Bennington holiday lettings

We found 1,618 holiday rentals — enter your dates for availability

Discover a selection of 18 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:17 Oct - 24 Oct

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.

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.

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

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.

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)
  • 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)
  • Mount Snow Golf Course (17.9 mi / 28.9 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?
Old Bennington is among the more sought-after neighbourhoods to book a holiday home in Bennington. Spend your getaway here and enjoy the privacy and convenience that comes with having a place all to yourselves.
What is the most popular type of holiday rental accommodation in Bennington?
The most sought-after types of holiday rentals in Bennington are houses. Ready for more choices? Vrbo has plenty of options to match the diverse needs of our guests, so you'll see holiday properties in all sizes and shapes. The perfect home away from home is waiting for you --- get yours today.
How much does it cost to rent a holiday rental in Bennington?
Different factors can influence how much you pay for a holiday rental in Bennington, such as the type of property, season and length of stay. But, all our holiday homes have one thing in common --- unbeatable value. Just add your travel dates to find your ideal match.
How much does it cost to rent a beach house in Bennington?
The average price for a holiday home near the beach in Bennington depends on when you're going and the style and size of property you're searching for. Find prices easily on Vrbo by entering your travel dates. Then make use of the filter tool to select the number of bedrooms and amenities essential to you, like a pool, WiFi and air conditioning.
Are there pet-friendly holiday rentals in Bennington?
Yes. There are. You'll have a choice of 418 holiday rentals that allow pets in Bennington. Several of our pet-friendly holiday rentals even come with space outdoors for your four-legged friend to have fun in, special dog beds, complimentary treats and proximity to parks and green space. Apply the "Pets allowed" filter to find your pawfect digs on Vrbo.
Can I rent a house with a pool in Bennington?
Add a whole new level of fun to your getaway by booking your crew into one of the 130 houses with a private pool in Bennington. Use our handy search filter to find the kind of property you want on Vrbo, and then spend carefree days playing and splashing in a swimming pool that's for your use only.
What are popular rental amenities in Bennington?
The most popular rental amenities people are searching for in Bennington include ski-in/ski-out facilities, a chef and a sauna. Whether you're on a trip with your besties, family or even pets, Vrbo holiday homes provide the best amenities for starting a new adventure with your loved ones.
Are there large group holiday rentals in Bennington?
With 158 properties that can host 10 guests or more in Bennington, there's no need to cross anyone off the invite list. From fun family get-togethers to special events like Christmas and birthday parties, Vrbo will help you find a large group rental to match the occasion.
Are there holiday rentals in Bennington that welcome kids?
Bennington has 417 family-friendly holiday rentals to choose from. And finding a stay that welcomes kiddos is easy with our "Properties good for families" filter. On top of having the whole place to yourselves, you'll also get perks and amenities like bunk beds, yards and private pools.
What are the top attractions for families in Bennington?
Keep the kids occupied at these fabulous family-friendly attractions in Bennington:

  • Woodford State Park
  • Bennington Centre for the Arts
  • Norman Rockwell Exhibition

Are there one-bedroom holiday rentals in Bennington?
Bennington has 44 one-bedroom rentals available. Often situated in prime areas due to their compact size, a one-bedroom property is ideal if you're getting away with your partner or a pal. And with plenty of home comforts like air conditioning and more privacy than a standard hotel, you'll be able to relax while enjoying this top destination.
Can I find two-bedroom holiday rentals in Bennington?
Bennington has 40 two-bedroom holiday rentals to select from. Go for a holiday home with all the privacy and comfort you need at a fantastic price on Vrbo.
Are there holiday rentals with WiFi in Bennington?
There are 175 holiday rentals with WiFi in Bennington. If you want to disconnect from the world on your trip, but still need to be connected to the web, these properties have what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Bennington?
You can choose from 237 Vrbo holiday rentals with air conditioning in Bennington offering that cooling breeze and extra element of comfort. Just enter your preferred dates of travel and then use our handy filters to find stays with air conditioning.
How old do you have to be to rent a holiday rental in Bennington?
The minimum age permitted can differ between properties on Vrbo, so be sure to check the rules of the holiday home in Bennington you want to book. But normally, it's 16, 18 or 21.
How long can I rent a holiday rental in Bennington for?
The amount of time you can stay in a Bennington holiday rental for depends on each property. Simply put in your preferred travel dates to browse options offering extended stays. They come with all you require to make your extended holiday more comfortable and convenient, like air conditioning and laundries. Some Vrbo holiday rentals may also offer weekly or monthly discounted prices, so you can stay even longer for less.

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