Search Cottages in Bennington

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
5 Sep - 7 Sep
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Cottages in Bennington

Our top choices for Bennington cottages

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Dining

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (227)
"We had an incredible time staying at the cottage and can't wait to visit again sometime! From hiking, sitting on the porch drinking coffee, cooking while listening to music, and enjoying time on the pond, everything about our stay was perfect. "
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access
Exterior

Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access

8.8 out of 10, Excellent, (3)
"Perfect cottage on the water!! Enjoyed kayaking and pedal boat with family. Beautiful greenery! Very quick respond."
Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access
Home with a spring-fed pond and mountain view.
Pool

Home with a spring-fed pond and mountain view.

10.0 out of 10, Exceptional, (118)
"Cute cottage with a lot of charm. The kiddos loved the concept of staying next to a pond. Convenient location to Manchester center and also to Bromley. Jeremy was quick to respond to all to all pf our questions."
Home with a spring-fed pond and mountain view.
Perfect for a peaceful get away in clean fresh Vermont air!
Exterior

Perfect for a peaceful get away in clean fresh Vermont air!

10.0 out of 10, Exceptional, (74)
"Enjoyed the cozy cabin feel. Property was extremely clean and when hit with snow the plow service was totally on top of it! A lovely stay!"
Perfect for a peaceful get away in clean fresh Vermont air!
Lake life at Woodford Cottage
Smart TV, fireplace

Lake life at Woodford Cottage

9.6 out of 10, Exceptional, (15)
"Perfect getaway for a family ski trip."
Lake life at Woodford Cottage
Bennington Gem w/ Smart TV Near Historic District!
House (1 Bedroom) | Interior

Bennington Gem w/ Smart TV Near Historic District!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We liked staying at the place as it had good amenities (washer, dryer, dishwasher, fridge with a freezer, fan, inflatable bed, wifi, cable, free parking spots. etc) and a lot of space. Where there is no central AC, it had a window unit which worked well - we had a comfortable stay in mid-July."
Bennington Gem w/ Smart TV Near Historic District!
This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.
Exterior

This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.

10.0 out of 10, Exceptional, (28)
"This was a great location… close to town but also close to skiing, hiking and skating."
This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.
< 6 Mi to Arlington: 'whimsical Stone Abode!'
Cottage (1 Bedroom) | Interior

< 6 Mi to Arlington: 'whimsical Stone Abode!'

3.0 star property
10.0 out of 10, Exceptional, (1)
"We came into town for a few days to visit friends. This was a perfect place. The home was clean and very inviting! Quiet location. Fully stocked kitchen with all the appliances and cooking ware you may need. You will not regret staying here. We loved the photo album of how the home was built! "
< 6 Mi to Arlington: 'whimsical Stone Abode!'
< 6 Mi to Arlington: 'Whimsical Stone Abode!'
Fridge, microwave, stovetop, dishwasher

< 6 Mi to Arlington: 'Whimsical Stone Abode!'

< 6 Mi to Arlington: 'Whimsical Stone Abode!'
Charming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!
Fridge, microwave, oven, stovetop

Charming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!

10.0 out of 10, Exceptional, (28)
"Loved Dorset and this house was great. Very clean and living area was nice to spend time with family. Also close to skiing which we took advantage of"
Charming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!
Spacious Home Near Bromley Mountain Ski Resort!
Exterior

Spacious Home Near Bromley Mountain Ski Resort!

3.0 star property
Spacious Home Near Bromley Mountain Ski Resort!
Manchester Center Home w/ Green Mtn Views!
House (2 Bedrooms) | Interior

Manchester Center Home w/ Green Mtn Views!

3.0 star property
Manchester Center Home w/ Green Mtn Views!
Beautiful Winter Escape on Bromley Mountain!
TV, fireplace, video-game console, books

Beautiful Winter Escape on Bromley Mountain!

3.0 star property
Beautiful Winter Escape on Bromley Mountain!
Enchanting Dorset Mountain Home w/ Stunning Views!
Fireplace

Enchanting Dorset Mountain Home w/ Stunning Views!

3.0 star property
6.0 out of 10, (1)
"The property was clean but run down compared to online photos. It would be helpful to have supplies such as wastebaskets in bathrooms, hand towels, dish clothes, pot holders, juice glasses/cups, extra towels, and paper towels and/or tissues. "
Enchanting Dorset Mountain Home w/ Stunning Views!
Cozy Cabin Between Stratton Resort & Mount Snow
TV, fireplace

Cozy Cabin Between Stratton Resort & Mount Snow

3.0 star property
Cozy Cabin Between Stratton Resort & Mount Snow
Nostalgic Vermont Escape in Manchester Center
Microwave, oven, stovetop, dishwasher

Nostalgic Vermont Escape in Manchester Center

3.0 star property
Nostalgic Vermont Escape in Manchester Center
Breathtaking Mtn Views: Stylish Rustic Retreat!
House (2 Bedrooms) | Interior

Breathtaking Mtn Views: Stylish Rustic Retreat!

3.0 star property
Breathtaking Mtn Views: Stylish Rustic Retreat!
Stylish Mountain Home Near Ski, Golf + Manchester!
Interior

Stylish Mountain Home Near Ski, Golf + Manchester!

3.0 star property
Stylish Mountain Home Near Ski, Golf + Manchester!
Stratton Mtn Ski Chalet w/ Giant Views in Winhall
House (3 Bedrooms) | Interior

Stratton Mtn Ski Chalet w/ Giant Views in Winhall

3.0 star property
Stratton Mtn Ski Chalet w/ Giant Views in Winhall
Secluded Home, 7 Mins to Stratton Mountain Resort
Exterior

Secluded Home, 7 Mins to Stratton Mountain Resort

3.0 star property
Secluded Home, 7 Mins to Stratton Mountain Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Bennington Hotel Reviews

Perfect for a peaceful get away in clean fresh Vermont air!

Perfect for a peaceful get away in clean fresh Vermont air!

10/10 Excellent
"We had an absolutely incredible vacation staying at Linda's cabin right on Big Pond. Having all the boats to use was great, our dog loved swimming everyday, and Linda was the best host"
Cathy G. 8-night trip
Posted 2 days ago
Perfect for a peaceful get away in clean fresh Vermont air!

Frequently asked questions

How much do cottages in Bennington cost?
Rates for cottages in Bennington range between and per night. Whatever your budget, you're sure to find the ideal place to get reacquainted with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Bennington with Expedia?
Reserving a cottage in Bennington is as easy as entering your travel dates and choosing an ideal place for a getaway in nature. From ritzy retreats to low-cost stays and cottages that offer amenities like a kitchenette, Expedia has something for all traveler tastes. As for awesome deals? We've got them as well!
How can I find cheap cottages in Bennington?
With Expedia's user-friendly filter tool, sourcing cheap cottages in Bennington has never been simpler. To view properties that'll make your hip pocket happy, narrow down your search by amenities, budget and star rating.