Best Old Bennington Hotels in 2026 from HK$692 - Fully Refundable Options

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Our top choices for Old Bennington hotels

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

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

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

A stone gate with a lantern, surrounded by trees and a grassy area.

1. The Four Chimneys Inn

Bennington

Robert

HK$1,856

HK$2,023 total

includes taxes & fees

1 Nov - 2 Nov

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

A hotel room with two beds, a desk with a television, and a window with a mountain view.

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

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

2. Hampton Inn Bennington

Bennington

Jacqueline

HK$1,216

HK$1,326 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

A hotel room with a bed, bedside tables, a sofa, a wooden coffee table, and a painting on the wall.

3. New Englander Inn Bennington

Bennington

Douglas

HK$720

HK$785 total

includes taxes & fees

25 Oct - 26 Oct

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

A modern conference room with round tables and orange chairs, large windows with a view of greenery, and a ceiling with a grid pattern and hanging lights.

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

4. Hotel Vervana, Trademark Collection by Wyndham

Bennington

Gloria

HK$827

HK$902 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

A formal dining room with a chandelier, fireplace, ornate mantelpiece, and a large floral carpet.

5. South Shire

Bennington

Jorge

HK$1,528

HK$1,751 total

includes taxes & fees

30 Oct - 31 Oct

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

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.

A motel with a swimming pool, lounge chairs, and a sign for Knotty Pine Motel.

6. Knotty Pine

Bennington

William

HK$1,064

HK$1,160 total

includes taxes & fees

15 Oct - 16 Oct

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

A modern living room with a fireplace, comfortable seating, a flat-screen TV, and a stone accent wall.

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.

7. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

C. David

HK$1,167

HK$1,304 total

includes taxes & fees

2 Nov - 3 Nov

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

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.

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

8. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Tara

HK$935

HK$1,045 total

includes taxes & fees

2 Nov - 3 Nov

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

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

A compact room with a television, a small desk with a chair, a wardrobe, and a patterned floor.

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

9. Bennington Motor Inn

Bennington

Jay

HK$887

HK$967 total

includes taxes & fees

13 Oct - 14 Oct

A large, multi-story building with a prominent stone facade and a metal roof, surrounded by landscaped gardens and a pedestrian bridge.

A spacious living area with a fireplace, wooden beams, and a large window.

A spacious interior with a wooden staircase, a seating area with patterned cushions, and large windows allowing natural light.

An outdoor seating area with stone fire pit, chairs, and a red building in the background.

10. The Williams Inn

Williamstown

Soleil

HK$1,594

HK$1,781 total

includes taxes & fees

8 Nov - 9 Nov

An outdoor seating area with Adirondack chairs and potted plants.

A reception area with a bulletin board, a 'no smoking' sign, a clock, and a 'STOP' sign.

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.

11. Cozy Corner Motel

Williamstown

Jonathan

HK$586

HK$692 total

includes taxes & fees

2 Nov - 3 Nov

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

A hotel room with two blue upholstered chairs, a wooden table with a lamp, a TV mounted on the wall, and a wooden dresser with drawers.

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

A hay bale display with pumpkins and scarecrows.

12. Willows Motel Williamstown

Williamstown

Charlene

HK$664

HK$741 total

includes taxes & fees

1 Nov - 2 Nov

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

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

A hotel room with two beds, a nightstand with a lamp, a television, and framed artwork on the wall.

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

13. The Villager Motel

Williamstown

DONNA

HK$620

HK$692 total

includes taxes & fees

1 Nov - 2 Nov

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

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

A row of colorful Victorian-style houses with a prominent red one labeled "PORCHES."

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

14. The Porches Inn at Mass MoCA

North Adams

Ram

HK$1,166

HK$1,478 total

includes taxes & fees

10 Nov - 11 Nov

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

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

A breakfast buffet setup with cereal, milk, juice, and pastries.

A swimming pool with lounge chairs and a fence.

15. Maple Terrace Motel

Williamstown

Deborah

HK$777

HK$868 total

includes taxes & fees

1 Nov - 2 Nov

A large tree with orange leaves in a grassy field.

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

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

A hotel room with a wooden floor, a bed with white bedding, a desk with a chair, a bedside table with a lamp, and a window with a view of greenery.

16. Starlight Inn

Bennington

Jeremia

HK$780

HK$850 total

includes taxes & fees

13 Oct - 14 Oct

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

A rectangular swimming pool with a wooden deck surrounding it.

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.

17. Howard Johnson by Wyndham Williamstown

Williamstown

Donna

HK$863

HK$964 total

includes taxes & fees

14 Oct - 15 Oct

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

A kitchen with a fireplace, dining area, and a large window with curtains.

18. Williamstown Motel

Williamstown

Ahmet

HK$629

HK$702 total

includes taxes & fees

1 Nov - 2 Nov

A stone fire pit surrounded by a grassy area with a tree and outdoor seating.

A snow-covered house with a red exterior, two lit lanterns, and a snow-covered entrance.

A wooden table with a glass, a knife, a napkin, salt and pepper shakers, and a candle holder.

A person sitting by a fireplace with stockings hanging above.

19. The Nutmeg

Wilmington

David

HK$1,413

HK$1,554 total

includes taxes & fees

2 Nov - 3 Nov

A spacious kitchen with large windows, a bar area, and a dining setup with chairs and tables.

A spacious restaurant with high ceilings, patterned flooring, and multiple seating areas.

A large, white colonial-style house with a porch, surrounded by lush greenery and trees.

A grand chandelier with multiple candle-like lights, a white balustrade, and an arched doorway in the background.

20. The White House Inn

Wilmington

Gordon

HK$1,300

HK$1,430 total

includes taxes & fees

1 Nov - 2 Nov

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Hotels recommended for families in Old Bennington

New Englander Inn Bennington

Bennington

HK$720

HK$785 total

includes taxes & fees

25 Oct - 26 Oct

Hampton Inn Bennington

Bennington

HK$1,216

HK$1,326 total

includes taxes & fees

1 Nov - 2 Nov

Hotel Vervana, Trademark Collection by Wyndham

Bennington

HK$827

HK$902 total

includes taxes & fees

1 Nov - 2 Nov

Cozy Corner Motel

Williamstown

HK$586

HK$692 total

includes taxes & fees

2 Nov - 3 Nov

Bennington Motor Inn

Bennington

HK$887

HK$967 total

includes taxes & fees

13 Oct - 14 Oct

The Villager Motel

Williamstown

HK$620

HK$692 total

includes taxes & fees

1 Nov - 2 Nov

Knotty Pine

Bennington

HK$1,064

HK$1,160 total

includes taxes & fees

15 Oct - 16 Oct

Willows Motel Williamstown

Williamstown

HK$664

HK$741 total

includes taxes & fees

1 Nov - 2 Nov

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Stay near popular Old Bennington attractions

Bennington Battle Monument

9.0/10 (202 reviews)

After visiting Bennington Battle Monument, make a plan to see the other sights and activities in Old Bennington. Discover the cafes and its art scene while you're in the area.

See properties

Bennington Museum

9.0/10 (50 reviews)

You can spend an afternoon exploring the galleries in Bennington Museum during your travels in Old Bennington. Discover the area's mountain views and cafes.

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Old First Congregational Church

9.6/10 (12 reviews)

Find out about the history of Old Bennington when you spend time at Old First Congregational Church. In the area, take in the art scene and mountain views.

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Learn more about Old Bennington

Venture to sights like Old First Congregational Church and Bennington Museum as you discover Old Bennington.

See all hotels in Old Bennington

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

Top Old Bennington Hotel Reviews

Willows Motel Williamstown

10/10 Excellent

"The room was very neat and clean. The bathroom was newly renovated. The staff was super friendly. Probably the best continental breakfast that you could ever ask for."

Howard Johnson by Wyndham Williamstown

10/10 Excellent

"Room was clean and comfortable. Easy access to Williamstown attractions."