Feb
Lovely ski-in/out condo steps from ski lift with trails and amazing views

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (206)
"Perfect get away. "
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Stratton 1 Bedroom Long Trail Condo, Walk to Village and Lifts

9.6 out of 10, Exceptional, (49)
"We had a great time staying at the Long Trail Lodge! The room was clean, as described, and easy to use! "
Stratton 1 Bedroom Long Trail Condo, Walk to Village and Lifts

Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside

10.0 out of 10, Exceptional, (10)
"We loved the carriage house! Everything about it was perfect. We loved sitting and watching movies while the fireplace roared before we would go on our adventures. It was the perfect spot for the two of us and couldn’t get enough of it. "
Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside

Cabin 7min to Ski Stratton-Wood Stove,Starry Skies,Fire Pit,Views,Dogs OK

2.0 star property
10.0 out of 10, Exceptional, (1)
"Cabin was as advertised and very close to the mountain. Would definitely stay again "
The price is AU$401
includes taxes & fees
23 Feb - 24 Feb
Cabin 7min to Ski Stratton-Wood Stove,Starry Skies,Fire Pit,Views,Dogs OK

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

10.0 out of 10, Exceptional, (163)
"This Vermont home is the perfect getaway in the winter. Deb and Ang have beautiful land for all of your cold weather needs. Their home is equipped with a REAL fireplace. Book here and you will not regret it!"
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.

Perfect Country Cottage

9.6 out of 10, Exceptional, (78)
"Host was great! On top of everything involved with the trip. The house worked out great for our ski trip. "
Perfect Country Cottage

Stratton Mtn Studio | Renovated | Walk to Lifts

10.0 out of 10, Exceptional, (27)
"Nicely renovated, well equipped condo very conveniently close to the main lodge and all it offers. It is small but for two people it certainly is fine and murphy bed is a clever solution. Well done!"
The price is AU$960
includes taxes & fees
19 Mar - 20 Mar
Stratton Mtn Studio | Renovated | Walk to Lifts

Stratton Mountain Resort Solstice Luxury 5 bedroom Ski-In/Out Vacation Home

9.8 out of 10, Exceptional, (50)
"Great location, ski in ski out, enjoyed the hot tub in the snow. Great for our group of 3 couples with young kids. Appreciated the well stocked kitchen. "
Stratton Mountain Resort Solstice Luxury 5 bedroom Ski-In/Out Vacation Home

The Stratton Cabin | Close to Stratton & Mt Snow!

10.0 out of 10, Exceptional, (2)
"The cabin was in a great location for us and was much nicer than we thought. It had everything we needed too. I’d rent this cabin again for sure "
The Stratton Cabin | Close to Stratton & Mt Snow!

Peaceful Stay at Birds of a Feather Farm & Spa

9.6 out of 10, Exceptional, (15)
"I arrived amidst freezing outdoor temperatures to a warm and cozy interior. I was visiting family and was concerned about snow and ice, Laurie had assured me that it would not be a problem and she was right. The unit was exactly as described in the ad. Laurie made sure that the snow was shoveled and I had no problems getting out in the morning! A wonderful, peaceful getaway!"
The price is AU$410
includes taxes & fees
24 Feb - 25 Feb
Peaceful Stay at Birds of a Feather Farm & Spa

Your own Private Lake - Breathtaking Views - Gym - Sauna - Hot Tub

10.0 out of 10, Exceptional, (25)
"We rented this property as a way to spend time with family right before the busy holiday season. We couldn’t have picked a better place to stay. The house was very cozy, clean, and had everything we needed and more! Check-in was super easy, and the host responded very quickly. The hot tub and sauna were great additions, but the view of the lake and mountains every morning was just what we wanted. We will definitely be recommending to friends and family!! "
Your own Private Lake - Breathtaking Views - Gym - Sauna - Hot Tub

5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio

9.8 out of 10, Exceptional, (16)
"I can’t rave about this condo enough. Super fair prices for staying directly across the street from the mountain and having a parking garage. The bed was super comfy and immediately after walking in I noticed how clean it was. The hot tub almost directly outside was the icing on the cake. If you’re going to stay in Stratton, this place is it. "
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio

Fabulous 3-bedroom townhome at the base of Magic Mountain in Londonderry, VT

10.0 out of 10, Exceptional, (1)
"This is exactly the type of property Vrbo was made for: it’s someone’s vacation home where you’re invited to stay for a few days. And you absolutely feel like a guest! They have everything you could want during your stay and it’s all things that they chose for comfort and enjoyment. It’s easy to feel right at home. We got an early check in and a late check out so we could maximize our ski time.And the location was fantastic! Views overlooking the mountain when you get up. And a closer walk to...
Fabulous 3-bedroom townhome at the base of Magic Mountain in Londonderry, VT

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

9.4 out of 10, Exceptional, (21)
"ideal for a large group of adult friends "
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

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

10.0 out of 10, Exceptional, (55)
"Great secluded place. Very clean couldn't ask for more. Great central location. Close to restaurants "
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

10.0 out of 10, Exceptional, (14)
"Family ski weekend. Our stay was very comfortable. Communication with host was phenomenal, always prompt and courteous Location is nice , very close to the ski resorts "
The price is AU$1,547
includes taxes & fees
24 Feb - 25 Feb
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Beautiful Manchester VT Mountain Retreat w/Hot Tub

10.0 out of 10, Exceptional, (31)
"We had 9 people in 2 family units staying at house. Then about another 6 that came each night to hang out. Plenty of room. 3 living room areas for everyone to spread out. Best stocked home EVER!!! There was literally everything and anything that we needed…..and then some. Inside sauna so cool. Unfortunately way too cold to go out and enjoy the hot tub. Decorations beyond beautiful. Owner very quick with communication. Highly recommend staying here. "
Beautiful Manchester VT Mountain Retreat w/Hot Tub
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 types of properties in Rupert you may be interested in

Kimpton Taconic Hotel by IHG

4.0 star property
9.4 out of 10, Exceptional, (746)
"We had a wonderful get-away! Lovely facilities. "
The price is AU$328
includes taxes & fees
3 Mar - 4 Mar
Kimpton Taconic Hotel by IHG

Hampton Inn and Suites Manchester

2.5 star property
9.6 out of 10, Exceptional, (1006)
"Always love staying here! "
The price is AU$232
includes taxes & fees
9 Mar - 10 Mar
Hampton Inn and Suites Manchester

The Equinox Golf Resort & Spa

4.5 star property
7.4 out of 10, Good, (454)
"We enjoyed our stay at the Equinox. We enjoyed the meals we had there and the general atmosphere. Front desk staff on Sunday, 2/16, could have been a bit more pleasant and/or helpful. One of the women at the desk was not particularly friendly or helpful in terms of what do with kids in the area during a storm. Also, there should be more coffee urns in the lobby to accommodate the volume of guests. I also thought they could have done a better job shoveling and salting the parking lot which was...
The price is AU$436
includes taxes & fees
9 Mar - 10 Mar
The Equinox Golf Resort & Spa
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.

Frequently asked questions

Are there holiday rentals in Rupert?

Yes, there are holiday rentals close to the most popular sights in Rupert, or you can select a more secluded option if you're looking for a relaxing stay. Rupert is known for its parks.

What are some of the best holiday rentals that Rupert has to offer?

Your Vermont Mountain Haven Pet Friendly home with Hot tub!: This holiday home rental outside of Rupert is located in the mountains, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals are there in Rupert?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Rupert stay.

What’s there to see and do in Rupert?

Green Mountain National Forest and Merck Forest Farmland Center are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Stratton Mountain Resort and Dorset Playhouse.

What’s a holiday rental in Rupert like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Rupert. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for family gatherings.