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Top cities in Bennington County

A garden with a central pathway, surrounded by neatly trimmed hedges and various plants.
Hotels

Manchester

Manchester

Find vacation rentals that suit your style

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Apartments
Apartments
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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Bennington County cottages

A cabin with a metal roof, wooden deck, and a small porch area.

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

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Winhall
9.6 out of 10, Exceptional, (262 reviews)
" Very Nice and Cozy, had everything we needed and the instructions were very thorough and easy to follow. Nice and quiet, relaxing atmosphere a great place to just get away and relax. "
United States
Sandra W.
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
A small white house with a chimney, a front porch, and a stone wall.

2. 12 Mi to Bromley Mtn Ski Resort: Quiet Hideaway

12 Mi to Bromley Mtn Ski Resort: Quiet Hideaway
3.0 star property
Manchester Center
8.0 out of 10, Very good, (1 review)
"Wonderful location, across the road from the mountain and the stream and an old barn. It literally feels like you are in the middle of nowhere. The bedrooms were well appointed, plenty of towels and sheets. There's also a washer and dryer in the kitchen. The hallway light was full of bugs and impossible for us to find the switch to turn it off. The front door is in serious need of repair. The property manager is woefully unskilled at her job."
United States
Sandra
12 Mi to Bromley Mtn Ski Resort: Quiet Hideaway
Two blue Adirondack chairs on a wooden dock overlooking a calm lake with a rainbow in the distance and autumn foliage.

3. Home with a spring-fed pond and mountain view.

Home with a spring-fed pond and mountain view.
Manchester
10.0 out of 10, Exceptional, (143 reviews)
"We enjoyed our stay immensely especially the the koi pond and the Vermont landscape including the farm. Jeremy is a wonderful host. We were not prepared for how well stocked the refrigerator was - the very fresh eggs were really a treat. Thank you very much!"
United States
Donald F.
Home with a spring-fed pond and mountain view.
A building with a red roof and a sign that reads "Woodford General Store".

4. Lake life at Woodford Cottage

Lake life at Woodford Cottage
Bennington
9.6 out of 10, Exceptional, (17 reviews)
"We were 4 nurses from Maine in Bennington volunteering at the annual RAM clinic. We put in long hours and were so grateful to have a clean, comfortable, safe place to lay our heads down at night. A dip in the pond after clinic was a refreshing treat! House was clean, well supplied and well stocked. Hosts were responsive and welcoming. 10/10 would recommend!"
United States
Alison G.
Lake life at Woodford Cottage
A grassy outdoor area with two green chairs and a fire pit.

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

Charming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!
Dorset
10.0 out of 10, Exceptional, (45 reviews)
"We loved staying here. Perfect location for a relaxing getaway."
United States
Eric K.
Charming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!
A house with a unique stone exterior and a small window.

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

< 6 Mi to Arlington: 'Whimsical Stone Abode!'
Sandgate
10.0 out of 10, Exceptional, (5 reviews)
"This was an amazing property! Great location, comfortable furnishings, and wonderful hosts! "
United States
Karla P.
< 6 Mi to Arlington: 'Whimsical Stone Abode!'
A view of a lake from a window, with a grassy area in the foreground and a forested hill in the background.

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

Perfect for a peaceful get away in clean fresh Vermont air!
Woodford
10.0 out of 10, Exceptional, (88 reviews)
"Cozy cabin with a big yard right on a beautiful lake."
United States
Adam a.
Perfect for a peaceful get away in clean fresh Vermont air!
A wooden cabin with a metal roof, surrounded by snow-covered ground and trees, with a mountain in the background.

8. Stratton Mtn Ski Chalet w/ Giant Views in Winhall

Stratton Mtn Ski Chalet w/ Giant Views in Winhall
3.0 star property
Bondville
Stratton Mtn Ski Chalet w/ Giant Views in Winhall
A covered porch with chairs, a view of a street with houses, and a parked car.

9. < 1 Mi to Historic District! Retreat in Bennington

< 1 Mi to Historic District! Retreat in Bennington
3.0 star property
Bennington
8.0 out of 10, Very good, (2 reviews)
"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."
United States
Anonymous traveller
< 1 Mi to Historic District! Retreat in Bennington
A house with a unique stone exterior and a small window.

10. < 6 Mi to Arlington: 'whimsical Stone Abode!'

< 6 Mi to Arlington: 'whimsical Stone Abode!'
3.0 star property
Arlington
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful unique space to get away and take a break!"
United States
William
< 6 Mi to Arlington: 'whimsical Stone Abode!'
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.
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Top reviews in Bennington County

A large building with a symmetrical facade, a central entrance with a glass door, and two smaller structures on either side.
Inn At Mount Snow

Inn At Mount Snow

Inn At Mount Snow
West Dover

10/10 Excellent

Tout était parfait endroit que je vais retourné sans hésiter. Nous réservons environ 40 hôtels par année et c'est de loin notre coup de coeur
Canada
marco
Reviewed September 10, 2026
Inn At Mount Snow

Frequently Asked Questions

How much do cottages in Bennington County cost?

Prepare to pay between CA $176 and CA $1,939 per night for cottages in Bennington County. Whatever your budget, an ideal stay is a click away on Expedia. 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.

How many cottages are there in Bennington County?

Bennington County has cottages to choose from. Enter your destination and dates and plan your ideal vacation today.

Why book your cottage in Bennington County with Expedia?

Reserving a cottage in Bennington County is as easy as deciding on your travel dates and picking your ideal place for a vacation in nature. From luxurious retreats to budget-friendly stays and cottages that have perks like free WiFi, Expedia has something for all traveler styles. As for epic deals? We've got you covered!

How can I find cheap cottages in Bennington County?

With Expedia's user-friendly filter tool, comparing cheap cottages in Bennington County is a breeze. To view properties that are friendly on the wallet, tailor your search results by budget, star rating and amenities.

What is there to do in Bennington County near my cottage?

Whether you're heading north, south, east or west in Bennington County, you'll find lots of fun things to immerse yourself in here. Planning a stop in Bennington? Harmen Hills Trail is a first-rate attraction to add to your itinerary.

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