Title: Bennington Chalets from CA $611 | Expedia.ca

[Hotels in Bennington](https://expedia.ca/Bennington-Hotels.d6057349.Travel-Guide-Hotels)[Vacation Rentals in Bennington](https://expedia.ca/Bennington-Vacation-Rentals.d6057349.Travel-Guide-VacationRentals)[Flights to Bennington](https://expedia.ca/Cheap-Flights-To-Bennington.d6057349.Travel-Guide-Flights)[Things to do in Bennington](https://expedia.ca/Things-To-Do-In-Bennington.d6057349.Travel-Guide-Activities)[Bennington Car Rentals](https://expedia.ca/Car-Rentals-In-Bennington.d6057349.Car-Rental-Guide)[Bennington Vacation Packages](https://expedia.ca/Bennington.d6057349.Destination-Travel-Guides)

![Historic Henry Covered bridge over the Walloomsac River e in Bennington, Vermont](https://images.trvl-media.com/place/6057349/ddd79da6-d04a-4703-8452-12989539524e.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Search Chalets in Bennington from CA $611

- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg)  
###  
Change your mind  
Book hotels with free cancellation
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg)  
###  
Treat yourself  
Sign in to save 10% or more on thousands of hotels  
[Sign in](https://www.expedia.ca/login)
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg)  
###  
Be picky  
Search almost a million properties worldwide

## Check prices for these dates

In two weeks

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6057349&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6057349&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6057349&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=6057349&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Bennington chalets

![Exterior](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/63238a28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/ad2f042c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/0c516aaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/47dfeff7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in Plymouth

[](https://www.expedia.ca/Plymouth-Hotels-BIGFOOT-CHALET.h106157385.Hotel-Information)

10/10

Exceptional

(14)

"Really enjoyed the setup at the location and the owners were very responsive to any queries!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ed N.

CA $309

CA $838 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Plymouth-Hotels-BIGFOOT-CHALET.h106157385.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/124000000/123360000/123354300/123354233/225c30fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books](https://images.trvl-media.com/lodging/124000000/123360000/123354300/123354233/3201c410.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123360000/123354300/123354233/c8edb36b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books](https://images.trvl-media.com/lodging/124000000/123360000/123354300/123354233/ff859ff4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in Charlemont

[](https://www.expedia.ca/Charlemont-Hotels-Joia-Verde-ChaletSleeps-8.h123354233.Hotel-Information)

CA $283

CA $868 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Charlemont-Hotels-Joia-Verde-ChaletSleeps-8.h123354233.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/c71f56f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/26cdcbb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/7665cd19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/e73412a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in Dover

[](https://www.expedia.ca/West-Dover-Hotels-MT-SNOW-SKI-BACK-TRAIL-FREE-SHUTTLE-Green-Mountain-House.h36777699.Hotel-Information)

9.8/10

Exceptional

(22)

"Decently-sized rooms, great lighting, plenty of space for families with kids to relax, enjoy the outdoor space, easy drive to Stratton and Wilmington. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

SZU YIN C.

CA $161

CA $611 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/West-Dover-Hotels-MT-SNOW-SKI-BACK-TRAIL-FREE-SHUTTLE-Green-Mountain-House.h36777699.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/a6a78255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/f2b8d538.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/d9c0ff94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/b3ddab44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in East Dover

[](https://www.expedia.ca/East-Dover-Hotels-Mandys-Mountain-Chalet-Minutes-From-Mount-Snow.h74683539.Hotel-Information)

9.8/10

Exceptional

(9)

"Easy to find! Clean! Cozy!! Would definitely stay again! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Roy-michael G.

CA $217

CA $672 total

includes taxes & fees

Jan 13 - Jan 14, 2026

[](https://www.expedia.ca/East-Dover-Hotels-Mandys-Mountain-Chalet-Minutes-From-Mount-Snow.h74683539.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/114000000/113100000/113092300/113092281/6da0ce7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/114000000/113100000/113092300/113092281/62ad9b82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/114000000/113100000/113092300/113092281/526de6a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113100000/113092300/113092281/d54b3197.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in Wardsboro

[](https://www.expedia.ca/Wardsboro-Hotels-The-Mont-Haus-Minutes-To-Mt-Snow-Stratton.h113092281.Hotel-Information)

10/10

Exceptional

(4)

"Impressively clean house! The owners were great to deal with and very responsive. Would certainly recommend to anyone traveling in the area."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kristen T.

CA $276

CA $702 total

includes taxes & fees

Jan 13 - Jan 14, 2026

[](https://www.expedia.ca/Wardsboro-Hotels-The-Mont-Haus-Minutes-To-Mt-Snow-Stratton.h113092281.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105990000/105982900/105982869/cc65421b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105990000/105982900/105982869/aaebfa4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/106000000/105990000/105982900/105982869/31c838bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105990000/105982900/105982869/83acf129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in Dover

[](https://www.expedia.ca/West-Dover-Hotels-Mountain-View-Chalet-Golf.h105982869.Hotel-Information)

9.8/10

Exceptional

(6)

"We spent the week, excellent location and the home was exactly as described in listing."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Chris R.

CA $1,132

CA $1,906 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/West-Dover-Hotels-Mountain-View-Chalet-Golf.h105982869.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/69000000/68860000/68850200/68850104/398175e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/69000000/68860000/68850200/68850104/40bc0fc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68860000/68850200/68850104/97cdf1bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/69000000/68860000/68850200/68850104/13b3aaae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in Chester

[](https://www.expedia.ca/Chester-Hotels-Spacious-Chalet-For-Picturesque-Fall-Getaway-Winter-Fun-At-Okemo.h68850104.Hotel-Information)

10/10

Exceptional

(10)

"We had a really sweet stay here. It was cozy and comfortable, and had everything as advertised. Plenty of towels and kitchen supplies when we needed them, and the beds were comfortable. We had a great trip to Okemo!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Carla C.

CA $602

CA $1,027 total

includes taxes & fees

Dec 24 - Dec 25

[](https://www.expedia.ca/Chester-Hotels-Spacious-Chalet-For-Picturesque-Fall-Getaway-Winter-Fun-At-Okemo.h68850104.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101360000/101355900/101355890/eda7773c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101360000/101355900/101355890/f7ab718d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101360000/101355900/101355890/909249f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101360000/101355900/101355890/ec10883e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in Wardsboro

[](https://www.expedia.ca/Wardsboro-Hotels-Brook-Haven-Retreat-Minutes-To-Mt-Snow-Stratton-Pet-Friendly.h101355890.Hotel-Information)

10/10

Exceptional

(14)

"Perfect weekend getaway "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Seth G.

CA $331

CA $700 total

includes taxes & fees

Jan 20 - Jan 21, 2026

[](https://www.expedia.ca/Wardsboro-Hotels-Brook-Haven-Retreat-Minutes-To-Mt-Snow-Stratton-Pet-Friendly.h101355890.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/76000000/75640000/75637200/75637196/d74e8c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/76000000/75640000/75637200/75637196/74c46c49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/76000000/75640000/75637200/75637196/6bb1cc24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/76000000/75640000/75637200/75637196/deccb16b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in Stratton

[](https://www.expedia.ca/Stratton-Hotels-HYGGE-HOUSE-Green-Mountain-Chalet-With-Sauna-And-Treehouse.h75637196.Hotel-Information)

10/10

Exceptional

(5)

"We had an amazing stay. It was the perfect location for 4 couples. The owners were super responsive. Amenities were great (our only kitchen recommendation is a non-glass cutting board and individual salt and pepper shakers). Would love to stay again in the summer next time! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nicholas D.

CA $446

CA $993 total

includes taxes & fees

Jan 13 - Jan 14, 2026

[](https://www.expedia.ca/Stratton-Hotels-HYGGE-HOUSE-Green-Mountain-Chalet-With-Sauna-And-Treehouse.h75637196.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/111000000/110990000/110980800/110980715/0d4d95fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110990000/110980800/110980715/w2180h1456x4y0-3d3ff46c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/111000000/110990000/110980800/110980715/33af9d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/111000000/110990000/110980800/110980715/e95e3631.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in Dover

[](https://www.expedia.ca/West-Dover-Hotels-NEW-Private-Chalet-4-Mins-To-Mt-Snow.h110980715.Hotel-Information)

10/10

Exceptional

(2)

"Mary and Adam were absolutely lovely hosts! From the initial booking to check-in and throughout our stay, they were incredibly responsive. The house was fantastic—completely updated, with a fully equipped kitchen, spacious bedrooms, and a beautiful living area with a cozy fireplace.Our only regret is that we couldn’t stay longer. Thank you, Mary and Adam, for a wonderful stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Patricia N.

CA $376

CA $968 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/West-Dover-Hotels-NEW-Private-Chalet-4-Mins-To-Mt-Snow.h110980715.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/121000000/120430000/120430000/120429915/a3e005f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120430000/120430000/120429915/407a0d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/121000000/120430000/120430000/120429915/cc9b5501.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/121000000/120430000/120430000/120429915/f3293a73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in Jamaica

[](https://www.expedia.ca/Jamaica-Hotels-PreLaunch-A-Frame-Hot-Tub-Sauna-EV-Stratton.h120429915.Hotel-Information)

CA $744

CA $1,541 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Jamaica-Hotels-PreLaunch-A-Frame-Hot-Tub-Sauna-EV-Stratton.h120429915.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/113000000/112680000/112675200/112675182/w1080h1071x0y2-62744863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112680000/112675200/112675182/w1080h1076x0y4-eec2a42e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112680000/112675200/112675182/8581675a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/113000000/112680000/112675200/112675182/w1070h1076x5y0-75daf8bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in Dover

[](https://www.expedia.ca/West-Dover-Hotels-Gorgeous-4-Bedroom-3-Bath-Chalet-In-Dover-10-Minutes-To-Mount-Snow-WIFI.h112675182.Hotel-Information)

10/10

Exceptional

(4)

"We had a great time at the Chalet. Great accommodations Jennifer made sure we had everything we needed She went above and beyond to accommodate our group. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Chris I.

CA $331

CA $800 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/West-Dover-Hotels-Gorgeous-4-Bedroom-3-Bath-Chalet-In-Dover-10-Minutes-To-Mount-Snow-WIFI.h112675182.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78500000/78494300/78494299/5f637af9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/79000000/78500000/78494300/78494299/6b8b3cc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/79000000/78500000/78494300/78494299/38bc7f77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/79000000/78500000/78494300/78494299/dcc44385.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in Dover

[](https://www.expedia.ca/West-Dover-Hotels-Charming-Chalet-W-Hot-Tub-1-Mile-To-Mt-Snow.h78494299.Hotel-Information)

10/10

Exceptional

(14)

"Place was super clean. My wife’s favorite video game pac man was down stairs which gave us all a chance to compete against each other and was a blast. We would love to go back A on this property "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rich H.

CA $689

CA $1,337 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/West-Dover-Hotels-Charming-Chalet-W-Hot-Tub-1-Mile-To-Mt-Snow.h78494299.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/110000000/109560000/109550900/109550875/76d2f10f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109560000/109550900/109550875/94109ab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/110000000/109560000/109550900/109550875/accd446a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, table tennis](https://images.trvl-media.com/lodging/110000000/109560000/109550900/109550875/f158318f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in Dover

[](https://www.expedia.ca/West-Dover-Hotels-Brand-New-Hot-Tub.h109550875.Hotel-Information)

10/10

Exceptional

(9)

"Helpful, fun and warm. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anthony S.

CA $878

CA $1,733 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/West-Dover-Hotels-Brand-New-Hot-Tub.h109550875.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-04&endDate=2026-01-05&regionId=6057349&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America&regionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-03-21&d1=2026-03-21&endDate=2026-03-24&d2=2026-03-24&lodging=CABIN)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America&regionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-03-21&d1=2026-03-21&endDate=2026-03-24&d2=2026-03-24&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America&regionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-03-21&d1=2026-03-21&endDate=2026-03-24&d2=2026-03-24&lodging=COTTAGE)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America&regionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-03-21&d1=2026-03-21&endDate=2026-03-24&d2=2026-03-24&lodging=APARTMENT)

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America&regionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-03-21&d1=2026-03-21&endDate=2026-03-24&d2=2026-03-24&lodging=APART_HOTEL)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America&regionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-03-21&d1=2026-03-21&endDate=2026-03-24&d2=2026-03-24&lodging=CONDO)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America&regionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-03-21&d1=2026-03-21&endDate=2026-03-24&d2=2026-03-24&lodging=CHALET)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America&regionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-03-21&d1=2026-03-21&endDate=2026-03-24&d2=2026-03-24&lodging=VILLA)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

Save an average of 15% on thousands of hotels when you're signed in

[Sign in

](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FBennington-Chalets.d6057349-aaChalets.Travel-Guide-Accommodation)[

Sign up, it's free

](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FBennington-Chalets.d6057349-aaChalets.Travel-Guide-Accommodation)

## Top Bennington Hotel Reviews

![Hotel Vervana, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/3000000/2580000/2577700/2577695/b33626c2_y.jpg)

### Hotel Vervana, Trademark Collection by Wyndham

10/10 Excellent

"Large rooms, great staff. Will stay again!"

[](https://expedia.ca/Bennington-Hotels-Paradise-Inn.h2577695.Hotel-Information)

![Hampton Inn Bennington](https://images.trvl-media.com/lodging/2000000/1200000/1192000/1191981/aadd5504_y.jpg)

### Hampton Inn Bennington

10/10 Excellent

"Clean room Comfy bed Great coffee Nice lotion in the bathroom"

[](https://expedia.ca/Bennington-Hotels-Hampton-Inn-Bennington.h1191981.Hotel-Information)

![Harwood Hill Motel](https://images.trvl-media.com/lodging/13000000/12360000/12354600/12354542/ffee6d77_y.jpg)

### Harwood Hill Motel

10/10 Excellent

"This was my third stay over the course of many years, and this motel is always reliable for its comfort, cleanliness, warm welcome and good continental breakfast. I'll be back for sure!"

[](https://expedia.ca/Bennington-Hotels-Harwood-Hill-Motel.h12354542.Hotel-Information)

![Knotty Pine](https://images.trvl-media.com/lodging/120000000/119110000/119106200/119106200/439bea3f_y.jpg)

### Knotty Pine

10/10 Excellent

"Yes"

[](https://expedia.ca/Bennington-Hotels-Knotty-Pine.h119106200.Hotel-Information)

![South Shire](https://images.trvl-media.com/lodging/77000000/76170000/76163200/76163190/0f420ffa_y.jpg)

### South Shire

10/10 Excellent

"Great period decor! Spacious rooms and an inviting living room to relax. Also walking distance to downtown shops and restaurants was a real plus!"

[](https://expedia.ca/Bennington-Hotels-South-Shire.h76163190.Hotel-Information)

![Best Western Bennington](https://images.trvl-media.com/lodging/1000000/20000/16400/16323/5ad1b90e_y.jpg)

### Best Western Bennington

10/10 Excellent

"Yes"

[](https://expedia.ca/Bennington-Hotels-Best-Western-Bennington.h16323.Hotel-Information)

![Bennington Motor Inn](https://images.trvl-media.com/lodging/2000000/1530000/1523000/1522906/0219b10e_y.jpg)

### Bennington Motor Inn

10/10 Excellent

"Great hotel for the price and convenient to downtown area.."

[](https://expedia.ca/Bennington-Hotels-Bennington-Motor-Inn.h1522906.Hotel-Information)

![Bennington Gem w/ Smart TV Near Historic District!](https://images.trvl-media.com/lodging/106000000/105900000/105898500/105898497/90671126_y.jpg)

### Bennington Gem w/ Smart TV Near Historic District!

6/10 Okay

"Two things can improved: 1). The bathroom needs to be renovated. It has a dirty look. 2). The security alarm was beeping irritatingly all the first night. This prevented us from getting anywhere near a good night sleep. I did not find the owner very responsive. He said someone would be there by 4 PM the next day"

[](https://expedia.ca/Bennington-Hotels-Bennington-Gem-W-Smart-TV-Near-Historic-District.h105898497.Hotel-Information)

![The Autumn Inn](https://images.trvl-media.com/lodging/3000000/2390000/2381300/2381247/be4d3e05_y.jpg)

### The Autumn Inn

10/10 Excellent

"Room was great for the price "

[](https://expedia.ca/Bennington-Hotels-The-Autumn-Inn.h2381247.Hotel-Information)

## Find out more about Bennington

## Bennington Chalets information

| Number of reviews | 94         |
| ----------------- | ---------- |
| Accommodation     | 19 Chalets |
| Lowest Price      | CA $611    |
| Highest Price     | CA $1,906  |

## Explore a world of travel with Expedia

- Lodging
- Flights
- Packages
- Cars
- More ways to book

- [4 Star Hotels in West Arlington ](https://www.expedia.ca/4Star-West-Arlington-Hotels.s40-0-d553248635976385881.Travel-Guide-Filter-Hotels)
- [B&B in Arlington ](https://www.expedia.ca/Arlington-Bed-And-Breakfast.d74695-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Hostels in Arlington ](https://www.expedia.ca/Arlington-Hostels.d74695-aaHostels.Travel-Guide-Accommodation)
- [Boutique Hotels in Arlington ](https://www.expedia.ca/Arlington-Hotels-Boutique-Hotel.0-0-d74695-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
- [Hotels with a Pool in Arlington ](https://www.expedia.ca/Arlington-Hotels-Hotel-With-Pool.0-0-d74695-tHotelwithPool.Travel-Guide-Filter-Hotels)
- [Pet-Friendly Hotels in Arlington ](https://www.expedia.ca/Arlington-Hotels-Pet-Friendly-Hotel.0-0-d74695-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [Ski Hotels in Arlington ](https://www.expedia.ca/Arlington-Hotels-Ski-Hotel.0-0-d74695-tSkiHotel.Travel-Guide-Filter-Hotels)
- [Winery Hotels in Arlington ](https://www.expedia.ca/Arlington-Hotels-Winery-Hotel.0-0-d74695-tWineryHotel.Travel-Guide-Filter-Hotels)
- [Arlington Hotels ](https://www.expedia.ca/Arlington-Hotels.d74695.Travel-Guide-Hotels)
- [Inns in Arlington ](https://www.expedia.ca/Arlington-Inns.d74695-aaInns.Travel-Guide-Accommodation)
- [Lodges in Arlington ](https://www.expedia.ca/Arlington-Lodges.d74695-aaLodges.Travel-Guide-Accommodation)
- [Motels in Arlington ](https://www.expedia.ca/Arlington-Motels.d74695-aaMotels.Travel-Guide-Accommodation)
- [Hotels near Bennington College ](https://www.expedia.ca/Bennington-College-Hotels.0-l6330089-0.Travel-Guide-Filter-Hotels)
- [Bennington County Hotels ](https://www.expedia.ca/Destinations-In-Bennington-County.d553248635996998200.Hotel-Destinations)
- [Aparthotels in East Arlington ](https://www.expedia.ca/East-Arlington-Apart-Hotels.d553248635976063348-aaApartHotels.Travel-Guide-Accommodation)
- [East Arlington Hotels ](https://www.expedia.ca/East-Arlington-Hotels.d553248635976063348.Travel-Guide-Hotels)
- [Hotels near Green Mountain National Forest ](https://www.expedia.ca/Green-Mountain-National-Forest-Hotels.0-l6115904-0.Travel-Guide-Filter-Hotels)
- [Hotels near Mount Snow ](https://www.expedia.ca/Mount-Snow-Hotels.0-l6115918-0.Travel-Guide-Filter-Hotels)
- [B&B in North Bennington ](https://www.expedia.ca/North-Bennington-Bed-And-Breakfast.d6140705-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Chalets in North Bennington ](https://www.expedia.ca/North-Bennington-Chalets.d6140705-aaChalets.Travel-Guide-Accommodation)
- [North Bennington Historic District Hotels ](https://www.expedia.ca/North-Bennington-Historic-District-North-Bennington-Hotels.0-n6329110-0.Travel-Guide-Filter-Hotels)
- [Cheap Hotels in North Bennington ](https://www.expedia.ca/North-Bennington-Hotels-Cheap-Hotels.0-0-d6140705-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in North Bennington ](https://www.expedia.ca/North-Bennington-Hotels-Luxury-Hotel.0-0-d6140705-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Mountain Hotels in North Bennington ](https://www.expedia.ca/North-Bennington-Hotels-Mountain-Hotels.0-0-d6140705-tMountainHotels.Travel-Guide-Filter-Hotels)
- [Ski Hotels in North Bennington ](https://www.expedia.ca/North-Bennington-Hotels-Ski-Hotel.0-0-d6140705-tSkiHotel.Travel-Guide-Filter-Hotels)
- [North Bennington Hotels ](https://www.expedia.ca/North-Bennington-Hotels.d6140705.Travel-Guide-Hotels)
- [Old Bennington Hotels ](https://www.expedia.ca/Old-Bennington-Hotels.d553248635976385350.Travel-Guide-Hotels)
- [B&B in Pownal ](https://www.expedia.ca/Pownal-Bed-And-Breakfast.d184068-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Cottages in Pownal ](https://www.expedia.ca/Pownal-Cottages.d184068-aaCottages.Travel-Guide-Accommodation)
- [Guest Houses in Pownal ](https://www.expedia.ca/Pownal-Guest-Houses.d184068-aaGuestHouses.Travel-Guide-Accommodation)
- [Cheap Hotels in Pownal ](https://www.expedia.ca/Pownal-Hotels-Cheap-Hotels.0-0-d184068-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Mountain Hotels in Pownal ](https://www.expedia.ca/Pownal-Hotels-Mountain-Hotels.0-0-d184068-tMountainHotels.Travel-Guide-Filter-Hotels)
- [Pownal Hotels ](https://www.expedia.ca/Pownal-Hotels.d184068.Travel-Guide-Hotels)
- [Inns in Pownal ](https://www.expedia.ca/Pownal-Inns.d184068-aaInns.Travel-Guide-Accommodation)
- [Motels in Pownal ](https://www.expedia.ca/Pownal-Motels.d184068-aaMotels.Travel-Guide-Accommodation)
- [Hotels near Prospect Mountain Nordic Ski Center ](https://www.expedia.ca/Prospect-Mountain-Nordic-Ski-Center-Hotels.0-l553248621532649082-0.Travel-Guide-Filter-Hotels)
- [Cheap Hotels in Readsboro ](https://www.expedia.ca/Readsboro-Hotels-Cheap-Hotels.0-0-d3000459721-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Readsboro Hotels ](https://www.expedia.ca/Readsboro-Hotels.d3000459721.Travel-Guide-Hotels)
- [Searsburg Hotels ](https://www.expedia.ca/Searsburg-Hotels.d553248635975857484.Travel-Guide-Hotels)
- [Hotels near Shaftsbury Historical Society Museum ](https://www.expedia.ca/Shaftsbury-Historical-Society-Museum-Hotels.0-l553248621551385180-0.Travel-Guide-Filter-Hotels)
- [Hotels & Resorts for Couples in Shaftsbury ](https://www.expedia.ca/Shaftsbury-Hotels-Couples-Resorts-Hotels.0-0-d184070-tCouplesResortsHotels.Travel-Guide-Filter-Hotels)
- [Pet-Friendly Hotels in Shaftsbury ](https://www.expedia.ca/Shaftsbury-Hotels-Pet-Friendly-Hotel.0-0-d184070-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [Shaftsbury Hotels ](https://www.expedia.ca/Shaftsbury-Hotels.d184070.Travel-Guide-Hotels)
- [Resorts in Shaftsbury ](https://www.expedia.ca/Shaftsbury-Resort-Hotels.d184070-aaResortHotels.Travel-Guide-Accommodation)
- [Aparthotels in Somerset ](https://www.expedia.ca/Somerset-Apart-Hotels.d3000437083-aaApartHotels.Travel-Guide-Accommodation)
- [B&B in Somerset ](https://www.expedia.ca/Somerset-Bed-And-Breakfast.d3000437083-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Guest Houses in Somerset ](https://www.expedia.ca/Somerset-Guest-Houses.d3000437083-aaGuestHouses.Travel-Guide-Accommodation)
- [Hotels with a Pool in Somerset ](https://www.expedia.ca/Somerset-Hotels-Hotel-With-Pool.0-0-d3000437083-tHotelwithPool.Travel-Guide-Filter-Hotels)
- [Somerset Hotels ](https://www.expedia.ca/Somerset-Hotels.d3000437083.Travel-Guide-Hotels)
- [Inns in Somerset ](https://www.expedia.ca/Somerset-Inns.d3000437083-aaInns.Travel-Guide-Accommodation)
- [Lodges in Somerset ](https://www.expedia.ca/Somerset-Lodges.d3000437083-aaLodges.Travel-Guide-Accommodation)
- [Motels in Somerset ](https://www.expedia.ca/Somerset-Motels.d3000437083-aaMotels.Travel-Guide-Accommodation)
- [Resorts in Somerset ](https://www.expedia.ca/Somerset-Resort-Hotels.d3000437083-aaResortHotels.Travel-Guide-Accommodation)
- [Hotels with Hot Tubs in Southern Vermont ](https://www.expedia.ca/Southern-Vermont-Hotels-Hotels-With-Hot-Tubs.0-0-d6057348-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Southern Vermont ](https://www.expedia.ca/Southern-Vermont-Hotels-Luxury-Hotel.0-0-d6057348-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Southern Vermont Hotels ](https://www.expedia.ca/Southern-Vermont-Hotels.d6057348.Travel-Guide-Hotels)
- [B&B in Stamford ](https://www.expedia.ca/Stamford-Bed-And-Breakfast.d3000459750-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Luxury Hotels in Stamford ](https://www.expedia.ca/Stamford-Hotels-Luxury-Hotel.0-0-d3000459750-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Stamford Hotels ](https://www.expedia.ca/Stamford-Hotels.d3000459750.Travel-Guide-Hotels)
- [Motels in Stamford ](https://www.expedia.ca/Stamford-Motels.d3000459750-aaMotels.Travel-Guide-Accommodation)
- [Cheap Hotels in Sunderland ](https://www.expedia.ca/Sunderland-Hotels-Cheap-Hotels.0-0-d6324879-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Hotels & Resorts for Couples in Sunderland ](https://www.expedia.ca/Sunderland-Hotels-Couples-Resorts-Hotels.0-0-d6324879-tCouplesResortsHotels.Travel-Guide-Filter-Hotels)
- [Historic Hotels in Sunderland ](https://www.expedia.ca/Sunderland-Hotels-Historic-Hotel.0-0-d6324879-tHistoricHotel.Travel-Guide-Filter-Hotels)
- [Hotels with a Pool in Sunderland ](https://www.expedia.ca/Sunderland-Hotels-Hotel-With-Pool.0-0-d6324879-tHotelwithPool.Travel-Guide-Filter-Hotels)
- [Hotels with smoking rooms in Sunderland ](https://www.expedia.ca/Sunderland-Hotels-Hotels-With-Smoking-Rooms.0-0-d6324879-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Sunderland ](https://www.expedia.ca/Sunderland-Hotels-Luxury-Hotel.0-0-d6324879-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Mountain Hotels in Sunderland ](https://www.expedia.ca/Sunderland-Hotels-Mountain-Hotels.0-0-d6324879-tMountainHotels.Travel-Guide-Filter-Hotels)
- [Pet-Friendly Hotels in Sunderland ](https://www.expedia.ca/Sunderland-Hotels-Pet-Friendly-Hotel.0-0-d6324879-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [Spa Hotels in Sunderland ](https://www.expedia.ca/Sunderland-Hotels-Spa-Hotel.0-0-d6324879-tSpaHotel.Travel-Guide-Filter-Hotels)
- [Sunderland Hotels ](https://www.expedia.ca/Sunderland-Hotels.d6324879.Travel-Guide-Hotels)
- [B&B in Woodford ](https://www.expedia.ca/Woodford-Bed-And-Breakfast.d553248635975848582-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Guest Houses in Woodford ](https://www.expedia.ca/Woodford-Guest-Houses.d553248635975848582-aaGuestHouses.Travel-Guide-Accommodation)
- [Cheap Hotels in Woodford ](https://www.expedia.ca/Woodford-Hotels-Cheap-Hotels.0-0-d553248635975848582-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Woodford Hotels ](https://www.expedia.ca/Woodford-Hotels.d553248635975848582.Travel-Guide-Hotels)
- [Inns in Woodford ](https://www.expedia.ca/Woodford-Inns.d553248635975848582-aaInns.Travel-Guide-Accommodation)
- [Lodges in Woodford ](https://www.expedia.ca/Woodford-Lodges.d553248635975848582-aaLodges.Travel-Guide-Accommodation)
- [Motels in Woodford ](https://www.expedia.ca/Woodford-Motels.d553248635975848582-aaMotels.Travel-Guide-Accommodation)
- [Vacation Homes in Woodford ](https://www.expedia.ca/Woodford-Private-Vacation-Homes.d553248635975848582-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Resorts in Woodford ](https://www.expedia.ca/Woodford-Resort-Hotels.d553248635975848582-aaResortHotels.Travel-Guide-Accommodation)

- [Flights to Arlington ](https://www.expedia.ca/Cheap-Flights-To-Arlington.d74695.Travel-Guide-Flights)
- [Flights to Pownal ](https://www.expedia.ca/Cheap-Flights-To-Pownal.d184068.Travel-Guide-Flights)
- [Flights to Sunderland ](https://www.expedia.ca/Cheap-Flights-To-Sunderland.d6324879.Travel-Guide-Flights)
- [Flights from Kingston to Southern Vermont ](https://www.expedia.ca/lp/flights/180034/6057348/kingston-to-southern-vermont)
- [Flights from Readsboro ](https://www.expedia.ca/lp/flights/3000459721/flights-from-readsboro)

- [Arlington Green Covered Bridge ](https://www.expedia.ca/Arlington-Green-Covered-Bridge-Arlington.d6179917.Vacation-Attraction)
- [Visit Bennington County ](https://www.expedia.ca/Bennington-County.dx553248635996998200)
- [Green Mountain National Forest ](https://www.expedia.ca/Green-Mountain-National-Forest-Vermont.d6115904.Vacation-Attraction)
- [Lake Shaftsbury State Park ](https://www.expedia.ca/Lake-Shaftsbury-State-Park-Shaftsbury.d553248621551385179.Vacation-Attraction)
- [Mount Snow ](https://www.expedia.ca/Mount-Snow-West-Dover.d6115918.Vacation-Attraction)
- [Visit Shaftsbury ](https://www.expedia.ca/Shaftsbury.dx184070)
- [Southern Vermont Vacations ](https://www.expedia.ca/Southern-Vermont.d6057348.Destination-Travel-Guides)
- [Sugar Shack ](https://www.expedia.ca/Sugar-Shack-Arlington.d553248621532665335.Vacation-Attraction)
- [Warlock's Woods ](https://www.expedia.ca/Warlocks-Woods-Wilmington.d553248635996618389.Vacation-Attraction)

- [Avis Rental Cars in Southern Vermont ](https://www.expedia.ca/Avis-Car-Rentals-In-Southern-Vermont.d6057348-c41.Car-Rental-Guide-Suppliers)
- [Economy Car Rentals near Back Draft ](https://www.expedia.ca/Economy-Car-Rentals-In-Back-Draft.d553248635996618773-tEconomy.Car-Rental-Guide-Class)
- [Enterprise Rental Cars in Woodford ](https://www.expedia.ca/Enterprise-Car-Rentals-In-Woodford.d553248635975848582-c15.Car-Rental-Guide-Suppliers)
- [Full-Size Car Rentals near Back Draft ](https://www.expedia.ca/Fullsize-Car-Rentals-In-Back-Draft.d553248635996618773-tFullsize.Car-Rental-Guide-Class)
- [National Car Rental Rental Cars in Southern Vermont ](https://www.expedia.ca/National-Car-Rental-Car-Rentals-In-Southern-Vermont.d6057348-c42.Car-Rental-Guide-Suppliers)
- [Premium Car Rentals near Back Draft ](https://www.expedia.ca/Premium-Car-Rentals-In-Back-Draft.d553248635996618773-tPremium.Car-Rental-Guide-Class)
- [Suv Car Rentals near Warlock's Woods ](https://www.expedia.ca/SUV-Car-Rentals-In-Warlocks-Woods.d553248635996618389-tSUV.Car-Rental-Guide-Class)

- [Book Chalets in Bennington on Expedia.com ](https://www.expedia.com/Bennington-Chalets.d6057349-aaChalets.Travel-Guide-Accommodation)