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

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Rupert holiday 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 £260
includes taxes & fees
13 Sept - 14 Sept
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
A wooden cabin with a green door, a small porch, and a set of stairs leading to the entrance.

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

Peaceful 1-bedroom bungalow with AC in charming Wells
Wells
The price is £178
includes taxes & fees
13 Sept - 14 Sept
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 £195
includes taxes & fees
16 Sept - 17 Sept
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A room with wooden walls, a window with a view of the sky and greenery, a hanging macrame wall decoration, and a vase with flowers on the windowsill.

4. Peaceful getaway at birds of a feather

Peaceful getaway at birds of a feather
Shaftsbury
9.8 out of 10, Exceptional, (38 reviews)
"Laurie was an amazing host, with an amazing property! What an adorable home with an adorable view."
United States
Michaela J.
The price is £203
includes taxes & fees
15 Sept - 16 Sept
Peaceful getaway at birds of a feather
A spacious kitchen with a central island, stainless steel appliances, and pendant lighting.

5. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is £584
includes taxes & fees
13 Sept - 14 Sept
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.

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)
"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 £385
includes taxes & fees
15 Sept - 16 Sept
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.

7. 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 £491
includes taxes & fees
16 Sept - 17 Sept
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A two-story white house with a front porch, a door with a wreath, and a chimney.

8. 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 £548
includes taxes & fees
19 Sept - 20 Sept
Cozy farmhouse in Manchester - short drive to multiple ski mountains!
A small cabin with a wooden deck, a front door, and large windows.

9. 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, (2 reviews)
"Phenomenal site, with stunning views. Highly recommend!"
United States
Jess M.
The price is £112
includes taxes & fees
14 Sept - 15 Sept
Runamuk Farm Camp Tiny House near Cambridge, New York
A room with a large window, a wooden table, two chairs, and a woven basket on the table.

10. 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, (1 review)
"Beautiful place Very spacious and super organized we love our stay "
United States
Rafael
Cozy 3 Bedroom Condo in the Heart of Manchester VT
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

11. 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, (14 reviews)
"Clean, lots of room, easy access to Stratton, responsive host."
United States
Mark H.
The price is £595
includes taxes & fees
16 Sept - 17 Sept
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A fire pit with Adirondack chairs in a forested area with a lake view.

12. 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 £602
includes taxes & fees
23 Sept - 24 Sept
Copeland Cabin - Charming Lake House in the Adirondacks
A two-story log cabin with a balcony on the upper level, surrounded by trees.

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

Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.
Stratton
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful stay! The location was extremely convenient to the mountain, and the house was clean, comfortable and spacious. We loved all of the seating in the living room, the large fireplace, and cozy hot tub."
United States
Steve M.
The price is £988
includes taxes & fees
15 Sept - 16 Sept
Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.
A snow-covered forest with a geodesic dome structure featuring a central fire.

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

Amanita Dome. All-inclusive food and drinks.
Cambridge
The price is £463
includes taxes & fees
20 Sept - 21 Sept
Amanita Dome. All-inclusive food and drinks.
A lodge with a large fireplace, a covered porch, and a staircase leading to the upper level.

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 £458
includes taxes & fees
13 Sept - 14 Sept
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 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 £835
includes taxes & fees
6 Oct - 7 Oct
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
"Best place ever."
Shannon 1-night trip
Posted 5 hours ago
The Palmer House Resort, an Ascend Collection Hotel

Find out more about Rupert

Rupert Holiday Homes information

Number of reviews
156
Accommodation
393 Holiday Homes
Lowest Price
£112
Highest Price
£988