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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Rupert holiday rentals

Dining

1. 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$941
HK$3,244 total
includes taxes & fees
1 Sept - 2 Sept
Historic Home with Colonial Charm in Manchester
Property grounds

2. 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, (1 review)
"We last minute booked this place just for a place to sleep that night. What we found was much more beauty. A place you could just sit outside watching the mountains and sky. The owners are as sweet as can be! We definitely want to come back soon for a quiet beautiful view!"
United States
Melissa
The price is HK$883
HK$1,165 total
includes taxes & fees
18 Aug - 19 Aug
Beautiful 1-bedroom cabin with AC in wonderful Wells
Coffee/tea maker, fridge, microwave, oven

3. Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.

Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.
Wallingford
10.0 out of 10, Exceptional, (2 reviews)
"Great stay as always. "
United States
debbie r.
The price is HK$671
HK$1,367 total
includes taxes & fees
16 Aug - 17 Aug
Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.
Children’s area

4. Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.6 out of 10, Exceptional, (17 reviews)
"Nice place "
United States
Janja L.
The price is HK$792
HK$2,691 total
includes taxes & fees
27 Aug - 28 Aug
Cozy Bromley Retreat
Exterior

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, (23 reviews)
"Great cabin , so cozy with the wood burning stove "
United States
Susan f.
The price is HK$1,405
HK$2,771 total
includes taxes & fees
16 Aug - 17 Aug
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
Property grounds

6. 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$1,951
HK$2,521 total
includes taxes & fees
1 Sept - 2 Sept
Tranquil Cabin Hideaway with Firepit and Riverfront Views on the Green River in Vermont
TV, fireplace

7. 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, (35 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$2,488 total
includes taxes & fees
14 Aug - 15 Aug
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Private kitchen

8. Modern Mountain Retreat w/ Chef’s Kitchen

Modern Mountain Retreat w/ Chef’s Kitchen
Manchester
The price is HK$1,445
HK$3,894 total
includes taxes & fees
1 Sept - 2 Sept
Modern Mountain Retreat w/ Chef’s Kitchen
Free WiFi, bed sheets

9. Schuyler Yacht Basin

Schuyler Yacht Basin
3.0 star property
Schuylerville
8.8 out of 10, Excellent, (24 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$1,335
HK$1,743 total
includes taxes & fees
7 Sept - 8 Sept
Schuyler Yacht Basin
Terrace/patio

10. Peaceful getaway at birds of a feather

Peaceful getaway at birds of a feather
Shaftsbury
9.8 out of 10, Exceptional, (37 reviews)
"Great place"
United States
Aidan K.
The price is HK$812
HK$1,999 total
includes taxes & fees
26 Aug - 27 Aug
Peaceful getaway at birds of a feather
Exterior

11. 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$1,779 total
includes taxes & fees
16 Aug - 17 Aug
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Property grounds

12. Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (64 reviews)
"This home was spacious, super clean, and in a great location. "
United States
Des C.
The price is HK$1,412
HK$2,013 total
includes taxes & fees
16 Aug - 17 Aug
Spacious apartment in beautiful, historic Arlington VT
Exterior

13. 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 HK$949
HK$1,124 total
includes taxes & fees
20 Aug - 21 Aug
Runamuk Farm Camp Tiny House near Cambridge, New York
Interior

14. Romantic New York Getaway near the Adirondacks

Romantic New York Getaway near the Adirondacks
Cambridge
The price is HK$906
HK$1,080 total
includes taxes & fees
16 Aug - 17 Aug
Romantic New York Getaway near the Adirondacks
Exterior

15. 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 HK$2,966
HK$5,861 total
includes taxes & fees
19 Aug - 20 Aug
Cozy farmhouse in Manchester - short drive to multiple ski mountains!
Outdoor spa tub

16. Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.6 out of 10, Excellent, (83 reviews)
"Nice place and great location!!!"
United States
William
The price is HK$2,465
HK$3,064 total
includes taxes & fees
17 Aug - 18 Aug
Long Trail House at Stratton Mountain Resort
Interior

17. 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$2,036 total
includes taxes & fees
26 Aug - 27 Aug
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Coffee/tea maker, fridge, microwave, oven

18. 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, (32 reviews)
"Great space, great location!"
United States
Jason S.
The price is HK$1,236
HK$3,117 total
includes taxes & fees
14 Aug - 15 Aug
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
Property grounds

19. Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton
8.0 out of 10, Very good, (1 review)
The price is HK$1,096
HK$3,188 total
includes taxes & fees
16 Aug - 17 Aug
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Terrace/patio

20. The Birchwood Cabin - Stunning Mountain Views

The Birchwood Cabin - Stunning Mountain Views
Sunderland
10.0 out of 10, Exceptional, (4 reviews)
"Excellent host very responsive. Beautiful cozy cabin with all the amenities you need. Highly recommend! "
United States
Robert V.
The price is HK$1,814
HK$5,037 total
includes taxes & fees
9 Sept - 10 Sept
The Birchwood Cabin - Stunning Mountain Views
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

Brittany Motel

Brittany Motel

10/10 Excellent
"We enjoyed our stay at this hotel. It is a little older but still in good condition. It was very clean! The staff was extremely responsive to any questions or needs that we had. We loved the little snack book and having coffee in the morning was great."
Jennie 1-night trip
Posted 7 hours ago
Brittany Motel

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?

Riverfront 2-bedroom house tons of light, AC, deck & patio Sleeps 8 Pet Friendly: This holiday home rental outside of Rupert is located on a river, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of books.

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.