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

Find Romantic Hotels in Bennington, VT

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Bennington Romantic Hotels

Next weekend
In two weeks

Our top choices for Bennington romantic hotels

Perfect for a peaceful get away in clean fresh Vermont air!

Perfect for a peaceful get away in clean fresh Vermont air!
Woodford
10.0 out of 10, Exceptional, (84 reviews)
"We had the most wonderful stay! The house and the property were beautiful, the amentities were excellent, and Linda Jane was an incredibly generous and accommodating host. We visit Bennington every year for Thanksgiving with family and we hope to rent with Linda Jane again in the future."
United States
Karissa A.
The price is AED 628
AED 1,415 total
includes taxes & fees
30 Jun - 1 Jul
Perfect for a peaceful get away in clean fresh Vermont air!

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (284 reviews)
"The property is very nice, well stocked amenities. Cozy and warm and perfect for a long weekend getaway. "
United States
Jonathan H.
The price is AED 661
AED 985 total
includes taxes & fees
29 Jun - 30 Jun
Berkshire Village Carriage House - Super Private!!

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 1,200 total
includes taxes & fees
5 Jul - 6 Jul
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

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 1,333 total
includes taxes & fees
9 Jul - 10 Jul
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

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, (106 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 1,142 total
includes taxes & fees
5 Jul - 6 Jul
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

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 1,121 total
includes taxes & fees
30 Jun - 1 Jul
Magic Mountain Trailside Condo - Ski In / Ski Out

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, (86 reviews)
"Beautiful and immaculately clean home located within walking distance to downtown, shopping, and restaurants. Very quiet location. We felt safe and comfortable at this home. Property has 3 bedrooms and 5 very comfortable beds. The attic bedroom has 3 single beds which is handy for larger families. Loved sitting around the fire pit and was pleased that our yard was separated from the neighbors. Thank you so much for sharing your hospitality."
United States
Kristen
The price is AED 496
AED 1,236 total
includes taxes & fees
29 Jun - 30 Jun
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

4 Season Cabin great location.

4 Season Cabin great location.
Mt Tabor
10.0 out of 10, Exceptional, (124 reviews)
"Excellent stay"
United States
Parsa R.
4 Season Cabin great location.

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 426
AED 955 total
includes taxes & fees
30 Jun - 1 Jul
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
8.4 out of 10, Very Good, (12 reviews)
"Great location and property. thank you"
United States
Christine P.
The price is AED 646
AED 1,186 total
includes taxes & fees
2 Jul - 3 Jul
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
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.

Top Bennington Hotel Reviews

Explore a world of travel with Expedia

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 Bennington Museum, Hemmings Motor News Car Lover's Convenience Store & Vehicle Display, 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 Bennington Museum, Hemmings Motor News Car Lover's Convenience Store & Vehicle Display, 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.