Bennington Vacation Rentals

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Vacation Rentals in Bennington

Mountain Sanctuary Dome Rustic Solitude 5BR

9.6 out of 10, Exceptional, (8)
"We had an awesome stay at Nate’s place! The stone architecture and wood oven fireplace gave a truly unique experience, and the house was very spacious. The fully equipped kitchen made for anxenjoyable cooking experience. Nate was also flexible and responsive. Definitely recommend this for your weekend getaway home!"
Mountain Sanctuary Dome Rustic Solitude 5BR

Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access

8.8 out of 10, Excellent, (3)
"Perfect cottage on the water!! Enjoyed kayaking and pedal boat with family. Beautiful greenery! Very quick respond."
Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

8.6 out of 10, Excellent, (32)
"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "
$285 nightly
The price is $304
Sep 22 - Sep 23
Total with taxes and fees
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Lake life at Woodford Cottage

9.6 out of 10, Exceptional, (15)
"Perfect getaway for a family ski trip."
Lake life at Woodford Cottage

Perfect for a peaceful get away in clean fresh Vermont air!

10.0 out of 10, Exceptional, (74)
"Loved the place and the stay. The pictures don’t do it justice. Its was everything we hoped for and more."
Perfect for a peaceful get away in clean fresh Vermont air!

Bennington Gem w/ Smart TV Near Historic District!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We liked staying at the place as it had good amenities (washer, dryer, dishwasher, fridge with a freezer, fan, inflatable bed, wifi, cable, free parking spots. etc) and a lot of space. Where there is no central AC, it had a window unit which worked well - we had a comfortable stay in mid-July."
Bennington Gem w/ Smart TV Near Historic District!

Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown

10.0 out of 10, Exceptional, (2)
"Everything was lovely and easy"
Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown

VT at its best! Near hiking trails, museums & colleges.

10.0 out of 10, Exceptional, (1)
"The property was even more beautiful than the detailed photos depicted. It is secluded and private and yet, only a short drive to downtown.The interior finishes were homey and classy at the same time.Courtney is a fantastic host, who communicated thoroughly and responded promptly.If you’re looking for a quiet get away, you will love this property. "
VT at its best! Near hiking trails, museums & colleges.

Meme's High Mountain Lake House

10.0 out of 10, Exceptional, (9)
"We loved this spot! From chilling by the water in the great yard and deck to explore nearby hiking spots, we couldn’t have asked for more! Jessica was very communicative as well. "
Meme's High Mountain Lake House

Green Mountain Getaway

2.0 star property
9.8 out of 10, Exceptional, (14)
"Great Location -- place was spotless and very accommodating"
$360 nightly
The price is $382
Sep 12 - Sep 13
Total with taxes and fees
Green Mountain Getaway

Breathtaking Mtn Views: Stylish Rustic Retreat!

10.0 out of 10, Exceptional, (29)
"Our family loved spending time exploring this gorgeous 100 acre property. The cabin is so charming and our daughters loved the “secret hideout” and I especially loved the bird watching! "
Breathtaking Mtn Views: Stylish Rustic Retreat!

Charming 2-bedroom apartment in superb Bennington with WiFi

9.6 out of 10, Exceptional, (4)
"The pictures don’t do the listing justice, much bigger than the puctures suggest. The location is great with minutes away from Main St. (bars restaurants). Robin is also a great host! Really enjoyed our stay look forward to booking again next winter "
Charming 2-bedroom apartment in superb Bennington with WiFi

Bennington Gem w/ Smart TV Near Historic District!

2.0 star property
10.0 out of 10, Exceptional, (1)
"Stayed for a wedding in the area & found the property suited our needs. Short walk to restaurants & shopping. Communication super quick with property contact."
Bennington Gem w/ Smart TV Near Historic District!

Breathtaking Mtn Views: Stylish Rustic Retreat!

3.0 star property
Breathtaking Mtn Views: Stylish Rustic Retreat!

Charming 3-bedroom cabin in Woodford private with mountain and pond view

Charming 3-bedroom cabin in Woodford private with mountain and pond view

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (228)
"Extremely cozy. Would highly recommend staying here."
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

★No Cleaning Fee★10% OFF★Walk To Mountain★Amenities+

10.0 out of 10, Exceptional, (53)
"From beginning to end, a great experience:the owners are very responsive throughout the process, check-in and parking was a breeze, condo is great, location is perfect -- right across the street from the village -- we had a wonderful time -- thank you Brandon!!"
★No Cleaning Fee★10% OFF★Walk To Mountain★Amenities+

Cozy ski retreat on the Stratton Access Road - 5 minutes to the slope!

9.8 out of 10, Exceptional, (18)
"Came for skiing and NYE, had a great time with a great location"
Cozy ski retreat on the Stratton Access Road - 5 minutes to the slope!

Long Trail House at Stratton Mountain Resort

3.0 star property
8.6 out of 10, Excellent, (74)
"Nice, clean room in prime location"
$312 nightly
The price is $352
Sep 2 - Sep 3
Total with taxes and fees
Long Trail House at Stratton Mountain Resort

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (21)
"This place was very enjoyable, it was just 3 of us so there was more than enough room. It is a very comfortable home and we enjoyed the easy trip into Manchester for some meals and a wonderful day of hiking some great nearby trails."
$562 nightly
The price is $630
Sep 2 - Sep 3
Total with taxes and fees
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Bennington Hotel Reviews

Find out more about Bennington

Find out more about Bennington

Everything you need to know about Bennington vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Bennington vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Bennington vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Bennington vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Bennington. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Bennington in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $304 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Bennington rentals

At Expedia, we put the best Bennington vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Bennington rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Bennington vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Bennington. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Bennington?

Yes, we have vacation rentals close to popular attractions in Bennington, or you can go with a more secluded option if you want a relaxing place to stay. Tourists who visit Bennington speak highly of the ski slopes and array of shops. While you're in the area, you can also enjoy the majestic mountain landscape and museums.

What are some of the best vacation rentals in Bennington?

Idyllic Lakefront House Suited Two Families: Visitors like this Bennington vacation home rental. It is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Bennington?

With 16 Expedia vacation rentals, you're sure to find just the right place for your Bennington stay.

What’s there to see and do in Bennington?

Enjoy the outdoors at Green Mountain National Forest and Harmen Hills Trail, or simply take in cultural attractions like Bennington Museum and Robert Frost Stone House Museum. While here, Old First Congregational Church and Bennington Battle Monument are other places worth a visit.

What’s a vacation rental in Bennington like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Bennington. Vacation rentals offer extras such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for a family trip.