Rupert Holiday Rentals

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Holiday Rentals in Rupert

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
Exterior
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
10.0 out of 10, Exceptional, (151)
"We had a wonderful stay at Creekside Camp. Home and property had everything we needed. Deck, creek, hot tub, comfortable beds and stocked kitchen. Area has great hiking, shopping and restaurants. Dan was very easy to communicate with and help with any issue. Thank you."
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
Long Trail House at Stratton Mountain Resort
Pool
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very good, (70)
"Amazing! Cannot get a better location! So close to everything! Quick walk to village shops and slopes. Very clean. Lots more room than I was expecting for two big 17 year old boys and parents. Kids had their own bedroom, bathroom and storage area on main floor, adult had master suite with own bathroom upstairs. Plenty of room in kitchen and family room. The only complaint is that hotels hot tubs and pool were over run with too many little kids. "
The price is HK$2,640
HK$3,195 total
includes taxes & fees
27 Jun - 28 Jun
Long Trail House at Stratton Mountain Resort
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Exterior
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
9.6 out of 10, Exceptional, (180)
"The bedroom overlooks a stream. The bed is very comfortable, and a third person could sleep next to the queen bed on the day bed. The bathroom with the shower and jacuzzi, kitchen, and sitting areas are all fabulous—like out of a magazine. It's very private. The only downside was when it was dark, the road was hard to see. But if you have GPS, you turn when it says turn, and you're fine. It's right off the main road, so it's very convenient. The property manager answered right away when I...
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
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Cabin in So. Vt enjoy the Mtns.
Exterior
Cabin in So. Vt enjoy the Mtns.
10.0 out of 10, Exceptional, (98)
"Great little cabin tucked in the countryside, very clean and had everything we could possibly need the owners were fantastic. I would highly recommend a stay here!"
Cabin in So. Vt enjoy the Mtns.
VT Cabin overlooking the West River and Village
Fridge, oven, stovetop, dishwasher
VT Cabin overlooking the West River and Village
10.0 out of 10, Exceptional, (20)
"The cabin was perfect for a getaway! Felt secluded however walkable to small village, and within 20 minutes to Stratton. Perfectly stocked to stay in for meals!"
The price is HK$1,554
HK$2,972 total
includes taxes & fees
28 Jun - 29 Jun
VT Cabin overlooking the West River and Village
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
Exterior
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
10.0 out of 10, Exceptional, (147)
"Beautiful home and property with plenty of space for our extended family members to connect and yet have privacy for each couple as well. We will definitely return!"
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
Private and Artistic cabin, Pet friendly, no cleaning fee
Property grounds
Private and Artistic cabin, Pet friendly, no cleaning fee
10.0 out of 10, Exceptional, (246)
"What a dream come true. This home is unlike any other and was truly the foundation for such a beautiful time shared with friends. Can’t wait to go back!"
Private and Artistic cabin, Pet friendly, no cleaning fee
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
Exterior
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
10.0 out of 10, Exceptional, (27)
"This was one of the best locations we have stayed at! We came up for a fundraiser at Stratton Mountain. Tommy was so helpful and provided great information from booking up until checkout. There is a great virtual guide that answers all important questions. The house and outdoors were exactly what we were looking for. Our dog loved running around and we enjoyed the hot tub. The house was very clean and had all the necessities we needed. Our favorite part was being cozy on the coach watching...
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
9 bedrooms, desk, iron/ironing board, free WiFi
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
9.4 out of 10, Exceptional, (17)
"Definitely recommend this place for large groups. Very clean, so much to do, and great communication with host. Very private location"
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Quaint lakefront home with great views & full kitchen - dog-friendly
Property grounds
Quaint lakefront home with great views & full kitchen - dog-friendly
8.6 out of 10, Excellent, (19)
"The cabin was pretty clean when we got there and it was a beautiful view."
Quaint lakefront home with great views & full kitchen - dog-friendly
Private Tavern, Hot Tub, 8-Fireplaces, Spa Baths, Fire Pit, Baths Ensuite - Shop or Ski!
Property grounds
Private Tavern, Hot Tub, 8-Fireplaces, Spa Baths, Fire Pit, Baths Ensuite - Shop or Ski!
10.0 out of 10, Exceptional, (40)
"This was an amazing property. The beauty of it made for a truly wonderful weekend experience! The initial booking was smooth and effortless. Communication with the host was stellar from start to finish! When we arrived two of the caretakers were on site to greet us. They thanked us for choosing to stay, offered to help with getting settled, and gave us vital advice on preventing bobcats and bears from being attracted. hey even left some farm fresh eggs for us! Our first stop on our setup tour...
Private Tavern, Hot Tub, 8-Fireplaces, Spa Baths, Fire Pit, Baths Ensuite - Shop or Ski!
Charming dog-friendly home with private deck, firepit, washer/dryer, & cable
Fridge, microwave, oven, stovetop
Charming dog-friendly home with private deck, firepit, washer/dryer, & cable
9.2 out of 10, Wonderful, (22)
"We enjoyed our time and it was very close to Okemo Mountain"
Charming dog-friendly home with private deck, firepit, washer/dryer, & cable
Views! Enjoy the Entire 3-floor Custom Chalet, AC+1gig internet on 18 acres.
Exterior
Views! Enjoy the Entire 3-floor Custom Chalet, AC+1gig internet on 18 acres.
9.8 out of 10, Exceptional, (93)
"The chalet was great! Close by to lakes, and offered beautiful views!"
Views! Enjoy the Entire 3-floor Custom Chalet, AC+1gig internet on 18 acres.
Stratton South Long Trail Studio Adjacent to the Village and Lifts
Property grounds
Stratton South Long Trail Studio Adjacent to the Village and Lifts
9.4 out of 10, Exceptional, (56)
"Right across the road from Stratton Mountain. Check in was easy. Place was clean and comfortable. Much nicer and roomier than a typical hotel room. Highly recommended"
Stratton South Long Trail Studio Adjacent to the Village and Lifts
Nature Retreat, Pet Friendly Cozy Cabin On 80 Acres With Fields & Forrest Trails
Exterior
Nature Retreat, Pet Friendly Cozy Cabin On 80 Acres With Fields & Forrest Trails
9.6 out of 10, Exceptional, (5)
"My husband, daughter, dog and I stayed at Pete's property for the Adirondack Balloon Festival and had a great time! The whole family, including Belle the dog, were super friendly and welcoming, chatting with us, showing us around the property and even hand delivered a half dozen fresh eggs from their chickens! The property is super fun-landing somewhere between a small farm and nature compound kind of feel. We were only there a couple days and spent the majority of the time out and about because...
Nature Retreat, Pet Friendly Cozy Cabin On 80 Acres With Fields & Forrest Trails
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Property grounds
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
10.0 out of 10, Exceptional, (185)
"Lovely, very private property that feels far away and yet is super convenient to Manchester. Great host … everything was easy."
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!
View from property
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!
10.0 out of 10, Exceptional, (51)
"Lovely"
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
Outdoor pool, a heated pool
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
9.6 out of 10, Exceptional, (8)
"Great place. Super close to everything. Host was super helpful. Everything you need for an amazing ski weekend."
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
Green Mountain Modern House: iconic modern getaway
Exterior
Green Mountain Modern House: iconic modern getaway
Green Mountain Modern House: iconic modern getaway
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Interior
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
7.6 out of 10, Good, (40)
"Can't beat the location. We had a great stay."
The price is HK$578
HK$2,235 total
includes taxes & fees
2 Jul - 3 Jul
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
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See all available properties in Rupert
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.

Other types of properties in Rupert you may be interested in

The Equinox Golf Resort & Spa
Exterior
The Equinox Golf Resort & Spa
4.5 star property
7.4 out of 10, Good, (361)
"The Equinox is a charming historic hotel in a stunning Vermont setting. Although it's close to all the shops and restaurants in Manchester, it feels serene and quiet. We've stayed there several times and will continue to go back."
The price is HK$1,306
HK$1,829 total
includes taxes & fees
2 Jul - 3 Jul
The Equinox Golf Resort & Spa
Kimpton Taconic Hotel, an IHG Hotel
Exterior
Kimpton Taconic Hotel, an IHG Hotel
4.0 star property
9.4 out of 10, Exceptional, (696)
"Great facility in a pretty town. Visit to The Lincoln family home - Hildene - is a must see"
The price is HK$1,610
HK$2,071 total
includes taxes & fees
30 Jun - 1 Jul
Kimpton Taconic Hotel, an IHG Hotel
Hampton Inn and Suites Manchester
Front of property – evening/night
Hampton Inn and Suites Manchester
2.5 star property
9.6 out of 10, Exceptional, (1002)
"The hotel website needs to make it very clear that dogs cannot be left alone in a room. It means restriction of a one or two hour visit to Manchester's outlets, not going out for dinner and not being able to go to the breakfast room without 5he dog."
The price is HK$1,398
HK$1,538 total
includes taxes & fees
30 Jun - 1 Jul
Hampton Inn and Suites Manchester
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.

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 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?

Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly: This holiday home rental outside of Rupert offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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?

While exploring the area, visit family-friendly sights like Sugar Shack, or get outside and enjoy nature at Merck Forest Farmland Center. In the wider area, you’ll find Dorset Playhouse and Equinox Preservation Trust.

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.

Recent reviews of Rupert properties
Expedia verified reviews

The Palmer House Resort, Ascend Hotel Collection

The Palmer House Resort, Ascend Hotel Collection

5/5 Excellent
"Pleasant Check In"
A verified traveller from Bridgeton stayed at The Palmer House Resort, Ascend Hotel Collection
Posted 3 days ago
The Palmer House Resort, Ascend Hotel Collection