Bennington holiday rentals

We found 1,739 holiday rentals — enter your dates for availability
Discover a selection of 16 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:18 Dec - 25 Dec

Two story living room with 70" smarttv, premium directtv and bluetooth turntable
Terrace/patio
Sun or snow, it's quite the show
Indoor hot tub
Exceptional
(10 reviews)

HotTub&GameRm&Traeger Smoker-15 min 2 Mt Snow, Across from Golf, 5 min to Lake

Wilmington

16% off
AU$11,953
for 7 nights, 1 chalet
AU$1,708 per night
includes taxes & fees
HotTub&GameRm&Traeger Smoker-15 min 2 Mt Snow, Across from Golf, 5 min to Lake
Enjoy chess, checkers or backgammon
A beautiful brook that runs through our lot
Summer view from the lake
Silestone counter top and Hickory cabinets
Exceptional
(101 reviews)

New Lakefront Log Home

Wilmington

12% off
AU$5,896
for 7 nights, 1 chalet
AU$842 per night
includes taxes & fees
New Lakefront Log Home
Terrace/patio
Living area
Dining
Room
Exceptional
(35 reviews)

Beautiful log home close to Mt. Snow with hot tub and sauna.

West Dover

8% off
AU$12,682
for 7 nights, 1 cabin
AU$1,812 per night
includes taxes & fees
Beautiful log home close to Mt. Snow with hot tub and sauna.
Exterior
Large living room with endless natural light
Property grounds
Interior
Exceptional
(17 reviews)

Private 6 bedroom Chalet 5min to Mt Snow

West Dover

8% off
AU$16,199
for 7 nights, 1 chalet
AU$2,314 per night
includes taxes & fees
Private 6 bedroom Chalet 5min to Mt Snow
King bed
Front of the house
Livingroom with a view.
Patio chairs and solo stove firepit
Exceptional
(16 reviews)

Chalet Mount Snow/Stratton Skiing/hiking

East Dover

8% off
AU$4,713
for 7 nights, 1 chalet
AU$673 per night
includes taxes & fees
Chalet Mount Snow/Stratton Skiing/hiking
Dining area, 10 Chairs are now black, Need a new picture!
View out front door
View from Kitchen sink
Open Kitchen with a wide open feel
Exceptional
(243 reviews)

Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews

Wilmington

8% off
AU$8,157
for 7 nights, 1 home
AU$1,165 per night
includes taxes & fees
Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews
Dining
Private kitchen
Interior
Interior
Exceptional
(7 reviews)

Tutti Farmhouse - 6 bedroom 3 bath 1847 Farmhouse Upstate NY

Cropseyville

8% off
AU$15,500
for 7 nights, 1 home
AU$2,214 per night
includes taxes & fees
Tutti Farmhouse - 6 bedroom 3 bath 1847 Farmhouse Upstate NY
Living area with wood stove
Kitchen and dining area.
Enjoy the infamous Moss Rock!
Living area with wood stove.
Exceptional
(26 reviews)

Vermont ski chalet near beautiful Mount Snow and the quaint town of Wilmington

West Dover

8% off
AU$5,530
for 7 nights, 1 chalet
AU$790 per night
includes taxes & fees
Vermont ski chalet near beautiful Mount Snow and the quaint town of Wilmington
Dining room
Living area
Back porch
Front door
Exceptional
(40 reviews)

Wishing Well Cabin

Jamaica

8% off
AU$3,775
for 7 nights, 1 cabin
AU$539 per night
includes taxes & fees
Wishing Well Cabin
Primary bedroom balcony
Interior
View from upstairs guest room
Sitting room looking into the kitchen.
Exceptional
(8 reviews)

Views of Stratton, Minutes from the Slopes, EV Charging Level 2

Bondville

8% off
AU$15,692
for 7 nights, 1 home
AU$2,242 per night
includes taxes & fees
Views of Stratton, Minutes from the Slopes, EV Charging Level 2
A look at the main floor family room from above.
Welcome to our 9 bedroom luxury home in the heart of Southern Vermont!
Complete privacy on our property!
Hot tub and firepit are great after a day of fun.
Exceptional
(22 reviews)

Luxury 9BRs Stratton Estate. Views! Hot Tub, Sauna, Game House, Swimming pool!

Bondville

8% off
AU$38,845
for 7 nights, 1 home
AU$5,549 per night
includes taxes & fees
Luxury 9BRs Stratton Estate. Views! Hot Tub, Sauna, Game House, Swimming pool!
Antique Cabin
Porch -Summer
Antique Cabin
Exterior
Exceptional
(89 reviews)

Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton

Jamaica

8% off
AU$5,997
for 7 nights, 1 home
AU$857 per night
includes taxes & fees
Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton
Gourmet kitchen has everything you need to prepare delicious meals
Beautiful period woodwork and Victorian details
Huge wraparound porch is perfect for visiting with family and friends
Walk to Spring Street and brand new Williams Bookstore
Exceptional
(157 reviews)

Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!

Williamstown

7% off
AU$8,433
for 7 nights, 1 home
AU$1,205 per night
includes taxes & fees
Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!
Bedroom 1: Queen Bed
Large open-concept living and kitchen area
Dining area
3-Season porch (new addition 2023)
Exceptional
(18 reviews)

Leonard’s Log Cabin— Mt. Snow/Stratton Ski House

Wardsboro

8% off
AU$8,634
for 7 nights, 1 cabin
AU$1,233 per night
includes taxes & fees
Leonard’s Log Cabin— Mt. Snow/Stratton Ski House
Private kitchen
Terrace/patio
Living area
Dining
Exceptional
(20 reviews)

Family-friendly, private three bedroom cottage in the beautiful Berkshires

Williamstown

16% off
AU$4,417
for 7 nights, 1 cottage
AU$631 per night
includes taxes & fees
Family-friendly, private three bedroom cottage in the beautiful Berkshires
Dining
Interior
Room
Bar (on property)
Exceptional
(79 reviews)

Western Mountain Lodge on River and Close to Stratton

Jamaica

17% off
AU$24,447
for 7 nights, 1 home
AU$3,492 per night
includes taxes & fees
Western Mountain Lodge on River and Close to Stratton
View of the Main house living room from the kitchen bar
Main house top floor river room with sounds of the river out the windows.
Main house top floor river room with deck overlooking the pool and backyard.
2nd - 3rd floor main house stairs
Exceptional
(38 reviews)

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Wardsboro

8% off
AU$22,156
for 7 nights, 1 home
AU$3,165 per night
includes taxes & fees
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Private kitchen
Exterior
Living area
Plenty of room for relaxing.
Exceptional
(33 reviews)

Winterfell chalet - quiet, relaxing & private with Stratton on your doorstep.

Bondville

8% off
AU$9,247
for 7 nights, 1 chalet
AU$1,321 per night
includes taxes & fees
Winterfell chalet - quiet, relaxing & private with Stratton on your doorstep.
Dining
Interior
Interior
Private kitchen
Exceptional
(55 reviews)

Skylight Ski Lodge VT Rustic Chic Near Stratton

Bondville

8% off
AU$17,836
for 7 nights, 1 home
AU$2,548 per night
includes taxes & fees
Skylight Ski Lodge VT Rustic Chic Near Stratton
Dining
Exterior
Games room
Living area
Exceptional
(39 reviews)

Beautiful Four Season Family Vacation Home

West Dover

12% off
AU$10,775
for 7 nights, 1 home
AU$1,539 per night
includes taxes & fees
Beautiful Four Season Family Vacation Home
Private kitchen
Property grounds
Living area
Exterior
Exceptional
(28 reviews)

Bear Pass Bunkhouse

Manchester

8% off
AU$3,111
for 7 nights, 1 home
AU$444 per night
includes taxes & fees
Bear Pass Bunkhouse
foyer for all skiing and outdoor stuff
Jacuzzi hot tub
main level living room area
kitchen
Exceptional
(26 reviews)

True Vermont Log Cabin Home at Mount Snow

West Dover

8% off
AU$9,505
for 7 nights, 1 cabin
AU$1,358 per night
includes taxes & fees
True Vermont Log Cabin Home at Mount Snow
Property grounds
Outdoor dining
Dining
Interior
Exceptional
(39 reviews)

Large, family-friendly farmhouse located in the beautiful Berkshires

Williamstown

20% off
AU$5,934
for 7 nights, 1 home
AU$848 per night
includes taxes & fees
Large, family-friendly farmhouse located in the beautiful Berkshires
Dining
Interior
Exterior
Private kitchen
Exceptional
(6 reviews)

Grateful Getaway - 5BR, 3.5B Home Sleeps 10 - Close to Mount Snow!

Wilmington

8% off
AU$10,519
for 7 nights, 1 home
AU$1,503 per night
includes taxes & fees
Grateful Getaway - 5BR, 3.5B Home Sleeps 10 - Close to Mount Snow!

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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)
  • 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 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.
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.
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 Stayz.
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.
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.
Are all fees included in the Bennington holiday homes prices shown on Stayz?
Stayz 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.
Are there any Bennington holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Bennington holiday homes?
You can find great discounts on holiday homes in Bennington on Stayz, 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.
Can I change or cancel my Bennington holiday home booking on Stayz?
To find Bennington holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Bennington?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Bennington holiday home?
Book your Bennington holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Bennington?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Bennington to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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