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Vacation rentals in Bennington

Book unique vacation rentals, houses, and more on Airbnb

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Popular amenities for Bennington vacation rentals

Stay near Bennington's top sights

Bennington Battle Monument72 locals recommend
Bennington Museum61 locals recommend
Madison Brewing Company Pub & Restaurant42 locals recommend
The Blue Benn40 locals recommend
Bennington Potters33 locals recommend
Allegro21 locals recommend

Other great vacation rentals in Bennington

Superhost
Home in Warrensburg
4.85 out of 5 average rating, 232 reviews

INCREDIBLE Adirondack Home (Lake George/Gore Mtn.)

RachelRating, 5 stars1 month ago
We loved our stay, the house was perfect for what we needed. Beautiful view from the back porch, clean, cute decor, lots of space and the kitchen had all we needed. Easy drive to Gore mountain. Easy entry and contact with owners. We will definitely rent again!
Guest favorite
Home in Monroe
4.93 out of 5 average rating, 14 reviews

The Camp

BrendaRating, 5 stars2 months ago
We enjoyed a short ski trip to Berkshire East. M's place was comfortable, spacious and clean. The kitchen had everything we needed to cook and make coffee. They even had dog bowls and treats for our pup! Snow removal was completed early, allowing us to get out and on the slopes for the day. As M says in the description, you definitely need a vehicle with AWD or 4X4 since you are nestled in the mountains. We enjoyed the bountiful binder with history of the small town and local attractions. I would caution people with young children and older folks about the steep staircase to the 2nd floor where the bedrooms are. The 1 full bath is on the first floor so if you're like me, you need to navigate the stairs in the middle of the night. We didn't mind this since it is part of the charm of a historic building and our family of four including two teens had no problems. We enjoyed our stay and would love to return!
Guest favorite
Home in Bellows falls
5 out of 5 average rating, 8 reviews

Amazing Views, Skiing Nearby and Amenities Galore!

GillianRating, 5 stars2 months ago
We absolutely loved our stay at Barbara’s home! It was spacious enough to accommodate 6 adults and 1 child with no issue. The kitchen is well appointed, allowing us to cook meals throughout our stay. We had a small storm roll through, which dropped 5” of snow overnight (great for our next day on the mountain!), and we were thrilled to see that the driveway and walkway had been cleared prior to 7am. The bedrooms were comfortable and the view from the great room is truly stunning. Would love to stay here again! Thank you, Barbara!
Guest favorite
Home in Dover
4.89 out of 5 average rating, 71 reviews

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.
Guest favorite
Home in Wilmington
4.88 out of 5 average rating, 105 reviews

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.
Top guest favorite
Home in Plymouth
5 out of 5 average rating, 16 reviews

Luxury Modern Cabin near Okemo & Killington

TariQRating, 5 stars1 month ago
Stephanie was an Incredible host! The listing matched her description and the property looked even better upon checking in. Stephanie maintains this property really well and I couldn’t have felt any more at home. The home was clean and had a perfect cozy feeling to it. In addition, this was really close to the mountain, which made the getaway even better. I enjoyed the privacy and waking up to a nice snow dusting before my trip to the mountain. I highly suggested staying at Stephanie’s property if you’re looking for a quick getaway. I certainly will be looking to book again soon. Thank you Stephanie!
Guest favorite
Home in Saratoga Springs
4.95 out of 5 average rating, 39 reviews

Great Saratoga House with Pool Walk to Everything!

CaitrinRating, 5 stars4 months ago
Loved staying here! It was super cozy and a lovely home away from home for the holidays. House is as described and very spacious. Fireplace makes it extra cozy when the weather got cold. Host was very proactive and responded to any question or issue almost immediately. We will definitely be staying here again!
Top guest favorite
Home in Saratoga Springs
4.96 out of 5 average rating, 151 reviews

Beautifully Restored Home Right in Downtown!

BethRating, 5 stars2 weeks ago
This booking is located on a tastefully renovated 2nd floor of a historic home in a beautiful neighborhood near downtown Saratoga Springs. It’s spacious, cozy, and comfortable. The addition of some antiques throughout the apartment was very charming. The caretaker living on the ground floor was kind and helpful. The house is walking/biking distance to the Convention Center, downtown restaurants, shops, and bars. There’s a Fresh Market and a great coffee shop 5 minutes driving. The neighborhood is quiet and peaceful and the kitchen is fully stocked. Easily one of the best Airbnbs we’ve stayed at. The hosts were very responsive, understanding and accommodating. I highly recommend staying here!

Quick stats about vacation rentals in Bennington

  • Total rentals

    40 properties

  • Nightly prices starting at

    ﺩ.ﺇ110 before taxes and fees

  • Total number of reviews

    2K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Bennington County
  5. Bennington