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Check prices for these dates

Next weekend
Sep 5 - Sep 7
In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26

Browse Select 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)
"The place was deserted "
The price is CA $98
CA $331 total
includes taxes & fees
Sep 1 - Sep 2
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
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 $159
CA $771 total
includes taxes & fees
Sep 1 - Sep 2
The Mountain Escape!
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 $240
CA $349 total
includes taxes & fees
Sep 4 - Sep 5
3-bedroom cottage on Cossayuna Lake
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 $334
CA $867 total
includes taxes & fees
Sep 14 - Sep 15
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
Peaceful Stay at Birds of a Feather Farm & Spa
Interior

Peaceful Stay at Birds of a Feather Farm & Spa

9.8 out of 10, Exceptional, (22)
"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 $161
CA $368 total
includes taxes & fees
Sep 3 - Sep 4
Peaceful Stay at Birds of a Feather Farm & Spa
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 $184
CA $568 total
includes taxes & fees
Sep 3 - Sep 4
Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming
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 $221
CA $708 total
includes taxes & fees
Sep 1 - Sep 2
Ski in Ski out Condo! Pool access
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 $246
CA $441 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
Amanita Dome. All-inclusive food and drinks.
Property grounds

Amanita Dome. All-inclusive food and drinks.

2.0 star property
The price is CA $273
CA $561 total
includes taxes & fees
Sep 3 - Sep 4
Amanita Dome. All-inclusive food and drinks.
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)
"EXCELLENT location managed by an amazing host who was very communicative and helpful!Hottub was perfect, plenty of sleeping and activities available at the house and in the immediate area (local food was AWESOME)."
The price is CA $159
CA $771 total
includes taxes & fees
Sep 11 - Sep 12
Mountain Oasis - Hot Tub, Sauna, Fire Pit, & MORE!
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 $349
CA $681 total
includes taxes & fees
Sep 1 - Sep 2
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
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 $371
CA $995 total
includes taxes & fees
Sep 1 - Sep 2
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Outdoor spa tub

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (21)
"This place was very enjoyable, it was just 3 of us so there was more than enough room. It is a very comfortable home and we enjoyed the easy trip into Manchester for some meals and a wonderful day of hiking some great nearby trails."
The price is CA $263
CA $865 total
includes taxes & fees
Aug 31 - Sep 1
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
This house is a 4 bedroom(s), 2.5 bathrooms, located in Jamaica, VT.
Fridge, microwave, oven, stovetop

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 $530
CA $1,085 total
includes taxes & fees
Sep 1 - Sep 2
This house is a 4 bedroom(s), 2.5 bathrooms, located in Jamaica, VT.
NEW Charming ski retreat w/heated plunge pool & endless views in peaceful Weston
Outdoor pool, a heated pool

NEW Charming ski retreat w/heated plunge pool & endless views in peaceful Weston

9.6 out of 10, Exceptional, (4)
"Absolutely gorgeous home with a lovely host! The endless views and cozy but elegant atmosphere of the property were exactly what we wanted for our Vermont stay. Highly recommend!"
The price is CA $742
CA $1,299 total
includes taxes & fees
Sep 2 - Sep 3
NEW Charming ski retreat w/heated plunge pool & endless views in peaceful Weston
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 $499
CA $1,164 total
includes taxes & fees
Sep 3 - Sep 4
5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton
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 $326
CA $810 total
includes taxes & fees
Sep 14 - Sep 15
Vermont Getaway near Stratton Mountain
Cozy 220 Year Colonial with a spectacular view
Property grounds

Cozy 220 Year Colonial with a spectacular view

9.6 out of 10, Exceptional, (5)
"The pictures do no justice to the homely beauty of the Tinmouth house. Every room is a treasure and it’s amenities are lovely. My friends and I are already planning a return visit."
The price is CA $381
CA $816 total
includes taxes & fees
Sep 21 - Sep 22
Cozy 220 Year Colonial with a spectacular view
Tranquil farmhouse in Manchester - perfect for ski or summer fun!
Exterior

Tranquil farmhouse in Manchester - perfect for ski or summer fun!

The price is CA $462
CA $944 total
includes taxes & fees
Sep 6 - Sep 7
Tranquil farmhouse in Manchester - perfect for ski or summer fun!
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 $780
CA $2,028 total
includes taxes & fees
Sep 10 - Sep 11
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

Find out more about Rupert

Find out more about Rupert

Rupert Vacation Homes information

Number of reviews
Accommodation
416 Vacation Homes
Lowest Price
CA $98
Highest Price
CA $742

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