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

Holiday Homes in Rupert

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Rupert holiday homes

A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

1. 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 AU$358
includes taxes & fees
31 Aug - 1 Sept
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A cabin with a sloped roof, large windows, and a balcony with outdoor seating.

2. 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, (23 reviews)
"Great cabin , so cozy with the wood burning stove "
United States
Susan f.
The price is AU$485
includes taxes & fees
31 Aug - 1 Sept
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
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.

3. Peaceful getaway at birds of a feather

Peaceful getaway at birds of a feather
Shaftsbury
9.8 out of 10, Exceptional, (38 reviews)
"Great place"
United States
Aidan K.
The price is AU$370
includes taxes & fees
31 Aug - 1 Sept
Peaceful getaway at birds of a feather
An outdoor dining area with tables and umbrellas, a wooden fence, and a building with large windows and lights.

4. 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 AU$752
includes taxes & fees
2 Sept - 3 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.

5. 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, (40 reviews)
"Our family had a wonderful vacation. The house and location were great. We will come back."
United States
Victoria L.
The price is AU$927
includes taxes & fees
31 Aug - 1 Sept
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
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 AU$1,058
includes taxes & fees
13 Sept - 14 Sept
1812 House, 2 Stays, 1 home
A small cabin with a wooden deck, a front door, and large windows.

7. 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 AU$203
includes taxes & fees
1 Sept - 2 Sept
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.

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 AU$1,042
includes taxes & fees
6 Sept - 7 Sept
Cozy farmhouse in Manchester - short drive to multiple ski mountains!
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.

9. 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 AU$530
includes taxes & fees
6 Sept - 7 Sept
Killington Retreat | Deck-Fire Pit-Mountain Views!
A modern two-story house with a front porch, a staircase, and a driveway.

10. Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Jamaica
9.6 out of 10, Exceptional, (30 reviews)
"House was perfect for a guys trip for skiing. Just as expected. Would stay again. "
United States
Michael A.
The price is AU$1,194
includes taxes & fees
31 Aug - 1 Sept
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
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, (13 reviews)
"Clean, lots of room, easy access to Stratton, responsive host."
United States
Mark H.
The price is AU$1,149
includes taxes & fees
15 Sept - 16 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 AU$1,102
includes taxes & fees
9 Sept - 10 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 AU$1,836
includes taxes & fees
2 Sept - 3 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 AU$875
includes taxes & fees
31 Aug - 1 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 AU$846
includes taxes & fees
31 Aug - 1 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 AU$1,452
includes taxes & fees
31 Aug - 1 Sept
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Rupert Hotel Reviews

The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent
"Nice room and property. With was down."
Amanda 1-night trip
Posted 11 hours ago
The Palmer House Resort, an Ascend Collection Hotel

Find out more about Rupert

Rupert Holiday Homes information

Number of reviews
242
Accommodation
415 Holiday Homes
Lowest Price
AU$203
Highest Price
AU$1,836