Search Bennington Cottage Accommodations

    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

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Cottages in Bennington

Comfy Cottage in Historic East Poultney
Exterior

Comfy Cottage in Historic East Poultney

10.0 out of 10, Exceptional, (7)
"We enjoyed our extended stay at the cottage! Nate was a great host and available, if needed. My 5 yr old still talks about her favorite stone in the shower Would highly recommend this location "
The price is AU$485
includes taxes & fees
24 Aug - 25 Aug
Comfy Cottage in Historic East Poultney
Historic Cottage- near Saratoga- on Summit Lake
Dining

Historic Cottage- near Saratoga- on Summit Lake

10.0 out of 10, Exceptional, (15)
"Overall it was great! Very nice and helpful hosts and great lake views!"
The price is AU$546
includes taxes & fees
25 Aug - 26 Aug
Historic Cottage- near Saratoga- on Summit Lake
3-bedroom cottage on Cossayuna Lake
Pool

3-bedroom cottage on Cossayuna Lake

7.6 out of 10, Good, (4)
"We had a good time. I was a little disappointed about the pool"
The price is AU$396
includes taxes & fees
29 Aug - 30 Aug
3-bedroom cottage on Cossayuna Lake
Terrific 3-bedroom cottage with AC in charming Cavendish
Private kitchen

Terrific 3-bedroom cottage with AC in charming Cavendish

The price is AU$897
includes taxes & fees
24 Aug - 25 Aug
Terrific 3-bedroom cottage with AC in charming Cavendish
Hilltop Cottage
Fridge, microwave, oven, stovetop

Hilltop Cottage

10.0 out of 10, Exceptional, (1)
"Beautiful cottage well kept. Created great environment "
Hilltop Cottage
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

Harwood Hill Motel

Harwood Hill Motel

10/10 Excellent
"Delightful country stay in North Bennington. Restaurant within walking distance. Excellent views. Love the artsy atmosphere. "
Melissa 1-night trip
Posted 2 days ago
Harwood Hill Motel

Frequently asked questions

How much do cottages in Bennington cost?
Cottages in Bennington range between and per night. These properties offer a chance to touch base with nature — at a price you can afford. This price was 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.
What is there to do in Bennington near my cottage?
Whatever your interests, Bennington has loads to keep you busy. Prospect Mountain Cross-Country Ski Centre, Woodford State Park and Prospect Mountain Nordic Ski Centre are on most travellers' sightseeing plans. Don't forget about Old First Congregational Church, Robert Frost Stone House Museum and Southern Vermont College either. With Expedia's hotel deals in Bennington, you can discover even more wonderful attractions like these with the money you save.