Find Romantic Hotels in Pittsfield, MA

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Compare Pittsfield Romantic Hotels room rates, reviews, and availability. Most hotels are fully refundable.

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Exterior

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3.0 star property
8.0 out of 10, Very Good, (701)
"Staff was very accommodating. The pool area was quite nice and it was deep"
The price is AED 364
AED 406 total
includes taxes & fees
5 Jan - 6 January 2025
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Hilton Garden Inn Lenox Pittsfield
Exterior

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (620)
"Check in and check out where quick and easy. The room was comfortable and clean. The staff were nice and accommodating. Central location to surrounding attractions. "
The price is AED 536
AED 599 total
includes taxes & fees
31 Dec - 1 January 2025
Hilton Garden Inn Lenox Pittsfield
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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Frequently asked questions

Searching for romantic hotels in Pittsfield?
Are you in need of a romantic escape? Our guests also enjoy Pittsfield for its theater scene and sporting events. If you want to explore the area, you might head to Berkshire Museum, Colonial Theater, or Bousquet Ski Area. If you’d like to stay close to a certain attraction, you can sort properties by neighborhood or distance to top landmarks, so you and your partner will get to see everything on your list.
How many romantic hotels can we expect to find in Pittsfield?
Expedia has 12 romantic Pittsfield hotels for you both to enjoy.
When is the best time of year for a romantic getaway to Pittsfield?
If you’re hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Pittsfield: 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 Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Pittsfield?
There’s nothing better than seeing a new destination with your sweetheart, so consider checking out all there is to see and do in Pittsfield. Adventurous pairs will enjoy Pittsfield for its sporting events. You might think about visiting Berkshire Museum, Colonial Theater, or Bousquet Ski Area.
What's the best way to get to Pittsfield and around town during my romantic getaway?
These transportation options in Pittsfield might help your romantic trip get off to a smooth start: The closest major airport is Pittsfield, MA (PSF-Pittsfield Municipal), located 2.5 mi (4 km) from the city center. To see more of the surrounding area, hop aboard a train at Pittsfield Intermodal Transportation Center or Pittsfield Station.