
Vacation rentals in Bennington
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Top-rated vacation rentals in Bennington
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Popular amenities for Bennington vacation rentals
Other great vacation rentals in Bennington
Guest favourite

Home in Monroe
4.93 out of 5 average rating, 14 reviewsThe 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 favourite

Home in Bellows falls
5 out of 5 average rating, 9 reviewsAmazing 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!
Superhost

Home in Manchester
4.86 out of 5 average rating, 35 reviewsYour VT Dream House: Fireplace, Pool, Dogs
AtulRating, 5 stars8 months ago
Beautiful area great amenity. Wish there was 1/2 bath downstairs. That was the only inconvenience.
Guest favourite

Home in Dover
4.89 out of 5 average rating, 71 reviewsLarge 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 favourite

Home in Wilmington
4.88 out of 5 average rating, 105 reviewsMtSnow * 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 favourite

Home in Plymouth
5 out of 5 average rating, 16 reviewsLuxury 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 favourite

Home in Saratoga Springs
4.95 out of 5 average rating, 39 reviewsGreat 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 favourite

Home in Saratoga Springs
4.96 out of 5 average rating, 151 reviewsBeautifully Restored Home Right in Downtown!
BethRating, 5 stars3 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
$41 CAD 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
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- Okemo Mountain Resort
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Saratoga Spa State Park
- Albany Center Gallery
- Saratoga Race Course
- West Mountain Ski Resort
- Berkshire East Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Mount Snow Ski Resort
- Mount Greylock Ski Club
- John Boyd Thacher State Park
- Mount Sugarloaf State Reservation
- Norman Rockwell Museum
- Bousquet Mountain Ski Area
- Otis Ridge
- Naumkeag
- Beartown State Forest
- Ekwanok Country Club
- Lake George Expedition Park
- Bretwood Golf Course
- Hooper Golf Course
- Butternut Ski Area and Tubing Center