Find Romantic Hotels in Stockbridge, MA from CA $287

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Check availability on Stockbridge Romantic Hotels

Our top choices for Stockbridge romantic hotels

Terrace/patio

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (277 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 CA $186
CA $287 total
includes taxes & fees
May 22 - May 23
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 CA $150
CA $330 total
includes taxes & fees
May 19 - May 20
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country 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 Stockbridge Hotel Reviews

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Breakfast was ordered off a small menu and delivered to the table. Very good quality."
J Kevin 3-night trip
Posted 7 hours ago
The Cornell Inn, Lenox & The Berkshires

Frequently asked questions

Searching for romantic hotels in Stockbridge?
If you and your partner need a romantic escape, we've got just the thing. Our guests also enjoy Stockbridge for its bars and historic landmarks. You might consider checking out some of the nearby sights and attractions such as Naumkeag Museum, National Shrine of the Divine Mercy, or Norman Rockwell Museum. If you'd like to stay close to a certain attraction, you can sort by neighborhood 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 Stockbridge?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Stockbridge: 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 27°F. The snowiest months in Stockbridge are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Stockbridge?
There's nothing better than wandering around a new destination with your sweetheart, so consider taking time to discover all there is to see and do in Stockbridge. If you're hoping to see some of the area's cultural attractions, you'll enjoy Stockbridge for its historic landmarks. You might think about stopping by Naumkeag Museum, National Shrine of the Divine Mercy, or Norman Rockwell Museum while you're seeing the sights.
What's the best way to get to Stockbridge and around town during my romantic getaway?
These transportation options in Stockbridge might help your romantic trip go off without a hitch: If you're looking to fly to Stockbridge, the closest major airport is Pittsfield, MA (PSF-Pittsfield Municipal), located 9.6 mi (15.5 km) from the city center. If you'd like to explore around the area, consider renting a car to take in more sights.

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