Bennington holiday lettings

We found 1,734 holiday rentals — enter your dates for availability

Discover a selection of 12 homes and other holiday rentals in Bennington that are perfect for your trip. Whether you're staying in a holiday rental with family or friends, you'll have the amenities that you expect and more, which might include Wi-Fi and a hot tub. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Bennington

Showing deals for:28 Aug - 4 Sept

Image gallery for Chalet /Stratton Mountain VT /5 minutes from base/Tesla Charger/5 bedrooms

Exterior
10 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)

Chalet /Stratton Mountain VT /5 minutes from base/Tesla Charger/5 bedrooms

Bondville

11% off
Price is £2,924
for 7 nights, 1 chalet
£418 per night
includes taxes & fees
Chalet /Stratton Mountain VT /5 minutes from base/Tesla Charger/5 bedrooms

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Why visit Bennington

  • Charming neighbourhoods: Explore Bennington's rich heritage and family-friendly activities in its picturesque surroundings.
  • Historic attractions: Visit notable colleges, universities, and local arts centres that showcase the area's cultural significance.
  • Outdoor pursuits: Enjoy skiing in winter and a variety of outdoor excursions throughout the year.
  • Affordable accommodation: Choose from delightful private holiday homes, cosy condos, and rustic cabins for an enjoyable stay.
  • Friendly atmosphere: Experience the warm hospitality of the locals and the unique vibe of Bennington.

Popular types of accommodation in Bennington

If you're considering a getaway to Bennington, you're in for a treat. Our most sought-after accommodation options include charming houses, cosy condos, and rustic cabins. Whether you're searching for a spacious apartment in Bennington, a delightful home rental, or VT rentals with multiple bedrooms, we’ve got just the place for you. Enjoy your stay with the comfort and reassurance of our transparent booking process.

  • Houses: The top choice among visitors to Bennington, these homes offer spacious and comfortable stays ideal for families or groups.
  • Condos: A popular selection, condos provide a blend of home-like amenities and hotel-style convenience for a delightful getaway.
  • Cabins: Perfect for those seeking a rustic escape, cabins offer a charming retreat surrounded by nature.
  • Apartments: A practical option for solo travellers or couples, apartments offer a homely atmosphere in the heart of the town.
  • Cottages: These quaint lodgings provide a warm and inviting environment, ideal for a romantic escape or peaceful retreat.**

Top attractions in and around Bennington

Bennington offers a delightful mix of skiing, adventure, and sports for holidaymakers. Visitors can explore a variety of attractions, including historic colleges and universities, arts centres, and national parks. This charming destination is perfect for those seeking cultural experiences, outdoor activities, and family-friendly fun, making it an ideal spot for a memorable getaway in the United States.

  • Bennington College: Nestled about 1.9km from the heart of Bennington, this historic institution is renowned for its vibrant arts and progressive educational philosophy, offering beautiful campus grounds and a rich cultural atmosphere.
  • Bennington Battle Monument: Located in the centre of Bennington, this impressive monument commemorates the pivotal Revolutionary War battle, providing visitors with stunning views and a deep sense of history.
  • Bennington Museum: Situated within Bennington, this museum showcases local history, art, and culture, featuring a diverse collection that highlights the region's unique heritage.

Things to do recommended for couples

Seeking a romantic getaway in Bennington? Enjoy the thrill of skiing together at Prospect Mountain Cross-Country Ski Center or venture 9.9km to Mount Snow for a stunning winter experience. The snowy landscapes offer a perfect backdrop for creating cherished memories as a couple.

Things to do recommended for families

Families visiting Bennington can explore the stars at Hopkins Observatory, enjoy nature at Windsor Lake Park, and discover art at The Georgi Museum. Each location offers a unique experience, perfect for creating lasting memories together.

Things to do recommended for groups

In Bennington, group travellers can indulge in the fascinating displays at Hemmings Motor News Car Lover's Convenience Store, hike the scenic Harmen Hills Trail, and enjoy the natural beauty at Harmon Hill, perfect for outdoor adventure and relaxation.

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

If you're travelling with a group, with family, bringing your pets, or seeking extended stays, be sure to refine your search according to your key preferences. Here are some helpful booking tips for using Vrbo.

  • Traveling to Bennington with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor space for social gatherings. Thankfully, you can easily filter for all these options, and more, on Vrbo.
  • Traveling to Bennington with young kids: Travelling with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable facilities, such as a private swimming pool. Additionally, it's wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Bennington: For many, a family holiday isn’t truly fulfilling without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations provide feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Bennington: If you're in search of holiday rentals with special offers for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. You might also want to include features such as a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in and around Bennington

Bennington, Vermont, offers an exciting blend of adventure and history, making it a perfect holiday destination. Nestled in Bennington County, the area boasts charming neighbourhoods rich in heritage and family-friendly activities. Whether you’re skiing in the winter or exploring local excursions, the friendly atmosphere and budget-friendly options will ensure a delightful stay. Don't miss the opportunity to experience the unique vibes and friendly people that make Bennington truly special.

  • Williamstown: Located 7.5km from Bennington, Williamstown is a charming town known for its vibrant cultural scene and outdoor adventures. Nestled in the scenic Berkshires, it attracts visitors with its skiing opportunities, including nearby ski resorts and fields perfect for winter sports enthusiasts. The town is home to Williams College, a historic institution that adds academic charm and offers beautiful architecture to explore. For nature lovers, the surrounding mountains and serene lakes provide stunning views and recreational activities, making Williamstown an ideal destination for both adventure seekers and those looking to relax in a picturesque setting.
  • North Adams: Situated 8.7km from Bennington, North Adams is a dynamic city that combines art and outdoor adventure. Known for its ski resorts and fields, it offers ample opportunities for winter sports. The city is also home to the renowned MASS MoCA, an art museum that showcases contemporary art and hosts various cultural events, making it a hub for creativity. With its public art installations and vibrant cultural centre, North Adams provides a unique blend of artistic expression and natural beauty, appealing to both art enthusiasts and outdoor adventurers alike.
  • Woodford: Just a short distance from Bennington, Woodford is a quaint village that offers a peaceful retreat for those seeking outdoor adventures. Renowned for its skiing activities, the village is surrounded by stunning landscapes that include a picturesque lake and the nearby Woodford State Park, which is perfect for hiking and exploring nature. The visitor centre provides insights into the area’s natural beauty and recreational opportunities, ensuring a fulfilling experience for guests. Woodford is an excellent choice for visitors looking to immerse themselves in Vermont's tranquil environment while enjoying outdoor pursuits.

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 simple

Are you hoping to cut costs on your next getaway? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, you could enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's clever Trip Board offers you a convenient space to plan new adventures, pick up from where you last left off, or review and organise your travel arrangements. 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/en-gb/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 holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Bennington

Do you want to find top things to see and do during your stay? Travellers enjoy Bennington for its skiing, hiking and golfing. Venture out of your cosy holiday rental and experience everything that makes Bennington a fun spot to go on holiday. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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 looking for adventure or just want to take in the scenery, Bennington is a great spot to appreciate mother nature. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • 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 21 cm and temperatures average -3°C.

Travelling to and around Bennington

Fly into Albany, NY (ALB-Albany Intl.), the closest airport, located 31.7 mi (51 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly 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 holiday rental?
When considering a holiday rental in Bennington, Vermont, one of the most appealing areas to stay is near the charming downtown district. This area offers a delightful mix of local shops, cafés, and restaurants, making it a great base for exploring the town. You'll find a variety of properties available, ranging from quaint cottages to more modern rentals, all within easy reach of the vibrant community atmosphere.

Another great option is the neighbourhood surrounding the Bennington Battle Monument, a key historical site that commemorates a pivotal battle in the American Revolution. Staying here not only places you close to this impressive 306-foot monument, which offers panoramic views of the region, but also near the Bennington Museum, where you can delve into local history and art.
How much does it cost to rent a holiday home in Bennington?
Prices for holiday 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 holiday 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, travellers should consider the nearby Stratton Mountain and Mount Snow ski areas, both of which are easily accessible within a short drive. In the Stratton area, visitors can find a variety of accommodations, including luxurious condos and charming chalets that often come equipped with modern amenities such as hot tubs, fireplaces, and fully stocked kitchens, great for unwinding after a day on the slopes.

The village of Stratton offers a vibrant après-ski scene, with local shops, restaurants, and cafes within walking distance from many rental properties. Additionally, properties in this area frequently include access to ski-in/ski-out trails, ensuring that guests can maximise their time on the mountain.

For those considering Mount Snow, the surrounding towns of West Dover and Wilmington provide a range of options from rustic mountain lodges to spacious family homes. Many rentals here feature amenities like game rooms, outdoor decks, and proximity to scenic hiking trails, allowing for year-round enjoyment. The local community also hosts seasonal events and markets that enhance the holiday experience.
What is the most popular type of holiday rental accomodation in Bennington?
In Bennington, holiday houses are the most popular type of holiday rental, with around 44 available throughout the area. These spacious homes typically feature multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxation, making them ideal for families or groups. Additionally, there are approximately 32 apartments that offer a more compact living experience, often equipped with kitchen facilities and comfortable living areas. For those seeking a rustic experience, about 20 cabins and 20 cottages are also on offer, providing a charming stay amidst the beautiful Vermont landscape.
Are there any family house rentals in Bennington?
In Bennington, Vermont, there are some family-friendly house rentals available, with around 22 options to choose from. This charming town is located in the picturesque Green Mountains, making it an ideal spot for families seeking both adventure and relaxation. Many of the properties offer spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can enjoy themselves.

Families will appreciate amenities such as Wi-Fi and laundry facilities, which can enhance the convenience of their stay. Nearby, attractions like Bennington Battle Monument and the local art scene provide opportunities for exploring history and culture.
Can I rent a holiday home with a pool or hot tub in Bennington?
In Bennington, Vermont, several holiday homes with pools and hot tubs are available for rent, offering a great retreat in this picturesque area. The town is surrounded by beautiful landscapes, making it an ideal spot for both relaxation and outdoor activities. Many of the rentals feature amenities such as private pools, hot tubs, spacious gardens, and fully equipped kitchens, which cater well to families and groups looking for comfort and convenience during their stay.

In addition to the amenities, the area boasts a rich cultural heritage with attractions such as the Bennington Battle Monument and the Bennington Museum, providing opportunities for exploration and education. Visitors can also enjoy hiking in the nearby Green Mountains or simply relax in the tranquil surroundings.
Can I find long-stay holiday rentals in Bennington?
A long-stay holiday 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, there are several pet-friendly house rentals available, with options that cater to various group sizes and preferences. Many of these properties offer features such as well-equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air.

The area is known for its charming surroundings, including easy access to scenic hiking trails and parks that are superb for walks with your furry companions. One great spot is the Bennington Battle Monument State Historic Site, which not only provides a glimpse into history but also offers expansive grounds for leisurely strolls.

Additionally, the nearby Green Mountain National Forest is a fantastic destination for outdoor enthusiasts, with numerous trails that welcome pets. The rentals in this region often combine comfort with a rustic feel, making them ideal for families or groups looking to unwind while enjoying the beauty of Vermont.
Are there any remote work holiday rentals in Bennington?
In Bennington, Vermont, there are numerous holiday rentals suitable for remote work, with around 112 options available. This picturesque town, known for its stunning autumn foliage and rich history, offers a variety of properties that cater to the needs of remote workers. Many rentals feature essential amenities such as free Wi-Fi, dedicated desk spaces, and comfortable desk chairs, ensuring a productive work environment.

Travellers can expect a mix of charming cottages, spacious homes, and modern apartments, often equipped with fully stocked kitchens, allowing for convenient self-catering during longer stays. The beautiful surroundings provide opportunities for outdoor activities during breaks, with nearby attractions like the Bennington Battle Monument and the scenic Green Mountains just a short drive away. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Bennington holiday rentals with parking?
Vrbo offers a wide selection of holiday 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 rental amenities include well-equipped kitchens, which allow guests to prepare their own meals, enhancing the home-like experience. Many properties also offer onsite parking, providing convenience for those travelling by car. A coffee and tea maker is typically available, ensuring that guests can enjoy warm beverages at their leisure. Additionally, many rentals are pet-friendly, accommodating travellers who wish to bring their furry companions along. Outdoor spaces such as decks or patios are also common, providing a lovely area for relaxation and enjoying the picturesque surroundings.
When is the best time to visit Bennington for a holiday rental?
March marks the beginning of the peak season in Bennington, Vermont, drawing in visitors who are eager to experience the region's stunning landscapes and vibrant local culture. From March to May, the area comes alive with activities that cater to outdoor enthusiasts and those looking to immerse themselves in the charm of small-town New England.

During March, temperatures typically range from -5 to 10 degrees Celsius, providing a comfortable climate for exploring the picturesque town and its surrounding natural beauty. This transitional month offers a great opportunity for hiking and enjoying the early spring blooms in local parks and gardens. Additionally, March is a wonderful time to visit local museums and historic sites, enhancing your understanding of Bennington's rich heritage.

For those seeking a more budget-friendly option, consider planning your visit in January. While it's the low season, the quiet atmosphere allows for a peaceful retreat, and you can enjoy the serene winter landscapes without the crowds. Plus, January can be a great month for those who appreciate winter sports, such as skiing and snowshoeing, in the nearby Green Mountains.

Ultimately, the best time to book a holiday rental in Bennington will depend on your preferences—whether you're drawn to the vibrant activities of spring or the tranquility of winter.
How early should I book a Bennington holiday rental?
Book your Bennington holiday 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 holiday 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 a variety of attractions that highlight the area's rich history and natural beauty. The Bennington Battle Monument, standing at 306 feet, is a must-visit, offering panoramic views of the surrounding countryside from its observation deck. Nearby, the Bennington Museum showcases local art and history, including works by renowned artist Grandma Moses.

For those interested in nature, the scenic Hump Brook Trail provides opportunities for hiking and enjoying the area's lush landscapes. The charming downtown area features historic buildings, quaint shops, and local eateries, great for leisurely strolls. Additionally, the nearby Bennington Potters offers an insight into handcrafted pottery, making it a unique stop for art enthusiasts.
Can I change or cancel my Bennington home rental booking on Vrbo?
To find Bennington holiday 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 cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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