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Featured Bennington Historic Hotels

The Four Chimneys Inn
The Four Chimneys Inn
4.0 out of 5.0 21 West Road, Bennington, VT
$239
5.0/5 (2 reviews)

We really enjoyed the Inn! Our room was beautifully decorated and comfortable. Fireplace was all ready and just needed to be lit. They even leave chocolates! Staff was so nice, gave us suggestions on places to go after a delicious hearty breakfast! Hope to go back again soon!

Reviewed on Nov 28, 2019
Renovated in 2016, The Four Chimneys Inn offers free WiFi in public areas, coffee in a common area, and express check-out. Free parking is available if you drive. ...
HistoricalGolfBreakfast
The Inn at Ormsby Hill
The Inn at Ormsby Hill
3.5 out of 5.0 1842 Main Street, Historic Route 7A, Manchester Center, VT
$137
4.7/5 (3 reviews)

Owners are lovely and hospitable, and the breakfast is delicious.

Reviewed on Jul 16, 2018
Guests staying at The Inn at Ormsby Hill enjoy free WiFi in public areas, a terrace, and wedding services. You can take advantage of free parking if you drive. ...
HistoricalGolfBreakfast
Kimpton Taconic Hotel
Kimpton Taconic Hotel
4.0 out of 5.0 3835 Main St., Manchester, VT
Free Cancellation
$149
4.6/5 (17 reviews)

We reserved two rooms: one king and two queens. When we arrived, a less than affable girl at the desk remarked that because we booked with Expedia, we forfeited the right to a double queen room accommodation! Whutt? We then showed her our online reservations; said then said our request did not register ...

Reviewed on Apr 20, 2019
Guests of Kimpton Taconic Hotel enjoy a 24-hour fitness center, free WiFi in public areas, and conference space. If you plan to drive, free valet parking is ...
HistoricalPet FriendlyDining
Wilburton Inn
Wilburton Inn
3.5 out of 5.0 257 Wilburton Dr, Manchester, VT
Free Cancellation
$144
4.3/5 (3 reviews)

What a beautiful hotel! It was immaculately clean, very bright, provided breathtaking mountain views, and it was very close to all of the fun that Manchester provides, including the Lincoln home. In addition, Jetson the dog happily greets you upon arrival! The staff was SO nice, professional, conversational ...

Reviewed on Jul 31, 2018
Guests of Wilburton Inn enjoy an outdoor tennis court, free WiFi in public areas, and conference space. If you drive, take advantage of free parking. The 24-hour ...
HistoricalFamily FriendlyGolf
The Equinox, a Luxury Collection Golf Resort & Spa, Vermont
The Equinox, a Luxury Collection Golf Resort & Spa, Vermont
4.5 out of 5.0 3567 Main Street Route 7A, Manchester, VT
$179
3.7/5 (7 reviews)

"Deluxe room with a view" equals average room with moldy bathroom and faulty sink and view of courtyard

Reviewed on Oct 12, 2016
A local mainstay since 1769, The Equinox, a Luxury Collection Golf Resort & Spa, Vermont offers a golf course, a full-service spa, and an indoor pool. Onsite ...
HistoricalLuxuryDining
Bennington Motor Inn
Bennington Motor Inn
2.0 out of 5.0 143 West Main Street, Bennington, VT
Free Cancellation
$75
3.4/5 (9 reviews)

A night stay before traveling to Mt Snow. Not much of a town. The Battle monument was impressive though. The place was pretty clean. The wicker chairs could have been more comfortable. Overall good value.

Reviewed on Feb 18, 2019
Guests staying at Bennington Motor Inn enjoy free WiFi in public areas and free newspapers. If you drive, put free parking to good use. The 24-hour front desk ...
HistoricalWifiRefrigerator
Paradise Inn
Paradise Inn
2.5 out of 5.0 141 West Main Street, Bennington, VT
$72
3.2/5 (11 reviews)

A hidden gem. From the front a very unassuming looking property. Hidden behind the main buildings are park-like grounds, an inviting looking pool area, and a tennis/pickleball court. My room was garden-variety,(their "economy" room) but comfortable and clean. One down note was the TV wasn't very ...

Reviewed on Aug 30, 2019
Guests staying at Paradise Inn enjoy a fitness center, outdoor tennis courts, and free WiFi in public areas. You can put free parking to good use if you drive. ...
HistoricalPet FriendlyPool
The INN at Willow Pond
The INN at Willow Pond
3.0 out of 5.0 74 Willow Pond Road, Manchester Center, VT
Guests of The INN at Willow Pond have access to an outdoor pool, a fitness center, and a sauna. If you plan to drive, free parking is available. Staff members ...
HistoricalGolfAdventure
Historic 1780 Manchester Farm House With Mountain Views and 7 Bedrooms
Historic 1780 Manchester Farm House With Mountain Views and 7 Bedrooms
Arlington, VT
At this vacation home, guests have access to a garden.
HistoricalTheme ParkFamily Friendly

Uncover the Intrigue of a Bennington Historic Hotel

Featuring a variety of historic hotels, Bennington offers travelers a rich tapestry of one-of-a-kind local experiences. Whether you choose opulence or rustic charm, you can embrace life in a different era for a night, a weekend, or an extended stay.

Upgrades and restores
Historic hotels have often been painstakingly restored to reflect their original glory or to update them with a contemporary vibe. You can choose to rough it in humble historic accommodations, or experience the good life in the area's sophisticated restored mansions and original hotels.

Historic hotels allow you to embrace each hotel’s heyday. Sip drinks in a retro bar, relish a candlelit dinner in a lavish dining room, or enjoy a private fire in your own well-appointed suite.

Many historic hotels even feature original grand facades and modern interiors with newly renovated lobbies and rooms. Others have been meticulously restored to reflect every historic detail of the building’s past. Choose how you wish to experience the history of Bennington!

Get a glimpse of the past at a Bennington historic hotel
Whether you’re looking for a retro experience or you want something from a different century, a stay at a famous hotel in Bennington offers an unforgettable escape that will take your vacation to a new and unexpected level.

Discover life in Bennington from a different perspective with a trip back in time and book your historic hotel stay today.

Recent Historic Hotels Reviews

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.