A covered bridge with a sign reading "Silk Road Bridge" and a height restriction of 10 feet 6 inches.

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Check availability on Bennington Luxury Hotels

Tonight
14 Oct - 15 Oct
Tomorrow
15 Oct - 16 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Bennington luxury hotels

A bedroom with a double bed, two chairs, a small table with a hat, and floral curtains.
A large, two-story house with a covered porch and multiple chimneys.
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

The Four Chimneys Inn
Bennington
₹22,539
₹24,568 total
includes taxes & fees
1 Nov - 2 Nov
The Four Chimneys Inn
A swimming pool with a view of a barn and mountains in the background.
A rustic room with wooden floors, a metal cart, shelves with plants, and a refrigerator.
A four-poster bed with a wooden frame, a bench, a small table with a lamp, and a mirror on the wall.
A wooden deck with potted plants, a white chair, and a scenic view of hills and trees.

2. Hill Farm Inn

Hill Farm Inn
Arlington
₹28,489
₹52,493 total
includes taxes & fees
26 Oct - 27 Oct
Hill Farm Inn
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 formal dining room with a chandelier, fireplace, ornate mantelpiece, and a large floral carpet.
A covered porch with wicker furniture, a patterned rug, and an American flag.

3. South Shire

South Shire
Bennington
₹18,761
₹21,488 total
includes taxes & fees
7 Nov - 8 Nov
South Shire
A restaurant with tables set for dining, chairs, and a fireplace in the background.
An outdoor dining area with a table set for six, surrounded by wicker chairs, in a garden setting with hanging planters and a lamp post.
A room with a brown leather sofa, a wooden chest labeled "The Honorable Lieutenant Captain Greenwood's Bay," and two windows with floral curtains.
A two-story building with a porch, American flag, and two white rocking chairs.

4. The Reluctant Panther Inn and Restaurant

The Reluctant Panther Inn and Restaurant
Manchester Village Historic District
  • Rustic luxury awaits at this Manchester inn where fireplaces and fine dining create mountain charm.
₹21,820
₹24,002 total
includes taxes & fees
27 Oct - 28 Oct
The Reluctant Panther Inn and Restaurant
A covered patio area with a wicker sofa, a round table with drinks, and a chair.
A room with a fireplace, a sofa, a dining table with chairs, and large windows offering a view of the outside.
A large indoor swimming pool with wooden beams and a central decorative element.
Two people toasting with drinks on a balcony overlooking a large building with columns.

5. The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa
Manchester Village Historic District
  • Luxurious mountain retreat with full-service spa offers indulgent massages and golf course views in this Vermont sanctuary.
₹9,577
₹15,568 total
includes taxes & fees
11 Nov - 12 Nov
The Equinox Golf Resort And Spa
A spacious dining area with a high ceiling, stone walls, and a fireplace.
A round wooden table set outdoors with white chairs, two glasses of wine, and a potted plant.
A white pergola with a stone pathway leading to a house.
A bar area with a long counter and multiple stools, a fireplace with a mantel, and a yellow armchair.

6. The Hermitage Inn Vermont

The Hermitage Inn Vermont
West Dover
₹34,848
₹38,333 total
includes taxes & fees
24 Oct - 25 Oct
The Hermitage Inn Vermont
A large, multi-story building with a prominent stone facade and a metal roof, surrounded by landscaped gardens and a pedestrian bridge.
A spacious interior with a wooden staircase, a seating area with patterned cushions, and large windows allowing natural light.
A spacious living area with a fireplace, wooden beams, and a large window.
An outdoor seating area with stone fire pit, chairs, and a red building in the background.

7. The Williams Inn

The Williams Inn
Williamstown
₹19,357
₹21,621 total
includes taxes & fees
8 Nov - 9 Nov
The Williams Inn
A white two-story house with a front porch, a covered patio, and a well-maintained garden.
A living room with a sofa, a coffee table, and a painting on the wall.
A white house with a porch, wooden chairs, and umbrellas.
A dining table with plates of food, two glasses of white wine, and a bottle of wine.

8. The Weston

The Weston
Weston
  • Elegant Vermont retreat offers pampering spa moments and daily manager's reception steps from Green Mountain National Forest.
₹33,672
₹36,703 total
includes taxes & fees
20 Oct - 21 Oct
The Weston
A large stone building with a steep roof, surrounded by dense forest and hills.
A hotel room with a bed, a nightstand, a lamp, a door, and a view into another room with a couch and a window.
A spacious living room with a fireplace, red sofas, a wooden coffee table, and a television.
A traditional bedroom with a four-poster bed, two armchairs, a wooden wardrobe, and a mirror.

9. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
₹20,620
₹22,476 total
includes taxes & fees
25 Oct - 26 Oct
Castle Hill Resort And Spa
A wooden deck with a solar panel, surrounded by lush greenery and a hill in the background.
A room with a stone fireplace, large windows with curtains, a patterned rug, and a plush chair.
A stone pathway leading to a porch with a wooden railing, surrounded by lush greenery and a lattice fence.
A large, white, two-story house with a steeply pitched roof, a balcony, and a staircase leading to the upper floor.

10. Windham Hill Inn

Windham Hill Inn
West Townshend
₹16,823
₹18,337 total
includes taxes & fees
28 Oct - 29 Oct
Windham Hill Inn
View all properties

Top Bennington Hotel Reviews

The Manchester View

The Manchester View

8/10 Good
"Great views !"
Matthew 2-night trip
Posted 20 hours ago
The Manchester View
Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

8/10 Good
"Pet friendly…if you are in building 3 you are pretty far from breakfast and lobby"
teresa 1-night trip
Posted 20 hours ago
Hotel Vervana, Trademark Collection by Wyndham
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

10/10 Excellent
"Good"
Kenton 2-night trip
Posted 1 day ago
The Equinox Golf Resort And Spa
Hampton Inn Bennington

Hampton Inn Bennington

10/10 Excellent
"Overnight stay Nice break from a long drive."
Randy 1-night trip
Posted 2 days ago
Hampton Inn Bennington
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"It's a great place to stay! I've been there several times in different seasons. Off-season or leaf peeper season the free breakfast is a lot less than the free breakfast during ski season. During ski season AKA winter, eggs, waffles, pancakes etc however during other seasons they only offer cold cereal, milk bagels toast and juice and coffee of course. Other than that it's a fantastic place and they're dog friendly"
Bridget 1-night trip
Posted 3 days ago
The Black Bear Lodge at Stratton Mountain Resort
Starlight Inn

Starlight Inn

8/10 Good
"Very nice old school Vermont motor inn. Dated decor, but all clean and well maintained. Except the shower. The shower was clean, but even with only a few people in the motel getting consistent hot/cold water was difficult. Literally our only complaint. Very good location to downtown, too. Only about 4 1/2 miles from Bennington College if you are visiting."
Tyler and Therese 2-night trip
Posted 9 days ago
Starlight Inn

Frequently asked questions

Are you searching for the perfect hotel for your luxury trip to Bennington?
Expedia can help you get a flight to Albany, NY (ALB-Albany Intl.) airport or Pittsfield, MA (PSF-Pittsfield Municipal) airport, and then you can select from a variety of places to stay that will deliver the luxury you seek. Amenities are important when you plan a holiday, so we make it easy to get what you want to make your stay relaxing and comfortable. If you want an upscale hotel that has fine dining, a spa or several swimming pools, Expedia can help you find the best luxury hotel experience that Bennington has to offer. During your visit, you might want to enjoy the mountain views and shopping which Bennington is known for.
When can I expect good weather in Bennington?
Planning for the weather is an important factor for making your trip to Bennington a success, especially when you're splurging. 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 Bennington are January, March, February and December, with each month seeing an average of 21 cm of snowfall.
What's there to see and do in Bennington?
Experience Bennington and visit Prospect Mountain Cross-Country Ski Center, Woodford State Park and Green Mountain National Forest. If you have spare time during your trip, you might want to make a stop at Old First Congregational Church and Bennington Museum.

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