Rupert Vacation Rentals

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Check prices for these dates

Tonight
Mar 4 - Mar 5
Tomorrow
Mar 5 - Mar 6
This weekend
Mar 7 - Mar 9
Next weekend
Mar 14 - Mar 16

Vacation Rentals in Rupert

Long Trail House at Stratton Mountain Resort
Condo, 2 Bedrooms | Pool

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very good, (73)
"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 CA $528
CA $656 total
includes taxes & fees
Apr 1 - Apr 2
Long Trail House at Stratton Mountain Resort
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Exterior

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

9.6 out of 10, Exceptional, (208)
"We absolutely loved our stay in the Honeymoon Cottage! Place was well stocked and clean. We loved the location, very private and close to the Appalachian Long Trail, which we enjoyed hiking. Location is close to Manchester for shopping, groceries and dining. Would happily return. Thank you for a lovely few romantic days."
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Unexpected Style in a Cosy, Convenient In-Town Apartment
Dining

Unexpected Style in a Cosy, Convenient In-Town Apartment

9.8 out of 10, Exceptional, (68)
"Beautiful place love the decor close to everything."
Unexpected Style in a Cosy, Convenient In-Town Apartment
Secluded home with game room, private hot tub, golf, river & mtn views, firepit
Fridge, microwave, oven, stovetop

Secluded home with game room, private hot tub, golf, river & mtn views, firepit

9.8 out of 10, Exceptional, (6)
"Very nice. Could use curtains or blinds in more rooms."
Secluded home with game room, private hot tub, golf, river & mtn views, firepit
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
Exterior

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

10.0 out of 10, Exceptional, (164)
"This was a perfect home base for our ski weekend. The house had more than enough to keep us comfortable during our stay, and the fireplace was a great place to relax at the end of the day."
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside
Interior

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

10.0 out of 10, Exceptional, (11)
"We had a very nice stay, the place is cozy and charming, exceptionally clean, easy to access, and had all the amenities we could've expected for a weekend away. It's comfortable and clearly cared for, and the kitchen is stocked with tools. Neighborhood is lovely and within easy commute to several ski areas. The property is very beautiful as well, though based on the photos and description we were expecting a more secluded siting. The unit is the second floor of a detached garage, located 20-30...
Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside
Mountain-view condo with private balcony, fireplace, & updated interior
Snow and ski sports

Mountain-view condo with private balcony, fireplace, & updated interior

8.2 out of 10, Very good, (13)
"A short walk to the base of Stratton, my son hiked to the peak and loved the views! It's close to other towns, and a perfectly outfitted condo with plenty of space and amenities. Dishwasher hadn't been emptied (a note for the cleaning service) but otherwise was neat and clean. Thank you!"
Mountain-view condo with private balcony, fireplace, & updated interior
Lovely ski-in/out condo steps from ski lift with trails and amazing views
TV, fireplace

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 CA $122
CA $428 total
includes taxes & fees
Mar 18 - Mar 19
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Stratton Mtn Studio | Renovated | Walk to Lifts
Exterior

Stratton Mtn Studio | Renovated | Walk to Lifts

10.0 out of 10, Exceptional, (28)
"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 CA $404
CA $847 total
includes taxes & fees
Mar 5 - Mar 6
Stratton Mtn Studio | Renovated | Walk to Lifts
Cabin 7 min to Ski Stratton, Wood-Fired Sauna, Brook View, Woodstove, Dogs OK
Exterior

Cabin 7 min to Ski Stratton, Wood-Fired Sauna, Brook View, Woodstove, Dogs OK

The price is CA $94
CA $237 total
includes taxes & fees
Mar 9 - Mar 10
Cabin 7 min to Ski Stratton, Wood-Fired Sauna, Brook View, Woodstove, Dogs OK
Perfect Country Cottage
Exterior

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
Bear Pass - Mountain View by RedAwning
Exterior

Bear Pass - Mountain View by RedAwning

10.0 out of 10, Exceptional, (1)
"Great house. 35 minutes from Stratton mountain. House had everything needed, plenty of supplies, towels, blankets, etc. highly recommended. Ad was exactly what you got"
The price is CA $343
CA $900 total
includes taxes & fees
Mar 6 - Mar 7
Bear Pass - Mountain View by RedAwning
Peaceful Stay at Birds of a Feather Farm & Spa
Interior

Peaceful Stay at Birds of a Feather Farm & Spa

9.6 out of 10, Exceptional, (16)
"The place was just as described and perfect for my stay while doing a workshop nearby. Host was easy to communicate with and helped me out as I forgot an item! "
The price is CA $159
CA $373 total
includes taxes & fees
Mar 22 - Mar 23
Peaceful Stay at Birds of a Feather Farm & Spa
Long Trail House Studio at Stratton Mountain Resort
Exterior

Long Trail House Studio at Stratton Mountain Resort

10.0 out of 10, Exceptional, (60)
"The studio condo we reserved had a last minute appliance issue so the owner upgraded us to a one bedroom and even accommodated an early check in. Everything worked out fine. The condo is next to village and to get to the lifts it’s a quick walk through the village and you’re there. Very clean unit with excellent water pressure and hot water. Plan to come back soon. "
Long Trail House Studio at Stratton Mountain Resort
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Interior

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

7.8 out of 10, Good, (45)
"Cleanliness was fine, but keys were missing when we checked in. Kitchen pots/pans we're good quality and fine for small meals but missing basics like a spatula and knivesBathroom had insufficient towels, no shampoo and only 1 small soap. Property manager did not bring replacements when called. Vacasa was the manager "
The price is CA $138
CA $458 total
includes taxes & fees
Mar 19 - Mar 20
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Your own Private Lake - Breathtaking Views - Gym - Sauna - Hot Tub
Exterior

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
Outdoor pool, a heated pool

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

9.6 out of 10, Exceptional, (20)
"The condo is the height of convenience. Cross the street to get the lifts and once you park your car in the heated garage you can leave it there. Condo is clean and well maintained. Owner was prompt and clear in all communication. Thank you!"
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
Sunny Stratton Mountain Retreat: 5BD Modern Oasis w/Hot Tub, Pond, & BBQ Deck
Fridge, microwave, oven, stovetop

Sunny Stratton Mountain Retreat: 5BD Modern Oasis w/Hot Tub, Pond, & BBQ Deck

9.4 out of 10, Exceptional, (6)
"We were absolutely thrilled to experience a fresh powder drop during our stay, which was a delightful surprise in an otherwise dry season. The house surpassed all our expectations, providing the perfect haven for our large group. It was impeccably clean, incredibly warm, and featured an abundance of comfortable beds, all while being conveniently close to the mountain. A standout feature for us was the Tesla charger in the garage, which met our specific needs perfectly. We are already eagerly...
Sunny Stratton Mountain Retreat: 5BD Modern Oasis w/Hot Tub, Pond, & BBQ Deck
By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.
TV, fireplace, DVD player, books

By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.

9.8 out of 10, Exceptional, (63)
"Rented this lodge based on other positive reviews - and they were spot on! Greeted by snowy landscape and cozy, warm, lodge wonderfully appointed More you looked, more you saw! Comfy beds, good showers, full service kitchen, spotless. Our family of 5 adults , 13 yr old twin granddaughters greed we felt like we were in a welcoming home. Brad, part owner/prop. manager immediately responded to call or text. We are looking forward to Dec 2025 to do it all again. Don’t miss Zoe’s grill in Manchester "
By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.
Beautiful Manchester VT Mountain Retreat w/Hot Tub
Fridge, microwave, oven, stovetop

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
Exterior

Kimpton Taconic Hotel by IHG

4.0 star property
9.4 out of 10, Exceptional, (748)
"We had a wonderful get-away! Lovely facilities. "
The price is CA $219
CA $291 total
includes taxes & fees
Mar 10 - Mar 11
Kimpton Taconic Hotel by IHG
Hampton Inn and Suites Manchester
Front of property - evening/night

Hampton Inn and Suites Manchester

2.5 star property
9.6 out of 10, Exceptional, (1006)
"Clean facilities with all the amenities. Front desk was courteous and friendly too. Would come back."
The price is CA $196
CA $215 total
includes taxes & fees
Mar 16 - Mar 17
Hampton Inn and Suites Manchester
Aspen At Manchester
Snow and ski sports

Aspen At Manchester

2.5 star property
8.6 out of 10, Excellent, (540)
"It was a wonderful setting to stay with our two labradors."
The price is CA $151
CA $182 total
includes taxes & fees
Apr 3 - Apr 4
Aspen At Manchester
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 vacation rentals in Rupert?

Yes, we give you a choice of vacation rentals near popular local attractions in Rupert, or you can go with a more secluded option if you're looking for a relaxing stay. Rupert is known for its parks.

What are some of the best vacation rentals in Rupert?

Bear Pass - Mountain View by RedAwning: This vacation home rental outside of Rupert offers a barbecue grill, a selection of books, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, an oven, and a microwave, so you can cook with friends or family.

How many vacation rentals are there in Rupert?

With 3 Expedia vacation rentals, you're sure 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 larger area, you’ll find R. K. Kittay Public Library and Stratton Mountain Resort.

What’s a vacation rental in Rupert like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in Rupert. Vacation rentals feature amenities like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for family gatherings.