Rupert holiday rentals

We found 381 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Rupert to find one that's perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll have the best amenities for spending time at your home away from home, which might include a hot tub and garden. At the end of the day, you'll be sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Rupert

Showing deals for:13 Nov - 20 Nov

Exterior
Interior
Dining
Interior
Exceptional
(54 reviews)

Skylight Ski Lodge VT Rustic Chic Near Stratton

Bondville

8% off
AU$14,475
for 7 nights, 1 home
AU$2,068 per night
includes taxes & fees
Skylight Ski Lodge VT Rustic Chic Near Stratton
great room with bridge to bedrooms, site-built timber truss and handhewn columns
Living area
spiral stair to lookout room
Dining and living rooms viewed from new kitchen
Exceptional
(92 reviews)

Vermont Lakefront Paradise

Wallingford

8% off
AU$6,268
for 7 nights, 1 room
AU$895 per night
includes taxes & fees
Vermont Lakefront Paradise
Dining
Interior
Interior
Living area
Exceptional
(5 reviews)

Spacious 5-bedroom w/ huge yard. Rural getaway!

Granville

8% off
AU$5,579
for 7 nights, 1 home
AU$797 per night
includes taxes & fees
Spacious 5-bedroom w/ huge yard. Rural getaway!
Room
Property grounds
Living area
Private kitchen
Exceptional
(23 reviews)

Bear Pass Bunkhouse

Manchester

8% off
AU$3,101
for 7 nights, 1 home
AU$443 per night
includes taxes & fees
Bear Pass Bunkhouse
Interior
Terrace/patio
Interior
Exterior
Exceptional
(57 reviews)

Modern mountain home - Vermont Ski House close to Stratton

East Dorset

8% off
AU$10,173
for 7 nights, 1 home
AU$1,453 per night
includes taxes & fees
Modern mountain home - Vermont Ski House close to Stratton
Private kitchen
Property grounds
Living area
Dining table with bay window
Exceptional
(12 reviews)

Log Cabin Escape: Well-stocked, clean, cozy & comfortable

Bondville

8% off
AU$6,345
for 7 nights, 1 cabin
AU$906 per night
includes taxes & fees
Log Cabin Escape: Well-stocked, clean, cozy & comfortable
living room
Outdoor dining
let it snow!
Stratton mtn fire tower view
Exceptional
(38 reviews)

Cozy Manchester Getaway with Amazing Views!!!

Bondville

7% off
AU$4,899
for 7 nights, 1 home
AU$700 per night
includes taxes & fees
Cozy Manchester Getaway with Amazing Views!!!
Fully enclosed loft space
Newly renovated kitchen with all major appliance, utensils, pots and pans.
Interior
Another view of our dining room and newly renovated kitchen.
Exceptional
(9 reviews)

Cozy Cabin - walking distance to town and 10 minutes to Bromley. Pet friendly!

Manchester Center

12% off
AU$3,932
for 7 nights, 1 cabin
AU$562 per night
includes taxes & fees
Cozy Cabin - walking distance to town and 10 minutes to Bromley. Pet friendly!
Dining
Property grounds
Exterior
Dining
Exceptional
(24 reviews)

Gorgeous Mountain View in Manchester, Shopping, Dining, Spa. 5 min walk to town.

Manchester

7% off
AU$6,824
for 7 nights, 1 home
AU$975 per night
includes taxes & fees
Gorgeous Mountain View in Manchester, Shopping, Dining, Spa. 5 min walk to town.
kitchen
deck
Living area
entrance view
Exceptional
(8 reviews)

Accessible Manchester Home with Amazing Views!

Manchester Center

8% off
AU$6,523
for 7 nights, 1 home
AU$932 per night
includes taxes & fees
Accessible Manchester Home with Amazing Views!
- Functional mudroom with wood bench and black modern accents - Hooks for coats and gear after outdoor adventures - Perfect transition space for guests exploring the outdoors
- Spacious open floor plan with bright natural lighting - Modern kitchen flows seamlessly into dining and living space - Ideal for entertaining with mountain views through large windows
- Sleek kitchen with black granite countertops and island seating - Fully equipped for cooking with stainless steel appliances - Open layout connects easily with living and dining area
- Open dining area with rustic wooden table and modern chairs - Seamless access to patio and backyard through sliding doors - Ideal for group meals with mountain view ambiance
Exceptional
(6 reviews)

Escape to The Clyde’s View Hideaway in Manchester, Vt. New Home 3 Bed 2 Bath

Manchester Center

11% off
AU$4,679
for 7 nights, 1 home
AU$668 per night
includes taxes & fees
Escape to The Clyde’s View Hideaway in Manchester, Vt. New Home 3 Bed 2 Bath
Interior
Outdoor dining
Property grounds
Exterior
Exceptional
(5 reviews)

Serene apartment in Dorset perfect for a relaxing getaway

Dorset

8% off
AU$1,372
for 7 nights, 1 apartment
AU$196 per night
includes taxes & fees
Serene apartment in Dorset perfect for a relaxing getaway
Private kitchen
Interior
Property grounds
Living room as part of an open flow design. French door to deck and hot tub
Exceptional
(28 reviews)

UNBELIEVABLE MOUNTAIN VIEWS! Convenient to Manchester,skiing,outlets

Arlington

16% off
AU$8,842
for 7 nights, 1 home
AU$1,263 per night
includes taxes & fees
UNBELIEVABLE MOUNTAIN VIEWS! Convenient to Manchester,skiing,outlets
Our meticulously cared for garden, which we love so much.
The sunniest sun room
Great room, is just that. Great..
Locally sourced slate countertops from down the road.
Exceptional
(20 reviews)

New! Lovingly restored Antique Vermont Farm House- Horse Friendly!

Rupert

8% off
AU$6,282
for 7 nights, 1 home
AU$897 per night
includes taxes & fees
New! Lovingly restored Antique Vermont Farm House- Horse Friendly!
Dining
Exterior
Enjoy a book, board game or foosball in cozy sunroom with large sleeper sofa
Front walkway
Exceptional
(78 reviews)

Minutes from Manchester Village/Center; near Stratton and Bromley Mtns

Manchester Center

5% off
AU$6,574
for 7 nights, 1 home
AU$939 per night
includes taxes & fees
Minutes from Manchester Village/Center; near Stratton and Bromley Mtns
Dorset Playhouse.
Seating for 6 at dining table, plus counter top seating for 3
Living area
Marble fire pit area with wooden Adirondack chairs.
Exceptional
(57 reviews)

The Nest at Birch Quarry

Dorset

8% off
AU$5,142
for 7 nights, 1 home
AU$735 per night
includes taxes & fees
The Nest at Birch Quarry
Property grounds
Dining
Exterior detail
Interior
Exceptional
(30 reviews)

A country getaway in upstate NY, surrounded by art and nature.

Salem

8% off
AU$1,616
for 7 nights, 1 apartment
AU$231 per night
includes taxes & fees
A country getaway in upstate NY, surrounded by art and nature.
Family Room
Bonnet House. A luxury home, steps from Main Street.
Family Room
Terrace/patio
Exceptional
(62 reviews)

BONNET HOUSE IS WHERE TIMELESS VERMONT CHARM MEETS MODERN LUXURY.

Manchester Center

8% off
AU$9,316
for 7 nights, 1 home
AU$1,331 per night
includes taxes & fees
BONNET HOUSE IS WHERE TIMELESS VERMONT CHARM MEETS MODERN LUXURY.
Dinning room/Kitchen
Outdoor dining
Living area
Kitchen
Exceptional
(23 reviews)

Cow Barn converted into a beautiful spacious home.

Danby

8% off
AU$4,599
for 7 nights, 1 home
AU$657 per night
includes taxes & fees
Cow Barn converted into a beautiful spacious home.
Al fresco dining!
A little ambiance.
Curl up by the fire!
Books, fireplace, smart flatscreen, games, chess table and lots of comfy seats!
Exceptional
(42 reviews)

Charming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!

Dorset

8% off
AU$3,788
for 7 nights, 1 cottage
AU$541 per night
includes taxes & fees
Charming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!
Terrace/patio
Dining
Living area
Exterior
Exceptional
(91 reviews)

Log Cabin In The Woods

Arlington

7% off
AU$2,742
for 7 nights, 1 cabin
AU$392 per night
includes taxes & fees
Log Cabin In The Woods
Living area
Interior
Room
Dining
Exceptional
(14 reviews)

TUCKED ABOVE: IN TOWN 3 BDR/2 BATH

Manchester Center

8% off
AU$8,514
for 7 nights, 1 home
AU$1,216 per night
includes taxes & fees
TUCKED ABOVE: IN TOWN 3 BDR/2 BATH
Interior
Exterior
Dining
X-Large Kitchen
Exceptional
(18 reviews)

8-bedroom vacation home just 16 minutes from Golf Club at Equinox

Dorset

16% off
AU$4,056
for 7 nights, 1 home
AU$579 per night
includes taxes & fees
8-bedroom vacation home just 16 minutes from Golf Club at Equinox
Kitchen
View of the Green Mountains
Exterior detail
Second living area in basement
Exceptional
(20 reviews)

The Manchester Center of it all!

Manchester Center

8% off
AU$3,766
for 7 nights, 1 home
AU$538 per night
includes taxes & fees
The Manchester Center of it all!

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The rustic city of Rupert awaits you

The countryside and parks provide a pleasant backdrop to your holiday home in Rupert. This relaxing city has many special qualities. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Rupert

Are you looking for things to do while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Rupert a fun place to get away to. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Golf Club at Equinox (10.2 mi / 16.4 km)
  • Sugar Shack (12.7 mi / 20.5 km)
  • Bromley Mountain Ski Resort (14.6 mi / 23.5 km)
  • Stratton Mountain Golf Course (18.5 mi / 29.7 km)
  • Stratton Mountain Resort (19.3 mi / 31 km)
  • Lake St Catherine Country Club (15.9 mi / 25.6 km)

Exploring the natural features in Rupert

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Rupert is a great place to get outside. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Merck Forest Farmland Center (2.7 mi / 4.4 km)
  • Equinox Preservation Trust (9.5 mi / 15.2 km)
  • Battenkill River (10.6 mi / 17 km)
  • Emerald Lake State Park (11.1 mi / 17.8 km)
  • Green Mountain National Forest (11.3 mi / 18.1 km)
  • Mount Equinox (11.3 mi / 18.2 km)

Transport options to and around Rupert

The nearest airport is in Glens Falls, NY (GFL-Floyd Bennett Memorial), located 20 mi (32.2 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 23.2 mi (37.3 km) away.

Frequently asked questions

What is the best area to stay in Rupert when booking a holiday rental?
When considering a holiday rental in Rupert, Vermont, the charming area of the town centre is an excellent choice. This quaint neighbourhood offers a delightful blend of picturesque landscapes and a sense of community. Staying here provides easy access to some of the region's top attractions, such as the stunning Merck Forest and Farmland Centre, where visitors can enjoy hiking trails and seasonal activities amidst beautiful scenery.Additionally, the nearby Battenkill River is superb for those who appreciate outdoor recreation, offering opportunities for fishing and kayaking. The properties available in this area vary, with a mix of charming cottages and spacious homes that cater to different preferences and group sizes.
Where are the best Rupert ski resort rentals?
For ski resort rentals in Rupert, Vermont, visitors should focus on the nearby area of Bromley Mountain, which is only a short drive away. The town of Manchester is a popular choice for accommodation, offering a variety of options ranging from quaint bed and breakfasts to spacious holiday homes. Many of these properties come equipped with essential amenities such as fully furnished kitchens, comfortable living areas, and some even feature hot tubs or fireplaces, superb for unwinding after a day on the slopes.In addition to the convenience of skiing at Bromley, Manchester offers a charming downtown area with shops, restaurants, and cultural attractions. Properties here often provide easy access to local trails for snowshoeing or cross-country skiing, and some rentals may include features like ski storage or shuttle services to the ski area.Additionally, the picturesque landscapes surrounding Rupert and Manchester create a beautiful backdrop for winter activities beyond skiing, such as snowmobiling or ice skating on local ponds.
What is the most popular type of holiday rental accomodation in Rupert?
In Rupert, holiday houses are among the most popular type of holiday rental, with several available in the area. These properties typically feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups seeking a comfortable retreat. Many of these homes are set in tranquil surroundings, offering a peaceful atmosphere away from the hustle and bustle. Additionally, there are also several villas available, which often provide upscale amenities, including private outdoor spaces and luxurious furnishings.
Are there any family house rentals in Rupert?
In Rupert, Vermont, there are several family-friendly house rentals available, making it a delightful spot for groups looking to enjoy the great outdoors. The area is surrounded by beautiful landscapes, with easy access to local attractions like the nearby Green Mountain National Forest, superb for hiking, biking, or simply enjoying nature.Many of these properties offer spacious living areas suitable for family gatherings, well-equipped kitchens ideal for preparing home-cooked meals, and outdoor spaces where children can play safely. Additional amenities such as Wi-Fi, laundry facilities, and sometimes even fireplaces enhance the comfort of your stay.Visitors can also explore nearby towns for dining and local shops, adding to the charm of a family getaway in this picturesque part of Vermont.
Can I rent a holiday home with a pool or hot tub in Rupert?
In Rupert, Vermont, there are several holiday homes available for rent that feature pools or hot tubs, making it an appealing destination for those seeking relaxation. The tranquil surroundings provide a picturesque backdrop, ideal for unwinding after a day of exploring the area. Many properties offer amenities such as private pools, hot tubs, spacious outdoor areas, and fully equipped kitchens, ensuring a comfortable and enjoyable stay for families or groups.The region is known for its beautiful landscapes, and visitors can take advantage of nearby outdoor activities, including hiking and skiing in the winter months.
Are there pet-friendly house rentals in Rupert?
In Rupert, Vermont, there are several pet-friendly house rentals available, making it an accommodating destination for travellers with furry companions. Many of these properties typically feature spacious living areas, fully equipped kitchens, and outdoor spaces where pets can enjoy the fresh air. Additionally, some rentals boast amenities such as fenced yards and nearby walking trails, allowing for convenient outings with pets.The picturesque surroundings of Rupert provide a serene backdrop, with opportunities for outdoor activities in the nearby Green Mountains. This area is great for those who appreciate nature and the tranquillity of rural life.
Are there any remote work holiday rentals in Rupert?
In Rupert, Vermont, there are 15 holiday rentals that cater to remote work needs. Many of these properties are equipped with reliable Wi-Fi, making it easy for guests to stay connected while enjoying the tranquillity of the area. Expect amenities such as comfortable workspaces, spacious living areas, and fully equipped kitchens, allowing for both productivity and relaxation during your stay.The picturesque surroundings of Rupert provide a serene environment, great for balancing work and leisure. Nearby attractions include the beautiful landscapes of the Green Mountains and local hiking trails, offering opportunities for outdoor activities once the workday is done. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Rupert?
In Rupert, popular holiday rental amenities typically include kitchens, which allow guests to prepare their own meals during their stay. Many properties also feature fireplaces, adding a cozy atmosphere, especially during the cooler months. Guests can expect outdoor spaces such as decks or patios, great for enjoying the picturesque surroundings. Additionally, some rentals may provide amenities like a blender for those who enjoy making smoothies or other beverages.
When is the best time to visit Rupert for a holiday rental?
March is the most popular time to visit Rupert, Vermont, as it marks the tail end of the peak season that runs from January to March. This period is particularly appealing for winter sports enthusiasts, with excellent skiing and snowboarding conditions at nearby resorts. The crisp, fresh air and stunning snowy landscapes create a picturesque setting for outdoor activities, making it an ideal time for those looking to embrace the winter wonderland.During March, temperatures in Rupert generally hover around -5 to 5 degrees Celsius, allowing for comfortable exploration of the area's winter attractions. Visitors can enjoy scenic snowshoeing trails or take leisurely walks through the charming town, where quaint shops and local eateries await.For those looking to enjoy a quieter experience with potentially better rates, consider visiting in February. This month, while still part of the winter season, typically sees fewer crowds, allowing for a more relaxed atmosphere where you can truly soak in the beauty of the snowy surroundings.Ultimately, the best time to book a holiday rental in Rupert depends on your preference for lively winter activities in March or a more peaceful getaway in February.
What are the top attractions in Rupert?
In Rupert, Vermont, visitors can explore the picturesque countryside and enjoy a variety of outdoor activities. The town is located near the stunning Green Mountain National Forest, which offers ample opportunities for hiking, wildlife viewing, and enjoying nature's beauty. The nearby Battenkill River is popular for fishing and kayaking, making it a great spot for outdoor enthusiasts.For those interested in local history and culture, the Rupert Historical Society provides insights into the town's past and heritage. Additionally, the charming small-town atmosphere is complemented by local farms and artisans, where visitors can experience Vermont's agricultural offerings.Just a short drive away, the town of Manchester offers additional attractions, including the Manchester Designer Outlets for shopping and the Southern Vermont Arts Centre for cultural experiences.
Are all fees included in the Rupert holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Rupert holiday homes with parking?
Stayz offers a wide selection of holiday homes in Rupert with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Rupert holiday homes?
You can find great discounts on holiday homes in Rupert on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Rupert holiday home booking on Stayz?
To find Rupert holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Rupert?
A long-stay holiday home in Rupert is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Rupert holiday home?
Book your Rupert holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Rupert?
Prices for holiday homes in Rupert vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Rupert to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.