Find Romantic Hotels in Stockbridge, MA from CA $291

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Check availability on Stockbridge Romantic Hotels

Tonight
Apr 1 - Apr 2
Tomorrow
Apr 2 - Apr 3
This weekend
Apr 3 - Apr 5
Next weekend
Apr 10 - Apr 12

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)
"Property was great- clean, well equipped and a perfect spot for us to spend the night and a quick visit in the Berkshires!! "
United States
christine b.
The price is CA $188
CA $291 total
includes taxes & fees
Apr 3 - Apr 4
Berkshire Village Carriage House - Super Private!!
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 CA $178
CA $361 total
includes taxes & fees
Apr 2 - Apr 3
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 CA $154
CA $334 total
includes taxes & fees
Apr 6 - Apr 7
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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"OK, the hotel needs updating, but the staff was so friendly and helpful it didn't even matter. We parked our car, walked everywhere, 2 min to the Colonial theater! Insider tip, if you buy a breakfast tix from the front desk it's less $ than paying at the restaurant. "
margaret 1-night trip
Posted 3 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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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