Bennington vacation rentals

We found 1,724 vacation rentals — enter your dates for availability

Discover a selection of 13 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:Jun 12 - Jun 19

Image gallery for New Lakefront Log Home

Summer view from the lake
9.8 out of 10, Exceptional, (100 reviews)
Exceptional
(100 reviews)

New Lakefront Log Home

Wilmington

13% off
Price is $689
$4,820 for 7 nights
All fees included
New Lakefront Log Home

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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:

  • 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)
  • Waubeeka Golf Links (15.7 mi / 25.3 km)
  • Mount Snow (15.7 mi / 25.3 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)
  • 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)

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, Vermont, United States of America when booking a vacation rental?
When considering the best area to stay in Bennington, Vermont, one highly recommended neighborhood is the downtown area. This vibrant section of the town offers a charming mix of history and modern amenities, making it an ideal base for your vacation. You'll find a variety of vacation rental options here, from cozy cottages to spacious homes, suiting different group sizes and preferences.

Staying in downtown Bennington allows easy access to some of the area's top attractions, such as the Bennington Museum, which showcases local art and history, and the iconic Bennington Battle Monument, offering stunning views of the surrounding landscape. Additionally, the area is known for its delightful dining options and unique shops, providing a great blend of relaxation and exploration.

Another appealing option is the nearby Old Bennington neighborhood, known for its historic architecture and picturesque surroundings. This area is close to the Bennington College campus, which often hosts cultural events and performances. Visitors can also enjoy the scenic beauty of the nearby Green Mountains, making it an excellent choice for outdoor enthusiasts.
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 the best ski resort rentals near Bennington, Vermont, travelers should consider accommodations in the nearby town of Wilmington, which is just a short drive from the Mount Snow ski area. Here, visitors can find a variety of vacation rentals ranging from cozy cabins to spacious chalets, many of which come equipped with amenities like hot tubs, wood-burning stoves, and fully stocked kitchens, superb for unwinding after a day on the slopes.

Additionally, the area around Stratton Mountain offers another excellent option, with a selection of ski-in/ski-out properties that provide utmost convenience for ski enthusiasts. These rentals often feature modern amenities such as large living areas, fireplaces, and balconies with scenic mountain views. The proximity to the Stratton Village also means easy access to shops, dining, and après-ski activities.

In both Wilmington and Stratton, visitors can enjoy the charming New England atmosphere, with local eateries and winter activities like snowshoeing and cross-country skiing available nearby.
What is the most popular type of vacation rental accomodation in Bennington?
In Bennington, vacation houses are the most common rental option, with about 11 available throughout the area. These homes often provide spacious living areas, multiple bedrooms, fully equipped kitchens, and outdoor spaces such as decks or gardens, making them ideal for families or larger groups. Additionally, several apartments, cottages, and cabins can be found, offering diverse choices for travelers seeking a cozy retreat.
Are there any family house rentals in Bennington?
In Bennington, Vermont, there are plenty of family-friendly house rentals available—specifically, around 22 options throughout the area. This charming town, located in the Green Mountains, is a wonderful place for families to explore together. Many of these properties offer spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces where children can play and enjoy the fresh air.

Visitors can find amenities such as Wi-Fi, air conditioning, and even cozy fireplaces for those cooler evenings. The town's proximity to attractions like the Bennington Battle Monument and the Bennington Museum makes it easy for families to engage in local history and culture. Additionally, the surrounding natural beauty offers opportunities for hiking, biking, and other outdoor activities.
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, making it an appealing destination for travelers seeking relaxation and recreation. The properties are often situated in scenic settings, providing a tranquil atmosphere superb for unwinding after a day of exploring the Green Mountains. Many rentals come equipped with spacious outdoor areas, allowing for enjoyable gatherings and activities.

Travelers can expect amenities such as private pools, hot tubs, fully equipped kitchens for home-cooked meals, and comfortable living spaces designed for family or group enjoyment. Find your rental in Bennington with a pool or a hot tub.
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, there are several pet-friendly house rentals available, offering travelers a comfortable stay while accommodating their furry friends. Many of these vacation homes come equipped with amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces where pets can play.

The rentals are often situated close to local parks and recreational areas, providing convenient opportunities for walks and outdoor activities with pets. For instance, Bennington Battle Monument Park features expansive grounds and trails ideal for exploring with dogs. Additionally, the nearby Green Mountain National Forest offers hiking paths and beautiful scenery, making it a great destination for those looking to enjoy nature with their pets.
Are there any remote work vacation rentals in Bennington?
In Bennington, Vermont, there are numerous remote work-friendly vacation rentals available, with around 28 options to choose from. Many of these properties are equipped with essential amenities such as free Wi-Fi, ensuring a reliable internet connection for those working remotely. Accommodations often include spacious work areas, comfortable furnishings, and well-equipped kitchens, allowing for a productive and enjoyable stay.

The town itself is rich in history and surrounded by beautiful landscapes, making it an ideal backdrop for a workcation. Travelers can explore nearby attractions like the Bennington Battle Monument and the picturesque Green Mountains during their downtime. 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 cater to a variety of traveler needs, ensuring a comfortable stay. Most rentals come equipped with kitchens, allowing guests to prepare their own meals, which is particularly convenient for families or groups. Onsite parking is commonly available, making it easy for visitors to explore the surrounding areas without the hassle of finding parking. Many properties also feature coffee and tea makers, superb for those who enjoy their morning brew. For pet owners, several rentals permit pets, offering a welcoming environment for furry companions. Additionally, many rentals include decks or patios, providing outdoor spaces to relax and enjoy the picturesque Vermont scenery.
When is the best time to visit Bennington for a vacation rental?
The best time to visit Bennington for a vacation rental is during the peak season from March to May. This period draws travelers who appreciate the blend of outdoor adventures and cultural experiences as the landscape transforms with the arrival of spring. As the temperatures rise, typically ranging from the low 30s to the mid-60s Fahrenheit, visitors can enjoy everything from hiking in the Green Mountains to exploring the charming downtown area filled with galleries and local shops.

March, in particular, stands out as a popular month to visit Bennington. During this time, outdoor enthusiasts can take advantage of the tail end of skiing conditions in nearby resorts while also witnessing the early buds of spring. The pleasant weather makes it a comfortable option for sightseeing and outdoor activities, allowing you to soak in the region's natural beauty.

For those seeking a more budget-friendly experience, consider planning your trip in January. This month offers a quieter atmosphere, great for cozy getaways and introspective walks through the snow-covered landscapes. The serene environment can be a delightful escape, providing a unique perspective on Bennington's winter charm.
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, Vermont, United States of America?
In Bennington, Vermont, visitors can explore a range of charming attractions that reflect the area's rich history and natural beauty. The Bennington Battle Monument stands tall, commemorating a significant Revolutionary War battle and offering stunning views from its observation deck. Nearby, the Bennington Museum showcases local art and history, including works by the renowned artist Grandma Moses.

The picturesque downtown area features quaint shops and eateries, superb for leisurely strolls. The Old First Church and its historic cemetery, where the poet Robert Frost is buried, add a touch of cultural significance to the area. For outdoor enthusiasts, the surrounding Green Mountains provide ample opportunities for hiking, especially in the nearby Bennington State Park, which offers scenic trails and stunning vistas.
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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