Vacation rentals in Bennington County

5 out of 5 average rating, 10 reviews

Home in Wilmington

Lake & Mountain View Cabin - Sauna, Hot Tub, Hikes

VanessaRating, 5 stars1 month ago

There is not a shortage of things to do at Anthony's place. The game tables, sauna and hot tub made the weekend really fun, especially for the non skiers of the group. The view from the house is also spectacular! We would definitely rent this place again.

4.85 out of 5 average rating, 13 reviews

A well-maintained entryway showcases wooden steps leading up to the front door, accompanied by a railing featuring horizontal cable wiring. Lush greenery and colorful flowers are planted alongside the steps, enhancing the welcoming approach to the home.

Home in Hoosick Falls

Enjoy Fall & Experience Beautiful Changing Colors

AnthonyRating, 5 stars2 months ago

We stayed here for a few months while we looked for a home to buy after a work move. Over these months Delia and the home were great. The house provided everything we needed, was well kept, and everything we needed was provided for us while our things were in storage. Delia was communicative throughout and helped us when we needed to stay longer. A great property with great views and a great host.

4.86 out of 5 average rating, 125 reviews

Home in Readsboro

Beautiful Vermont! (Pet Friendly)

JudahRating, 5 stars4 months ago

This stay was an absolute gem! The host’s charming old house radiates character and warmth, with every detail carefully curated to make you feel at home. Her hospitality was unmatched—gracious, attentive, and genuine. Clear directions were thoughtfully placed everywhere, making the stay seamless and stress-free.

4.91 out of 5 average rating, 98 reviews

Two blue Adirondack chairs are positioned on a wooden deck overlooking a lush green lawn and Sadawga Lake. A gas grill is situated nearby. Soft shadows are cast on the deck from the chairs, with the sky above featuring scattered clouds and sunlight.

Tiny home in Whitingham

Cozy Lakeside Tiny Home, Near Skiing

MelissaRating, 5 stars1 month ago

We had a lovely time at this tiny home. It was quiet and relaxing which is exactly what we were looking for. We enjoyed the hot tub and the sunny living room. It was cozy and cute. We took a few trips to Wilmington for food. It’s a cute town. We’d like to come back when the weather is better to enjoy some kayaking and hiking in the area.

4.91 out of 5 average rating, 134 reviews

An open door leads to a private balcony, where a serene tree offers shade. A large, relaxed dog rests on the balcony floor. Bright greenery is visible, enhancing the tranquil outdoor atmosphere.

Apartment in Wilmington

Globetrotter Retreat too - Minutes to the Mountain

XianlongRating, 5 stars3 weeks ago

Thanks for the host making this place like home. Furnitures are well organized. My partner and I love the sofa in the living room. There is a big sofa and single arm chair sofa. It’s good for staying with partner to kiss cuddle and more. We love the well organized kitchen. Very well-equipped. They even have some stock of food, coffee and tea bags just in case if you are hungry in mid night. We came here for skiing trip. It’s just 15 min to Mt Snow, 1.5h to Okemo. Stratton is also around this area. Great location for mountain staycation.

5 out of 5 average rating, 70 reviews

An aerial view captures a chalet with a steeply pitched roof, softly illuminated by warm outdoor lighting. The wrap-around deck features comfortable seating and a fire pit area. The surrounding lawn is lush, enhanced by charming landscape elements and the peaceful ambiance of evening light.

Cabin in Wilmington

Modern Chalet-private deck/firepit/ clubhouse pool

LoremyRating, 5 stars2 months ago

Michelle and this property are absolute gems. The place is spotless, full of clean and well-maintained pots, pans, kitchen utensils, appliances, and tableware. All the rooms are well appointed and comfortable. We have learned from past rentals that the home is not always cleaned properly. So we normally wipe down all the counters, faucets and tables prior to use. This is the only home that we’ve rented that came away with ZERO dirt. Michelle’s very prompt communication contains very detailed information regarding the house and things to-do around the area. We are in awe of this house and Michelle. We hope that all future renters continue to respect the property so that many more can continue to enjoy it for years to come.

5 out of 5 average rating, 10 reviews

A modern cabin is situated among snow-covered trees, showcasing large windows that reflect the evening sky. The triangular roofline and dark exterior contrast with the white snow, while a cozy glow emanates from within.

Home in Peru

Highland Haus: stunning ski getaway with hot tub

ChristopherRating, 5 stars1 month ago

Beautiful home that is about 15min from Manchester, which is wonderful to walk around (shops, restaurants). The home is secluded on a nice piece of property in the woods. It was a charming getaway with a wood-burning fireplace and great amenities (games, dart board, hot tub, etc). Highly recommend!

Vacation rentals for every style

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Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Bennington County vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Bennington County

4.85 out of 5 average rating, 227 reviews

An outdoor deck features white railing and steps leading up to the entrance of the house. Two chairs are positioned on the deck, surrounded by a grassy area and trees in the background. A red umbrella stands at one corner, providing shade.

Home in Manchester

Keys to Vermont

ElizabethRating, 5 stars1 month ago

Mary’s place was a great location for us to stay during our ski trip to Bromley. We were within a 10min drive to skiing and 5 minute drive to the restaurants in town. The beds were very comfortable and the bathrooms nice and clean. We randomly had cassette tapes with us and Mary had a tape player, the kids were soo excited to use it. She also had games and books for the kids. We had a great time! Thank you!

4.95 out of 5 average rating, 42 reviews

A tranquil lakeside view is framed by a large window, showcasing lush greenery and a grassy area leading down to the water. A glider swing sits nearby, with a small group of colorful chairs arranged on the lawn. The calm lake reflects the surrounding trees.

Cottage in Woodford

HoneyBear Lake Cottage

CarinaRating, 5 stars8 months ago

We had a wonderful peaceful stay at Honey Bear, Linda Jane is a fantastic host and her home is beautiful and relaxing. It rained a lot of our stay, but we did get to make the most of our stay when it was nice out with all the wonderful inclusions. The boats and games were a fanatic added bonus. Thank you so much

4.95 out of 5 average rating, 57 reviews

The image captures a serene lake scene with swimmers enjoying the water near a rocky shore. A sailboat glides peacefully across the sparkling surface, surrounded by lush green hills under a partly cloudy sky.

Condo in Dover

Condo w/ great amenities 4-seasons! Ski in Ski out

DavidRating, 5 stars2 weeks ago

Christine is very easy to work with and very responsive. she answered us back right away before and during our stay. the place is great! very cozy and comfortable. I can't wait to go back to her place next time we're in town!

4.98 out of 5 average rating, 48 reviews

A pair of large, framed windows offer views of a mountainous landscape, featuring snow-capped peaks and dense green forests. Natural light filters into the room, highlighting the soft textures of nearby seating and creating a cozy ambiance.

Condo in Dover

Mountain View Ski Escape

CarolynRating, 5 stars1 month ago

What a fantastic family weekend (2 families, 5 kids total ages 10 to 6). Andrew was super responsive to questions we had about the sleep set up (two bunks as well as a large single bed w/ trundle) for the kids. But more importantly, he was proactive! He sent clear notes on check in, how to get a fire going, local amenities, shuttles and more. The Community Center was fabulous; a large indoor, heated pool and hot tub, game room, library, TV room w/ bean bag chairs, common room w/ fire, popcorn, hot cocoa and even a little apres ski party on Saturday from 4-6pm. The condo is super close to Mt Snow, easy to find and park. Andrew even had sleds in the front closet which came in handy when the lifts shut down due to wind (but sledding in the backyard was a breeze). Highly recommend this great tri-story condo!

4.89 out of 5 average rating, 71 reviews

A hot tub is situated on a wooden deck, surrounded by a misty forest of bare trees. Snowflakes lightly cover the edge of the tub, while steam rises gently from the water, creating a serene winter atmosphere.

Home in Dover

Large Mount Snow Ski House with Hot Tub

AndyRating, 5 stars1 month ago

Big group of friends and I stayed at Michele's place for a ski-weekend at Mount Snow. House was comfortable and fun with lots of games in the basement and space for us to hang out as a group in the main living area. Hot tub was 🧑‍🍳 perfection. Michele was responsive and helpful via messages.

4.88 out of 5 average rating, 105 reviews

Home in Wilmington

MtSnow * HotTub * Pool * Air Hockey * PingPong * Darts

JamesRating, 5 stars1 week ago

Place was great! Less than 10 minutes to Mount Snow. We had fun playing ping-pong, air hokey, pool, and darts! Relaxed by the wood burning stove. Lots of rooms and beds.

4.88 out of 5 average rating, 58 reviews

Home in Stratton

Visit Vermont - Home Minutes to Mt. Snow/ Stratton

JamesRating, 5 stars1 month ago

Great place for March 2015 Ski trip. Friendly owner. The house is well stocked and has everything you could need. Pictures were accurate for the cabin like feel. Highly recommend.