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

Rupert Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Rupert holiday rentals

A wooden deck with a white lattice base, a metal roof, and a house with a garage door in the background.

1. Beautiful 1-bedroom cabin with AC in wonderful Wells

Beautiful 1-bedroom cabin with AC in wonderful Wells
Wells
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful location with Mountain views. Property owners were wonderful hosts."
United States
Jane
The price is HK$882
HK$1,164 total
includes taxes & fees
28 Sept - 29 Sept
Beautiful 1-bedroom cabin with AC in wonderful Wells
A dining room with a wooden table, four chairs, a vase with flowers, and a view of greenery outside.

2. Historic Home with Colonial Charm in Manchester

Historic Home with Colonial Charm in Manchester
Manchester
10.0 out of 10, Exceptional, (2 reviews)
"The accommodations were absolutely amazing. We had a wonderful time. The home is beautiful. The host is very communicative."
United States
Victor G.
The price is HK$932
HK$3,021 total
includes taxes & fees
29 Sept - 30 Sept
Historic Home with Colonial Charm in Manchester
A red barn, a hammock, a fire pit, and a chair in a grassy area with trees and a stream in the background.

3. Tranquil Cabin Hideaway with Firepit and Riverfront Views on the Green River in Vermont

Tranquil Cabin Hideaway with Firepit and Riverfront Views on the Green River in Vermont
Sandgate
The price is HK$1,797
HK$2,207 total
includes taxes & fees
30 Sept - 1 Oct
Tranquil Cabin Hideaway with Firepit and Riverfront Views on the Green River in Vermont
A sunroom with a large window, wicker furniture, and a fish mounted on the wall.

4. Quaint, friendly cottage with lakefront location & water views

Quaint, friendly cottage with lakefront location & water views
Poultney
9.4 out of 10, Exceptional, (60 reviews)
"The cottage is in a nice spot on the lake. It is accurately depicted in the listing and was great for our trip"
United States
Jim V.
The price is HK$824
HK$3,199 total
includes taxes & fees
9 Oct - 10 Oct
Quaint, friendly cottage with lakefront location & water views
A cabin with a sloped roof, large windows, and a balcony with outdoor seating.

5. 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 HK$1,405
HK$2,604 total
includes taxes & fees
28 Sept - 29 Sept
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
A bedroom with a bed, a window, and a door.

6. Schuyler Yacht Basin

Schuyler Yacht Basin
3.0 star property
Schuylerville
9.0 out of 10, Wonderful, (26 reviews)
"Love this place and the ease of the check in and check out! Quiet and peaceful! Would have like to seen the pub open though! See you all next year!"
United States
Jean Paul
The price is HK$1,334
HK$1,742 total
includes taxes & fees
28 Sept - 29 Sept
Schuyler Yacht Basin
A playground with slides and climbing structures surrounded by trees.

7. Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (20 reviews)
"Nice place "
United States
Janja L.
The price is HK$1,010
HK$2,791 total
includes taxes & fees
30 Sept - 1 Oct
Cozy Bromley Retreat
A green wooden door with a circular moon and sun decoration.

8. Serenity Ridge. Enchanting 1-bedroom cabin in Wells perfect for a cozy getaway

Serenity Ridge. Enchanting 1-bedroom cabin in Wells perfect for a cozy getaway
Wells
The price is HK$1,530
HK$1,889 total
includes taxes & fees
7 Oct - 8 Oct
Serenity Ridge. Enchanting 1-bedroom cabin in Wells perfect for a cozy getaway
A modern kitchen with a central island, stainless steel appliances, pendant lighting, and a view to the dining area.

9. Modern Mountain Retreat w/ Chef’s Kitchen

Modern Mountain Retreat w/ Chef’s Kitchen
Manchester
10.0 out of 10, Exceptional, (1 review)
"Communication with Caroline was top notch and speedy! Very clear instructions for accessing the property and check out. Even though this place is connected with two other rooms/units ( I think that is what it is) we never heard them and hopefully we didn't bother them either!The house was amazing inside and out. The location was exceptional!Thank you for a beautiful stay!"
United States
Eva G.
The price is HK$1,291
HK$3,444 total
includes taxes & fees
27 Oct - 28 Oct
Modern Mountain Retreat w/ Chef’s Kitchen
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

10. 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 HK$585
HK$1,956 total
includes taxes & fees
30 Sept - 1 Oct
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A yurt with a red door, a visible interior with a fire, and snow outside.

11. Off-Grid Mongolian Yurt on Vermont Sheep Farm

Off-Grid Mongolian Yurt on Vermont Sheep Farm
Poultney
The price is HK$784
HK$1,142 total
includes taxes & fees
28 Sept - 29 Sept
Off-Grid Mongolian Yurt on Vermont Sheep Farm
A building with a sign reading 'Fire Tower Restaurant & Tavern.'

12. Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Stratton
The price is HK$585
HK$1,734 total
includes taxes & fees
28 Sept - 29 Sept
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

13. Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (65 reviews)
"Excellent place, fantastic hosts, highly recommend."
United States
Mike K.
The price is HK$1,412
HK$1,933 total
includes taxes & fees
6 Oct - 7 Oct
Spacious apartment in beautiful, historic Arlington VT
A living room with a sofa, a television, a fireplace, and a dining area with chairs and a table.

14. Lovely ski-in/out condo steps from ski lift with trails and amazing views

Lovely ski-in/out condo steps from ski lift with trails and amazing views
Stratton
8.4 out of 10, Very good, (36 reviews)
"I have stayed in this condo a few times now, and for my needs it is a great value; affordable, comfortable and ideal location. "
United States
eric m.
The price is HK$585
HK$2,354 total
includes taxes & fees
28 Sept - 29 Sept
Lovely ski-in/out condo steps from ski lift with trails and amazing views
A spacious kitchen with a central island, stainless steel appliances, and pendant lighting.

15. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is HK$2,266
HK$5,654 total
includes taxes & fees
29 Sept - 30 Sept
1812 House, 2 Stays, 1 home
A small cabin with a wooden deck, a front door, and large windows.

16. 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 HK$984
HK$1,158 total
includes taxes & fees
28 Sept - 29 Sept
Runamuk Farm Camp Tiny House near Cambridge, New York

17. Romantic New York Getaway near the Adirondacks

Romantic New York Getaway near the Adirondacks
Cambridge
The price is HK$939
HK$1,113 total
includes taxes & fees
30 Sept - 1 Oct
Romantic New York Getaway near the Adirondacks
An outdoor dining area with tables and umbrellas, a wooden fence, and a building with large windows and lights.

18. 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 HK$2,647
HK$3,763 total
includes taxes & fees
28 Sept - 29 Sept
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
A room with a large window, a wooden table, two chairs, and a woven basket on the table.

19. 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 HK$1,788
HK$4,120 total
includes taxes & fees
5 Oct - 6 Oct
Cozy 3 Bedroom Condo in the Heart of Manchester VT
A modern kitchen with dark cabinetry, stainless steel appliances, and a bar area with stools.

20. Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
Stratton Mountain
10.0 out of 10, Exceptional, (35 reviews)
"Great space, great location!"
United States
Jason S.
The price is HK$2,016
HK$4,326 total
includes taxes & fees
26 Oct - 27 Oct
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
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

Aspen At Manchester

Aspen At Manchester

10/10 Excellent
"The grounds and rooms are simple and clean. Location is close shops and restaurants. You are able to access to staff when needed. The only comment I will make is that I wish there was a bench or something like it where the guests have a place their personal item in the bathroom."
Karen 2-night trip
Posted 6 hours ago
Aspen At Manchester

Find out more about Rupert

Search for holiday rentals in Rupert on Expedia! You can easily find your home rentals, villas, holiday apartments in Rupert using one of the methods below:

  • View our selection of featured holiday rentals in Rupert
  • Use the map to find apartments and other holiday homes in the Rupert neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Rupert while they last

Look no further and take a look at our great range of rental properties in Rupert!

Frequently asked questions

Are there holiday rentals in Rupert?

Yes, there are holiday rentals close to the most popular sights in Rupert, or you can select a more secluded option if you're looking for a relaxing stay. Rupert is known for its parks.

What are some of the best holiday rentals that Rupert has to offer?

Beautifully Remodeled VT Mountain Oasis with Stratton Views and private Hot Tub: This holiday home rental outside of Rupert offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Rupert?

With 4 Expedia holiday rentals, you're guaranteed to find just the right place for your Rupert stay.

What’s there to see and do in Rupert?

Merck Forest Farmland Center and Green Mountain National Forest are a couple of lovely local spots to get outside and enjoy nature. While here, R. K. Kittay Public Library and Haystack Mountain are other places worth a visit.

What’s a holiday rental in Rupert like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Rupert. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for family gatherings.