Rupert Vacation Rentals

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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Rupert vacation rentals

Spa

Comfy Cottage in Historic East Poultney

Comfy Cottage 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 ￥25,414
￥50,879 total
includes taxes & fees
Apr 27 - Apr 28
Comfy Cottage in Historic East Poultney
TV, books

Peaceful Cottage Retreat

Peaceful Cottage Retreat
cambridge
9.8 out of 10, Exceptional, (47 reviews)
"Perfect little stay. Best parts of being out in the middle of the woods that also has great cell service. Everything you'd need to enjoy a couple days out in "
United States
Victor L.
The price is ￥19,856
￥29,975 total
includes taxes & fees
Apr 19 - Apr 20
Peaceful Cottage Retreat
Property grounds

Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (61 reviews)
"Love staying here! Kate is so friendly, and the place is the perfect spot to rest and recover after ski days. Spacious kitchen allows us to cook and enjoy our own meals. We will book again!"
United States
Eric W.
The price is ￥27,163
￥38,429 total
includes taxes & fees
Apr 29 - Apr 30
Spacious apartment in beautiful, historic Arlington VT
Outdoor spa tub

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 ￥54,326
￥67,526 total
includes taxes & fees
Apr 23 - Apr 24
Long Trail House at Stratton Mountain Resort
Exterior

Romantic Riverbed Treehouse - hot tub & new sauna!

Romantic Riverbed Treehouse - hot tub & new sauna!
londonderry
9.0 out of 10, Wonderful, (6 reviews)
"Great little space"
United States
John
The price is ￥29,878
￥103,224 total
includes taxes & fees
May 4 - May 5
Romantic Riverbed Treehouse - hot tub & new sauna!
Dining

Sowilo Retreat All Inclusive Oak House

Sowilo Retreat All Inclusive Oak House
Cambridge
9.0 out of 10, Wonderful, (2 reviews)
"One of the best getaways that I have ever experienced! The food was amazing the service was A and the scenery was absolutely breathtaking. I will definitely be returning!"
United States
Anthony
Sowilo Retreat All Inclusive Oak House
Interior

Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
Londonderry
8.2 out of 10, Very Good, (11 reviews)
"We had a wonderful stay."
United States
Joshua
The price is ￥52,182
￥90,022 total
includes taxes & fees
Apr 20 - Apr 21
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
Living area

Gorgeous couples barn with WiFi & hot tub in lovely Londonderry

Gorgeous couples barn with WiFi & hot tub in lovely Londonderry
Londonderry
10.0 out of 10, Exceptional, (2 reviews)
"The converted barn was absolutely stunning. Kitchen was well appointed and the family room spacious and comfortible."
United States
Tim M.
The price is ￥126,087
￥193,632 total
includes taxes & fees
Apr 26 - Apr 27
Gorgeous couples barn with WiFi & hot tub in lovely Londonderry
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 ￥34,770
￥144,292 total
includes taxes & fees
Apr 19 - Apr 20
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Exterior

Insanely romantic treehouse perched next to a stream and rolling hills.

Insanely romantic treehouse perched next to a stream and rolling hills.
Londonderry
10.0 out of 10, Exceptional, (2 reviews)
"Very nice secluded treehouse. We would definitely recommend!"
United States
Beth H.
The price is ￥62,901
￥141,797 total
includes taxes & fees
Apr 20 - Apr 21
Insanely romantic treehouse perched next to a stream and rolling hills.
Fridge, oven, stovetop, dishwasher

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

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Londonderry
7.0 out of 10, Good, (2 reviews)
"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 ￥40,314
￥79,657 total
includes taxes & fees
Apr 21 - Apr 22
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Exterior

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, (25 reviews)
"Absolutely a wonderful place to vacation. The house is comfortable and warming. The hosts went above and beyond to make our stay great and responded to our questions promptly. We will definitely rent again. "
United States
Lee Anna C.
The price is ￥34,770
￥142,317 total
includes taxes & fees
Apr 23 - Apr 24
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Smart TV, fireplace

Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!

Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
Londonderry
10.0 out of 10, Exceptional, (10 reviews)
"Great location, well-designed house, and a beautiful view."
United States
Marcel P.
The price is ￥39,315
￥101,869 total
includes taxes & fees
Apr 21 - Apr 22
Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
Exterior

Family-friendly A-Frame near Stratton, Bromley & Magic — hot tub retreat in the quiet, peaceful woods

Family-friendly A-Frame near Stratton, Bromley & Magic — hot tub retreat in the quiet, peaceful woods
Jamaica
8.8 out of 10, Excellent, (8 reviews)
"Great location. House was recently updated but has some older charm in parts. Fun and cozy. Hot tub was great the first day but smell seemed off the next day. Perhaps more chlorine was needed. Great time , great trip. Pet friendly is a bonus and the house looks never used so the cleaning crew is doing great work. Will rent again next year perhaps !"
United States
Michael C.
The price is ￥52,417
￥116,252 total
includes taxes & fees
Apr 26 - Apr 27
Family-friendly A-Frame near Stratton, Bromley & Magic — hot tub retreat in the quiet, peaceful woods
Property grounds

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, (21 reviews)
"A great weekend. The property was clean and comfortable."
United States
Joan P.
The price is ￥21,127
￥61,721 total
includes taxes & fees
Apr 17 - Apr 18
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Property grounds

Amanita Dome. All-inclusive food and drinks.

Amanita Dome. All-inclusive food and drinks.
Cambridge
The price is ￥47,655
￥92,616 total
includes taxes & fees
Apr 19 - Apr 20
Amanita Dome. All-inclusive food and drinks.
Terrace/patio

Peaceful getaway at birds of a feather

Peaceful getaway at birds of a feather
Shaftsbury
9.8 out of 10, Exceptional, (32 reviews)
"Great place!!"
United States
Margaret D.
The price is ￥15,154
￥38,322 total
includes taxes & fees
Apr 30 - May 1
Peaceful getaway at birds of a feather
Interior

Idyllic Village Estate: Luxury Villa Historic Barn

Idyllic Village Estate: Luxury Villa Historic Barn
Manchester
9.4 out of 10, Exceptional, (14 reviews)
"It was a fantastic stay! The house is beautiful with stunning views in every direction. It is well-appointed and very comfortable. It has special amenities like a hot tub and party barn. Communication with the host was easy; he responded almost immediately and was quite pleasant. He gave us lots of useful information and even honored a couple of unique requests. This is a super special property. "
United States
Elizabeth C.
The price is ￥128,660
￥289,157 total
includes taxes & fees
Apr 17 - Apr 18
Idyllic Village Estate: Luxury Villa Historic Barn
Outdoor spa tub

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Winhall
9.4 out of 10, Exceptional, (37 reviews)
"Our family had a wonderful time staying in this home."
United States
Meghan C.
The price is ￥31,347
￥105,314 total
includes taxes & fees
Apr 22 - Apr 23
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Dining

Sowilo Pine House. All-inclusive food and drinks.

Sowilo Pine House. All-inclusive food and drinks.
Cambridge
10.0 out of 10, Exceptional, (4 reviews)
"BEAUTIFUL HOME GREAT VIEWS, CLEAN, SPACIOUS, AND A VERY HELPFUL PROPERTY MANAGER. CLOSE TO OUR WEDDING DESTINATION. HAD A WONDERFUL TIME. WOULD HIGHLY RECOMMEND THIS PROPERTY."
United States
diane
Sowilo Pine House. All-inclusive food and drinks.
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

Toll Road Inn

Toll Road Inn

10/10 Excellent
"Great property! The location is perfect and the hot tub was very relaxing. I also appreciate how they have you reserve time slots for the hot tub so you can relax and enjoy yourself. "
Andrew 2-night trip
Posted 10 hours ago
Toll Road Inn

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:

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

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?

Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!: This vacation home rental outside of Rupert is located in the mountains and has a garden, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.