Old Bennington Holiday Rentals, Bennington: Private House Rentals

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Our top choices for Old Bennington hotels

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

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

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

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

1. Hampton Inn Bennington

Bennington

Jacqueline

฿5,343

฿5,823 total

includes taxes & fees

25 Oct - 26 Oct

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

Mike

฿3,083

฿3,360 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 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 tree with a fallen trunk in a grassy area with a blue building in the background.

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

3. Hotel Vervana, Trademark Collection by Wyndham

Bennington

John

฿3,968

฿4,325 total

includes taxes & fees

7 Oct - 8 Oct

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

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

4. South Shire

Bennington

Jorge

฿7,145

฿8,154 total

includes taxes & fees

29 Oct - 30 Oct

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

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

5. Knotty Pine

Bennington

William

฿4,606

฿5,021 total

includes taxes & fees

1 Oct - 2 Oct

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

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

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.

6. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

C. David

฿5,586

฿6,239 total

includes taxes & fees

18 Oct - 19 Oct

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

A reception area with a large landscape painting, a dark reception desk, and a potted plant.

7. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Alexandra

฿4,539

฿5,070 total

includes taxes & fees

14 Oct - 15 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 bar area with wooden beams, red chairs, and a long wooden table.

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

8. The Williams Inn

Williamstown

Soleil

฿7,531

฿8,412 total

includes taxes & fees

18 Oct - 19 Oct

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

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

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

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

9. Bennington Motor Inn

Bennington

Jay

฿2,520

฿2,747 total

includes taxes & fees

1 Oct - 2 Oct

An outdoor seating area with Adirondack chairs and potted plants.

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.

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

10. Cozy Corner Motel

Williamstown

Jonathan

฿3,325

฿3,897 total

includes taxes & fees

5 Oct - 6 Oct

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

A hay bale display with pumpkins and scarecrows.

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

11. Willows Motel Williamstown

Williamstown

Linda

฿3,478

฿3,884 total

includes taxes & fees

1 Oct - 2 Oct

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.

12. The Porches Inn at Mass MoCA

North Adams

Ram

฿6,662

฿8,192 total

includes taxes & fees

29 Oct - 30 Oct

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

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

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.

13. Howard Johnson by Wyndham Williamstown

Williamstown

Donna

฿3,123

฿3,488 total

includes taxes & fees

1 Oct - 2 Oct

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

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

A swimming pool with lounge chairs and a fence.

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

14. Maple Terrace Motel

Williamstown

Deborah

฿4,332

฿4,839 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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.

15. The Villager Motel

Williamstown

DONNA

฿3,325

฿3,714 total

includes taxes & fees

1 Oct - 2 Oct

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.

16. Starlight Inn

Bennington

Jeremia

฿3,341

฿3,642 total

includes taxes & fees

1 Oct - 2 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, coffee table, and fireplace. There is a kitchen area with cabinets and a refrigerator.

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

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.

17. Williamstown Motel

Williamstown

Ahmet

฿3,597

฿4,018 total

includes taxes & fees

1 Oct - 2 Oct

A row of single-story cabins with individual porches, each featuring a chair and a small table.

A room with a television on a wooden dresser, a chair, and a lamp.

A row of single-story cabins with porch seating and a covered walkway.

A small boat with three people on a calm lake surrounded by greenery and houses.

18. West Road Motel

Bennington

Wesley G

฿3,325

฿3,624 total

includes taxes & fees

1 Oct - 2 Oct

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

A person sitting by a fireplace with stockings hanging above.

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

A room with a blue sofa, a plant, a lamp, and framed artwork on the wall.

19. The Nutmeg

Wilmington

David

฿7,053

฿7,758 total

includes taxes & fees

25 Oct - 26 Oct

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

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.

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

20. The White House Inn

Wilmington

John

฿6,776

฿7,453 total

includes taxes & fees

25 Oct - 26 Oct

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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

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.

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.

See properties

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

The White House Inn

10/10 Excellent

"Patrick was very warm and welcoming! The room had its own outside entrance,spacious and clean. The bed was so comfortable.Beautiful bed and breakfast with lots of history and charm. Grounds also beautiful! Will definitely recommend to friends"

Hideaway Inn Mt. Snow

10/10 Excellent

"I appreciate the fact that the staff help me out with checking in early. Thank you so much"

Knotty Pine

10/10 Excellent

"We had a nice stay at the Knotty Pine Motel. The room was clean, spacious, and comfortable, and check-in was quick and easy. Overall, everything was well kept and made for a pleasant stay. The only downside for me was that the bed was a bit harder than I prefer, but that’s a personal preference. Overall, a good place to stay, definitely would stay there again."

Hotel Vervana, Trademark Collection by Wyndham

10/10 Excellent

"Lovely clean room with very comfortable beds. The shower was absolutely amazing, super clean, all new and great pressure!! A lovely little patio and a funky lobby."

Willows Motel Williamstown

10/10 Excellent

"The staff was very helpful and the breakfasts were great! Lots of healthy options and plenty of excellent fresh fruit and some for the road, too. We'll be back."

The Williams Inn

10/10 Excellent

"Great"

The Porches Inn at Mass MoCA

10/10 Excellent

"Great stay"

Blue Vista Motor Lodge

10/10 Excellent

"The mountain view is beautiful. The room was clean. Staff suggested a great restaurant for dinner, which we enjoyed. I recommend staying at this motel."

Valley Craft Ales

10/10 Excellent

"My husband and I enjoyed our stay in Wilmington. The room was as pictured, basic, but cozy and clean. Convenient location close to shops and restaurants. Seamless virtual check in. Great place to stay at this price point."

More cheap stays in Old Bennington

Bennington Motor Inn

143 West Main Street Bennington VT

฿2,520

฿2,747 total

1 Oct - 2 Oct

includes taxes & fees

7.6/10 Good! (496 reviews)

Valley Craft Ales

18 N Main St Wilmington VT

฿3,292

฿3,621 total

27 Oct - 28 Oct

includes taxes & fees

8.4/10 Very good! (251 reviews)

Willows Motel Williamstown

480 Main St Williamstown MA

฿3,478

฿3,884 total

1 Oct - 2 Oct

includes taxes & fees

9.2/10 Wonderful! (1,000 reviews)

Hotel Vervana, Trademark Collection by Wyndham

141 West Main Street Bennington VT

฿3,968

฿4,325 total

7 Oct - 8 Oct

includes taxes & fees

8.2/10 Very good! (1,001 reviews)

Knotty Pine

130 Northside Dr Bennington VT

฿4,606

฿5,021 total

1 Oct - 2 Oct

includes taxes & fees

8.2/10 Very good! (173 reviews)

Inn At Mount Snow

401 Vermont Rte 100 West Dover VT

฿5,767

฿6,344 total

14 Oct - 15 Oct

includes taxes & fees

Frequently asked questions

Where is the best place for a stay in Old Bennington?

Based on our traveller data, The Four Chimneys Inn is one of the top choices for your stay. This B&B is a short 1-minute walk from Green Mountain National Forest, and it offers free breakfast and free parking. Other good choices for your visit to the area are Hotel Downstreet, an Ascend Collection Hotel and The Williams Inn. See all available top hotels, or vacation rentals in Old Bennington.

If I need to cancel my hotel reservation in Old Bennington, will I receive a refund?

Yes! The majority of room reservations are refundable provided that you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If your reservation is non-refundable, it might still be possible to cancel it and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Old Bennington.

How is it staying in Old Bennington?

Visitors will definitely enjoy all that Old Bennington has to offer. There are 1012 hotels and other accommodation options in the surrounding area. Find out more about Old Bennington.

What are the top places to visit in Old Bennington?

A couple of favourite places to visit are Old First Congregational Church and Bennington Museum. You'll also find Bennington Center for the Arts and Robert Frost Stone House Museum in the area. Take a look at what more there is to see and do in Expedia's Old Bennington guide.

What's the weather like in Old Bennington?

The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Old Bennington are January, March, February and December, with each month seeing an average of 21 cm of snowfall.

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Book Hotels in Old Bennington on Expedia.com

Find hotels in Old Bennington, VT from ฿2,747

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Old Bennington

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Old Bennington hotels

1. Hampton Inn Bennington

2. New Englander Inn Bennington

3. Hotel Vervana, Trademark Collection by Wyndham

4. South Shire

5. Knotty Pine

6. Fairfield Inn & Suites by Marriott Williamstown

7. Hotel Downstreet, an Ascend Collection Hotel

8. The Williams Inn

9. Bennington Motor Inn

10. Cozy Corner Motel

11. Willows Motel Williamstown

12. The Porches Inn at Mass MoCA

13. Howard Johnson by Wyndham Williamstown

14. Maple Terrace Motel

15. The Villager Motel

16. Starlight Inn

17. Williamstown Motel

18. West Road Motel

19. The Nutmeg

20. The White House Inn

Stay near popular Old Bennington attractions

Bennington Battle Monument

Old First Congregational Church

Bennington Museum

Learn more about Old Bennington

Top Old Bennington Hotel Reviews

The White House Inn

Hideaway Inn Mt. Snow

Knotty Pine

Hotel Vervana, Trademark Collection by Wyndham

Willows Motel Williamstown

The Williams Inn

The Porches Inn at Mass MoCA

Blue Vista Motor Lodge

Valley Craft Ales

More cheap stays in Old Bennington

Bennington Motor Inn

Valley Craft Ales

Willows Motel Williamstown

Hotel Vervana, Trademark Collection by Wyndham

Knotty Pine

Inn At Mount Snow

Frequently asked questions

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