A rural landscape with a barn on a hill, surrounded by autumn-colored trees.

Rupert Vacation Rentals

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Rupert vacation rentals

A wooden deck with a white lattice base, a metal roof, and a house with a garage door in the background.

1. 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, (2 reviews)
"Beautiful location with Mountain views. Property owners were wonderful hosts."
United States
Jane
$133 nightly
The price is $148
Oct 4 - Oct 5
Total with taxes and fees
Beautiful 1-bedroom cabin with AC in wonderful Wells
A sunroom with a large window, wicker furniture, and a fish mounted on the wall.

2. Quaint, friendly cottage with lakefront location & water views

Quaint, friendly cottage with lakefront location & water views
Poultney
9.4 out of 10, Exceptional, (60 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.
$385 nightly
The price is $431
Oct 9 - Oct 10
Total with taxes and fees
Quaint, friendly cottage with lakefront location & water views
A dining room with a wooden table, four chairs, a vase with flowers, and a view of greenery outside.

3. 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.
$385 nightly
The price is $435
Nov 3 - Nov 4
Total with taxes and fees
Historic Home with Colonial Charm in Manchester
A playground with slides and climbing structures surrounded by trees.

4. Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (20 reviews)
"Nice place "
United States
Janja L.
$333 nightly
The price is $376
Oct 8 - Oct 9
Total with taxes and fees
Cozy Bromley Retreat
A cabin with a sloped roof, large windows, and a balcony with outdoor seating.

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, (24 reviews)
"Great cabin , so cozy with the wood burning stove "
United States
Susan f.
$315 nightly
The price is $350
Oct 4 - Oct 5
Total with taxes and fees
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
A wooden cabin interior with a wooden dresser, a floral chair, a teal refrigerator, and a shelf with mugs and a coffee maker.

6. Peaceful 1-bedroom bungalow with AC in charming Wells

Peaceful 1-bedroom bungalow with AC in charming Wells
Wells
10.0 out of 10, Exceptional, (1 review)
"Clean comfy quiet spot."
United States
Dillon B.
$212 nightly
The price is $237
Oct 4 - Oct 5
Total with taxes and fees
Peaceful 1-bedroom bungalow with AC in charming Wells
Property grounds

7. Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (65 reviews)
"Excellent place, fantastic hosts, highly recommend."
United States
Mike K.
$227 nightly
The price is $254
Oct 6 - Oct 7
Total with taxes and fees
Spacious apartment in beautiful, historic Arlington VT
A green wooden door with a circular moon and sun decoration.

8. Serenity Ridge. Enchanting 1-bedroom cabin in Wells perfect for a cozy getaway

Serenity Ridge. Enchanting 1-bedroom cabin in Wells perfect for a cozy getaway
Wells
$223 nightly
The price is $250
Oct 7 - Oct 8
Total with taxes and fees
Serenity Ridge. Enchanting 1-bedroom cabin in Wells perfect for a cozy getaway
A bedroom with a bed, a window, and a door.

9. Schuyler Yacht Basin

Schuyler Yacht Basin
3.0 star property
Schuylerville
9.0 out of 10, Wonderful, (26 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
$221 nightly
The price is $243
Oct 4 - Oct 5
Total with taxes and fees
Schuyler Yacht Basin
A modern kitchen with a central island, stainless steel appliances, pendant lighting, and a view to the dining area.

10. Modern Mountain Retreat w/ Chef’s Kitchen

Modern Mountain Retreat w/ Chef’s Kitchen
Manchester
10.0 out of 10, Exceptional, (1 review)
"Communication with Caroline was top notch and speedy! Very clear instructions for accessing the property and check out. Even though this place is connected with two other rooms/units ( I think that is what it is) we never heard them and hopefully we didn't bother them either!The house was amazing inside and out. The location was exceptional!Thank you for a beautiful stay!"
United States
Eva G.
$421 nightly
The price is $476
Nov 3 - Nov 4
Total with taxes and fees
Modern Mountain Retreat w/ Chef’s Kitchen
A yurt with a red door, a visible interior with a fire, and snow outside.

11. Off-Grid Mongolian Yurt on Vermont Sheep Farm

Off-Grid Mongolian Yurt on Vermont Sheep Farm
Poultney
$134 nightly
The price is $150
Nov 2 - Nov 3
Total with taxes and fees
Off-Grid Mongolian Yurt on Vermont Sheep Farm
A room with a large window, a wooden table, two chairs, and a woven basket on the table.

12. Cozy 3 Bedroom Condo in the Heart of Manchester VT

Cozy 3 Bedroom Condo in the Heart of Manchester VT
Manchester
10.0 out of 10, Exceptional, (1 review)
"Beautiful place Very spacious and super organized we love our stay "
United States
Rafael
$551 nightly
The price is $559
Oct 4 - Oct 5
Total with taxes and fees
Cozy 3 Bedroom Condo in the Heart of Manchester VT
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

13. 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
$227 nightly
The price is $256
Oct 5 - Oct 6
Total with taxes and fees
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A spacious living room with wooden floors, a high ceiling with exposed beams, a dining area with a table and chairs, and large windows offering a view of the outdoors.

14. Killington Retreat | Deck-Fire Pit-Mountain Views!

Killington Retreat | Deck-Fire Pit-Mountain Views!
Clarendon
9.2 out of 10, Wonderful, (5 reviews)
"The living area is bigger than we expected, and we loved watching the horses next door. It's a short drive to downtown Rutland, and it's quiet. "
United States
Ahmad H.
$411 nightly
The price is $417
Oct 24 - Oct 25
Total with taxes and fees
Killington Retreat | Deck-Fire Pit-Mountain Views!
A living room with a wooden floor, a central rug, a sofa, a coffee table, and a door with a 'GUEST' sign.

15. Peaceful Cottage Retreat

Peaceful Cottage Retreat
cambridge
9.8 out of 10, Exceptional, (50 reviews)
"Nice cozy little home Was well welcomed and host very communicative"
United States
Caleb N.
$170 nightly
The price is $189
Oct 4 - Oct 5
Total with taxes and fees
Peaceful Cottage Retreat
A building with a sign reading 'Fire Tower Restaurant & Tavern.'

16. 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
$199 nightly
The price is $224
Oct 7 - Oct 8
Total with taxes and fees
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
A living room with a sofa, a television, a fireplace, and a dining area with chairs and a table.

17. 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, (36 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.
$278 nightly
The price is $314
Oct 4 - Oct 5
Total with taxes and fees
Lovely ski-in/out condo steps from ski lift with trails and amazing views
A small cabin with a wooden deck, a front door, and large windows.

18. 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, (4 reviews)
"Phenomenal site, with stunning views. Highly recommend!"
United States
Jess M.
$145 nightly
The price is $148
Oct 5 - Oct 6
Total with taxes and fees
Runamuk Farm Camp Tiny House near Cambridge, New York
A wooden cabin with multiple windows, a deck, and a thatched roof.

19. Romantic New York Getaway near the Adirondacks

Romantic New York Getaway near the Adirondacks
Cambridge
$140 nightly
The price is $142
Oct 4 - Oct 5
Total with taxes and fees
Romantic New York Getaway near the Adirondacks
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

20. 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, (41 reviews)
"Our family had a wonderful vacation. The house and location were great. We will come back."
United States
Victoria L.
$591 nightly
The price is $663
Oct 19 - Oct 20
Total with taxes and fees
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
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

The Inn at Manchester

The Inn at Manchester

10/10 Excellent
"Just a wonderful place. We grabbed a fresh baked chocolate chip cookie as a snack. Breakfast to order was great."
Kevin 1-night trip
Posted 3 hours ago
The Inn at Manchester

Find out more about Rupert

Everything you need to know about Rupert vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Rupert vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Rupert vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Rupert vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Rupert. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Rupert in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $224 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Rupert rentals

At Expedia, we put the best Rupert vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Rupert rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Rupert vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Rupert. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Beautifully Remodeled VT Mountain Oasis with Stratton Views and private Hot Tub: This vacation home rental outside of Rupert offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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. While here, R. K. Kittay Public Library and Haystack Mountain are other places worth a visit.

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.