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Rupert Vacation Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Rupert vacation rentals

Interior

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 AED 274
AED 953 total
includes taxes & fees
29 Jun - 30 Jun
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Exterior

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 AED 274
AED 833 total
includes taxes & fees
26 Jun - 27 Jun
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
TV, fireplace

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)
"Appeared dated"
United States
John B.
The price is AED 274
AED 1,165 total
includes taxes & fees
26 Jun - 27 Jun
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Terrace/patio

Peaceful getaway at birds of a feather

Peaceful getaway at birds of a feather
Shaftsbury
9.8 out of 10, Exceptional, (33 reviews)
"Great place"
United States
Aidan K.
The price is AED 364
AED 909 total
includes taxes & fees
30 Jun - 1 Jul
Peaceful getaway at birds of a feather
Children's area

Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.6 out of 10, Exceptional, (12 reviews)
"The best stay ever!!! Very clean, great location, super cozy, all the amenities you would need. 5/5 stars, we will be coming back :)"
United States
Carolina I.
The price is AED 333
AED 1,190 total
includes taxes & fees
28 Jun - 29 Jun
Cozy Bromley Retreat
Exterior detail

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Jamaica
9.6 out of 10, Exceptional, (29 reviews)
"EXCELLENT location managed by an amazing host who was very communicative and helpful!Hottub was perfect, plenty of sleeping and activities available at the house and in the immediate area (local food was AWESOME)."
United States
s w.
The price is AED 1,184
AED 3,828 total
includes taxes & fees
13 Jul - 14 Jul
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Fridge, microwave, oven, stovetop

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, (31 reviews)
"Great space, great location!"
United States
Jason S.
The price is AED 493
AED 1,341 total
includes taxes & fees
28 Jun - 29 Jun
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
Cottage (1 Bedroom) | Interior

< 6 Mi to Arlington: 'whimsical Stone Abode!'

< 6 Mi to Arlington: 'whimsical Stone Abode!'
3.0 star property
Arlington
10.0 out of 10, Exceptional, (1 review)
"We came into town for a few days to visit friends. This was a perfect place. The home was clean and very inviting! Quiet location. Fully stocked kitchen with all the appliances and cooking ware you may need. You will not regret staying here. We loved the photo album of how the home was built! "
United States
Dale
The price is AED 720
AED 1,262 total
includes taxes & fees
29 Jun - 30 Jun
< 6 Mi to Arlington: 'whimsical Stone Abode!'
Fridge, microwave, oven, stovetop

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, (1 review)
"Great stay as always. "
United States
debbie r.
The price is AED 314
AED 640 total
includes taxes & fees
26 Jun - 27 Jun
Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.
TV, DVD player

Quaint, friendly cottage with lakefront location & water views

Quaint, friendly cottage with lakefront location & water views
Poultney
9.4 out of 10, Exceptional, (59 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 AED 386
AED 1,585 total
includes taxes & fees
28 Jun - 29 Jun
Quaint, friendly cottage with lakefront location & water views
Free WiFi, bed sheets

Schuyler Yacht Basin

Schuyler Yacht Basin
3.0 star property
Schuylerville
8.6 out of 10, Excellent, (20 reviews)
"Great place to stay while visiting the area!"
United States
David R.
The price is AED 625
AED 816 total
includes taxes & fees
30 Jun - 1 Jul
Schuyler Yacht Basin
Outdoor dining

Tranquil Brookside Retreat with Hot Tub & Firepit

Tranquil Brookside Retreat with Hot Tub & Firepit
Peru
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful place. Comfortable and well furnished. "
United States
Michael B.
Tranquil Brookside Retreat with Hot Tub & Firepit
Sauna

Magic Mountain Trailside Condo - Ski In / Ski Out

Magic Mountain Trailside Condo - Ski In / Ski Out
Londonderry
9.8 out of 10, Exceptional, (14 reviews)
"Nice and we enjoyed our stay"
United States
Gretchen H.
The price is AED 459
AED 1,121 total
includes taxes & fees
8 Jul - 9 Jul
Magic Mountain Trailside Condo - Ski In / Ski Out
Interior

Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester

Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
Londonderry
9.6 out of 10, Exceptional, (24 reviews)
"Super attentive and accommodating host! It was a perfect cozy getaway on a frigid weekend, and the fireplace and hot tub were just the ticket. "
United States
Meghan R.
The price is AED 1,043
AED 2,532 total
includes taxes & fees
30 Jun - 1 Jul
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
Spa

Comfy Cottage with Private Hot Tub in Historic East Poultney

Comfy Cottage with Private Hot Tub in Historic East Poultney
Poultney
10.0 out of 10, Exceptional, (13 reviews)
"Very comfortable and clean cottage in a beautiful village. The shower in the bath is incredible. "
United States
Karen C.
The price is AED 790
AED 1,411 total
includes taxes & fees
7 Jul - 8 Jul
Comfy Cottage with Private Hot Tub in Historic East Poultney
Smart TV, fireplace, books, stereo

Vermont A-Frame | Sleeps10, Hot Tub, Sauna, EV, AC

Vermont A-Frame | Sleeps10, Hot Tub, Sauna, EV, AC
Jamaica
10.0 out of 10, Exceptional, (3 reviews)
"Great peaceful stay. Hosts were always in communication with us. Close to Stratton. Hot tube & sauna were a great top off to a day of skiing. "
United States
fran g.
The price is AED 1,055
AED 3,028 total
includes taxes & fees
29 Jun - 30 Jun
Vermont A-Frame | Sleeps10, Hot Tub, Sauna, EV, AC
Exterior

4 Season Cabin great location.

4 Season Cabin great location.
Mt Tabor
10.0 out of 10, Exceptional, (124 reviews)
"Excellent stay"
United States
Parsa R.
4 Season Cabin great location.
Property grounds

Quaint lakefront home with great views & full kitchen

Quaint lakefront home with great views & full kitchen
Poultney
The price is AED 386
AED 1,585 total
includes taxes & fees
30 Jun - 1 Jul
Quaint lakefront home with great views & full kitchen
Exterior

Romantic New York Getaway near the Adirondacks

Romantic New York Getaway near the Adirondacks
Cambridge
The price is AED 420
AED 502 total
includes taxes & fees
28 Jun - 29 Jun
Romantic New York Getaway near the Adirondacks
Exterior

Runamuk Farm Camp Tiny House near Cambridge, New York

Runamuk Farm Camp Tiny House near Cambridge, New York
Cambridge
The price is AED 420
AED 502 total
includes taxes & fees
1 Jul - 2 Jul
Runamuk Farm Camp Tiny House near Cambridge, New York
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
"I love the Brittany! It’s a wonderful place to stay with good vibes at a reasonable price"
Andrew 1-night trip
Posted 2 hours ago
Brittany Motel

Frequently asked questions

Are there vacation rentals in Rupert?

Yes, we give you a choice of vacation rentals near popular local attractions in Rupert, or you can go with a more secluded option if you're looking for a relaxing stay. Rupert is known for its parks.

What are some of the best vacation rentals in Rupert?

Riverfront 2-bedroom house with tons of light, AC, deck & patio. Pet Friendly: This vacation home rental outside of Rupert is located on a river and has a balcony, a garden, and a barbecue grill 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 vacation with amenities like a selection of books.

How many vacation rentals are there in Rupert?

With 4 Expedia vacation rentals, you're sure 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. In the larger area, you’ll find R. K. Kittay Public Library and Dorset Playhouse.

What’s a vacation rental in Rupert like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in Rupert. Vacation rentals feature amenities like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for family gatherings.