Rupert Vacation Rentals

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Vacation Rentals in Rupert

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

10.0 out of 10, Exceptional, (166)
"This place is magical for a mental health reset. The water, the trees, everything was perfect! "
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (212)
"Cabin was beautiful! Love the little stream outside. Very close to restaurants, shopping, and hiking trails. "
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (17)
"This place was very enjoyable, it was just 3 of us so there was more than enough room. It is a very comfortable home and we enjoyed the easy trip into Manchester for some meals and a wonderful day of hiking some great nearby trails."
The price is CA $280
CA $891 total
includes taxes & fees
Apr 20 - Apr 21
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Long Trail House at Stratton Mountain Resort

3.0 star property
8.6 out of 10, Excellent, (74)
"Nice, clean room in prime location"
The price is CA $444
CA $553 total
includes taxes & fees
Apr 23 - Apr 24
Long Trail House at Stratton Mountain Resort

NEW Charming ski retreat w/heated plunge pool & endless views in peaceful Weston

NEW Charming ski retreat w/heated plunge pool & endless views in peaceful Weston

Secluded home with game room, private hot tub, golf, river & mtn views, firepit

9.8 out of 10, Exceptional, (6)
"Very nice. Could use curtains or blinds in more rooms."
Secluded home with game room, private hot tub, golf, river & mtn views, firepit

Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

10.0 out of 10, Exceptional, (22)
"Great location close to the slopes. Clean and comfortable. Loved the fireplace. "
Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

9.4 out of 10, Exceptional, (22)
"The 2 houses were able to accommodate 21 people and 2 dogs. There was plenty of room and the houses were clean. House included linens and a few towels in each bedroom. The grounds are beautiful and it was nice to walk around and take in the scenery. We came here to ski at mt snow and was about 13 minutes to the mountain. The weather was real cold in the low single digits and they got hit with a foot of snow a few days earlier. We had 5 vehicles and Parking was a little tight. This was...
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

10.0 out of 10, Exceptional, (55)
"Great secluded place. Very clean couldn't ask for more. Great central location. Close to restaurants "
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

Beautiful Manchester VT Mountain Retreat w/Hot Tub

10.0 out of 10, Exceptional, (32)
"We had 9 people in 2 family units staying at house. Then about another 6 that came each night to hang out. Plenty of room. 3 living room areas for everyone to spread out. Best stocked home EVER!!! There was literally everything and anything that we needed…..and then some. Inside sauna so cool. Unfortunately way too cold to go out and enjoy the hot tub. Decorations beyond beautiful. Owner very quick with communication. Highly recommend staying here. "
Beautiful Manchester VT Mountain Retreat w/Hot Tub

Lovely ski-in/out condo steps from ski lift with trails and amazing views

8.8 out of 10, Excellent, (23)
"Wonderful location and comfortable. Appliances were a bit dated, but that didn’t impact our stay. The unit was not cleaned from the previous occupants upon our check in and took a few hours to do so. This is not the fault of the owner, but did impact our initial experience. Overall wonderful though. Great location and comfortable with a working fireplace. Would stay here again. "
The price is CA $98
CA $387 total
includes taxes & fees
Apr 24 - Apr 25
Lovely ski-in/out condo steps from ski lift with trails and amazing views

Long Trail House Studio at Stratton Mountain Resort

10.0 out of 10, Exceptional, (63)
"Great location, the studio feels bigger than it seems on pictures. "
Long Trail House Studio at Stratton Mountain Resort

By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.

9.8 out of 10, Exceptional, (63)
"Rented this lodge based on other positive reviews - and they were spot on! Greeted by snowy landscape and cozy, warm, lodge wonderfully appointed More you looked, more you saw! Comfy beds, good showers, full service kitchen, spotless. Our family of 5 adults , 13 yr old twin granddaughters greed we felt like we were in a welcoming home. Brad, part owner/prop. manager immediately responded to call or text. We are looking forward to Dec 2025 to do it all again. Don’t miss Zoe’s grill in Manchester "
By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.

Summer Adventures Await -- Book now for the Horse Show & Explore Manchester

10.0 out of 10, Exceptional, (50)
"We enjoyed skylight lodge. We get together with family and friends each year to do an annual fundraising event. The house was perfect for our group. The big fireplace was a great way to relax after a day of skiing or snowshoeing. "
Summer Adventures Await -- Book now for the Horse Show & Explore Manchester

Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.

10.0 out of 10, Exceptional, (165)
"The place was amazing; perfect location between killington and stratton. We definitely want to come back here and stay again in peak winter!"
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.

Peaceful Stay at Birds of a Feather Farm & Spa

9.6 out of 10, Exceptional, (17)
"Wonderful get away for the week in VT. Place was clean and beautiful, host was very helpful, and views were gorgeous! "
The price is CA $152
CA $360 total
includes taxes & fees
Apr 19 - Apr 20
Peaceful Stay at Birds of a Feather Farm & Spa

Vermont Lake House

10.0 out of 10, Exceptional, (17)
"Host was great and it was in a great location "
Vermont Lake House

Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester

8.8 out of 10, Excellent, (17)
"From the time we got there to the time we left, we very much enjoyed David’s home. He was a wonderful host! Although we didn’t get to enjoy a fire in the pit, my daughter figured out how to make the s’mores in the air fryer! The coffeemaker was a very welcome appliance! lol. Can’t wait to book this again!"
Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester

Schuyler Yacht Basin

3.0 star property
8.0 out of 10, Very good, (12)
"Great place to stay while visiting the area!"
Schuyler Yacht Basin

Adirondack Lakefront home with private dock

10.0 out of 10, Exceptional, (17)
"Friends and I chose this location to have our annual ice fishing contest. It did not disappoint! House is very clean, user friendly, and the property sits on a small pond with direct access.Communication from the owner was outstanding. Overall, highly recommend and hope to return for a summer stay."
Adirondack Lakefront home with private dock
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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Other types of properties in Rupert you may be interested in

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

10.0 out of 10, Exceptional, (166)
"This place is magical for a mental health reset. The water, the trees, everything was perfect! "
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

The Equinox Golf Resort & Spa

4.5 star property
7.4 out of 10, Good, (466)
"Very nice location"
The price is CA $139
CA $226 total
includes taxes & fees
Apr 20 - Apr 21
The Equinox Golf Resort & Spa

Kimpton Taconic Hotel by IHG

4.0 star property
9.4 out of 10, Exceptional, (761)
"Amazng stay"
The price is CA $209
CA $278 total
includes taxes & fees
Apr 27 - Apr 28
Kimpton Taconic Hotel by IHG
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.

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?

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style: Visitors like this Rupert vacation home rental. It is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a garden, 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 3 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.