A rural landscape with a barn on a hill, surrounded by autumn-colored trees.

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Our top choices for Rupert vacation homes

1. Long Trail House 368 condo in Stratton Village, walk to the lifts

Long Trail House 368 condo in Stratton Village, walk to the lifts
Stratton
The price is ¥13,396
¥41,933 total
includes taxes & fees
Nov 16 - Nov 17
Long Trail House 368 condo in Stratton Village, walk to the lifts

2. Peaceful 1-bedroom bungalow with AC in charming Wells

Peaceful 1-bedroom bungalow with AC in charming Wells
Wells
9.6 out of 10, Exceptional, (4 reviews)
"This is the most amazing spot. Our second time staying here after the horse races and we will definitely be back next summer. You guys are awesome!"
United States
Donna A.
The price is ¥32,777
¥39,934 total
includes taxes & fees
Nov 30 - Dec 1
Peaceful 1-bedroom bungalow with AC in charming Wells

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

Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
shushan
9.6 out of 10, Exceptional, (27 reviews)
"Great cabin , so cozy with the wood burning stove "
United States
Susan f.
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views

4. Cozy 3 Bedroom Condo in the Heart of Manchester VT

Cozy 3 Bedroom Condo in the Heart of Manchester VT
Manchester
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful accommodations. Great communication with host."
United States
Peggy S.
The price is ¥43,138
¥92,983 total
includes taxes & fees
Nov 15 - Nov 16
Cozy 3 Bedroom Condo in the Heart of Manchester VT

5. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is ¥47,753
¥117,559 total
includes taxes & fees
Dec 1 - Dec 2
1812 House, 2 Stays, 1 home

6. Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.

Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
Manchester
10.0 out of 10, Exceptional, (13 reviews)
"Very clean and convenient to the town and very helpful host!"
United States
Corry B.
The price is ¥57,517
¥82,326 total
includes taxes & fees
Nov 15 - Nov 16
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.

7. Wonderful hilltop house with breathtaking views

Wonderful hilltop house with breathtaking views
Dorset
The price is ¥71,951
¥84,883 total
includes taxes & fees
Nov 29 - Nov 30
Wonderful hilltop house with breathtaking views

8. Amanita Dome. Inclusive Brunch & Dinner Experience

Amanita Dome. Inclusive Brunch & Dinner Experience
Cambridge
The price is ¥47,967
¥95,176 total
includes taxes & fees
Nov 23 - Nov 24
Amanita Dome. Inclusive Brunch & Dinner Experience

9. Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Winhall
9.2 out of 10, Wonderful, (45 reviews)
"Our family had a wonderful vacation. The house and location were great. We will come back."
United States
Victoria L.
The price is ¥34,533
¥116,005 total
includes taxes & fees
Nov 16 - Nov 17
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

10. Cozy farmhouse in Manchester - short drive to multiple ski mountains!

Cozy farmhouse in Manchester - short drive to multiple ski mountains!
Manchester
9.4 out of 10, Exceptional, (3 reviews)
"The hosts were very friendly and responsive during our stay. Loved that the house is close to the main town as well as close to the ski slopes (Bromley). "
United States
Marissa H.
The price is ¥60,393
¥113,379 total
includes taxes & fees
Nov 25 - Nov 26
Cozy farmhouse in Manchester - short drive to multiple ski mountains!

11. Copeland Cabin - Charming Lake House in the Adirondacks

Copeland Cabin - Charming Lake House in the Adirondacks
Fort Ann
10.0 out of 10, Exceptional, (49 reviews)
"Extremely charming house! Perfect for a quiet get away!"
United States
Halley S.
The price is ¥60,249
¥124,512 total
includes taxes & fees
Nov 23 - Nov 24
Copeland Cabin - Charming Lake House in the Adirondacks

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

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Winhall
10.0 out of 10, Exceptional, (15 reviews)
"Clean, lots of room, easy access to Stratton, responsive host."
United States
Mark H.
The price is ¥45,729
¥119,969 total
includes taxes & fees
Nov 17 - Nov 18
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

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

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Londonderry
7.0 out of 10, Good, (2 reviews)
"I was "sold" & excited when I saw the pictures online bc the barn looked really neat. Although the barn was a neat concept, the pictures ARE NOT accurate, it is not as updated as pictured & it was VERY DISAPPOINTING. I now understand the non-refundable policy bc what you see online is definitely NOT what you walked into when you opened the door & they don't want to have to give people their back. Although we had fun, the accommodations were VERY misleading & disappointing. "
United States
Christine M.
The price is ¥40,550
¥76,332 total
includes taxes & fees
Nov 17 - Nov 18
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

14. Gorgeous couples barn with WiFi & hot tub in lovely Londonderry

Gorgeous couples barn with WiFi & hot tub in lovely Londonderry
Londonderry
10.0 out of 10, Exceptional, (2 reviews)
"The converted barn was absolutely stunning. Kitchen was well appointed and the family room spacious and comfortible."
United States
Tim M.
The price is ¥118,342
¥174,528 total
includes taxes & fees
Nov 17 - Nov 18
Gorgeous couples barn with WiFi & hot tub in lovely Londonderry

15. Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.

Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.
Jamaica
8.8 out of 10, Excellent, (8 reviews)
"Beautiful home, we enjoyed our stay!"
United States
Luke B.
The price is ¥66,145
¥92,643 total
includes taxes & fees
Nov 17 - Nov 18
Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.

16. 5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton

5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton
Stratton
10.0 out of 10, Exceptional, (20 reviews)
"Great spot for a large group. "
United States
Brian G.
The price is ¥74,029
¥156,876 total
includes taxes & fees
Nov 30 - Dec 1
5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton
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

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Rupert Vacation Homes information

Number of reviews
190
Accommodation
326 Vacation Homes
Lowest Price
¥39,934
Highest Price
¥174,528