Silk Road covered bridge with trees showing fall colors near Paper Mill Village, Vermont.

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Our top choices for Bennington romantic hotels

Outdoor pool, a heated pool

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is AED 250
AED 1,195 total
includes taxes & fees
14 Jun - 15 Jun
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
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)
"3rd year at this listing, absolutely love it. Close to okemo and mount snow. Host got back to me very quickly when reached out to. "
United States
Jake D.
The price is AED 624
AED 1,358 total
includes taxes & fees
16 Jun - 17 Jun
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Terrace/patio

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (281 reviews)
"Beautiful “New England” layout and area!!!"
United States
Peter S.
The price is AED 661
AED 985 total
includes taxes & fees
15 Jun - 16 Jun
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

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, (105 reviews)
"The host was very responsive and helpful. The property itself was also fantastic, with plenty of amenities and kept very clean."
United States
Jon
The price is AED 426
AED 1,146 total
includes taxes & fees
22 Jun - 23 Jun
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Property grounds

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, (110 reviews)
"Clean great cozy place!"
United States
Himanshu P.
The price is AED 496
AED 1,232 total
includes taxes & fees
12 Jun - 13 Jun
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Indoor pool

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Hancock
9.8 out of 10, Exceptional, (22 reviews)
"Great skiing and proximity to mountain. Great for families"
United States
John F.
The price is AED 437
AED 931 total
includes taxes & fees
15 Jun - 16 Jun
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
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, "
United States
Bryan R J.
The price is AED 545
AED 1,111 total
includes taxes & fees
14 Jun - 15 Jun
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Sauna

Magic Mountain Trailside Condo - Ski In / Ski Out

Magic Mountain Trailside Condo - Ski In / Ski Out
Londonderry
9.8 out of 10, Exceptional, (14 reviews)
"Nice and we enjoyed our stay"
United States
Gretchen H.
The price is AED 459
AED 1,150 total
includes taxes & fees
30 Jun - 1 Jul
Magic Mountain Trailside Condo - Ski In / Ski Out
Exterior

4 Season Cabin great location.

4 Season Cabin great location.
Mt Tabor
10.0 out of 10, Exceptional, (124 reviews)
"Excellent weekend getaway! My dog and I loved the cabin and the property! The hosts were top-notch! Can’t wait to return. Thanks for the hospitality ❤️"
United States
Corinna
The price is AED 680
AED 1,152 total
includes taxes & fees
28 Jun - 29 Jun
4 Season Cabin great location.
Interior

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (85 reviews)
"Great proximity to mountain and Ludlow downtown area."
United States
Yasmine O.
The price is AED 551
AED 1,299 total
includes taxes & fees
29 Jun - 30 Jun
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
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 Bennington Hotel Reviews

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

10/10 Excellent
"unique place, super friendly staff, helped us with late check in. room was clean and quiet. great location in the berkshires."
Brian 1-night trip
Posted 1 day ago
Hotel Vervana, Trademark Collection by Wyndham
New Englander Inn Bennington

New Englander Inn Bennington

8/10 Good
"This was the second time I’ve stayed at this location, first time under New Englander Inn name. Both times I was impressed by how clean and organized the breakfast area was. A staff member was constantly in and out cleaning up and restocking the breakfast items."
Deb 1-night trip
Posted 10 days ago
New Englander Inn Bennington

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Frequently asked questions

Searching for romantic hotels in Bennington?
If you and your partner need a romantic escape, we've got just the ticket. Our guests also love Bennington for its skiing, hiking, and major shopping area. You might consider checking out some of the nearby sights and attractions such as Old First Congregational Church, Bennington Museum, or Bennington Center for the Arts. If you're interested in staying close to a certain attraction, you can sort by neighborhood and proximity to top sights, so you and your partner will get to see everything on your list.
When is the best time of year for a romantic getaway to Bennington?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Bennington: The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 26°F. The snowiest months in Bennington are January, March, February, and December, with each month seeing an average of 8 inches of snowfall.
What is there to do in Bennington?
There's nothing better than seeing a new place with your sweetheart, so consider checking out all that Bennington has to offer. If you and your partner are planning an adventurous vacation, you'll love Bennington for its skiing, hiking, and golfing. You might think about stopping by Old First Congregational Church, Bennington Museum, or Bennington Center for the Arts while you're seeing the sights.
What's the best way to get to Bennington and around town during my romantic getaway?
These transportation options in Bennington might help your romantic trip get off to a smooth start: If you're looking to fly to Bennington, the closest major airport is Albany Intl. Airport (ALB), located 31.7 mi (51 km) from the city center. If you'd like to explore around the area, you may want a rental car for your journey.