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
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 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, (27 reviews)
"Great cabin , so cozy with the wood burning stove "
United States
Susan f.
The price is £264
includes taxes & fees
28 Oct - 29 Oct
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

2. 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 £193
includes taxes & fees
9 Nov - 10 Nov
Long Trail House 368 condo in Stratton Village, walk to the lifts
A room with a large window, a wooden table, two chairs, and a woven basket on the table.

3. 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 £465
includes taxes & fees
29 Oct - 30 Oct
Cozy 3 Bedroom Condo in the Heart of Manchester VT
A spacious kitchen with a central island, stainless steel appliances, and pendant lighting.

4. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is £618
includes taxes & fees
10 Nov - 11 Nov
1812 House, 2 Stays, 1 home
A rustic interior with a wooden ceiling, a bar area with stools, a sofa, and a dining table.

5. Wonderful hilltop house with breathtaking views

Wonderful hilltop house with breathtaking views
Dorset
The price is £607
includes taxes & fees
9 Nov - 10 Nov
Wonderful hilltop house with breathtaking views
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
9.2 out of 10, Wonderful, (44 reviews)
"Our family had a wonderful vacation. The house and location were great. We will come back."
United States
Victoria L.
The price is £546
includes taxes & fees
28 Oct - 29 Oct
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A street view at dusk with a restaurant and a shop with a mannequin in the window.

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 £415
includes taxes & fees
9 Nov - 10 Nov
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
Eatery

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

Amanita Dome. All-inclusive food and drinks.
Cambridge
The price is £471
includes taxes & fees
28 Oct - 29 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.

9. 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 £554
includes taxes & fees
9 Nov - 10 Nov
Cozy farmhouse in Manchester - short drive to multiple ski mountains!
A fire pit with Adirondack chairs in a forested area with a lake view.

10. 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 £536
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.

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, (15 reviews)
"Clean, lots of room, easy access to Stratton, responsive host."
United States
Mark H.
The price is £609
includes taxes & fees
28 Oct - 29 Oct
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A rustic kitchen with wooden beams, a large island, and a hanging light fixture.

12. 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 £369
includes taxes & fees
9 Nov - 10 Nov
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.

13. 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 £825
includes taxes & fees
28 Oct - 29 Oct
Gorgeous couples barn with WiFi & hot tub in lovely Londonderry
A spacious kitchen with a large island, wooden ceiling beams, and a view to the outside.

14. 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 £771
includes taxes & fees
9 Nov - 10 Nov
5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton
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 £390
includes taxes & fees
28 Oct - 29 Oct
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 wooden cabin with a green door, a small porch, and a set of stairs leading to the entrance.

16. 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 £180
includes taxes & fees
29 Oct - 30 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 Manchester View

The Manchester View

10/10 Excellent
"beautiful location clean rooms and very friendly and helpful staff"
Maureen 2-night trip
Posted 6 hours ago
The Manchester View

Find out more about Rupert

Rupert Holiday Homes information

Number of reviews
189
Accommodation
394 Holiday Homes
Lowest Price
£180
Highest Price
£825