Bennington vacation rentals

We found 1,720 vacation rentals — enter your dates for availability

Discover a selection of 14 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:Apr 17 - Apr 24

Image gallery for Country Getaway Lodge/Ranch near Saratoga Springs

Living area
9.8 out of 10, Exceptional, (51 reviews)
Exceptional
(51 reviews)

Country Getaway Lodge/Ranch near Saratoga Springs

valley Falls

26% off
Price is $521
$3,647 for 7 nights
All fees included
Country Getaway Lodge/Ranch near Saratoga Springs

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Find out more about Bennington

Why visit Bennington

  • Outdoor Adventure: Enjoy skiing, hiking, and family-friendly activities in the nearby national and state parks.
  • Rich History: Explore Bennington's historical sites, including museums and landmarks that highlight its cultural heritage.
  • Vibrant Arts Scene: Discover local arts centers featuring galleries, performances, and community events.
  • Charming Neighborhoods: Stroll through picturesque neighborhoods filled with friendly locals and unique shops.
  • Diverse Accommodations: Choose from cozy cabins, stylish condos, or private vacation homes for a perfect stay.

Popular types of accommodation in Bennington

Planning a getaway to Bennington? You're in for a treat. Discover the charm of Vermont with our top-notch vacation rentals, including houses, cozy cabins, and stylish condos. Whether you’re looking for spacious house rentals or comfortable bedroom rentals, Bennington has the perfect option for you. Enjoy transparency and savings as you explore your ideal vt rentals and Vermont apartments. Your unforgettable vacation starts here.

  • Houses: The top choice for travelers in Bennington, offering spacious and comfortable accommodations ideal for families or groups.
  • Condos: A popular option for visitors seeking modern amenities and convenient locations, perfect for a relaxing stay.
  • Cabins: Cozy and charming, cabins provide a rustic retreat surrounded by nature, ideal for a peaceful getaway.
  • Apartments: A practical choice for solo travelers or couples, offering home-like comfort in the heart of Bennington.
  • Cottages: Quaint and inviting, cottages are perfect for a romantic escape or a quiet family vacation.**

Top attractions in and around Bennington

Bennington, Vermont, offers a perfect blend of adventure and culture for travelers. From skiing and outdoor sports to exploring historic colleges and vibrant arts centers, there's something for everyone. The nearby national and state parks provide breathtaking scenery and family-friendly activities, making it an ideal destination for those seeking both relaxation and excitement. Enjoy the rich history and natural beauty that Bennington has to offer.

  • Bennington College: Nestled 3 miles from Bennington, this historic college is known for its progressive education and vibrant arts scene, attracting creative minds and offering a unique cultural atmosphere.
  • Bennington Battle Monument: Located in the heart of Bennington, this impressive monument commemorates a pivotal Revolutionary War battle, providing visitors with a deep sense of history and stunning views from its observation deck.
  • Bennington Museum: Situated downtown, this museum showcases local history and art, featuring exhibits on the region's heritage, including its famous Bennington Pottery and a notable collection of American art.

Things to do recommended for couples

For a romantic getaway in Bennington, indulge in outdoor adventures at Mount Snow, just 16 miles away, or enjoy the cozy atmosphere at Prospect Mountain Cross-Country and Nordic Ski Centers. Embrace the snowy landscapes together and create unforgettable memories in this charming Vermont town.

Things to do recommended for families

Families visiting Bennington can explore the stars at Hopkins Observatory, enjoy the serene beauty of Windsor Lake Park, and appreciate art at The Georgi Museum. Each location offers unique experiences that blend fun and relaxation, perfect for creating lasting memories together.

Things to do recommended for groups

Groups visiting Bennington can explore the Hemmings Motor News Car Lover's Convenience Store for a unique automotive experience. Hiking the scenic Harmen Hills Trail offers adventure and beautiful outdoor views, while visiting Harmon Hill provides a perfect spot to soak in the area's natural beauty.

*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 Bennington

When planning your trip—whether you're traveling with a group, family, pets, or seeking extended stays—be sure to use the appropriate filters to match your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Bennington with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Bennington with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, and look for amenities that cater to their age, like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Bennington: For many families, a trip isn't truly satisfying without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds to ensure that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Bennington: If you're searching for vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in and around Bennington

Bennington, Vermont, offers a delightful blend of adventure and history, making it an ideal destination for tourists. From thrilling ski resorts to charming family-friendly neighborhoods, visitors can enjoy a vibrant atmosphere filled with friendly locals. Explore the beautiful Bennington County, with its rich historical sites and shopping opportunities nearby. Whether you seek cozy family homes or budget-friendly accommodations, Bennington promises an unforgettable vacation experience for everyone.

  • Williamstown: Nestled 12 miles from Bennington, Williamstown is a charming city known for its rich cultural heritage and outdoor adventures. Visitors flock here for skiing and other sports, with access to fantastic ski resorts and fields. The city is home to the prestigious Williams College, where you can explore historic architecture and beautiful campus grounds. The surrounding mountains and serene lake provide stunning backdrops for hiking, photography, and relaxation, making Williamstown a perfect blend of adventure and tranquility.
  • North Adams: Located 14 miles away from Bennington, North Adams is a vibrant city that offers a unique mix of outdoor and cultural experiences. Known for its adventurous spirit, visitors can enjoy skiing at nearby resorts or explore the stunning landscapes of the surrounding mountains. North Adams is also home to the renowned Massachusetts Museum of Contemporary Art (Mass MoCA), which showcases cutting-edge art and hosts various cultural events. The city's public art installations and cultural centers further enhance its artistic vibe, making it a must-visit for art lovers and outdoor enthusiasts alike.
  • Woodford: Just a short distance from Bennington, Woodford is a picturesque village perfect for those seeking outdoor adventure. Known for its skiing opportunities, visitors can hit the slopes at the nearby ski resorts and enjoy the stunning natural surroundings. Woodford is also home to beautiful lakes and the scenic Woodford State Park, where you can hike, fish, or simply unwind in nature. The local visitor center provides valuable information on the area’s trails and attractions, making it an ideal base for exploring the great outdoors.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 LowSlightly Low
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 CloudyAverageAverage
November36.9°F (2.7°C)Light RainMostly SunnyModerately LowAverage
December28.2°F (-2.1°C)Light RainMostly CloudyAverageSlightly High

Booking with Vrbo is a breeze

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

Unlock savings with One Key

Plan your group getaway by booking an eligible Vrbo and earn OneKeyCash on your reservation. Being the organizer really pays off. When you join our travel rewards program, One Key, you can immediately access member discounts and earn OneKeyCash on qualifying bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or easily manage your travel arrangements. You can find the properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/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:

  • Mount Snow (15.7 mi / 25.3 km)
  • Stratton Mountain Resort (21.5 mi / 34.6 km)
  • Prospect Mountain Nordic Ski Center (6.8 mi / 10.9 km)
  • Prospect Mountain Cross-Country Ski Center (7.2 mi / 11.6 km)
  • Sugar Shack (14.4 mi / 23.1 km)
  • The Hermitage Club (15.9 mi / 25.5 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)
  • Harriman Reservoir (16.5 mi / 26.5 km)
  • Mount Greylock State Reservation (16.8 mi / 27 km)
  • Mount Equinox (16.9 mi / 27.2 km)
  • Mount Greylock (17.2 mi / 27.6 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 planning a vacation in Bennington, Vermont, one of the best areas to consider for your stay is the downtown district. This charming area is not only picturesque, but it also offers a vibrant atmosphere filled with quaint shops, local eateries, and a rich history. Staying here places you within walking distance of attractions like the Bennington Museum, which showcases the region's artistic heritage, and the historic Bennington Battle Monument, providing stunning views and a glimpse into the area's Revolutionary War history. There are numerous vacation rental properties available in this area, offering a variety of options to suit different preferences and budgets.

Another great neighborhood to explore is the Old Bennington area, known for its beautiful historic homes and serene surroundings. This neighborhood is close to the Bennington Center for the Arts, which hosts a variety of exhibits and performances, and the charming Robert Frost Stone House Museum, where you can delve into the life and works of the famed poet. The Old Bennington area typically has a good selection of vacation rentals that provide a cozy and tranquil retreat, great for unwinding after a day of exploration.

Both areas offer great experiences that allow you to enjoy the best of Bennington while being conveniently located to access its many attractions.
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 traveling 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. To get the best value, book early and take advantage of Vrbo's free rewards program.
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, travelers should consider accommodations in the nearby areas of Wilmington and Stratton. Wilmington, located approximately 20 minutes from Bennington, offers a variety of vacation rentals that cater to ski enthusiasts, particularly those heading to the Stratton Mountain Resort. Many properties in this area provide amenities such as ski-in/ski-out access, hot tubs, and spacious living areas, making them ideal for families or groups looking to enjoy the slopes.

In Stratton, visitors can find a range of lodgings, from luxurious condos to cozy cabins, often featuring wood-burning stoves or fireplaces, fully equipped kitchens, and outdoor decks with beautiful views of the mountains. This area is known for its vibrant après-ski scene, with various dining and shopping options close by, ensuring that guests have plenty to do after a day on the slopes.

Additionally, the picturesque town of Bennington itself offers charming inns and bed-and-breakfasts, which provide a more intimate experience. These accommodations often include complimentary breakfasts and cozy common areas, great for unwinding after a day of skiing. The surrounding Green Mountains also offer hiking trails and scenic vistas for those looking to explore beyond the ski resorts.
What is the most popular type of vacation rental accomodation in Bennington?
In Bennington, vacation houses are the most popular type of rental, with about 15 available throughout the area. These homes typically feature multiple bedrooms, spacious living areas, and often come with outdoor spaces for relaxation and gatherings. Many vacation houses also include fully equipped kitchens, making it convenient for families or groups to prepare their meals. Additionally, there are several apartments, cottages, and cabins available, offering a variety of choices for travelers seeking a different experience. These options tend to provide a cozy atmosphere, ideal for enjoying the picturesque Vermont landscape and exploring local attractions like Bennington Battle Monument and the charming downtown area.
Are there any family house rentals in Bennington?
In Bennington, Vermont, there are numerous family-friendly house rentals available, with around 23 options throughout the area. Visitors can find properties located within charming neighborhoods that capture the essence of New England. Many homes feature spacious living rooms superb for family gatherings, fully equipped kitchens for preparing meals together, and outdoor spaces like decks or yards for children to play.

The locale is rich in natural beauty, with the Green Mountains offering ample opportunities for hiking and outdoor activities. Families can also enjoy local attractions such as the Bennington Battle Monument, which provides historical insights and stunning views.
Can I rent a vacation home with a pool or hot tub in Bennington?
In Bennington, Vermont, there are several vacation homes available for rent that feature pools and hot tubs. This charming town is surrounded by beautiful landscapes, making it an excellent destination for travelers seeking relaxation and outdoor activities. Many of the rentals come equipped with private pools, hot tubs, and spacious outdoor areas where guests can unwind and enjoy the serene environment. Inside, you can expect modern amenities such as fully equipped kitchens, comfortable living spaces, and often additional features like fireplaces and game rooms, which are great for family gatherings or a cozy retreat.
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. 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 Bennington?
In Bennington, travelers can find a variety of pet-friendly house rentals that cater to those looking to enjoy the picturesque Vermont landscape. With around 14 options available, many of these rentals come equipped with amenities such as spacious backyards, fully equipped kitchens, and cozy living areas, making them ideal for families or groups traveling with pets.

The area is rich in outdoor activities, with nearby parks and nature spots like the Bennington Battle Monument and the Green Mountain National Forest providing plenty of opportunities for hiking and exploring the beautiful surroundings. These locations often welcome pets, allowing visitors to enjoy the great outdoors together. Additionally, some rentals may feature amenities like fire pits and outdoor seating areas, superb for relaxing after a day of adventure. See all pet-friendly rentals in Bennington.
Are there any remote work vacation rentals in Bennington?
In Bennington, Vermont, there are numerous options for remote work vacation rentals, with around 30 available throughout the area. Many of these properties cater specifically to remote workers, offering essential amenities such as high-speed Wi-Fi, dedicated office spaces, and comfortable workstations with desks and chairs. This makes it easy to maintain productivity while enjoying a scenic getaway.

The town itself is rich in history and surrounded by beautiful landscapes, providing a great backdrop for breaks between work sessions. Nearby attractions include the Bennington Battle Monument and the serene parks that offer walking trails and picturesque views. Travelers can expect charming accommodations that often feature cozy living areas and full kitchens, allowing for a comfortable and convenient stay. 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 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 Bennington?
In Bennington, popular vacation rental amenities typically include WiFi, kitchens, coffee and tea makers, onsite parking, and patios. These amenities provide travelers with the comforts of home, allowing them to prepare their meals, stay connected, and enjoy the fresh air in private outdoor spaces.
When is the best time to visit Bennington for a vacation rental?
March marks the beginning of the peak season in Bennington, Vermont, drawing visitors eager to enjoy the stunning landscape and vibrant local culture. From March through May, travelers can immerse themselves in a variety of outdoor activities, including hiking and exploring the region's rich history, all while enjoying the refreshing spring temperatures that typically range from the upper 30s to the mid-60s Fahrenheit.

During this peak period, the charming town of Bennington comes alive with events and festivals, inviting you to experience art walks, farmers' markets, and more. The scenery is particularly captivating as the snow begins to melt, revealing lush greenery and blooming flowers, superb for leisurely strolls and photography.

For those who are budget-conscious yet still wish to experience Bennington, January offers a quieter alternative. While the temperatures can dip into the low 20s Fahrenheit, this month is ideal for cozying up in a vacation rental and enjoying the peaceful winter atmosphere. You can also take advantage of off-season rates, which provide excellent value for your stay.

Ultimately, the best time to visit Bennington depends on whether you prefer the bustling energy of spring and early summer or the tranquil charm of winter.
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 explore several attractions that showcase the town's rich history and beautiful landscapes. The Bennington Battle Monument, located in the historic district, offers panoramic views of the surrounding area and is a significant site commemorating the Revolutionary War. The charming downtown area features unique shops, galleries, and restaurants, providing a taste of local culture.

Nature enthusiasts can visit the Bennington Museum, which houses a collection of American art and historical artifacts, including works by local artists. Nearby, the picturesque Park McCullough House offers a glimpse into 19th-century architecture and history.

For those who enjoy the outdoors, the surrounding Green Mountains provide opportunities for hiking, especially at the nearby Long Trail, which is famous for its scenic vistas and diverse wildlife.
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 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 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.
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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