The Bennington County Court House with a white facade, green shutters, and a gold dome.

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Check availability on Southern Vermont Historic Hotels

Next weekend
31 Jul - 2 Aug
In two weeks
7 Aug - 9 Aug

Our top choices for Southern Vermont historic hotels

Exterior

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (169 reviews)
"We had a very lovely stay. The kitchen was well-equipped and the whole home was very cozy. There was wood for the wood stove and lots of games and puzzles to do. Check-in and check-out was simple. Just what we were looking for! "
United States
Eleanor D.
The price is AED 624
AED 1,353 total
includes taxes & fees
27 Jul - 28 Jul
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
TV, books

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
9.6 out of 10, Exceptional, (9 reviews)
"This was a very cute rental in a beautiful part of New Hampshire, but it was much smaller than we imagined."
United States
Kelly
The price is AED 966
AED 1,140 total
includes taxes & fees
27 Jul - 28 Jul
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Property grounds

Entire Farmhouse with lots of open space 15 min north of Keene

Entire Farmhouse with lots of open space 15 min north of Keene
Walpole
10.0 out of 10, Exceptional, (39 reviews)
"Lovely place would definitely book again"
United States
Sean M.
The price is AED 1,181
AED 1,445 total
includes taxes & fees
27 Jul - 28 Jul
Entire Farmhouse with lots of open space 15 min north of Keene
Front of property

Castle Hill Resort And Spa

Castle Hill Resort And Spa
3.5 star property
Cavendish
9.0 out of 10, Wonderful, (120 reviews)
"This was our second time staying here and it never disappoints! I booked this trip during our kids' spring break for a quick getaway and to use the amazing heated outdoor pool. It's a great location convenient to all the amazing sites Vermont has to offer. Would love to go back again in the fall!"
United States
Jennifer
The price is AED 840
AED 916 total
includes taxes & fees
30 Jul - 31 Jul
Castle Hill Resort And Spa
Coffee/tea maker, fridge, microwave, oven

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (113 reviews)
"Clean great cozy place!"
United States
Himanshu P.
The price is AED 843
AED 1,683 total
includes taxes & fees
28 Jul - 29 Jul
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Smart TV, fireplace, books

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (109 reviews)
"Great location right in town and close to Okemo."
United States
Justin P.
The price is AED 687
AED 1,287 total
includes taxes & fees
12 Aug - 13 Aug
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Dining

A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (57 reviews)
"Comfortable lovely home with everything we needed to have a great weekend. "
United States
Margaret C.
The price is AED 841
AED 1,781 total
includes taxes & fees
3 Aug - 4 Aug
A roomy remodeled retreat close to MassMoCA
Pool

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Hancock
9.8 out of 10, Exceptional, (25 reviews)
"We stayed here twice this season and it was wonderful. The unit was clean, conveniently located and was fully equipped with all the essentials, making our stay comfortable and seamless from start to finish. We will definitely be back!"
United States
Kristina L.
The price is AED 393
AED 874 total
includes taxes & fees
27 Jul - 28 Jul
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Coffee/tea maker, fridge, microwave, oven

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Hoosick Falls
9.8 out of 10, Exceptional, (107 reviews)
"This is the third time we’ve stayed at this lovely home and it’s always a treat! Very clean, with a Well stocked kitchen, comfy beds and huge back yard plus a fenced in portion, your dog will love-close to Bennington and walking trails with lots to do. A home away from home! "
United States
Anita T.
The price is AED 691
AED 1,476 total
includes taxes & fees
27 Jul - 28 Jul
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Southern Vermont Hotel Reviews

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

8/10 Good
"The room was nice and very clean. The bar and waitstaff were friendly and helpful. The biggest disappointment was the outdoor patio/fire pit area because management said that there was a problem with the gas line (but it's been out for at least a week or two), so it was dark and cold on the patio. They did nothing to help rectify the problem when in fact there were at least 30 people trying to enjoy the outdoors. Many requests were made for management to assist, but nothing. It took the friendly bar staff to come up with a solution. She grabbed lanterns from the inside tables to brighten up the darkness - this made people want to stay longer and enjoy drinks with friends. She made the difference that night! Her name started with a "P" and deserves recognition for making a decision that night."
Lynn 1-night trip
Posted less than an hour ago
The Equinox Golf Resort & Spa

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