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Check availability on Bennington Romantic Hotels

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 225
AED 1,147 total
includes taxes & fees
11 Jun - 12 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 1,329 total
includes taxes & fees
11 Jun - 12 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 981 total
includes taxes & fees
10 Jun - 11 Jun
Berkshire Village Carriage House - Super Private!!
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 441
AED 935 total
includes taxes & fees
15 Jun - 16 Jun
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
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 940
AED 1,813 total
includes taxes & fees
7 Jul - 8 Jul
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
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, (109 reviews)
"Couldn’t have picked a better place! Warm and comfy and sooo close to okemo "
United States
Erica B.
The price is AED 496
AED 1,220 total
includes taxes & fees
10 Jun - 11 Jun
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
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!
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
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 617
AED 1,187 total
includes taxes & fees
16 Jun - 17 Jun
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
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.
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
"Great staff and the stay was what we needed in a quiet peaceful town. Thank you"
Richard 1-night trip
Posted 4 days 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 8 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.