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Vacation Rentals in Bennington, Vermont

about Bennington

Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Bennington, Vermont vacation rentals and inquire about your favorites. If you cant find what youre looking for, consider nearby destinations, or come back for a visit - vacation home rentals in Bennington are added and updated every week!

Compared to hotels, Bennington vacation rentals are much more family-friendly and flexible, offering a lot more space, a lot more savings, and a lot more amenities - like private pools, gourmet kitchens, and pet-friendly accommodations! Tip: Save money by taking advantage of cheap weekly rates.

Bennington, Vermont Vacation Rentals and Tourism

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Bennington things to do


Bennington Battle Monument

A good highlight for such a small town as Bennington. If you happen to be in Bennington, you should go visit more


Mass Museum of Contemporary Art

I saw sad to hear that Wilco was taking a skip year, but we went to Mass MOCA anyway. The 13 acres in the old factory are filled with new art from all more


Clark Art Institute

The collection is fabulous. I was so impressed and surprised as a native NYCer to find such an extensive collection of art from so many famous periods more


Vermont Arts Exchange

Their Mission Statement says it all.....To strengthen communities and neighborhoods through the arts and to bring art, art education, exhibition more


Mt. Anthony Country Club

Pretty decent greens. Challenging to walk and cart fee is $20. Too many blind shots. No water to drink on the more


Oldcastle Theatre Company

What a great little gem this is! I have only been to two performances there so far but both have been extraordinary. Great seating and layout. Both more


The Yoga Place

I attended a different class on Friday morning with Carol. This was a longer class then the Monday evening class. Carol's class was a workout and a half; more


Bennington CrossFit

Great instruction, good people, nice and more


Robert Frost Stone House Museum

To tell you the truth, I wasn't expecting much from this experience. Compared to other historic homes (especially ones so close to the recent past), more


Park McCullough House

While visiting my daughter & family in Bennington, I had one afternoon free. I have always loved touring other people's houses, seeing how others lived more


Images Cinema

This is a fantastic little theatre in Williamstown! From blankets to organic popcorn and butter and candy this great theatre has it all... except more


Bennington Museum

*Spoiler Alert* The best piece of art in the entire museum is called "Happy Naked Princess Leia". The actual name is something dumb like "Nirvana", more


Cinema 7

Pretty much the only theatre in Southern Vermont! Cinema 7 offers most of the current box offer favorites. The prices work since you don't have any more


Anytime Fitness

This gym was my friend for my first 2 weeks away from home, away from the city. Thanks to the 14-day free trial deal! The equipments are new. The more


Williamstown Theatre Festival

We took a vacation in the area, and found the performance of "The Elephant Man'" with it's 12 day run, which we managed to get tickets to. Spectacular! more

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Meadowood Farm
Bennington House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $400 - $450 /nt
    $1,300 - $1,500 /wk
    $4,000 - $6,000 /mth

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Labor Day Weekend Now Available due to last minute cancellation!
Bennington Apartment Rental Picture
  • bedrooms 1
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $135 - $199 /nt
    $945 - $1,050 /wk

33 reviews write a review

Private Pool, hot tub and the fabulous mountains outside your door!
Bennington Barn Rental Picture
  • bedrooms 3
  • rental type Barn
  • sleeps 12
  • baths 1
  • rates (USD) $165 - $215 /nt
    $1,155 /wk

2 reviews write a review

Escape to our Country Estate w/Guest House, 350 acres with ponds, woods & trails
Bennington House Rental Picture
  • bedrooms 6
  • rental type House
  • owner badgeowner badge
  • sleeps 12
  • baths
  • rates (USD) $350 - $450 /nt
    $2,300 - $2,600 /wk

17 reviews write a review