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

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 $247
CA $487 total
includes taxes & fees
Sep 11 - Sep 12
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 CA $254
CA $320 total
includes taxes & fees
Sep 11 - Sep 12
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 $103
CA $355 total
includes taxes & fees
Sep 14 - Sep 15
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
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 CA $466
CA $696 total
includes taxes & fees
Sep 14 - Sep 15
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, (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 $272
CA $901 total
includes taxes & fees
Sep 14 - Sep 15
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
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.

6. 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 CA $160
CA $372 total
includes taxes & fees
Sep 15 - Sep 16
Peaceful getaway at birds of a feather
A two-story white house with a front porch, a door with a wreath, and a chimney.

7. 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 $521
CA $1,016 total
includes taxes & fees
Sep 16 - Sep 17
Cozy farmhouse in Manchester - short drive to multiple ski mountains!
A spacious kitchen with a central island, stainless steel appliances, and pendant lighting.

8. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is CA $426
CA $1,085 total
includes taxes & fees
Sep 13 - Sep 14
1812 House, 2 Stays, 1 home
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 CA $173
CA $203 total
includes taxes & fees
Sep 20 - Sep 21
Runamuk Farm Camp Tiny House near Cambridge, New York
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.

10. 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 $585 total
includes taxes & fees
Sep 20 - Sep 21
Killington Retreat | Deck-Fire Pit-Mountain Views!
A room with a large window, a wooden table, two chairs, and a woven basket on the table.

11. 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
The price is CA $443
CA $926 total
includes taxes & fees
Oct 5 - Oct 6
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.

12. 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 CA $435
CA $1,140 total
includes taxes & fees
Sep 16 - Sep 17
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A snow-covered forest with a geodesic dome structure featuring a central fire.

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

Amanita Dome. All-inclusive food and drinks.
Cambridge
The price is CA $414
CA $857 total
includes taxes & fees
Sep 20 - Sep 21
Amanita Dome. All-inclusive food and drinks.
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 $572
CA $840 total
includes taxes & fees
Sep 13 - Sep 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.
A fire pit with Adirondack chairs in a forested area with a lake view.

15. 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 $501
CA $1,116 total
includes taxes & fees
Sep 23 - Sep 24
Copeland Cabin - Charming Lake House in the Adirondacks
A two-story log cabin with a balcony on the upper level, surrounded by trees.

16. 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 CA $651
CA $1,864 total
includes taxes & fees
Sep 15 - Sep 16
Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.
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 CA $712
CA $1,590 total
includes taxes & fees
Sep 14 - Sep 15
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 Manchester View

The Manchester View

10/10 Excellent
"Totally renovated motel type property. Beautiful and spacious rooms. Great views, pool, fire pit, breakfast, etc. I booked a terrace king because the pics of the room showed two chairs and a round table, but it did not have a table so no place to open the lap top and work. Nice balcony and beautiful views."
Sandra 1-night trip
Posted 4 hours ago
The Manchester View

Find out more about Rupert

Rupert Vacation Homes information

Number of reviews
161
Accommodation
392 Vacation Homes
Lowest Price
CA $203
Highest Price
CA $1,864

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