Bennington vacation rentals

We found 1,612 vacation rentals — enter your dates for availability

Discover a selection of 16 homes and other vacation rentals in Bennington that are perfect for your trip. Whether you're staying in a vacation rental with friends, family, or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include WiFi and a washer and dryer. You're sure to find a rental to meet everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Bennington

Showing deals for:Nov 21 - Nov 28

Image gallery for Cozy 2-bedroom cabin near Mount Snow 3 min drive

Exterior
9.6 out of 10 rating
Exceptional
(8 reviews)

Cozy 2-bedroom cabin near Mount Snow 3 min drive

West Dover, VT

10% off
Price is CA $267
CA $2,606 total
includes taxes & fees
Cozy 2-bedroom cabin near Mount Snow 3 min drive

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Find out more about Bennington

Find out more about Bennington

Why visit Bennington

  1. Adventure Sports: Bennington is a prime location for skiing and outdoor activities, perfect for thrill-seekers.
  2. Cultural Richness: Experience a blend of historic colleges and vibrant arts centres that showcase local talent.
  3. Scenic Neighborhoods: Explore charming areas like North Bennington, offering a relaxing atmosphere and friendly vibes.
  4. Family-Friendly Activities: Enjoy a variety of excursions suitable for all ages, ensuring fun for the entire family.
  5. Unique Accommodations: Choose from private homes, cozy condos, and charming cabins for a memorable stay.

Popular types of accommodation in Bennington

If you're exploring vacation rentals in Bennington, you're in for a treat! Our most sought-after accommodations include houses, cozy condos, and charming cabins. Whether you're looking for a spacious apartment in Bennington or a quaint getaway, we have various options to suit your needs. Discover the perfect bennington properties for your next adventure, ensuring transparency, savings, and reassurance throughout your stay.

  • Houses: The top choice among travellers, offering spacious accommodations ideal for families or groups seeking comfort and privacy.
  • Condos: A popular option for those desiring modern amenities and a central location, perfect for enjoying local attractions.
  • Cabins: Ideal for nature enthusiasts, these rentals provide a rustic experience while being surrounded by Vermont's stunning landscapes.
  • Apartments: A convenient choice for couples or solo travellers looking for a home-like atmosphere in the heart of Bennington.
  • Cottages: These quaint and charming retreats offer a cozy ambiance, perfect for a romantic getaway or peaceful escape.**

Top attractions in Bennington

Bennington, Vermont, is a fantastic destination for skiing and adventure sports, offering a rich blend of historic colleges, vibrant arts centres, and beautiful national and state parks. This charming locale provides a perfect mix of cultural experiences and outdoor activities, making it ideal for families and travellers seeking both relaxation and adventure. Explore the area’s unique attractions and immerse yourself in the captivating local culture during your visit.

  1. Bennington College: Established in a picturesque setting, this historic college offers a rich cultural atmosphere with beautiful architecture and lush grounds, perfect for leisurely strolls and appreciating the arts.
  2. Bennington Battle Monument: A striking tribute to the Revolutionary War, this towering monument provides a glimpse into American history and offers stunning views of the surrounding landscape.
  3. Bennington Center for the Arts: This vibrant arts centre showcases a diverse range of exhibits and performances, making it a hub for creativity and cultural enrichment in the community.

Things to do recommended for couples

Planning a romantic getaway in Bennington? Enjoy skiing together at nearby Mount Snow, just 25.7km away. For a more local vibe, visit the Prospect Mountain Cross-Country Ski Center or the Prospect Mountain Nordic Ski Center, both offering beautiful trails for an adventurous couple experience.

Things to do recommended for families

Your family will love exploring the cosmos at the Hopkins Observatory, relaxing at Windsor Lake Park, and appreciating art at The Georgi Museum, all offering enjoyable experiences within a short drive from Bennington. These destinations provide a perfect blend of entertainment and relaxation for everyone.

Things to do recommended for groups

Groups visiting Bennington can explore the Hemmings Motor News Car Lover's Convenience Store, showcasing classic vehicles. For outdoor enthusiasts, Harmon Hill offers beautiful scenery, while the Harmen Hills Trail provides a thrilling hiking adventure amidst nature's beauty.

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

When planning your trip, whether you're going 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 for you.

  • Traveling to Bennington with a group: Think about how many bedrooms you require, along with amenities like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Bennington with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, as well as access to suitable amenities, like a private swimming pool. Additionally, thinking about your location in relation to family-friendly attractions can greatly enhance your experience.
  • Taking your pets with you to Bennington: For many, a family getaway wouldn’t feel complete without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Bennington: If you're in search of vacation rentals offering discounts for 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 options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Bennington

Bennington, Vermont, offers a delightful mix of adventure and cultural exploration. From the charming streets of North Bennington to the tranquil atmosphere of the quiet north end, visitors will find a perfect vacation home to unwind. Enjoy family-friendly excursions and immerse yourself in the vibrant arts scene. Discover the welcoming vibe of the surrounding neighborhoods, including the enchanting Oregonian Oasis, making your stay in Bennington a memorable experience filled with friendly faces and exciting activities.

  • Williamstown: Nestled 19.3km from Bennington, Williamstown is a charming city that attracts visitors with its vibrant outdoor activities and sports experiences. Renowned for its ski resorts and adventure opportunities, this locale is a winter wonderland for skiing enthusiasts. Beyond skiing, visitors can explore the local historic college university, which adds a touch of culture and academia to your travels. The surrounding mountainous landscapes and pristine lakes offer breathtaking views and ample opportunities for hiking and relaxation. Williamstown is a perfect blend of outdoor adventure and historical significance.
  • Woodford: Just a stone’s throw from Bennington, Woodford is a picturesque village that captivates nature lovers and adventure seekers alike. Known for its outdoor experiences, this village is home to ski fields and resorts that promise exhilarating winter sports. The nearby lakes and the expansive national state park provide a serene backdrop for hiking, fishing, and wildlife viewing. Don't forget to visit the local visitor centre for insights on the area’s natural beauty and recreational activities. Woodford is a perfect getaway for those looking to immerse themselves in Vermont's stunning landscapes.
  • Old Bennington: Located in the vicinity of Bennington, Old Bennington is a quaint village steeped in history and outdoor charm. Visitors flock here for skiing and adventure sports, with nearby ski fields and resorts catering to winter sports enthusiasts. The area boasts beautiful lakes and notable landmarks such as monuments and stadiums that highlight its rich heritage. Old Bennington is an ideal destination for those wishing to experience both the thrill of outdoor activities and the allure of historical attractions, making it a delightful stop on your Vermont journey.

Best time to go to Bennington

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

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January21.2°F (-6.0°C)Light RainMostly CloudyAverageSlightly High
February23.4°F (-4.8°C)Light RainMostly CloudyModerately HighSlightly High
March31.5°F (-0.3°C)Light RainMostly CloudyAverageAverage
April43.7°F (6.5°C)Light RainMostly CloudyModerately LowSlightly Low
May56.5°F (13.6°C)Light RainMostly SunnyModerately LowAverage
June63.9°F (17.7°C)Light RainMostly SunnyAverageAverage
July70.0°F (21.1°C)Light RainMostly SunnyModerately HighAverage
August68.2°F (20.1°C)Light RainMostly SunnyModerately HighAverage
September61.0°F (16.1°C)Light RainMostly SunnyAverageSlightly Low
October49.3°F (9.6°C)Light RainMostly CloudyAverageSlightly Low
November36.9°F (2.7°C)Light RainMostly SunnyModerately LowAverage
December28.2°F (-2.1°C)Light RainMostly CloudyAverageSlightly High

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay often results in significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to refine your search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers a user-friendly platform for planning your trips. You can easily start new journeys, continue from where you last left off, or manage and view your travel arrangements. All the properties you've saved or reserved are neatly organized into categories: Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Adventurous Bennington will entice you

Enjoy the museums and other features of Bennington. This city's skiing, mountain views and hiking draw many visitors. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Bennington

Do you want to discover attractions to visit in the city? Travelers enjoy Bennington for its skiing, hiking and golfing. Venture out of your cozy vacation rental and experience everything that makes Bennington a fun spot to vacation. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Prospect Mountain Cross-Country Ski Center (7.2 mi / 11.6 km)
  • Sugar Shack (14.4 mi / 23.1 km)
  • Waubeeka Golf Links (15.7 mi / 25.3 km)
  • Mount Snow (15.7 mi / 25.3 km)
  • The Hermitage Club (15.9 mi / 25.5 km)
  • The Hermitage Golf Club (16.5 mi / 26.6 km)

Exploring the mountains and other natural features in Bennington

Whether you're an active traveler or just want to take in the scenery, Bennington is a great place to spend some time outside. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city center:

  • Lake Shaftsbury State Park (9.6 mi / 15.4 km)
  • Grafton Lakes State Park (14.1 mi / 22.7 km)
  • Taconic Lake (14.4 mi / 23.1 km)
  • Campers Beach (15 mi / 24.1 km)
  • Windsor Lake Park (15 mi / 24.1 km)
  • Harriman Reservoir (16.5 mi / 26.5 km)

Seasonal weather averages in Bennington

Bennington is well known for its skiing. If you've planned your trip around snowy activities, consider visiting in January, March, February or December, when snowfall averages 8 inches and temperatures average 26°F.

Traveling to and around Bennington

Fly into Albany Intl. Airport (ALB), the closest airport, located 31.7 mi (51 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Pittsfield, MA (PSF-Pittsfield Municipal), which is 31.9 mi (51.4 km) away.

Frequently asked questions

What is the best area to stay in Bennington when booking a vacation rental?
When considering a vacation rental in Bennington, Vermont, the downtown area is an excellent choice. This vibrant neighbourhood boasts a charming atmosphere, with a variety of shops, cafes, and restaurants that cater to all tastes. Staying here puts you within walking distance of great attractions such as the Bennington Battle Monument, which offers stunning views of the surrounding landscape, and the Bennington Museum, where you can explore fascinating exhibits related to the region's history and art. The downtown area typically has a decent selection of properties, ranging from cosy apartments to more spacious homes, making it suitable for different group sizes and preferences.
How much does it cost to rent a vacation home in Bennington?
Prices for vacation rentals in Bennington 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. Vrbo offers something for every taste and budget, from affordable rentals in Bennington to more spacious homes.
Are there any discounts for Bennington vacation house rentals?
You can find great discounts on house rentals in Bennington 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 Bennington ski resort rentals?
For ski resort rentals near Bennington, Vermont, travellers will want to consider the nearby area of Mount Snow, which is approximately a half-hour drive away. In the charming town of Wilmington, just a short distance from Mount Snow, visitors can find a variety of rental options, including cosy chalets and spacious cabins that cater to both families and groups. Many of these properties feature essential amenities such as fully equipped kitchens, comfortable living areas with fireplaces, and outdoor spaces superb for enjoying the scenic mountain views.

Further along, the Stratton Mountain area also offers additional accommodation options. Here, travellers can discover ski-in/ski-out lodges and townhouses that provide easy access to the slopes. These rentals typically come equipped with modern conveniences like Wi-Fi, hot tubs, and community amenities such as heated pools or fitness centres, enhancing the overall experience after a day on the mountain.
What is the most popular type of vacation rental accomodation in Bennington?
In Bennington, vacation houses are the most popular type of rental accommodation, with about 15 available throughout the area. These houses typically provide spacious living areas, fully equipped kitchens, and outdoor spaces, making them ideal for families or groups looking for comfort and flexibility. Additionally, there are several apartments, cottages, and cabins scattered around town, each offering a unique charm and a cozy feel. Many of these properties are located near local attractions such as the Bennington Battle Monument and the picturesque downtown area, allowing guests to easily explore the rich history and natural beauty of the region.
Are there any family house rentals in Bennington?
In Bennington, Vermont, there are numerous family-friendly house rentals available—approximately 25 options to choose from. This charming town offers a range of accommodations suitable for families, with many properties located near the scenic Green Mountains. Visitors can find homes that provide spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces superb for children to run and play.
Can I rent a vacation home with a pool or hot tub in Bennington?
In Bennington, there are several vacation homes available for rent that feature pools and hot tubs, making it an appealing destination for those seeking relaxation and leisure. The town, located in the picturesque Green Mountains of Vermont, offers a variety of neighbourhoods where these properties can be found, often set against a backdrop of stunning natural beauty.
Can I find long-stay vacation rentals in Bennington?
A long-stay vacation rental in Bennington 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Bennington?
In Bennington, Vermont, there are several pet-friendly house rentals available that cater to travellers looking to enjoy the beauty of the Green Mountain State. Many of these properties come equipped with convenient amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can roam freely.

The area offers a charming mix of rural and small-town vibes, providing easy access to local attractions and outdoor activities. Not far from Bennington, visitors can explore the scenic landscapes of the Green Mountain National Forest, offering hiking trails that are great for adventures with pets. Additionally, the nearby Bennington Battle Monument and local parks provide opportunities for leisurely strolls and outdoor enjoyment.
Are there any remote work vacation rentals in Bennington?
In Bennington, Vermont, there are numerous remote work vacation rentals available, with around 32 options to choose from. This charming town, located in the picturesque Green Mountains, offers a variety of properties that cater to remote workers. Many of these rentals come equipped with essential amenities such as high-speed Wi-Fi, dedicated workspace areas with desks and chairs, and even computer monitors for a more comfortable setup. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Bennington vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Bennington 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 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 Bennington?
In Bennington, popular vacation rentals typically feature essential amenities for a comfortable stay, with most properties offering a fully equipped kitchen, including a microwave, stovetop, and refrigerator. Many rentals also provide cookware, dishware, and utensils, allowing guests to prepare their own meals during their visit.
When is the best time to visit Bennington for a vacation rental?
March is the most popular time to visit Bennington, Vermont, as it marks the beginning of the peak season that extends through May. This vibrant period attracts visitors who are eager to experience the beauty of the Green Mountains as they awaken from winter. Outdoor enthusiasts will find a wealth of activities, from exploring picturesque hiking trails to enjoying the local arts scene, all while surrounded by stunning landscapes that Vermont is famous for.

During these spring months, temperatures begin to rise, typically hovering in the low teens Celsius. This makes for comfortable conditions to explore Bennington's charming downtown area, where you can discover unique shops, art galleries, and delightful eateries. Spring also brings the opportunity to witness the stunning transformation of the region, with blooming flowers and lush greenery enhancing the already picturesque scenery.

For those looking for a more budget-friendly option, consider visiting in January. This month, while quieter, offers a unique charm with its winter wonderland backdrop. You can enjoy outdoor activities like snowshoeing or cross-country skiing, and you may find some great deals on vacation rentals during this off-peak period.
How early should I book a Bennington vacation rental?
Book your Bennington 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 Bennington?
In Bennington, Vermont, visitors can immerse themselves in a rich tapestry of history and natural beauty. One of the top attractions is the Bennington Battle Monument, which offers panoramic views of the surrounding landscape and commemorates a significant Revolutionary War battle. The nearby Bennington Museum showcases local art and history, including works by popular American artists and exhibits on the region's heritage.
Can I change or cancel my Bennington home rental booking on Vrbo?
To find Bennington 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 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 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Bennington 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.

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