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

Rupert Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Rupert vacation homes

A cabin with a sloped roof, large windows, and a balcony with outdoor seating.

1. 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, (24 reviews)
"Great cabin , so cozy with the wood burning stove "
United States
Susan f.
The price is CA $255
CA $502 total
includes taxes & fees
Oct 4 - Oct 5
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
A wooden cabin interior with a wooden dresser, a floral chair, a teal refrigerator, and a shelf with mugs and a coffee maker.

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

Peaceful 1-bedroom bungalow with AC in charming Wells
Wells
10.0 out of 10, Exceptional, (1 review)
"Clean comfy quiet spot."
United States
Dillon B.
The price is CA $262
CA $331 total
includes taxes & fees
Oct 4 - Oct 5
Peaceful 1-bedroom bungalow with AC in charming Wells
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

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

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Stratton
The price is CA $106
CA $366 total
includes taxes & fees
Oct 5 - Oct 6
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Room

4. Runamuk Farm Camp Tiny House near Cambridge, New York

Runamuk Farm Camp Tiny House near Cambridge, New York
Cambridge
10.0 out of 10, Exceptional, (4 reviews)
"Phenomenal site, with stunning views. Highly recommend!"
United States
Jess M.
The price is CA $178
CA $210 total
includes taxes & fees
Oct 8 - Oct 9
Runamuk Farm Camp Tiny House near Cambridge, New York
A two-story white house with a front porch, a door with a wreath, and a chimney.

5. 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 CA $538
CA $1,058 total
includes taxes & fees
Oct 15 - Oct 16
Cozy farmhouse in Manchester - short drive to multiple ski mountains!
A spacious kitchen with a central island, stainless steel appliances, and pendant lighting.

6. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is CA $483
CA $1,174 total
includes taxes & fees
Oct 21 - Oct 22
1812 House, 2 Stays, 1 home
An outdoor dining area with tables and umbrellas, a wooden fence, and a building with large windows and lights.

7. 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)
"Beautiful cozy house with plenty of beds and space. We drove here in a snowstorm and were so thankful that the host had cleared the driveway and walkways for us. Overall a great stay."
United States
Greg W.
The price is CA $480
CA $731 total
includes taxes & fees
Oct 7 - Oct 8
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

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

Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Winhall
9.4 out of 10, Exceptional, (41 reviews)
"Our family had a wonderful vacation. The house and location were great. We will come back."
United States
Victoria L.
The price is CA $281
CA $930 total
includes taxes & fees
Oct 28 - Oct 29
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

9. 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 CA $584
CA $1,351 total
includes taxes & fees
Oct 20 - Oct 21
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A spacious kitchen with a large island, a stone fireplace, and wooden beams.

10. Views for Days | Hot Tub, Sauna, EV, A/C | 6 Min to Stratton, 15 to Bromley

Views for Days | Hot Tub, Sauna, EV, A/C | 6 Min to Stratton, 15 to Bromley
Winhall
10.0 out of 10, Exceptional, (13 reviews)
"House was great for our family ski trip! "
United States
Brooke S.
Views for Days | Hot Tub, Sauna, EV, A/C | 6 Min to Stratton, 15 to Bromley
A spacious living room with wooden floors, a high ceiling with exposed beams, a dining area with a table and chairs, and large windows offering a view of the outdoors.

11. Killington Retreat | Deck-Fire Pit-Mountain Views!

Killington Retreat | Deck-Fire Pit-Mountain Views!
Clarendon
9.2 out of 10, Wonderful, (5 reviews)
"The living area is bigger than we expected, and we loved watching the horses next door. It's a short drive to downtown Rutland, and it's quiet. "
United States
Ahmad H.
The price is CA $199
CA $591 total
includes taxes & fees
Oct 24 - Oct 25
Killington Retreat | Deck-Fire Pit-Mountain Views!
A snow-covered forest with a geodesic dome structure featuring a central fire.

12. Amanita Dome. All-inclusive food and drinks.

Amanita Dome. All-inclusive food and drinks.
Cambridge
The price is CA $427
CA $870 total
includes taxes & fees
Nov 2 - Nov 3
Amanita Dome. All-inclusive food and drinks.
A fire pit with Adirondack chairs in a forested area with a lake view.

13. Copeland Cabin - Charming Lake House in the Adirondacks

Copeland Cabin - Charming Lake House in the Adirondacks
Fort Ann
10.0 out of 10, Exceptional, (47 reviews)
"Extremely charming house! Perfect for a quiet get away!"
United States
Halley S.
The price is CA $515
CA $1,150 total
includes taxes & fees
Oct 5 - Oct 6
Copeland Cabin - Charming Lake House in the Adirondacks
A lodge with a large fireplace, a covered porch, and a staircase leading to the upper level.

14. 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 CA $590
CA $850 total
includes taxes & fees
Nov 1 - Nov 2
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.
A large estate with a swimming pool, tennis court, and a spacious lawn.

15. The Privacy of a home & Perks of a Resort! Pool, Tennis, Views, Dogs, 6 baths!

The Privacy of a home & Perks of a Resort! Pool, Tennis, Views, Dogs, 6 baths!
Manchester
9.6 out of 10, Exceptional, (7 reviews)
"Great proximity to Bromley and Stratton, with easy access to plenty of restaurants in Manchester."
United States
Jessica G.
The price is CA $1,922
CA $3,084 total
includes taxes & fees
Oct 21 - Oct 22
The Privacy of a home & Perks of a Resort! Pool, Tennis, Views, Dogs, 6 baths!
A spacious kitchen with a large island, wooden ceiling beams, and a view to the outside.

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 CA $672
CA $1,534 total
includes taxes & fees
Oct 26 - Oct 27
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

The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent
"Interesting upscale older property. Rooms are motel -like, and definitely not like chains. Grounds are pretty with good activities for families."
Preston 1-night trip
Posted 7 hours ago
The Palmer House Resort, an Ascend Collection Hotel

Find out more about Rupert

Rupert Vacation Homes information

Number of reviews
160
Accommodation
392 Vacation Homes
Lowest Price
CA $210
Highest Price
CA $3,084

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