Rupert vacation rentals

We found 366 vacation rentals — enter your dates for availability

Scroll through and select from vacation rentals in Rupert to find one that's perfect for your trip. Whether you’re staying in a vacation home with your kids and pets or just with friends, you'll have the best amenities for spending time at your home away from home, such as air conditioning and a TV. Whatever you're looking for, you'll find a rental that has what everyone needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Rupert

Showing deals for:Jul 3 - Jul 10

Image gallery for Beautiful Manchester VT Mountain Retreat w/Hot Tub

Aerial view
10 out of 10, Exceptional, (43 reviews)
Exceptional
(43 reviews)

Beautiful Manchester VT Mountain Retreat w/Hot Tub

Bondville

8% off
Price is $499
$3,493 for 7 nights
All fees included
Beautiful Manchester VT Mountain Retreat w/Hot Tub

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Find out more about Rupert

Why visit Rupert

  • Outdoor Adventures: Experience thrilling skiing, hiking, and exploration of stunning lakes and national parks.
  • Quaint Farmhouse Charm: Enjoy the idyllic Vermont farmhouse atmosphere, perfect for a relaxing getaway.
  • Romantic Escapes: Discover secluded spots and friendly locals in nearby West Rupert for a romantic retreat.
  • Diverse Accommodations: Choose from cozy cabins, inviting condos, and spacious vacation homes tailored to your needs.
  • Seasonal Activities: Embrace vibrant seasonal experiences, from winter sports to summer lake activities.

Popular types of accommodation in Rupert

Planning a getaway to Rupert? You're in for a treat. Discover the charm of Houses, inviting Condos, and cozy Cabins that make for the perfect stay. Whether you're searching for a spacious family home or a charming country house, Rupert has the ideal rental to suit your needs. Explore our selection of house rentals, including the popular Carver House, and enjoy a memorable vacation experience.

  • Houses: The top choice for visitors to Rupert, offering spacious and comfortable accommodations perfect for families or groups.
  • Condos: A popular option for travelers seeking modern amenities and convenience, often located near local attractions.
  • Cabins: Ideal for those wanting a rustic escape, these rentals provide a cozy retreat amidst nature.
  • Cottages: These quaint spaces are perfect for a romantic getaway or a peaceful stay, blending charm with comfort.
  • Apartments: A practical choice for solo travelers or couples, offering a home-like atmosphere in the heart of Rupert.**

Top attractions in and around Rupert

Rupert, Vermont, is a fantastic destination for outdoor enthusiasts, offering thrilling ski and adventure opportunities. Visitors can explore stunning lakes, national parks, and golf courses, making it an ideal spot for those seeking outdoor activities, cultural experiences, and beautiful scenery. Whether you're looking to relax or embark on an adventure, Rupert has something for everyone to enjoy during your vacation.

  • Golf Club at Equinox: Located 10 miles from Rupert, this stunning golf course offers a unique blend of adventure and relaxation amidst picturesque landscapes. Perfect for golf enthusiasts, it provides a challenging course with breathtaking views, making it an ideal spot for both play and leisure.
  • Equinox Preservation Trust: Just 9 miles away, this family-friendly nature reserve invites visitors to explore its diverse trails and natural beauty. Enjoy outdoor adventures in a serene environment, perfect for hiking, picnicking, and wildlife watching.
  • Merck Forest Farmland Center: Situated within Rupert, this working farm offers an immersive experience in agriculture and nature. Engage in outdoor activities, enjoy scenic views, and learn about sustainable farming practices in a charming rural setting.

Things to do recommended for couples

For a romantic getaway in Rupert, Vermont, explore the snowy slopes at Stratton Mountain Resort or Bromley Mountain Ski Resort, both offering thrilling outdoor adventures. For a unique experience, take a scenic ride on the American Express Ski Lift, perfect for couples seeking adventure together.

Things to do recommended for families

Your family will love exploring Dana L. Thompson Memorial Park for relaxation, enjoying the thrills of the Bromley Alpine Slide, and discovering art at The Georgi Museum, all within a short drive from Rupert. These kid-friendly spots offer fun and memorable experiences for everyone.

Things to do recommended for groups

Enjoy a night of culture and entertainment at the Dorset Playhouse, just 6 miles from Rupert. For shopping enthusiasts, visit the Manchester Designer Outlets, located 10 miles away, offering a mix of family fun and city vibes. Don't miss the Sugar Shack, a charming store 13 miles from town.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Rupert

When traveling with a group, family, or pets, or if you're seeking extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Rupert with a group: Think about how many bedrooms you require and any specific amenities you might want, like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these features and many others on Vrbo.
  • Traveling to Rupert with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Rupert: For many families, a getaway wouldn't feel complete without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Rupert: If you're searching for vacation rentals with discounts for extended stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a spacious kitchen, or a private pool in your search as well.

Where to stay near Rupert

Rupert, Vermont, offers a delightful blend of outdoor adventures and a serene atmosphere, making it an ideal destination for travelers seeking both relaxation and excitement. Explore the idyllic Vermont farmhouse charm and experience the quintessential Vermont getaway. Nearby West Rupert boasts friendly locals and secluded spots perfect for a romantic escape. Whether you’re skiing in winter or enjoying the vibrant seasons, Rupert promises an unforgettable vacation experience.

  • Manchester: Located approximately 10 miles from Rupert, Manchester is a vibrant city known for its thrilling ski adventures and outdoor sports experiences. Nestled in the picturesque Green Mountains, visitors can enjoy world-class ski resorts and expansive ski fields that attract winter sports enthusiasts year-round. Beyond skiing, Manchester offers stunning views of lakes, mountains, and valleys, making it a perfect destination for nature lovers. With charming shops, dining options, and cultural attractions, Manchester combines adventure with a welcoming community atmosphere.
  • Manchester Center: Also situated around 10 miles from Rupert, Manchester Center is a bustling hub for outdoor activities and sports. This charming city provides easy access to ski resorts, where visitors can partake in exhilarating winter sports. The area's breathtaking landscapes, featuring serene lakes and majestic mountains, create a stunning backdrop for outdoor adventures. Manchester Center is also known for its quaint shops and local eateries that offer a taste of authentic Vermont, ensuring a delightful experience for all travelers.
  • Dorset: Just 6 miles from Rupert, Dorset is a picturesque town that invites adventure seekers to explore its outdoor offerings. Known for its proximity to ski fields and resorts, Dorset is a haven for winter sports enthusiasts. The town boasts beautiful natural attractions, including a national state park, serene lakes, and stunning mountain views. With its tranquil atmosphere and opportunities for hiking, skiing, and enjoying the great outdoors, Dorset is an ideal destination for those looking to immerse themselves in Vermont's natural beauty.

Best time to go to Rupert

If you're planning a trip to Rupert, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in January, March, September and November, while off-peak times, like February and December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January21.0°F (-6.1°C)Light RainMostly CloudyHighSlightly High
February23.2°F (-4.9°C)Light RainMostly CloudyLowSlightly High
March31.5°F (-0.3°C)Light RainMostly CloudyHighAverage
April43.5°F (6.4°C)Light RainMostly CloudyAverageSlightly Low
May56.3°F (13.5°C)Light RainMostly SunnyAverageSlightly Low
June63.7°F (17.6°C)Light RainMostly SunnyAverageAverage
July69.6°F (20.9°C)Light RainMostly SunnyAverageAverage
August68.0°F (20.0°C)Light RainMostly SunnyAverageAverage
September60.8°F (16.0°C)Light RainMostly SunnyHighAverage
October49.3°F (9.6°C)Light RainMostly SunnyAverageSlightly Low
November37.0°F (2.8°C)Light RainMostly SunnyHighAverage
December28.0°F (-2.2°C)Light RainMostly CloudyLowSlightly High

Booking with Vrbo is a breeze

Are you hoping to cut costs on your upcoming adventure? Being open to adjusting your travel dates can help, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board feature offers a convenient way to plan your travels, allowing you to start new trips, pick up where you left off, or manage your existing plans with ease. You can easily find the properties you've saved or booked under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The rustic city of Rupert awaits you

The countryside and parks provide a pleasant backdrop to your vacation home in Rupert. This relaxing city has many special qualities. A vacation 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 attractions to visit while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Rupert a fun place to get away. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

  • 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 Resort (19.3 mi / 31 km)
  • Lake St Catherine Country Club (15.9 mi / 25.6 km)
  • Wild Wings Ski Touring Center (16 mi / 25.7 km)

Exploring the natural features in Rupert

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

  • Merck Forest Farmland Center (2.7 mi / 4.4 km)
  • Equinox Preservation Trust (9.5 mi / 15.2 km)
  • Dana L. Thompson Memorial Park (10 mi / 16.1 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)

Transportation 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 center. If you can't find a flight that works for your travel itinerary, you could also fly into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 23.2 mi (37.3 km) away.

Frequently asked questions

How much does it cost to rent a vacation home in Rupert?
Prices for vacation rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Rupert to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Rupert vacation house rentals?
You can find great discounts on house rentals in Rupert on Vrbo, 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.
Where are the best Rupert ski resort rentals?
For the best ski resort rentals near Rupert, Vermont, travelers should consider the nearby area of Bromley Mountain, which is just a short drive away. The town of Manchester, a charming New England community, offers a variety of vacation rentals suitable for skiers. Many of these accommodations include cozy cabins and charming homes that feature amenities such as fireplaces, well-equipped kitchens, and spacious living areas, superb for relaxing after a day on the slopes.

In Manchester, visitors can also find properties that provide easy access to local shops, restaurants, and cultural attractions. Many rentals here come with outdoor spaces, such as decks or patios, where guests can enjoy the beautiful mountain views. Additionally, some homes may include hot tubs or game rooms, adding to the comfort and entertainment options for families or groups.

For those looking for an even closer experience to skiing, the area around Bromley Mountain offers additional options, including ski-in/ski-out accommodations that allow for immediate access to the slopes. These properties typically come equipped with ski storage, making it convenient for guests to prepare for their skiing adventures.
What is the most popular type of vacation rental accomodation in Rupert?
In Rupert, vacation houses and villas are the most popular types of rental accommodations, with several options available throughout the area. These properties typically feature spacious interiors, multiple bedrooms, and fully equipped kitchens, making them suitable for families or groups seeking a comfortable and home-like atmosphere. Many rentals also include outdoor spaces, such as private yards or decks, allowing guests to enjoy the serene surroundings of Vermont.
Are there any family house rentals in Rupert?
In Rupert, Vermont, there are some family-friendly house rentals available, superb for those looking to enjoy a cozy getaway. The area is known for its picturesque landscapes and proximity to outdoor activities, making it an excellent choice for families. Many of these homes offer spacious living rooms, fully equipped kitchens for easy meal preparation, and outdoor spaces where children can play or families can gather for barbecues.

Visitors can explore the scenic surroundings, including nearby hiking trails and local parks, providing ample opportunities for outdoor adventures. Additionally, the charming town atmosphere ensures that families can enjoy local shops and eateries, enhancing their overall experience.
Can I rent a vacation home with a pool or hot tub in Rupert?
In Rupert, Vermont, travelers can find several vacation homes available for rent that feature pools and hot tubs, making it an attractive destination for those seeking relaxation and recreation. The town is surrounded by picturesque landscapes, offering a serene escape into nature. Many of these rentals come equipped with amenities such as private pools, hot tubs, spacious outdoor decks, and fully equipped kitchens, providing a comfortable setting for families or groups. Additionally, the properties often include cozy living spaces and may have features like fire pits or barbecue grills, great for enjoying evenings outdoors.
Can I find long-stay vacation rentals in Rupert?
A long-stay vacation rental in Rupert is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Rupert?
In Rupert, Vermont, there are several pet-friendly house rentals available, making it an excellent choice for travelers looking to bring their furry companions along. Many of these vacation homes come equipped with amenities such as spacious yards, fully stocked kitchens, and comfortable living areas that cater to both pets and their owners.

The surrounding area offers beautiful landscapes and outdoor activities, great for pet owners. Nearby parks and nature trails provide great opportunities for walks and exploration, allowing pets to enjoy the fresh Vermont air. Additionally, the charming small-town atmosphere of Rupert enhances the overall experience, with local shops and eateries that may welcome pets on patios or have outdoor seating.
Are there any remote work vacation rentals in Rupert?
In Rupert, Vermont, there are several vacation rentals suitable for remote work. Travelers can expect properties equipped with reliable Wi-Fi, ensuring a productive environment. Many of these rentals feature spacious living areas and dedicated workspaces, making it easier to balance work and relaxation. The serene countryside surrounding Rupert offers a peaceful backdrop for remote working, while also providing opportunities for outdoor activities during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Rupert vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Rupert with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo 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.
What are popular rental amenities in Rupert?
In Rupert, popular vacation rental amenities include kitchens, which allow guests to prepare their own meals during their stay. Many rentals also feature cozy fireplaces, providing a warm atmosphere for relaxation after a day of outdoor activities. Decks or patios are common, giving guests a private outdoor space to enjoy the scenic surroundings. Additionally, some properties are equipped with blenders for making smoothies or cocktails, enhancing the convenience for those who enjoy cooking.
When is the best time to visit Rupert for a vacation rental?
The best time to visit Rupert for a vacation rental is during the peak season, which spans from January to March. March, in particular, is a favorite among travelers seeking the thrill of winter sports and the charm of the snowy landscape. During this time, visitors can enjoy skiing, snowboarding, and snowshoeing at nearby resorts, all while surrounded by the picturesque views of the Green Mountains.

In March, temperatures typically range from the low 20s to mid-40s Fahrenheit, providing a brisk yet invigorating atmosphere great for outdoor activities. The snow conditions are generally excellent, allowing for memorable days on the slopes or cozy evenings by the fire. Additionally, this period attracts a vibrant community of winter sports enthusiasts, creating a lively yet comfortable environment for adventure seekers.

For those looking for a more budget-friendly option, February is a wonderful month to consider. While it may be considered the low season, it still offers a chance to experience the winter wonderland without the crowds. Visitors can enjoy the tranquility of the snow-covered trails and perhaps even find some hidden gems off the beaten path.

Ultimately, your ideal time to visit Rupert will depend on whether you prefer the bustling energy of peak winter activities in March or the quieter charm of February's serene landscapes.
How early should I book a Rupert vacation rental?
Book your Rupert vacation rental 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 Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Rupert, Vermont, United States of America?
In Rupert, Vermont, visitors can enjoy the serene beauty of the Green Mountains, with many outdoor activities available throughout the year. The town's picturesque landscape makes it a great spot for hiking and enjoying nature's tranquility. Nearby, the Taconic Mountains offer additional opportunities for hiking, especially in the nearby state parks, such as Bomoseen State Park, which features a lovely lake for swimming and picnicking.

The charming village area of Rupert itself boasts a quaint rural atmosphere, where visitors can find local artisan shops and cozy cafes. The Rupert Historical Society operates a small museum that showcases the town's rich history, providing insights into the region's past.

For those interested in skiing and winter sports, nearby areas like the Okemo Mountain Resort and Killington are easily accessible, offering a variety of winter activities. In the summer, the scenic Vermont countryside is great for biking and exploring the local farms, where visitors can savor fresh produce and homemade goods.
Can I change or cancel my Rupert home rental booking on Vrbo?
To find Rupert vacation rentals with free cancellation, just use Vrbo'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". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Rupert vacation rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

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