Find Romantic Hotels in Windsor, MA from CA $291

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Check availability on Windsor Romantic Hotels

Tonight
Apr 4 - Apr 5
Tomorrow
Apr 5 - Apr 6
Next weekend
Apr 10 - Apr 12
In two weeks
Apr 17 - Apr 19

Our top choices for Windsor 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 7 - Apr 8
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 $179
CA $361 total
includes taxes & fees
Apr 7 - Apr 8
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 $146
CA $324 total
includes taxes & fees
Apr 8 - Apr 9
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 Windsor Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

6/10 Okay
"Great dinner, nice room. Only complaint is that none of the 3 elevators would come to the 6 floor in the morning. It was a long walk with our baggage."
patrick 1-night trip
Posted 10 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Frequently asked questions

Searching for romantic hotels in Windsor?
Are you looking for a romantic escape? If you want to see some sights and attractions in the greater Windsor area, you might head to Wahconah Falls State Park, Susan B. Anthony Birthplace Museum, or Mount Greylock State Reservation Visitor Center. If you're interested in staying 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 Windsor?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Windsor: The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Windsor are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Windsor?
There's nothing better than seeing a new destination with your sweetheart, so consider taking time to discover all that Windsor has to offer. If you're interested in seeing some of the area's sights and attractions, you might make a stop at Wahconah Falls State Park or Susan B. Anthony Birthplace Museum.
What's the best way to get to Windsor and around town during my romantic getaway?
These transportation options in Windsor might help your romantic getaway go off without a hitch: To get to Windsor, you can fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is the closest major airport, located 13.8 mi (22.2 km) from the city center. If you'd like to explore around the area, you may want to rent a car for your trip.

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