Bennington Vacation Rentals

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Vacation Rentals in Bennington

Fridge, microwave, oven, stovetop
Victorian Home in Bennington, Vermont
10.0 out of 10, Exceptional, (78)
"The house fit our needs so well that we stayed an extra day. High ceilings, lots of light, more than ample room. We used it as a home base for ski slopes less than an hour away. Great work-from-home setup for a non-skier. Thank you for hosting us!"
Victorian Home in Bennington, Vermont
Interior
Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
9.8 out of 10, Exceptional, (7)
"Beautiful property! Responsive and helpful hosts. Short walk into downtown Bennington. We had a blast!"
Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
Fridge, microwave, oven, stovetop
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
9.0 out of 10, Wonderful, (24)
"The cabin was clean and quiet and suited our needs for the weekend. The hot tub was enjoyable, although I would recommend that the owners purchase stairs to make exit and entry a bit easier."
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
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Exterior
Great Place to get away and have clean fresh air surround you!
9.8 out of 10, Exceptional, (120)
"The house has a beautiful view of the lake and is very clean. It is beautifully decorated, and has all the supplies that are needed for comfortable stay. The owner is very thoughtful and the house is nicely organized. We appreciated the Christmas decorations during our holiday stay, extra towels prepared for the dog and the dog treats. The house is nicely stocked with family games, and there is beautiful trail in walking distance: up the hill to vast trail, and path through the forest to Little...
Great Place to get away and have clean fresh air surround you!
Fridge, microwave, oven, stovetop
Escape to Serenity: Cozy 3 bedroom apartment
The price is CA $146
CA $533 total
includes taxes & fees
Jun 11 - Jun 12
Escape to Serenity: Cozy 3 bedroom apartment
Panoramic House | Private kitchen
Two Brooks Lodge
3.0 star property
4.8 out of 10, (3)
"Strong dog smell, dirty shabby condition of interior surfaces. Obvious makeshift repairs, spongy floors, torn, flaking couch. Kitchen counter had multiple burn marks and some sticky substance, corner held down with duct tape. Screen door off tracks, laying against wall. Wife was stung by insect in the unit, had to go to hospital. We moved out after only 3 hours, and literally slept in the car rather than go back. Owner uncaring, rude and greedy. Slow to return security deposit. I've...
Two Brooks Lodge
Exterior
Perfect for a peaceful get away in clean fresh Vermont air!
10.0 out of 10, Exceptional, (67)
"We travel to Vermont frequently. This was the best rental we have had. The property is sparkling clean and very cozy. The location is beautiful, and the host is very responsive, taking great pride in her property. I wish I could add more stars to my recommendation. My husband and I will definitely return."
Perfect for a peaceful get away in clean fresh Vermont air!
Smart TV, fireplace
Lake life at Woodford Cottage
9.6 out of 10, Exceptional, (11)
"Stayed Fri - Mon over Columbus Day weekend - overall the cabin itself was very nice. Clean, cozy and all the amenities listed. Some things to note: -There’s no dishwasher so bring paper plates and bowls to make life easier! -There’s a washer dryer combo in the kitchen but only the dryer is available for use -The front door is tricky with the lock but you’ll quickly get the hang of it -The shower is also tricky at first but you’ll also get the hang of that! -Not really any closet or drawer space...
Lake life at Woodford Cottage
View from property
Meme's High Mountain Lake House
10.0 out of 10, Exceptional, (3)
"How was better than advertised. Really appreciated the owners leaving the essentials, including the spices and condiments. Linens, too. They really take pride in the place. Highly recommend."
Meme's High Mountain Lake House
Interior
Bennington Cabin w/ Deck & Views of 3 States!
10.0 out of 10, Exceptional, (22)
"The lodging, location and view exceeded our expectations. The owner was extremely helpful and responsive. We definitely want to return."
Bennington Cabin w/ Deck & Views of 3 States!
Fridge, microwave, oven, stovetop
Traveler Dream Space in the Center of Downtown Bennington Steps From Everything!
9.4 out of 10, Exceptional, (14)
"Great, large apartment in downtown Bennington, Vermont. Walk to restaurants and shops. Short drive to area attractions. Small amount of traffic noise did not bother us at all. We slept well each night."
Traveler Dream Space in the Center of Downtown Bennington Steps From Everything!
Interior
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
3.0 star property
10.0 out of 10, Exceptional, (1)
"The host was so kind and helpful. I will definitely cime abck here. "
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
Exterior
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
9.6 out of 10, Exceptional, (177)
"We stayed the weekend for our 26th anniversary and had a wonderful time. Very private and everything was as described. The cottage is super charming! Will definitely be going back!"
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Property grounds
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
10.0 out of 10, Exceptional, (183)
"The barn was spacious and had everything we needed. The property is breathtaking, great location to the town, and Jeff was a great host. Our dogs were welcome, living their best life running around the property, and it was so special to see the mountains and just breathe in the air there. Would love to come back in the warmer weather!"
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Condo, 2 Bedrooms | Pool
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very good, (69)
"The unit was perfect for our ski race weekend. Very accessible, underground parking included (ski boxes on top of SUVs will not fit - thankfully we left ours at home), really nice place with everything we needed!"
The price is CA $430
CA $521 total
includes taxes & fees
May 30 - May 31
Long Trail House at Stratton Mountain Resort
Private kitchen
2 block walk to Manchester shops! Short drive to slopes! Pet friendly.
2 block walk to Manchester shops! Short drive to slopes! Pet friendly.
Property grounds
By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.
9.8 out of 10, Exceptional, (57)
"We loved our stay at the lodge. We had two couples and kids ranging in age from 2 to 12. We did lots of skiing at Bromley but loved having Manchester so close to explore. The pinball arcade was a great rainy day activity for kids! The house was amazing and bigger than we imagined, we were all extremely comfortable. The only thing to mention is the stairs and upstairs loft are a bit scary for little ones. We blocked them with a baby gate and didn’t let the two year old up there, but it was fine...
By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.
Exterior
Dragonfly Cottage -Luxurious Mountain View A-Frame -quiet street close to town.
10.0 out of 10, Exceptional, (11)
"Peter and Becky were fantastic hosts. Their cottage was a home away from home. It is beautifully appointed and perfectly located. I look forward to staying here again on my next trip to Vermont."
Dragonfly Cottage -Luxurious Mountain View A-Frame -quiet street close to town.
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
10.0 out of 10, Exceptional, (205)
"Very comfortable stay in a peaceful and private setting. Would definitely back again."
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Pool
Home with a spring-fed pond and mountain view.
10.0 out of 10, Exceptional, (101)
"We had a great stay with our pup for a late ski season weekend! The house was clean, well-stocked, and very cozy. The location was beautiful and perfectly situated a few minutes away from everything you could want to do in Manchester. We will definitely be back!"
Home with a spring-fed pond and mountain view.
Don't see what you're looking for?
See all available properties in Bennington
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.

Bennington Vacation Rental Travel Info

Number of vacation rentals
2
Popular accommodation
Bennington private vacation homes
Known landmarks
Prospect Mountain Cross-Country Ski Center, Prospect Mountain Nordic Ski Center and Woodford State Park
International airport
Albany, NY (ALB-Albany Intl.)

Other types of properties in Bennington you may be interested in

Front of property
The Autumn Inn
2.0 star property
7.8 out of 10, Good, (501)
"Independent motel, somewhat dated but clean with updated bathroom. Gentleman who assisted me was lovely. Short visit to Bennington to visit an elderly family member. Convenient, although I wish I could find better coffee close by. I launched early morning on low grade."
The price is CA $122
CA $133 total
includes taxes & fees
May 27 - May 28
The Autumn Inn
Exterior
Hampton Inn Bennington
2.5 star property
8.6 out of 10, Excellent, (871)
"Serviceable. Clean, consistent with other Hampton inn properties. Friendly, responsive staff."
The price is CA $220
CA $240 total
includes taxes & fees
Jun 9 - Jun 10
Hampton Inn Bennington
In-room safe, blackout drapes, iron/ironing board
Best Western Bennington
2.5 star property
7.8 out of 10, Good, (705)
"Converted motel but nicely done"
The price is CA $163
CA $178 total
includes taxes & fees
Jun 9 - Jun 10
Best Western Bennington
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.

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Bennington vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Bennington vacation rentals we have selected for you start as low as CA $146 per night. Entering your travel dates in the search wizard 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?

Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms: This highly rated vacation home rental in Bennington is located in the city center and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 6 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 selection of games and a spa tub. Other favorite homes for rent in Bennington are Victorian Home in Bennington, Vermont and Two Brooks Lodge, Beautiful Waterfront Vermont Retreat.

How many vacation rentals will I find in Bennington?

With 13 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 Woodford State Park 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.

Recent reviews of Bennington properties
Expedia verified reviews

Bennington Motor Inn

Bennington Motor Inn

5/5 Excellent
"Great stay at Bennington Motor Inn! "
A verified traveller from New York stayed at Bennington Motor Inn
Posted 6 days ago
Bennington Motor Inn