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

Bennington Romantic Hotel

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Check availability on Bennington Romantic Hotel

This weekend
3 Jul - 5 Jul
Next weekend
10 Jul - 12 Jul

Our top choices for Bennington romantic hotels

Exterior

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 HK$1,490
HK$3,188 total
includes taxes & fees
21 Jul - 22 Jul
Perfect for a peaceful get away in clean fresh Vermont air!
Terrace/patio

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (285 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 HK$1,412
HK$2,093 total
includes taxes & fees
2 Jul - 3 Jul
Berkshire Village Carriage House - Super Private!!
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 HK$534
HK$2,561 total
includes taxes & fees
5 Jul - 6 Jul
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)
"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 HK$1,333
HK$2,845 total
includes taxes & fees
14 Jul - 15 Jul
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
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, (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 HK$910
HK$2,420 total
includes taxes & fees
5 Jul - 6 Jul
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
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 HK$1,094
HK$2,282 total
includes taxes & fees
1 Jul - 2 Jul
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Beach

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 HK$1,165
HK$2,252 total
includes taxes & fees
1 Jul - 2 Jul
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
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 HK$1,080
HK$2,169 total
includes taxes & fees
1 Jul - 2 Jul
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, (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 HK$1,595
HK$3,290 total
includes taxes & fees
1 Jul - 2 Jul
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

The Four Chimneys Inn

The Four Chimneys Inn

10/10 Excellent
"Wonderful place to stay!"
Peg 2-night trip
Posted 2 days ago
The Four Chimneys Inn

Frequently asked questions

Searching for romantic hotels in Bennington?
If you and your partner need a romantic holiday, we'd like to help you plan for it. 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 near a certain attraction, you can sort by neighbourhood or distance to top landmarks, 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 looking forward to lots of outings with your partner, take a look at these details about year-round temperatures in Bennington: The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Bennington are January, March, February and December, with each month seeing an average of 21 cm 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 holiday, 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 in Albany, NY (ALB-Albany Intl.), located 31.7 mi (51 km) from the city centre. If you'd like to explore around the area, you may want to rent a car for your trip.

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