Rupert Vacation Rentals

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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16
In four months
Dec 12 - Dec 14

Browse Select Rupert Vacation Homes

Our top choices for Rupert vacation homes

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, (50)
"Great condo in great location. Easy walk to restaurants and lifts."
The price is CA $98
CA $333 total
includes taxes & fees
Aug 25 - Aug 26
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
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, (20)
"Great little quiet and peaceful spot that was still very close to Bennington and Manchester.Neighborhood was good for walks or gravel rides."
The price is CA $162
CA $372 total
includes taxes & fees
Aug 25 - Aug 26
Peaceful Stay at Birds of a Feather Farm & Spa
Ski in Ski out Condo! Pool access
Terrace/patio

Ski in Ski out Condo! Pool access

9.0 out of 10, Wonderful, (2)
"Great location with plenty of space for the whole family. Highly recommend!"
The price is CA $232
CA $725 total
includes taxes & fees
Aug 25 - Aug 26
Ski in Ski out Condo! Pool access
The Mountain Escape!
Outdoor spa tub

The Mountain Escape!

9.8 out of 10, Exceptional, (18)
"Easy booking, clean home, great location and the owner very easy to get in touch with."
The price is CA $169
CA $788 total
includes taxes & fees
Sep 1 - Sep 2
The Mountain Escape!
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
House, 3 Bedrooms | Exterior

Bear Pass - Mountain View 4 Bedroom Home by RedAwning

3.0 star property
8.0 out of 10, Very good, (1)
"Cozy cottage. Very clean and everything you need is there. Nice kitchen and fireplace. Lots of room and 3 bathrooms as well. Reasonably close to the ski mountains. "
The price is CA $332
CA $867 total
includes taxes & fees
Aug 25 - Aug 26
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming
Fridge, microwave, oven, stovetop

Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming

9.0 out of 10, Wonderful, (2)
"Our family had the best time staying here. The home was spacious and gave our two young children plenty of room to roam and explore. It was also close enough to the main road where everything was accessible but also isolated enough where you feel like you're getting away. Erin was great about answering any questions and making sure our stay was comfortable. We'd definitely return here!"
The price is CA $228
CA $626 total
includes taxes & fees
Aug 25 - Aug 26
Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming
Mountain Oasis - Hot Tub, Sauna, Fire Pit, & MORE!
Outdoor spa tub

Mountain Oasis - Hot Tub, Sauna, Fire Pit, & MORE!

9.8 out of 10, Exceptional, (26)
"Amazing stay. Perfect weekend friend getaway"
The price is CA $169
CA $788 total
includes taxes & fees
Sep 11 - Sep 12
Mountain Oasis - Hot Tub, Sauna, Fire Pit, & MORE!
3-bedroom cottage on Cossayuna Lake
Pool

3-bedroom cottage on Cossayuna Lake

7.6 out of 10, Good, (4)
"We had a good time. I was a little disappointed about the pool"
The price is CA $242
CA $351 total
includes taxes & fees
Aug 29 - Aug 30
3-bedroom cottage on Cossayuna Lake
Amanita Dome. All-inclusive food and drinks.
Property grounds

Amanita Dome. All-inclusive food and drinks.

2.0 star property
The price is CA $275
CA $575 total
includes taxes & fees
Aug 25 - Aug 26
Amanita Dome. All-inclusive food and drinks.
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
Exterior

Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views

10.0 out of 10, Exceptional, (15)
"Husband and i stayed for an overnight get-away. Perfect for relaxing, great views from porch. Great for a couple or small family"
The price is CA $248
CA $441 total
includes taxes & fees
Aug 25 - Aug 26
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
Alpine 5, cozy Vermont retreat
1 bedroom, desk, iron/ironing board, WiFi

Alpine 5, cozy Vermont retreat

The price is CA $145
CA $214 total
includes taxes & fees
Aug 27 - Aug 28
Alpine 5, cozy Vermont retreat
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Exterior

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

10.0 out of 10, Exceptional, (4)
"Great location, large space for family, good amenities, love the fireplace and coffee set up."
The price is CA $373
CA $1,005 total
includes taxes & fees
Aug 26 - Aug 27
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Room 4 - Prickly Pear double room
1 bedroom, desk, iron/ironing board, travel crib

Room 4 - Prickly Pear double room

The price is CA $145
CA $214 total
includes taxes & fees
Sep 1 - Sep 2
Room 4 - Prickly Pear double room
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
2 bedrooms, WiFi, bed sheets

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

2.0 star property
The price is CA $351
CA $686 total
includes taxes & fees
Aug 25 - Aug 26
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Room 7 - family room sleeps 4
Property grounds

Room 7 - family room sleeps 4

The price is CA $145
CA $214 total
includes taxes & fees
Sep 15 - Sep 16
Room 7 - family room sleeps 4
This house is a 4 bedroom(s), 2.5 bathrooms, located in Jamaica, VT.
Smart TV, fireplace, offices

This house is a 4 bedroom(s), 2.5 bathrooms, located in Jamaica, VT.

9.0 out of 10, Wonderful, (6)
"Great location. House was recently updated but has some older charm in parts. Fun and cozy. Hot tub was great the first day but smell seemed off the next day. Perhaps more chlorine was needed. Great time , great trip. Pet friendly is a bonus and the house looks never used so the cleaning crew is doing great work. Will rent again next year perhaps !"
The price is CA $534
CA $1,098 total
includes taxes & fees
Aug 25 - Aug 26
This house is a 4 bedroom(s), 2.5 bathrooms, located in Jamaica, VT.
5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton
Fridge, microwave, oven, stovetop

5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton

10.0 out of 10, Exceptional, (14)
"Everything was exactly as it was listed. Great communication"
The price is CA $531
CA $1,226 total
includes taxes & fees
Aug 26 - Aug 27
5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton
6 Bam Boo Cozy escape in the heart of Vermont
Exterior

6 Bam Boo Cozy escape in the heart of Vermont

The price is CA $160
CA $230 total
includes taxes & fees
Aug 27 - Aug 28
6 Bam Boo Cozy escape in the heart of Vermont
Vermont Getaway near Stratton Mountain
Fridge, microwave, oven, stovetop

Vermont Getaway near Stratton Mountain

9.0 out of 10, Wonderful, (11)
"The owner was quick to respond and more than accommodating on short notice. Would definitely come back. "
The price is CA $329
CA $801 total
includes taxes & fees
Sep 14 - Sep 15
Vermont Getaway near Stratton Mountain
Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.
4 bedrooms, iron/ironing board, WiFi, bed sheets

Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.

2.0 star property
10.0 out of 10, Exceptional, (7)
"Awesome."
The price is CA $747
CA $1,978 total
includes taxes & fees
Aug 26 - Aug 27
Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.
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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Top Rupert Hotel Reviews

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"Very nice property with friendly staff; excellent food at the restaurant; was only there for 16 hours but definitely want to go back to stay longer."
Julia 1-night trip
Posted 4 days ago
Kimpton Taconic Hotel by IHG