Find Romantic Hotels in The Berkshires

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Romantic Hotels

Top Romantic Hotels in The Berkshires

Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (687)
"Fun place and very clean. Friendly staff and an amazing outdoor area to hang out."
The price is S$229
includes taxes & fees
26 Aug - 27 Aug
Berkshires Untold
The Williams Inn
Front of property – evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (486)
"The property was spacious but still had a cozy feel. "
The price is S$321
includes taxes & fees
7 Sept - 8 Sept
The Williams Inn
The Constance by the Lenox Collection
Free WiFi, bed sheets

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (523)
"Great place , love it, will return"
The price is S$214
includes taxes & fees
15 Sept - 16 Sept
The Constance by the Lenox Collection
The Red Lion Inn
Outdoor pool, pool loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1008)
"Loved our visit"
The price is S$318
includes taxes & fees
26 Aug - 27 Aug
The Red Lion Inn
The Dewey
Exterior

The Dewey

3.5 star property
8.8 out of 10, Excellent, (321)
"excellent stay!! The Dewey is a cozy getaway location!"
The price is S$247
includes taxes & fees
15 Sept - 16 Sept
The Dewey
Simsbury 1820 House
Front of property

Simsbury 1820 House

4.0 star property
9.2 out of 10, Wonderful, (980)
"Great place to stay and eat."
The price is S$272
includes taxes & fees
24 Aug - 25 Aug
Simsbury 1820 House
The Wilmington Inn
Porch

The Wilmington Inn

3.5 star property
10.0 out of 10, Exceptional, (179)
"Right in downtown Wilmington - easy to find, yet hidden away. Shops and dining in easy walking distance. Nice firepit outside residence. Charlie was friendly and welcoming during check in. "
The price is S$306
includes taxes & fees
31 Aug - 1 Sept
The Wilmington Inn
Simsbury Inn
Exterior

Simsbury Inn

3.5 star property
9.2 out of 10, Wonderful, (266)
"Lovely property Everyone kind and gracious. "
The price is S$366
includes taxes & fees
1 Sept - 2 Sept
Simsbury Inn
Brook Farm Inn
1 bedroom, premium bedding, iron/ironing board, rollaway beds

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (158)
"Inn was gorgeous and staff exceptional!"
Brook Farm Inn
Gateways Inn & Restaurant
Iron/ironing board, free WiFi, bed sheets

Gateways Inn & Restaurant

3.0 star property
7.8 out of 10, Good, (189)
"Very well kept property, nice restaurant and is in a great area"
The price is S$426
includes taxes & fees
1 Sept - 2 Sept
Gateways Inn & Restaurant
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 The Berkshires Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Liked the fact there are 2 pools, an indoor and an outdoor."
MARK 2-night trip
Posted 3 days ago
Vacation Village in the Berkshires