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.

Guest favorite
Apartment in Bennington
NEW Escape the City- Vermont Studio
Our newly renovated studio apartment is located minutes from Bennington College, and sits on 7 acres of land in the Green Mountain National Forest. It's on the second floor of our home through a private entrance with a personal deck and outdoor seating. Take an afternoon to stroll to the Mile Around Woods, or hike to the white rocks! Walk the Ninja trail from the college to see the historic covered bridges, or drive 20-30 miles N to enjoy Vermont's best skiing, and shopping at designer outlets!
Dec 23 – 30
ﺩ.ﺇ294 per night
4.94 out of 5 average rating, 154 reviews
Guest favorite
Cabin in Woodford
Lakeview Cabin in the Mountains - beautiful
Lovely log sided cabin situated across from Woodford lake with view. Large Great room cathedral ceiling, halfmoon window, pine ceiling & floors, dining table,woodstove, corner gas fireplace, full kitchen. Beautiful ambiance, rustic yet elegant. 2 bedrooms, full bath with clawfoot tub, romantic sleeping loft w sitting area. Basement play area heated with 2 beds for children. Central heat, washer/dryer TV/Roku, ceiling fans. Great getaway for nature lovers, skiers, snowmobilers, hikers. Wifi.
May 9 – 16
ﺩ.ﺇ573 per night
4.91 out of 5 average rating, 131 reviews
Guest favorite
Guesthouse in North Bennington
Birch House - lake, green trees + modern comforts
Birch House is a little guest house near a lake in Vermont with green trees + modern comforts. Perfect for couples + individuals looking to relax + enjoy nature. Renovated, air conditioned light space with cozy, minimalist vibes. We're a small modern cabin that's peaceful + private. Tucked into a quiet neighborhood. Main home is a separate building next door. Near Bennington College. 12 minutes to downtown Bennington. Please note that due to a severe allergy, we cannot accommodate animals.
May 18 – 25
ﺩ.ﺇ443 per night
4.98 out of 5 average rating, 141 reviews

Popular amenities for Bennington vacation rentals

Stay near Bennington's top sights

Bennington Battle Monument72 locals recommend
The Blue Benn40 locals recommend
Madison Brewing Company Pub & Restaurant42 locals recommend
Ramunto's Brick Oven Pizza16 locals recommend
Apple Barn Country Bake Shop10 locals recommend
Sunny Side Diner3 locals recommend

Other great vacation rentals in Bennington

Superhost
Home in Readsboro
Vermont March Madness! (Pet Friendly)
Sep 4 – 11
ﺩ.ﺇ249 per night
4.86 out of 5 average rating, 118 reviews
Guest favorite
Tiny home in Jamaica
Apple Blossom Cottage: A Tiny House
Feb 5 – 12
ﺩ.ﺇ315 per night
4.94 out of 5 average rating, 1129 reviews
Guest favorite
Guest suite in Wilmington
Architectural GuestSuite
Nov 25 – Dec 2
ﺩ.ﺇ376 per night
4.92 out of 5 average rating, 708 reviews
Guest favorite
Barn in Marlboro
The Studio With a View. Bring your dog, too!
Jan 24 – 31
ﺩ.ﺇ446 per night
4.95 out of 5 average rating, 260 reviews
Guest favorite
Cabin in Shaftsbury
Renovated Log Cabin Lodge-EV & Pets-Hike-Hot Tub
Dec 19 – 26
ﺩ.ﺇ1,605 per night
5.0 out of 5 average rating, 108 reviews
Guest favorite
Cabin in Pownal
Historic Cozy Cabin Six
May 22 – 29
ﺩ.ﺇ346 per night
4.97 out of 5 average rating, 171 reviews
Superhost
Cabin in Bennington
Vermont Cabin - Secluded Woods on South Stream
Apr 27 – May 4
ﺩ.ﺇ328 per night
4.81 out of 5 average rating, 99 reviews
Guest favorite
Home in Shaftsbury
Cheerful 1 bedroom cottage
Nov 25 – Dec 2
ﺩ.ﺇ265 per night
4.92 out of 5 average rating, 95 reviews
Guest favorite
Farm stay in Bennington
The Farm cottage
Dec 30 – Jan 6
ﺩ.ﺇ514 per night
4.96 out of 5 average rating, 76 reviews
Guest favorite
Apartment in Bennington
Cozy Loft steps from VT downtown
Apr 10 – 17
ﺩ.ﺇ461 per night
4.86 out of 5 average rating, 37 reviews
Guest favorite
Apartment in Bennington
North Bennington, VT conveniently located unit.
Dec 2 – 9
ﺩ.ﺇ327 per night
4.78 out of 5 average rating, 32 reviews
Guest favorite
Cottage in Bennington
Cozy, bright 3-bedroom Cottage with fireplace.
Dec 12 – 19
ﺩ.ﺇ1,102 per night
5.0 out of 5 average rating, 52 reviews

Quick stats about vacation rentals in Bennington

Total rentals

40 properties

Rentals with dedicated workspaces

20 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

1.9K reviews

Nightly prices starting at

ﺩ.ﺇ110 before taxes and fees

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Bennington?

    Yes! Work meets play with ease at over 20 vacation rentals in Bennington featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Bennington?

    Four-legged friends are welcome in Bennington. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there family-friendly vacation rentals in Bennington?

    Bennington has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do apartment rentals in Bennington have wifi?

    Absolutely! We offer over 10 apartment rentals with wifi in Bennington. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Bennington?

    Experience the best of Bennington with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Bennington have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Bennington. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Bennington?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, over 10 homes with free parking, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do apartment rentals in Bennington have free parking?

    Absolutely! We offer over 10 apartment rentals with free parking in Bennington. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore

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