Find Romantic Hotels in Bennington, VT

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Check availability on Bennington Romantic Hotels

Our top choices for Bennington romantic hotels

Free WiFi, bed sheets
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort
3.0 star property
Stratton
7.6 out of 10, Good, (940)
"We like that getting to Stratton Mountain and the downtown area was very walkable or easy to get there by regularly running shuttle buses."
United States
Mark
The price is AED 673
AED 814 total
includes taxes & fees
7 Jan - 8 January 2026
The Black Bear Lodge at Stratton Mountain Resort
Exterior
The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel
3.0 star property
Manchester Center
8.4 out of 10, Very Good, (864)
"Nice staff, big room, comfortable bed, walking distance to downtown-overall great stay! "
United States
Amanda
The price is AED 393
AED 493 total
includes taxes & fees
17 Dec - 18 Dec
The Palmer House Resort, an Ascend Collection Hotel
Exterior
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa
4.5 star property
Manchester Village Historic District
7.4 out of 10, Good, (576)
"Beautiful hotel! "
United States
sarah
The price is AED 679
AED 955 total
includes taxes & fees
17 Dec - 18 Dec
The Equinox Golf Resort & Spa
Property grounds
The Inn at Manchester

The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (280)
"Great establishment "
United States
Brenda
The price is AED 606
AED 667 total
includes taxes & fees
4 Jan - 5 January 2026
The Inn at Manchester
Reception
South Shire

South Shire

South Shire
4.0 star property
Bennington
9.2 out of 10, Wonderful, (118)
"Great period decor! Spacious rooms and an inviting living room to relax. Also walking distance to downtown shops and restaurants was a real plus!"
United States
Roseann
The price is AED 599
AED 693 total
includes taxes & fees
23 Dec - 24 Dec
South Shire
Signature Room, King plus Twin Bed, Private Bathroom, Porch, Accessible, RM-10 | Premium bedding, individually decorated, individually furnished
The Four Chimneys Inn

The Four Chimneys Inn

The Four Chimneys Inn
4.0 star property
Bennington
9.4 out of 10, Exceptional, (280)
"What an absolutely amazing stay!! Everything was perfect. Highly recommend having dinner onsite. "
United States
Jon
The Four Chimneys Inn
Deluxe Room | Frette Italian sheets, premium bedding, iron/ironing board
The Reluctant Panther Inn and Restaurant

The Reluctant Panther Inn and Restaurant

The Reluctant Panther Inn and Restaurant
4.0 star property
Manchester Village Historic District
9.8 out of 10, Exceptional, (331)
"Wonderful stay! The room was spacious and the bed was heaven. The breakfast was amazing and they were even able to offer gluten free options!"
United States
Abbie
The price is AED 658
AED 724 total
includes taxes & fees
14 Dec - 15 Dec
The Reluctant Panther Inn and Restaurant
Front of property
The Inn at Ormsby Hill

The Inn at Ormsby Hill

The Inn at Ormsby Hill
3.5 star property
Manchester Center
9.8 out of 10, Exceptional, (150)
"Lovely place to stay Jack and Maryann excellent hosts"
United States
Lenny
The price is AED 731
AED 804 total
includes taxes & fees
14 Dec - 15 Dec
The Inn at Ormsby Hill
Garden
Arlington Inn

Arlington Inn

Arlington Inn
3.0 star property
Arlington
8.8 out of 10, Excellent, (187)
"Excellent stay! Very friendly staff."
United States
Mercedita
The price is AED 741
AED 808 total
includes taxes & fees
4 Jan - 5 January 2026
Arlington Inn
Front of property
Hill Farm Inn

Hill Farm Inn

Hill Farm Inn
4.0 star property
Arlington
9.6 out of 10, Exceptional, (173)
"This Inn is spectacular! The rooms, grounds, decor, staff and restaurant all were the best for stops on our vacation."
United States
Kenneth
The price is AED 625
AED 1,507 total
includes taxes & fees
11 Jan - 12 January 2026
Hill Farm Inn
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

Best Western Bennington

Best Western Bennington

10/10 Excellent
"Yes"
Clark 4-night trip
Posted 6 days ago
Best Western 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 Battle Monument. 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 Battle Monument 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.