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

Holiday Homes in Rupert

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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 €316
includes taxes & fees
15 Oct - 16 Oct
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
A room with a large window, a wooden table, two chairs, and a woven basket on the table.

2. 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, (2 reviews)
"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 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 €238
includes taxes & fees
19 Oct - 20 Oct
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Property grounds

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 €136
includes taxes & fees
15 Oct - 16 Oct
Runamuk Farm Camp Tiny House near Cambridge, New York
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 €674
includes taxes & fees
21 Oct - 22 Oct
1812 House, 2 Stays, 1 home
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

6. 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, (43 reviews)
"Our family had a wonderful vacation. The house and location were great. We will come back."
United States
Victoria L.
The price is €574
includes taxes & fees
15 Oct - 16 Oct
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
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.

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

Killington Retreat | Deck-Fire Pit-Mountain Views!
Clarendon
9.2 out of 10, Wonderful, (5 reviews)
"Beautiful house! It had everything we needed for a fun and relaxing week. "
United States
Joshua
The price is €367
includes taxes & fees
24 Oct - 25 Oct
Killington Retreat | Deck-Fire Pit-Mountain Views!
An outdoor dining area with tables and umbrellas, a wooden fence, and a building with large windows and lights.

8. 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 €513
includes taxes & fees
10 Nov - 11 Nov
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
A snow-covered forest with a geodesic dome structure featuring a central fire.

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

Amanita Dome. All-inclusive food and drinks.
Cambridge
The price is €560
includes taxes & fees
26 Oct - 27 Oct
Amanita Dome. All-inclusive food and drinks.
A two-story white house with a front porch, a door with a wreath, and a chimney.

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 €663
includes taxes & fees
21 Oct - 22 Oct
Cozy farmhouse in Manchester - short drive to multiple ski mountains!
A modern two-story house with a front porch, a staircase, and a driveway.

11. 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 €765
includes taxes & fees
20 Oct - 21 Oct
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
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, (48 reviews)
"Extremely charming house! Perfect for a quiet get away!"
United States
Halley S.
The price is €689
includes taxes & fees
8 Nov - 9 Nov
Copeland Cabin - Charming Lake House in the Adirondacks
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

13. 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 €741
includes taxes & fees
1 Nov - 2 Nov
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A rustic kitchen with wooden beams, a large island, and a hanging light fixture.

14. 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 €442
includes taxes & fees
27 Oct - 28 Oct
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
A spacious room with wooden beams, large windows, and a cozy seating area with white furniture.

15. 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 €1,098
includes taxes & fees
3 Nov - 4 Nov
Gorgeous couples barn with WiFi & hot tub in lovely Londonderry
A lodge with a large fireplace, a covered porch, and a staircase leading to the upper level.

16. 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 €532
includes taxes & fees
1 Nov - 2 Nov
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.

17. 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 €945
includes taxes & fees
19 Oct - 20 Oct
5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton
A wooden cabin interior with a wooden dresser, a floral chair, a teal refrigerator, and a shelf with mugs and a coffee maker.

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

Peaceful 1-bedroom bungalow with AC in charming Wells
Wells
9.4 out of 10, Exceptional, (3 reviews)
"Clean comfy quiet spot."
United States
Dillon B.
The price is €216
includes taxes & fees
18 Oct - 19 Oct
Peaceful 1-bedroom bungalow with AC in charming Wells
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 Inn at Manchester

The Inn at Manchester

10/10 Excellent
"Amazing place in a beautiful setting!"
Dawn 1-night trip
Posted 2 hours ago
The Inn at Manchester

Find out more about Rupert

Rupert Holiday Homes information

Number of reviews
145
Accommodation
394 Holiday Homes
Lowest Price
€136
Highest Price
€945