Bennington vacation rentals

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Discover a selection of 17 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

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Find out more about Bennington

Find out more about Bennington

Why visit Bennington

  1. Outdoor Adventures: Enjoy skiing, hiking, and exploring stunning national parks and beautiful lakes.
  2. Rich Local History: Immerse yourself in the area's cultural heritage while discovering historical sites.
  3. Scenic Beauty: Take in breathtaking landscapes and picturesque views that define the region.
  4. Family-Friendly Activities: Engage in a variety of activities suitable for all ages, ensuring fun for the whole family.
  5. Charming Accommodations: Choose from cozy condos, spacious homes, and inviting apartments for a memorable stay.

Popular types of accommodation in Bennington

Planning a getaway to Bennington, Vermont? You’re in for a treat! Discover the charm of this beautiful town by choosing from a variety of popular vacation rentals, including condos, private homes, and apartments. Whether you're looking for a cozy retreat or a spacious family vacation home, Bennington has the perfect spot for you. Explore your options and find the ideal place to stay during your visit to this picturesque destination!

  • Condos: The top choice for visitors in Bennington, condos offer modern amenities and a comfortable stay.
  • Houses: These homes provide spacious living and a home-like atmosphere for families and groups.
  • Apartments: Ideal for solo travelers or couples, apartments combine convenience with a local feel.
  • Cabins: Perfect for those seeking a rustic escape, cabins immerse you in nature.
  • Cottages: Cozy and charming, cottages are great for a romantic getaway or a peaceful retreat.**

Top attractions in Bennington

Bennington, Vermont, is a fantastic destination for outdoor enthusiasts and adventure seekers. With its stunning national parks, inviting ski resorts, and beautiful lakes, there are plenty of activities to enjoy. Visitors can immerse themselves in the rich culture while exploring the area's natural beauty. Whether you're skiing, hiking, or simply soaking in the scenery, Bennington offers a memorable experience for all types of travelers.

  1. Bennington College: Nestled three miles from Bennington, this historic college boasts stunning architecture and a vibrant arts scene. The campus is a hub of creativity, offering visitors a glimpse into its rich cultural heritage.
  2. Bennington Battle Monument: Located in the heart of Bennington, this impressive monument commemorates a pivotal Revolutionary War battle. Visitors can climb to the top for panoramic views and immerse themselves in local history.
  3. Bennington Museum: Situated in Bennington, this museum showcases a diverse collection of art, history, and artifacts, reflecting the region's cultural evolution and artistic contributions.

Things to do recommended for couples

For a romantic getaway in Bennington, embrace the thrill at Mount Snow, just 16 miles away, or take an adventurous ride on the Grand Summit Express Ski Lift, 17 miles from town. Don't miss the serene beauty of the Prospect Mountain Cross-Country Ski Center right in the area.

Things to do recommended for families

Families visiting Bennington can experience the wonders of the universe at Hopkins Observatory, relax at Windsor Lake Park, and explore art at The Georgi Museum, creating unforgettable memories together in a welcoming, family-friendly atmosphere.

Things to do recommended for groups

Explore the Hemmings Motor News Car Lover's Convenience Store for a unique vehicle display, then hike the scenic Harmen Hills Trail for outdoor adventure. Finally, enjoy the beautiful surroundings at Harmon Hill, perfect for relaxation and group bonding.

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

No matter if you're traveling with a group, your family, pets, or planning an extended stay, it's important to filter your options based on your specific needs. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Bennington with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search on Vrbo to include these options and much more.
  • Traveling to Bennington with young kids: Traveling with young children can be a bit daunting. It's important to prioritize their comfort and safety, along with ensuring that there are suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Bennington: For many families, a trip isn’t truly complete without their furry companion. If that resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly options come equipped with feeding bowls and cozy beds, ensuring that everyone feels 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 rental options. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to enhance your search experience.

Where to stay in Bennington

Bennington, Vermont, is a treasure trove for adventure seekers and outdoor enthusiasts. Nestled in Bennington County, it offers a blend of family-friendly activities and romantic spots, all steeped in rich local history. Just a short drive away, the scenic Hudson Valley and Clifton Park provide additional exploration opportunities, showcasing friendly people and vibrant art scenes. Whether you're skiing or simply enjoying the breathtaking landscapes, Bennington promises an unforgettable travel experience.

  • Williamstown: Situated 12 miles from Bennington, Williamstown is a charming town renowned for its outdoor adventures and cultural experiences. Travelers flock to this picturesque location for skiing and other sports activities, with easy access to ski fields and resorts. The town is also home to the prestigious Williams College, where you can explore its historic campus and enjoy the beautiful surrounding mountains and serene lakes. With its blend of natural beauty and academic charm, Williamstown offers a unique travel experience for visitors seeking both adventure and tranquility.
  • Manchester: Located 21 miles from Bennington, Manchester is a delightful destination that combines outdoor excitement with small-town charm. Known for its excellent skiing options, visitors can enjoy various winter sports at nearby ski resorts. The town features breathtaking views of the mountains and is dotted with beautiful parks and serene lakes, perfect for leisurely strolls or picnics. While in Manchester, don’t miss the opportunity to explore local shops and restaurants that showcase the region’s unique character and culinary delights, making it an ideal spot for relaxation and adventure.
  • West Dover: Just 19 miles from Bennington, West Dover is a haven for outdoor enthusiasts. This small town is celebrated for its lively ski scene, with ample opportunities for skiing and snowboarding at nearby resorts. The stunning landscapes encompass beautiful lakes, majestic mountains, and lush valleys, providing an ideal backdrop for hiking, biking, and other outdoor activities. West Dover's inviting atmosphere and recreational offerings make it a perfect getaway for those looking to experience the best of Vermont's natural beauty and adventure.

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 CloudyAverageModerately High
February23.4°F (-4.8°C)Light RainMostly CloudyModerately HighModerately High
March31.5°F (-0.3°C)Light RainMostly CloudyAverageAverage
April43.7°F (6.5°C)Light RainMostly CloudyModerately LowModerately 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 SunnyAverageModerately Low
October49.3°F (9.6°C)Light RainMostly CloudyAverageAverage
November36.9°F (2.7°C)Light RainMostly SunnyModerately LowModerately Low
December28.2°F (-2.1°C)Light RainMostly CloudyAverageModerately High

Booking with Vrbo is simple

Are you hoping to save money on your upcoming trip? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that aligns with your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll receive OneKeyCash™ on the full booking amount. Being the organizer truly has its rewards! By joining our One Key rewards program, you can take advantage of exclusive member discounts and earn OneKeyCash™ on eligible stays. Sign up today and start reaping the benefits!

Vrbo Trips: Effortless planning

Vrbo's user-friendly Trip Board offers you a convenient way to plan new trips, pick up right where you left off, or review and organize your travel plans. You can easily 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 booked during 2023 and 2024.

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)
  • Windsor Lake Park (15 mi / 24.1 km)
  • Lake Lauderdale (16.4 mi / 26.4 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?
Old Bennington is one of the more desired locations to book a vacation home in Bennington. Spend your getaway here to enjoy the convenience and privacy that comes with having the whole place to yourself.
What is the most popular type of vacation rental accommodation in Bennington?
The most sought-after types of vacation rentals in Bennington are condos. Want something different? Vrbo has plenty of options to match the needs of our guests, so you’ll see vacation homes in all shapes and sizes. The perfect fit is ready and waiting for you — get yours today.
How much does it cost to rent a vacation rental in Bennington?
The average price for a vacation home in Bennington is based on several factors, such as season, length of stay and property type. Whether you’d like a sprawling villa with a pool or a quaint cabin ideal for just you and the kids, just add your travel dates to find stays with fantastic value.
How much does it cost to rent a beach house in Bennington?
Prices for beach houses in Bennington can vary depending on the type and size of the property and when you plan to travel. All you have to do is enter your travel dates into Vrbo and how many guests to view your rental options and prices. From there you can use our filter tool to tailor your search by amenities, ratings, nearby activities and more.
Are there pet-friendly vacation rentals in Bennington?
You’re in luck. There are. You’ll have your pick of 460 stays that welcome pets in Bennington on Vrbo. Our furry friends deserve a break too, so simply use our search function for pet-friendly vacation rentals to book a perfect pad where your puppy can lap up the good times.
Can I rent a house with a pool in Bennington?
Check the “pool” box in our handy filter tool and choose from 148 houses with private pools in Bennington on Vrbo. Lazy soak or ball games and races? How you spend your free time is up to you when your vacation home boasts a swimming pool.
What are popular rental amenities in Bennington?
The most popular rental amenities people prefer in Bennington include a nearby waterfront, a sauna and a water view. Whether you’re on the road with family, friends or even pets, Vrbo vacation rentals have the best amenities for making epic memories with the people closest to you.
Are there large group vacation rentals in Bennington?
You can pick from 176 vacation rentals in Bennington that can sleep 10 or more guests. Whether you’re organizing a trip with the family or a special event like a birthday party, there’s enough room to get your group together under the same roof.
Are there vacation rentals in Bennington that welcome kids?
Bring the entire family together for a fun-filled adventure in Bennington at one of our 459 family-friendly properties. A lot of these stays offer conveniences that are suitable for getaways with the kids, including laundries, extra bedrooms and private pools. Simply click on the “Properties good for families” filter and book your favorite.
What are the top attractions for families in Bennington?
There are lots of amazing things to see and do with the family in Bennington, such as:

  • Harmen Hills Trail
  • Bennington Potters Yard
  • Bennington Arts Guild Gallery

Are there one-bedroom vacation rentals in Bennington?
Yes, you can pick from 50 one-bedroom rentals in Bennington. Whether you’d like a cozy chalet or a fancy condo, Vrbo’s one-bedroom rentals are great if you don’t require lots of space. One of the major perks of having your own place? You’ll never need to share your adventure with strangers.
Can I find two-bedroom vacation rentals in Bennington?
Gather your loved ones and experience complete comfort and privacy in one of the 43 two-bedroom vacation homes Bennington has to offer.
Are there vacation rentals with WiFi in Bennington?
Whether you want to keep up with the latest headlines, write a few emails or post a pic to social media, there are 206 vacation homes with WiFi in Bennington. Check the “WiFi” box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Bennington?
You’ll have a choice of 268 vacation rentals with air conditioning in Bennington giving you that gentle, cool breeze and extra comfort level. Simply enter your desired travel dates and then use our handy filters to locate stays with air conditioning.
How old do you have to be to rent a vacation rental in Bennington?
It’s a good idea to check with the Bennington vacation rental you want on Vrbo as the minimum age differs. However, normally it’s 16, 18 or 21.
How long can I rent a vacation rental in Bennington for?
It all depends on the Bennington property. To see all available options offering extended stays, simply type your travel dates and guest number into Vrbo. You can look forward to having the property to yourself, as well as comforts such as a kitchen, air conditioning and an outdoor space where the kids can play. Be on the lookout for any long-term stays that offer discounted weekly or monthly prices.
Does Vrbo offer discounts for vacation homes in Bennington?
On Vrbo, you’ll find fabulous bargains and discounts for Bennington. Take a look at our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you’re looking for a mini getaway or an extended escape, Vrbo has a variety of options for every style and budget.

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