A tall, narrow obelisk with a pointed top, surrounded by trees and a clear blue sky.

Hotels in Old Bennington

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Where to stay in Old Bennington?

A bedroom with a double bed, two chairs, a small table with a hat, and floral curtains.

A dining room with a brick floor, large windows, and a chandelier.

A large, two-story house with a covered porch and multiple chimneys.

A cozy living room with a fireplace, comfortable seating, and a view of the outdoors.

1. The Four Chimneys Inn

Bennington

$249

$271 total

includes taxes & fees

Nov 2 - Nov 3

A hotel reception area with a modern design, featuring a reception desk, seating area, and artwork on the walls.

A modern kitchen area with built-in appliances, wooden tables, and red chairs.

A two-story hotel with a covered entrance, large windows, and a landscaped front yard with flower beds.

A hotel room with a large bed, a nightstand with a lamp, a small table with flowers, and a sliding glass door leading to an outdoor area with chairs.

2. New Englander Inn Bennington

Bennington

$92

$100 total

includes taxes & fees

Oct 25 - Oct 26

A hotel room with a large bed, a desk with a chair, a balcony with a view, and a TV mounted on the wall.

A hotel room with two beds, a desk, a chair, a TV, and a window with a view of greenery.

A hotel room with a red sofa, a round wooden table, a black armchair, a bed, and a large window with a view of greenery.

A tree with a fallen trunk in a grassy area with a blue building in the background.

3. Hotel Vervana, Trademark Collection by Wyndham

Bennington

$99

$107 total

includes taxes & fees

Nov 2 - Nov 3

An indoor swimming pool with clear water, metal railings, and lounge chairs.

A hotel lobby with a fireplace, seating area, and a bar.

A hotel reception area with a reception desk, a chandelier, framed pictures, and a coffee station.

A Hampton Inn hotel with a covered entrance and a clear sign indicating a 16-foot clearance.

4. Hampton Inn Bennington

Bennington

$155

$169 total

includes taxes & fees

Nov 1 - Nov 2

A two-story building with a white exterior, a porch with a white railing, and a staircase leading to the upper floor.

A BENNINGTON MOTOR INN sign with amenities like free continental breakfast and free wireless internet.

A hotel room with two beds, a rocking chair, a door, and a window with curtains.

A bathroom with a sink, two hair dryers, and a mirror.

5. Bennington Motor Inn

Bennington

$75

$82 total

includes taxes & fees

Nov 5 - Nov 6

An outdoor seating area with Adirondack chairs and potted plants.

A sign with the word "CLARM" on a grassy field with a road and trees in the background.

A hotel room with a large bed, two bedside lamps, a nightstand, a framed picture on the wall, and a window with curtains.

A building with a double door labeled "WELCOME" and "OFFICE," a "PARKING ONLY" sign, and flower baskets on either side of the entrance.

6. Cozy Corner Motel

Williamstown

$75

$88 total

includes taxes & fees

Nov 2 - Nov 3

A kitchen with a countertop, a refrigerator, and a window.

A kitchen with a refrigerator, a coffee maker, and a microwave.

A park with picnic tables, a playground, and a large coniferous tree.

A motel named 'The Villager Motel' with a 'VACANCY' sign, a picnic table, and a red planter on the lawn.

7. The Villager Motel

Williamstown

$75

$84 total

includes taxes & fees

Nov 16 - Nov 17

A large tree with orange leaves in a grassy field.

A motel with a row of rooms, a flagpole, and a large tree in the foreground.

A room with wooden paneling, a window with a white curtain, an air conditioning unit, and a wooden hanger rack.

8. Starlight Inn

Bennington

$99

$108 total

includes taxes & fees

Oct 25 - Oct 26

A patio area with wooden chairs and tables, surrounded by dense greenery and trees.

A hotel room with a TV, a desk, a chair, a dresser, a bed with a patterned bedspread, and a microwave.

A white two-story building with a porch, labeled as a motel.

A hay bale display with pumpkins and scarecrows.

9. Willows Motel Williamstown

Williamstown

$89

$99 total

includes taxes & fees

Nov 1 - Nov 2

A small, single-story building with a green roof and a white exterior. There are two large trees in front of the building, each with a flower pot on top. The surrounding area has grass, a few pumpkins, and a small garden with red flowers.

A living room with a sofa, chairs, a coffee table, and a rug. There is a kitchen area with a refrigerator and a water dispenser.

A living room with a sofa, coffee table, and fireplace. There is a kitchen area with cabinets and a refrigerator.

A blue wooden deck with white picket railings, surrounded by a well-maintained lawn and colorful autumn foliage.

10. Williamstown Motel

Williamstown

$80

$89 total

includes taxes & fees

Nov 1 - Nov 2

A spacious living room with a fireplace, a piano, and a dining area with round tables and chairs.

A kitchen with wooden cabinets, a stainless steel sink, a microwave, a kettle, a toaster, and a refrigerator.

A white motel named Knotty Pine with a signboard, windows, and flower planters.

A compact kitchen with a microwave, utensils, and a sink. A sliding door leads to a bedroom with a bed and a radiator.

11. Knotty Pine

Bennington

$151

$164 total

includes taxes & fees

Oct 25 - Oct 26

A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.

A modern hotel building with the name "Hotel Downtown" on the facade.

A modern cafe with a wooden accent wall, a coffee machine, and black chairs.

A modern interior with a large window, a wooden table, and bar stools.

12. Hotel Downstreet, an Ascend Collection Hotel

North Adams

$119

$133 total

includes taxes & fees

Nov 12 - Nov 13

A garden with a swing set, a blue chair, and a flower bed.

A swimming pool with lounge chairs and a fence.

A house with a porch, snow-covered ground, and a Christmas tree with lights.

A garden with a wooden pergola, potted plants, and a lawn with chairs.

13. Maple Terrace Motel

Williamstown

$99

$111 total

includes taxes & fees

Nov 1 - Nov 2

A room with wooden paneling, a piano, a chair, and a door leading to another room.

A two-story house with a front porch, a flag, and a gravel driveway.

A covered porch with wicker furniture, a patterned rug, and an American flag.

A traditional living room with a wooden ceiling, green curtains, a fireplace, and a large armchair.

14. South Shire

Bennington

$196

$224 total

includes taxes & fees

Oct 29 - Oct 30

A building with a covered parking area and a grassy front yard.

A dining area with wooden chairs and tables, a kitchen counter with appliances, and framed pictures on the wall.

A motel with multiple rooms, a parking area, and a large tree in the foreground.

A hotel room with a large bed, two bedside tables with lamps, a desk with a chair, and a small window.

15. Howard Johnson by Wyndham Williamstown

Williamstown

$100

$112 total

includes taxes & fees

Nov 22 - Nov 23

A fire feature with a metal frame and a brick wall in the background.

A Fairfield Inn & Suites by Marriott hotel with a brick facade, large windows, and a covered outdoor seating area.

A modern restaurant with a long counter, multiple seating areas, and pendant lighting.

A reception area with a wooden reception desk, a bar area in the background, and a decorative wall piece.

16. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

$144

$161 total

includes taxes & fees

Nov 15 - Nov 16

A spacious living area with a high ceiling, a wooden staircase, and a built-in kitchen visible through an open door.

A spacious living room with a wooden staircase, a television, a sofa set, and a fireplace.

A living room with a sofa, a coffee table, a chess table, a TV, and a gaming console.

A building with a covered outdoor area, wooden benches, and potted plants.

17. Brittany Motel

Manchester Center

$86

$95 total

includes taxes & fees

Nov 2 - Nov 3

A bedroom with a bed, dresser, TV, and a chair.

A bathroom with a double sink, a large mirror, and a bed with a blue patterned bedspread.

A two-story house with a red roof and grey siding, a front porch, and a stack of firewood.

A panoramic view of a lake surrounded by forested hills.

18. Doveberry Inn

West Dover

$122

$134 total

includes taxes & fees

Oct 25 - Oct 26

A spacious lounge area with multiple seating options, including sofas and chairs, arranged around a central coffee table.

A cozy lounge area with a stone fireplace, comfortable seating, and a 'Hi' sign above.

A swimming pool with a gazebo, outdoor seating, and a view of trees.

A long dining table with chairs, large windows, and hanging disco balls.

19. Hideaway Inn Mt. Snow

West Dover

$117

$129 total

includes taxes & fees

Oct 26 - Oct 27

A wooden deck overlooking a river with rocks and dense greenery.

A rustic interior with a long wooden table, a sofa, and a sign reading "VALLEY CRAFT ALES PRESENTS".

A spacious indoor area with wooden tables and chairs, some with laptops and papers, suggesting a co-working or meeting space.

A red building with a sign reading "Valley Craft Ales" and a covered outdoor area.

20. Valley Craft Ales

Wilmington

$98

$108 total

includes taxes & fees

Oct 27 - Oct 28

View all properties

Go beyond your typical stay in Old Bennington

Top landmarks in Old Bennington

Bennington Battle Monument

9.0/10 (202 reviews)

Bennington Battle Monument is 0.4 mi (0.6 km) from central Old Bennington, why not stop by during your stay.

See properties

Bennington Museum

9.0/10 (50 reviews)

If museums are on your list of things to see, then you might want to head to Bennington Museum, located in the heart of Old Bennington.If you want to see more of the museums in Old Bennington, Robert Frost Stone House Museum isn't far either.

See properties

Old First Congregational Church

9.6/10 (12 reviews)

If you're planning a bit of sightseeing during your trip, head to Old First Congregational Church— just one of the monuments in central Old Bennington. You can also discover the museums and art galleries in the area— your sightseeing tour starts here.

See properties

Learn more about Old Bennington

Old Bennington is well-known for its attractions such as Old First Congregational Church and Bennington Museum.

See all hotels in Old Bennington

Check out reviews of Old Bennington hotels guests love

The Four Chimneys Inn

Bennington

10/10 Exceptional

10/10 Exceptional

Lisa

A modern living room with a fireplace, large windows, and a cozy seating area.

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

A modern living room with a large sofa, a coffee table, and a fireplace.

A modern hotel room with a large bed, a desk, and a chair. There is a window with curtains, a painting of mountains, and a TV on the wall.

Inn At Mount Snow

West Dover

10/10 Exceptional

We visited during leaf-peeping season, so the property was not fully occupied. It was clean, well-maintained and tastefully renovated very recently. Location was ideal and the breakfast was sufficiently stocked with all of the basics. The staff was very attentive and responsive, providing suggestions for dining and local activities. Only suggestion is for side-sleepers like myself, to bring your own pillow. The ones provided were too large and stiff for my taste.

Steven

Brittany Motel

Manchester Center

10/10 Exceptional

Heaven

Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.

Two people sitting by a campfire in a wooded area with benches and a clear view of the surrounding trees.

A cozy living room with a fireplace, a red armchair, a bookshelf, and a coffee table.

A hallway with a collection of plates on the walls, leading to a staircase.

A stone fire pit surrounded by rocks, with a tree in the background and a building with a red roof to the left.

A living room with a stone wall, a television, and a fireplace.

A two-story house with a dark brown exterior, a dark blue front door, and a small porch area.

A fireplace with a fire burning inside, a metal screen, and a handle on the right side.

Deerfield Valley Inn

West Dover

10/10 Exceptional

Raul

Frequently Asked Questions

What hotels do travelers recommend in Old Bennington?

Guests like The Four Chimneys Inn, Hotel Vervana, Trademark Collection by Wyndham and Knotty Pine.

Can I book refundable accommodations in Old Bennington?

If you're looking for the flexibility to change your plans to Old Bennington, most properties provide refundable* bookable rates. You can find these properties by searching our site and using the "fully refundable" filter to narrow down the results.

What will the weather in Old Bennington be like during my trip?

The warmest months in Old Bennington are usually July and August with an average temp of 66°F. January and February are the chilliest months when the average temp is 26°F. The rainiest months are October and June.

Why should I book my Old Bennington accommodation with Hotels.com?

There are plenty of reasons to book your Old Bennington travel with us: our free cancellations on selected hotels* gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.