Old Bennington Holiday Rentals, Bennington: Private House Rentals

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

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

1. The Four Chimneys Inn

Bennington

Robert

Rp4.243.234

Rp4.625.125 total

includes taxes & fees

1 Nov - 2 Nov

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.

2. Hampton Inn Bennington

Bennington

Victoria

Rp3.068.216

Rp3.344.355 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 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

Rp1.643.495

Rp1.791.410 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 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.

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.

4. Hotel Vervana, Trademark Collection by Wyndham

Bennington

Gloria

Rp1.905.913

Rp2.077.445 total

includes taxes & fees

15 Nov - 16 Nov

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.

5. South Shire

Bennington

Jorge

Rp3.531.904

Rp4.045.300 total

includes taxes & fees

7 Nov - 8 Nov

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

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

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

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

6. Knotty Pine

Bennington

William

Rp2.648.928

Rp2.887.396 total

includes taxes & fees

25 Oct - 26 Oct

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

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.

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

7. Bennington Motor Inn

Bennington

Jay

Rp1.343.620

Rp1.464.546 total

includes taxes & fees

29 Oct - 30 Oct

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

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.

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

8. The Williams Inn

Williamstown

Joshua

Rp3.644.105

Rp4.070.465 total

includes taxes & fees

8 Nov - 9 Nov

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

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

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

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

9. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Tara

Rp2.138.210

Rp2.388.380 total

includes taxes & fees

5 Nov - 6 Nov

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

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

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.

10. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

C. David

Rp2.509.885

Rp2.803.541 total

includes taxes & fees

15 Nov - 16 Nov

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.

11. Cozy Corner Motel

Williamstown

Jonathan

Rp1.339.969

Rp1.581.773 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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

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

12. The Porches Inn at Mass MoCA

North Adams

Ram

Rp2.665.049

Rp3.377.595 total

includes taxes & fees

15 Nov - 16 Nov

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 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.

13. Starlight Inn

Bennington

Jeremia

Rp1.873.549

Rp2.042.195 total

includes taxes & fees

20 Oct - 21 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.

14. The Villager Motel

Williamstown

DONNA

Rp1.345.350

Rp1.502.846 total

includes taxes & fees

16 Nov - 17 Nov

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

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

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.

15. Howard Johnson by Wyndham Williamstown

Williamstown

Barbara

Rp1.790.121

Rp1.999.586 total

includes taxes & fees

18 Oct - 19 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 garden with a wooden pergola, potted plants, and a lawn with chairs.

A swimming pool with lounge chairs and a fence.

16. Maple Terrace Motel

Williamstown

Deborah

Rp1.775.862

Rp1.983.584 total

includes taxes & fees

1 Nov - 2 Nov

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.

17. Willows Motel Williamstown

Williamstown

David

Rp1.513.699

Rp1.690.759 total

includes taxes & fees

11 Nov - 12 Nov

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 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.

18. Williamstown Motel

Williamstown

Ahmet

Rp1.434.030

Rp1.601.812 total

includes taxes & fees

11 Nov - 12 Nov

A fire pit with four Adirondack chairs arranged around it, overlooking a snowy landscape with distant mountains.

A large, single-story building with a red and white exterior, surrounded by green fields and a winding road.

A hotel room with two beds, a desk, a chair, a lamp, and a view of the mountains.

A sauna room with wooden walls, a bench, a heater, and a door leading to an outdoor area.

19. Blue Vista Motor Lodge

North Adams

William

Rp3.447.044

Rp3.643.619 total

includes taxes & fees

12 Nov - 13 Nov

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 large, white, two-story house with a central balcony and a covered porch.

20. The White House Inn

Wilmington

Teresa

Rp2.970.533

Rp3.267.586 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.

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

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

Inn At Mount Snow

10/10 Excellent

"This was one of the nicest, most comfortable places we have stayed. Everything was just as it said in their web pages. It was very cozy and comfortable. The manager was very helpful. I didn't see access for disabled. There were stairs up to the rooms and down to the breakfast area. If you can't do stairs, you may want to call and check before you book. I would recommend this Inn to everyone."

Hideaway Inn Mt. Snow

10/10 Excellent

"This was a nice place. The staff was great as there were prompt responses to my inquiries. The property is a little dated but clean. We were not there long enough to enjoy the amenities. I would stay again."

Brittany Motel

8/10 Good

"Everything was totally fine except there was like one outlet in the entire room and the mini fridge was inexplicably loud when it would turn on and back off. It woke me up several times and I thought something serious was happening, but then it was just the fridge :/"

Valley Craft Ales

8/10 Good

"Beautiful view. I stayed Sunday so it was nice and quiet."

The White House Inn

8/10 Good

"It was a beautiful property with friendly staff. The room was very pretty but the mattress was very soft and the pillows were tiny. We loved the fireplace as well but when you lay down you can't see the fire and it was uncomfortable to sit at the end of the bed. A cozy area should be in front of the fire place. However I would still stay there again."

Hampton Inn Bennington

10/10 Excellent

"Overnight stay Nice break from a long drive."

Howard Johnson by Wyndham Williamstown

8/10 Good

"Room was good for an overnight stay. Location near Williamstown was a plus. Hope they install a vent to take out humidity out of bath."

Knotty Pine

8/10 Good

"I felt a little abandoned by the manager because she had very limite hours when she was available. The was pleasant and responsive when we did see her, but . . . Bathroom was clean and all, but design didn't allow space for a woman to lay out makeup and personal items. Very limited. Beds were very comfortable. Glad to have frig and microwave."

The Four Chimneys Inn

10/10 Excellent

"Very nice, quiet place. Relaxing and cute."

More cheap stays in Old Bennington

Bennington Motor Inn

143 West Main Street Bennington VT

Rp1.343.620

Rp1.464.546 total

29 Oct - 30 Oct

includes taxes & fees

7.6/10 Good! (503 reviews)

Willows Motel Williamstown

480 Main St Williamstown MA

Rp1.513.699

Rp1.690.759 total

11 Nov - 12 Nov

includes taxes & fees

Valley Craft Ales

18 N Main St Wilmington VT

Rp1.758.103

Rp1.933.913 total

27 Oct - 28 Oct

includes taxes & fees

8.4/10 Very good! (264 reviews)

Hotel Vervana, Trademark Collection by Wyndham

141 West Main Street Bennington VT

Rp1.905.913

Rp2.077.445 total

15 Nov - 16 Nov

includes taxes & fees

Knotty Pine

130 Northside Dr Bennington VT

Rp2.648.928

Rp2.887.396 total

25 Oct - 26 Oct

includes taxes & fees

8.2/10 Very good! (178 reviews)

Inn At Mount Snow

401 Vermont Rte 100 West Dover VT

Rp2.692.852

Rp2.962.137 total

1 Nov - 2 Nov

includes taxes & fees

10/10 Exceptional! (135 reviews)

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 Rp1.346.485

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. The Four Chimneys Inn

2. Hampton Inn Bennington

3. New Englander Inn Bennington

4. Hotel Vervana, Trademark Collection by Wyndham

5. South Shire

6. Knotty Pine

7. Bennington Motor Inn

8. The Williams Inn

9. Hotel Downstreet, an Ascend Collection Hotel

10. Fairfield Inn & Suites by Marriott Williamstown

11. Cozy Corner Motel

12. The Porches Inn at Mass MoCA

13. Starlight Inn

14. The Villager Motel

15. Howard Johnson by Wyndham Williamstown

16. Maple Terrace Motel

17. Willows Motel Williamstown

18. Williamstown Motel

19. Blue Vista Motor Lodge

20. The White House Inn

Stay near popular Old Bennington attractions

Bennington Battle Monument

Bennington Museum

Old First Congregational Church

Learn more about Old Bennington

Top Old Bennington Hotel Reviews

Inn At Mount Snow

Hideaway Inn Mt. Snow

Brittany Motel

Valley Craft Ales

The White House Inn

Hampton Inn Bennington

Howard Johnson by Wyndham Williamstown

Knotty Pine

The Four Chimneys Inn

More cheap stays in Old Bennington

Bennington Motor Inn

Willows Motel Williamstown

Valley Craft Ales

Hotel Vervana, Trademark Collection by Wyndham

Knotty Pine

Inn At Mount Snow

Frequently asked questions

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