Old Bennington Vacation Rentals

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Vacation Rentals in Old Bennington

Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
Interior
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
9.4 out of 10, Exceptional, 47 reviews
"We loved our stay at the chalet. It's perfectly situated in the cutest little neighborhood, while also feeling very secluded. The chalet had everything we needed for our stay. While visiting we walked a few of the trails nearby, part of the Valley Trail and the Hoot, Toot and Whistle. They were both perfect for our pups, especially during hunting season. We gave our pups an extra squeeze in honor of Scarlet. Thank you for sharing your place with us! We would love to stay again!!"
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Fridge, microwave, oven, stovetop
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
10.0 out of 10, Exceptional, 28 reviews
"This is a great spot for a getaway! The space was spotless. There was a lot of privacy. The location was close to everything we needed. The space is cozy and super fun with the hot tub and fore pit! We we are able to enjoy the included breakfast, which was great before skiing!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Spacious apartment in beautiful, historic Arlington VT
Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils
Spacious apartment in beautiful, historic Arlington VT
10.0 out of 10, Exceptional, 30 reviews
"Apartment was immaculately clean. Beds all comfortable and rooms very spacious. Host Late was A with communication. We were very lick to find this wonderful place. "
The price is $190
$237 total
includes taxes & fees
Jun 16 - Jun 17
Spacious apartment in beautiful, historic Arlington VT
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SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Property grounds
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
8.8 out of 10, Excellent, 38 reviews
"The home location, layout were awesome. Pics must be older as there was maintenance needed on the basketball/tennis court, pool, and shuffleboard room. Our bachelor party had a good time, once some updates are done, could be a 5 start spot."
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
10.0 out of 10, Exceptional, 206 reviews
"Very comfortable stay in a peaceful and private setting. Would definitely back again."
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Wilmington Vacation Rental Near Hiking and Skiing!
TV, fireplace, books
Wilmington Vacation Rental Near Hiking and Skiing!
10.0 out of 10, Exceptional, 9 reviews
"Beatiful weekend get away."
Wilmington Vacation Rental Near Hiking and Skiing!
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
Fridge, microwave, oven, stovetop
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
10.0 out of 10, Exceptional, 101 reviews
"We were looking for a quick getaway to Vermont and this gorgeous home was perfect! The views are every bit as spectacular as the photos. The home is clean and modern with stunning views of the mountains from the kitchen, living room, and back deck. The living room is large and comfortable for gathering. The adjoining kitchen is clean, modern, and has everything you need to cook a meal or just prepare a quick snack. There are dishes and cooking supplies available, which made meal prep a breeze....
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Golf
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
10.0 out of 10, Exceptional, 93 reviews
"Everything is basic but solid and comfortable. Beds were nice and firm, my preference. Host was lovely. Wish we could have stayed longer to explore the area more."
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Great Place to get away and have clean fresh air surround you!
Exterior
Great Place to get away and have clean fresh air surround you!
9.8 out of 10, Exceptional, 120 reviews
"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!
Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
Interior
Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
9.8 out of 10, Exceptional, 8 reviews
"House was perfect for our family to gather and celebrate my son’s graduation from Bennington. Sean was very quick to respond to questions."
The price is $600
$1,108 total
includes taxes & fees
Jun 16 - Jun 17
Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Property grounds
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
10.0 out of 10, Exceptional, 195 reviews
"We loved everything about this house. The view was amazing. Location was perfect and everyone enjoyed the pool table, shuffle board and ping pong table. If we had more time, we would have taken advantage of the kayaks but our stay was just too short to fit that in. The host was terrific and quick to respond. If our travels ever take us to Vermont, we’d definitely stay here again."
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
The Brown House. Indoor pool - Spa - Sauna - Gameroom
Fridge, microwave, oven, stovetop
The Brown House. Indoor pool - Spa - Sauna - Gameroom
8.0 out of 10, Very Good, 19 reviews
"We had a large crew and this house had plenty of room for all. Large table and lots of room to hang out. The location to the mountain is great- so close! You can walk through the snow to a restaurant. Unfortunately, the new pool was not ready yet, but it looks like it will be gorgeous and we would come back again."
The Brown House. Indoor pool - Spa - Sauna - Gameroom
Mount Snow's Best View - Sleeps 8-10
Fridge, microwave, oven, stovetop
Mount Snow's Best View - Sleeps 8-10
10.0 out of 10, Exceptional, 39 reviews
"We loved this condo! It was so gorgeous and clean, and has an awesome view of the mountain. There was so much space and all of our needs were met! We would go back again for sure."
Mount Snow's Best View - Sleeps 8-10
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Property grounds
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
8.6 out of 10, Excellent, 19 reviews
"Good Condo in a great location"
The price is $74
$336 total
includes taxes & fees
Jun 21 - Jun 22
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Walk to Mount Snow, Cozy, Clean and Comfortable!
Pool
Walk to Mount Snow, Cozy, Clean and Comfortable!
9.6 out of 10, Exceptional, 28 reviews
"Overall property was good, and the unit was very good. Our needs were minimal, but if we had questions, Tiago was very quick and to respond."
Walk to Mount Snow, Cozy, Clean and Comfortable!
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Terrace/patio
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
9.6 out of 10, Exceptional, 36 reviews
"The house was perfect for our larger family event. The bedrooms were quiet and each one had their own bathroom. The owner was responsive to any needs. We had a wonderful event."
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Spacious Mount Snow condo near slopes with private hot tub, sauna & fireplace
Interior
Spacious Mount Snow condo near slopes with private hot tub, sauna & fireplace
8.4 out of 10, Very Good, 12 reviews
"Property was great. We were there to ski at Mt Snow and the location did not disappoint. We were not ski-on ski-off but were so close it didn’t matter. Overall the house was clean and the owner was super responsive. Have it saved to stay again next season."
Spacious Mount Snow condo near slopes with private hot tub, sauna & fireplace
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
Fridge, microwave, oven, stovetop
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
9.0 out of 10, Wonderful, 24 reviews
"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."
The price is $230
$427 total
includes taxes & fees
Jun 28 - Jun 29
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
Old Ark Retreat | Secluded & spacious dog-friendly home in Wilmington
Fridge, microwave, oven, stovetop
Old Ark Retreat | Secluded & spacious dog-friendly home in Wilmington
7.0 out of 10, Good, 4 reviews
"We had a great time here, it was clean and spacious. We thoroughly enjoyed the multiple living areas and the outdoor space."
Old Ark Retreat | Secluded & spacious dog-friendly home in Wilmington
Perfect Country Cottage
Exterior
Perfect Country Cottage
9.6 out of 10, Exceptional, 73 reviews
"This house is in a great location and has everything you need to feel at home. Great house to cook in or sit out on the porch. Quick rides to town or out for a hike. More importantly Nick was so great to work with; anyone who stays here is in good hands. Thank you for everything Nick! Can’t wait to come back."
Perfect Country Cottage
Don't see what you're looking for?
See all available properties in Old 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.

Other types of properties in Old Bennington you may be interested in

The Four Chimneys Inn
Signature Room, King plus Twin Bed, Private Bathroom, Porch, Accessible, RM-10 | Premium bedding, individually decorated, individually furnished
The Four Chimneys Inn
4.0 star property
9.4 out of 10, Exceptional, 257 reviews
"We quite liked this hotel as it was charming and well thought out in many ways. We especially loved the dinner we had the first night. Our room had a fireplace and we loved that feature because it was a bit chillier than we expected. The only thing we would have wished for was a mini fridge in the room, but that’s not a huge deal breaker for us to return someday. It Is a nice walkable area and an easy to navigate town. Sadly, Bennington Pottery store isn’t open to the public anymore, but the...
The price is $269
$293 total
includes taxes & fees
Jun 16 - Jun 17
The Four Chimneys Inn
Hotel Downstreet
Hypo-allergenic bedding, laptop workspace, blackout drapes
Hotel Downstreet
3.0 star property
8.6 out of 10, Excellent, 929 reviews
"I really liked everything about it "
The price is $134
$150 total
includes taxes & fees
Jun 24 - Jun 25
Hotel Downstreet
Mountaineer Inn
Fireplace
Mountaineer Inn
2.0 star property
9.2 out of 10, Wonderful, 291 reviews
"Loved that this is a legit old ski lodge and still has the feel while having modernized what needed to be. Loved it here."
The price is $123
$149 total
includes taxes & fees
Jun 16 - Jun 17
Mountaineer Inn
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 Old 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 Old 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 Old Bennington vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Old Bennington vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Old 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 Old 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 $74 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 Old Bennington rentals

At Expedia, we put the best Old 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 Old 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 Old 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 Old 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 Old Bennington?

Yes, you can find vacation rentals near the most popular points of interest in Old Bennington, or you can choose a more remote option if you're looking for relaxation.

What are some of the best vacation home rentals in Old Bennington?

SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW! : This vacation home rental outside Old Bennington offers an indoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 12 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a pool table so you can immerse yourself in your vacation.

What’s there to see and do in Old Bennington?

Explore the area and cultural attractions such as Bennington Museum, or visit a family-friendly sight such as Sugar Shack. Other places in town to visit include Bennington Battle Monument and Old First Congregational Church.

What’s a vacation rental in Old Bennington like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Old Bennington. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for family trips or small group gatherings.

Recent reviews of Old Bennington properties
Expedia verified reviews

The Williams Inn

The Williams Inn

5/5 Excellent
"Wonderful stay and meal was very yummy. Even though waiter said we ordered too my co. But we were hungry. "
A verified traveler stayed at The Williams Inn
Posted 17 hours ago
The Williams Inn