Rupert Holiday Rentals

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Check prices for these dates

Tonight
19 Nov - 20 Nov
Tomorrow
20 Nov - 21 Nov
This weekend
21 Nov - 23 Nov
Next weekend
28 Nov - 30 Nov

Holiday Rentals in Rupert

Private kitchen
Beautiful country cabin with hot tub and outdoor shower in Londonderry

Beautiful country cabin with hot tub and outdoor shower in Londonderry

2.0 star property
Londonderry
10.0 out of 10, Exceptional, (2)
"On a farm in the country…..stars blazing at night for hot tub. Cozy loft had amazing mattress and pillows! Our dog enjoyed the surrounding field. Beautiful! "
United States
Laurel
The price is HK$1,154
HK$2,807 total
includes taxes & fees
25 Nov - 26 Nov
Beautiful country cabin with hot tub and outdoor shower in Londonderry
Fridge, microwave, oven, stovetop
Cozy Bromley Retreat

Cozy Bromley Retreat

Bromley Mountain
9.8 out of 10, Exceptional, (7)
"There is no place I’d rather stay in VT. It’s a perfect condo and the recent renovations are really nice. It’s got all the comforts of home and great touches throughout. Bromley is a great community to be in, it’s close to town, obviously the slopes, and just a overall stay!"
United States
Vanessa P.
The price is HK$705
HK$2,527 total
includes taxes & fees
20 Nov - 21 Nov
Cozy Bromley Retreat
Exterior
Comfy Cottage in Historic East Poultney

Comfy Cottage in Historic East Poultney

Poultney
10.0 out of 10, Exceptional, (12)
"My in-laws were in town for a week and this was the perfect place for them. Easily accessible entrance and bathroom. The house is clean and very comfortable. They had a great time. Thank you!"
United States
Carol G.
The price is HK$1,259
HK$2,482 total
includes taxes & fees
20 Nov - 21 Nov
Comfy Cottage in Historic East Poultney
Terrace/patio
Mountain Dream Escape

Mountain Dream Escape

2.0 star property
Sandgate
10.0 out of 10, Exceptional, (1)
"Beautiful location and home! The apartment was beautifully decorated and so cozy. The hot tub was a great place for stargazing! It was wonderful for our anniversary weekend but would also be great for a longer stay.Great communication with hosts and they were super helpful when we had a minor issue with check in."
United States
Morgan C.
The price is HK$921
HK$3,539 total
includes taxes & fees
20 Nov - 21 Nov
Mountain Dream Escape
Exterior
Peaceful Cottage Retreat

Peaceful Cottage Retreat

cambridge
9.8 out of 10, Exceptional, (44)
"Host was awesome as usual. Check on is as easy as can be. Amenities are always in order.I've been there many times (twice this summer) and will be back at least twice more this year...Place is just as advertised....peaceful, quiet and relaxing. Great for a getaway- or if you plan to attend events in Saratoga or surrounding areas."
United States
Ralph I.
The price is HK$875
HK$1,359 total
includes taxes & fees
20 Nov - 21 Nov
Peaceful Cottage Retreat
Pool
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, (77)
"Nice, clean room in prime location"
United States
Kristin
The price is HK$2,343
HK$2,912 total
includes taxes & fees
20 Nov - 21 Nov
Long Trail House at Stratton Mountain Resort
Interior
Peaceful Stay at Birds of a Feather Farm & Spa

Peaceful Stay at Birds of a Feather Farm & Spa

Shaftsbury
9.8 out of 10, Exceptional, (28)
"Beautiful location and very cozy place to stay. Thank you!"
United States
Kristin G.
The price is HK$631
HK$1,735 total
includes taxes & fees
20 Nov - 21 Nov
Peaceful Stay at Birds of a Feather Farm & Spa
1 bedroom, WiFi, bed sheets
Romantic Riverbed Treehouse - hot tub & new sauna!

Romantic Riverbed Treehouse - hot tub & new sauna!

londonderry
10.0 out of 10, Exceptional, (2)
"We had a great stay. The cabin was well lit and perfect for two people. Very clean, warm, and comfortable. There was a snow storm the night before we left and they kept the driveway plowed for us. Gorgeous views and close to everything."
United States
Karen L.
The price is HK$1,462
HK$4,982 total
includes taxes & fees
20 Nov - 21 Nov
Romantic Riverbed Treehouse - hot tub & new 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
8.6 out of 10, Excellent, (27)
"We loved staying at the townhome. It was a welcome place to stay while we traveled around, enjoying fall. It was very comfortable and the village amenities were great."
United States
John N.
The price is HK$599
HK$2,240 total
includes taxes & fees
23 Nov - 24 Nov
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Fridge, microwave, oven, stovetop
Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming

Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming

South Londonderry
9.6 out of 10, Exceptional, (4)
"Host was accommodating with responses."
United States
Michael S.
The price is HK$1,050
HK$3,224 total
includes taxes & fees
20 Nov - 21 Nov
Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming
Exterior
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!

Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!

Fort Ann
10.0 out of 10, Exceptional, (23)
"Great little get away with the family and the dogs! Met both Linda and her husband. Both very friendly and accommodating "
United States
Allan G.
The price is HK$1,448
HK$2,911 total
includes taxes & fees
2 Dec - 3 Dec
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
Dining
Bromley Aframe - King Master Bed, Wood Fireplace

Bromley Aframe - King Master Bed, Wood Fireplace

Peru
9.6 out of 10, Exceptional, (14)
"This house was great for my family's spring vacation. The stream was beautiful and relaxing. "
United States
Loni N.
The price is HK$1,402
HK$3,216 total
includes taxes & fees
30 Nov - 1 Dec
Bromley Aframe - King Master Bed, Wood Fireplace
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
7.8 out of 10, Good, (52)
"Location was great, pool, hot tubs and sauna were great"
United States
Lin M.
The price is HK$715
HK$2,145 total
includes taxes & fees
23 Nov - 24 Nov
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
2 bedrooms, WiFi, bed sheets
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

2.0 star property
Londonderry
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. "
United States
Christine M.
The price is HK$1,973
HK$3,864 total
includes taxes & fees
1 Dec - 2 Dec
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Outdoor spa tub
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Jamaica
9.6 out of 10, Exceptional, (21)
"House was perfect and just what we were looking for! Very clean, great hot tub, loved the fire pit!Cassie was incredibly helpful with local recommendations and going above and beyond!Highly recommend!"
United States
Neal T.
The price is HK$1,634
HK$5,303 total
includes taxes & fees
3 Dec - 4 Dec
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Interior
Stratton Mtn Studio | Renovated | Walk to Lifts

Stratton Mtn Studio | Renovated | Walk to Lifts

Stratton Mountain
10.0 out of 10, Exceptional, (30)
"Great location."
United States
Jeffrey
The price is HK$1,392
HK$3,260 total
includes taxes & fees
21 Nov - 22 Nov
Stratton Mtn Studio | Renovated | Walk to Lifts
Exterior
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, (20)
"Lovely home. Very pet friendly. "
United States
Kimberly D.
The price is HK$1,749
HK$2,925 total
includes taxes & fees
23 Nov - 24 Nov
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
Outdoor spa tub
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

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

Jamaica
9.8 out of 10, Exceptional, (27)
"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 HK$1,650
HK$5,330 total
includes taxes & fees
23 Nov - 24 Nov
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Outdoor spa tub
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Winhall
9.6 out of 10, Exceptional, (30)
"It was exactly what we wanted. Fireplace , hot tub, and ample sleeping arrangements "
United States
Craig F.
The price is HK$1,581
HK$5,018 total
includes taxes & fees
23 Nov - 24 Nov
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Terrace/patio
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

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

Stratton
7.4 out of 10, Good, (20)
"Proximity to southern Vermont towns, and shopping and dining in the village."
United States
Steven L.
The price is HK$1,065
HK$2,714 total
includes taxes & fees
1 Dec - 2 Dec
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
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

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"Staff was great. Our room was okay… broken blinds and lots of scuffs on walls"
Christine 1-night trip
Posted 3 days ago
Kimpton Taconic Hotel by IHG

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?

Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing: This holiday home rental outside of Rupert is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals are there in Rupert?

With 3 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?

Green Mountain National Forest and Merck Forest Farmland Center are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find R. K. Kittay Public Library and Stratton Mountain Resort.

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.