Search Vacation Homes in Rupert
Bundle & SaveGet more, spend less whenever you see Bundle & Save deals
OneKeyCashEarn OneKeyCash on all your eligible bookings
Upfront pricingWe are not like the others - we include taxes and fees
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Rupert vacation homes
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible viewsshushan
9.6 out of 10, Exceptional, (20)
"Lovely home. Very pet friendly. "
Kimberly D.
$337 nightly
The price is $374
Dec 23 - Dec 24
Total with taxes and fees
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Enjoy this authentic and cozy VT Barn with Brand New Hot TubLondonderry
8.0 out of 10, Very Good, (1)
"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. "
Christine M.
$439 nightly
The price is $496
Dec 25 - Dec 26
Total with taxes and fees
$446 nightly
The price is $461
Dec 23 - Dec 24
Total with taxes and fees
Cozy 220 Year Colonial with a spectacular view
Cozy 220 Year Colonial with a spectacular viewTinmouth
9.6 out of 10, Exceptional, (5)
"Beautiful place. We had a great time. "
Laurel W.
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 LiftsStratton
7.8 out of 10, Good, (52)
"Location was great, pool, hot tubs and sauna were great"
Lin M.
$378 nightly
The price is $427
Jan 14 - Jan 15, 2026
Total with taxes and fees
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
Bear Pass - Mountain View 4 Bedroom Home by RedAwningArlington
8.0 out of 10, Very Good, (1)
"Cozy cottage. Very clean and everything you need is there. Nice kitchen and fireplace. Lots of room and 3 bathrooms as well. Reasonably close to the ski mountains. "
Manish
$616 nightly
The price is $679
Jan 6 - Jan 7, 2026
Total with taxes and fees
Bear Pass - Mountain View by RedAwning
Bear Pass - Mountain View by RedAwningSunderland
9.6 out of 10, Exceptional, (5)
"We loved our stay at Bear Pass! The kitchen was more than adequately stocked. The hous was great for our extended family and our 3 dogs"
Megan G.
$605 nightly
The price is $678
Jan 4 - Jan 5, 2026
Total with taxes and fees
6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT
6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VTManchester Center
10.0 out of 10, Exceptional, (51)
"This was the most well-stocked house we've ever rented. It's like being in the comfort of your own home. Lots of herbs and spices in the kitchen and all sorts of pots and pans that make it possible to cook anything. Great location and clean."
Anonymous traveler
$1,860 nightly
The price is $2,102
Jan 5 - Jan 6, 2026
Total with taxes and fees
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.
Find vacation rentals that suit your style
Cabins
Aparthotels
Save an average of 15% on thousands of hotels when you're signed in
Top Rupert Hotel Reviews
Aspen At Manchester
10/10 Excellent
Find out more about Rupert
Rupert Vacation Homes information
Number of reviews | 218 |
|---|---|
Accommodation | 365 Vacation Homes |
Lowest Price | $374 |
Highest Price | $2,580 |
Explore a world of travel with Expedia
- Hotels near Merck Forest Farmland Center
- B&B in Dorset
- Cottages in Dorset
- Vacation Homes in Dorset
- Motels in Dorset
- Cabin Rentals in Dorset
- Farmstay in Dorset
- Guest Houses in Dorset
- B&B in Pawlet
- Vacation Homes in Pawlet
- Cottages in Pawlet
- Hotels near Dorset Playhouse
- Dorset Hotels
- Pet-friendly Hotels in Dorset
- Hotels with Bars in Dorset
- Hotels with Tennis Courts in Dorset
- Luxury Hotels in Dorset
- Romantic Hotels in Dorset
- 3 Star Hotels in Dorset
- 5 Star Hotels in Dorset
- 4 Star Hotels in Dorset
- Family Hotels in Dorset
- Hotels with Connecting Rooms in Dorset
- Non-Smoking Hotels in Dorset
- Pawlet Hotels
- 3 Star Hotels in Pawlet
- West Pawlet Hotels
- Manchester Hotels
- Hotels near Equinox Preservation Trust
- Hotels near Southern Vermont Arts Center
- Cabin Rentals in Manchester
- B&B in Manchester
- Motels in Manchester
- Cottages in Manchester
- Guest Houses in Manchester
- Resorts in Manchester
- Inns in Manchester
- Lodges in Manchester
- Chalets in Manchester
- Condo Rentals in Manchester
- Apartments in Manchester Center
- Guest Houses in Manchester Center
- B&B in Manchester Center
- Cabin Rentals in Manchester Center
- Motels in Manchester Center
- Vacation Homes in Manchester Center
- Condo Rentals in Manchester Center
- Hotels near Dana L. Thompson Memorial Park
- Pet-friendly Hotels in Manchester
- Hotels with an Indoor Pool in Manchester
- 5 Star Hotels in Manchester
- Hotels near American Museum of Fly Fishing
- Cheap Hotels in Manchester
- Resorts & Hotels with Spas in Manchester
- Hotels with an Outdoor Pool in Manchester
- Hotels with Restaurants in Manchester
- Hotels with Fireplaces in Manchester
- Hotels with Free Breakfast in Manchester
- Ski Hotels in Manchester
- Historic Hotels in Manchester
- Boutique Hotels in Manchester
- Romantic Hotels in Manchester
- Hotels with Bars in Manchester
- Golf Hotels in Manchester
- 3 Star Hotels in Manchester
- Luxury Hotels in Manchester
- Family Hotels in Manchester
- Hotels with Tennis Courts in Manchester
- Hotels with Connecting Rooms in Manchester
- Hotel Wedding Venues Hotels in Manchester
- Hotels with Laundry Facilities in Manchester
- Car rentals near West Rupert
- Car rentals near Merck Forest Farmland Center
- Car rentals near Dorset
- Foco Rental Cars in Dorset
- Alamo Rent A Car Rental Cars in Dorset
- Rent A Wreck Rental Cars in Dorset
- Car rentals near Pawlet
- Car rentals near West Pawlet
- Car rentals near Sandgate
- Car rentals near Equinox Preservation Trust
- Car rentals near Manchester
- Car rentals near Manchester Center