Search Cottages in Bennington

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
9.6 out of 10, Exceptional, (195)
"A great place to unwind and snuggle with my spouse to celebrate our Anniversary!"
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Home with a spring-fed pond and mountain view.
10.0 out of 10, Exceptional, (110)
"Very nice and cozy place to getaway for a few nights! Very close to Manchester and places to eat and things to do. Koi pond was very pretty and we enjoyed feeding them! Loved having coffee on the deck with a view of the mountains, before we went on our adventures! "
Home with a spring-fed pond and mountain view.
Great Place to get away and have clean fresh air surround you!
9.8 out of 10, Exceptional, (131)
"This was one of our favorite family trips ever! So fun using the paddle boat and seeing the misty mornings and starry nights in the lake."
Great Place to get away and have clean fresh air surround you!
Perfect for a peaceful get away in clean fresh Vermont air!
10.0 out of 10, Exceptional, (70)
"What a lovely stay! The cabin was stocked with everything we needed and it was very clean and well organized. The photos don't quite do it justice. Peaceful lake views all day with mountains in the distance - what's not to like? We used the queen bedroom on the main floor and the bed was so very comfortable. We were there for two weeks, so we definitely used the kitchen - again, a well-planned space and well stocked. We hope to be there again!"
Perfect for a peaceful get away in clean fresh Vermont air!
Lake life at Woodford Cottage
9.4 out of 10, Exceptional, (13)
"Very comfortable beds! This property is what you would expect from a cottage in Vermont, but there's so much more! We were surprised by the very well equipped kitchen and the vicinity to Woodford State Park also worked out really well for us. Would definitely recommend!"
Lake life at Woodford Cottage
This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.
10.0 out of 10, Exceptional, (22)
"Wonderful place to stay in great location. Private, quiet- less than a block away from equinox resort. Walking distance to restaurants. Manchester is a sweet little town with beautiful homes and history"
This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.
Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!
10.0 out of 10, Exceptional, (21)
"Not often in life do all things congeal to make an experience perfect. However, this was our sense of out Dorset vacation. We would repeat it without a second thought!"
Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
3.0 star property
10.0 out of 10, Exceptional, (1)
"The host was so kind and helpful. I will definitely cime abck here. "
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
Spacious Home Near Bromley Mountain Ski Resort!
3.0 star property
Spacious Home Near Bromley Mountain Ski Resort!
Beautiful Winter Escape on Bromley Mountain!
3.0 star property
Beautiful Winter Escape on Bromley Mountain!
Manchester Center Home w/ Green Mtn Views!
3.0 star property
Manchester Center Home w/ Green Mtn Views!
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!
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!
Cozy Cabin Between Stratton Resort & Mount Snow
3.0 star property
Cozy Cabin Between Stratton Resort & Mount Snow
Nostalgic Vermont Escape in Manchester Center
3.0 star property
Nostalgic Vermont Escape in Manchester Center
Breathtaking Mtn Views: Stylish Rustic Retreat!
3.0 star property
Breathtaking Mtn Views: Stylish Rustic Retreat!
Secluded Home, 7 Mins to Stratton Mountain Resort
3.0 star property
Secluded Home, 7 Mins to Stratton Mountain Resort
Stylish Mountain Home Near Ski, Golf + Manchester!
3.0 star property
Stylish Mountain Home Near Ski, Golf + Manchester!
Whimsical Winhall Cottage w/ Private Hot Tub!
3.0 star property
Whimsical Winhall Cottage w/ Private Hot Tub!
Londonderry Vacation Home w/ Deck + Gas Grill!
3.0 star property
Londonderry Vacation Home w/ Deck + Gas Grill!
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.
Don't see what you're looking for?
See all available properties in Bennington
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Bennington

Great Place to get away and have clean fresh air surround you!
9.8 out of 10, Exceptional, (131)
"This was one of our favorite family trips ever! So fun using the paddle boat and seeing the misty mornings and starry nights in the lake."
Great Place to get away and have clean fresh air surround you!
Victorian Home in Bennington, Vermont
10.0 out of 10, Exceptional, (86)
"The home is spacious, clean, bright, nicely decorated and well-equipped. An easy walk to shops and restaurants. It was great for our annual family gathering in southwestern Vermont."
Victorian Home in Bennington, Vermont
Perfect for Leaf Peeping w/Bar Room, Hot Tub
9.8 out of 10, Exceptional, (10)
"We had 15 members of my family in this old house. Another 5 at another VRBO , and 4 others that joined us all day Saturday. Good weather and the annual recognition of the Battle of Bennington was a wonderful surprise The house needs many repairs. The kitchen was a big disappointment "
Perfect for Leaf Peeping w/Bar Room, Hot Tub
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.

Frequently asked questions

Why book your cottage in Bennington with Expedia?
We think that holidays should be simple, so if you’re looking for cottages in Bennington at the perfect price, Expedia can help. Save those pennies and select a cheap option surrounded by wilderness, or book a 5-star cottage to spoil your loved ones.
How can I find cheap cottages in Bennington?
An excellent way to track down cheap cottages in Bennington is with Expedia’s useful filter tool. Refine your search by star rating, budget and amenities to grab unbeatable prices with only a few clicks.
What is there to do in Bennington near my cottage?
No matter your interests, Bennington has plenty to keep you on the hop. Prospect Mountain Cross-Country Ski Centre, Woodford State Park and Prospect Mountain Nordic Ski Centre are on many travellers’ schedules. Don’t go home without exploring Old First Congregational Church, Norman Rockwell Exhibition and Robert Frost Stone House Museum either. With Expedia’s Bennington hotel deals, you can discover more renowned attractions like these with the cash you save.