Romantic Hotels in Pittsfield, Massachusetts

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Check availability on Pittsfield Romantic Hotels

Top Pittsfield Romantic Hotels

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (823)
"Very convenient location, downtown, short drive to local attractions "
The price is P7,363
P8,225 total
includes taxes & fees
Jul 27 - Jul 28
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is P11,214
P12,526 total
includes taxes & fees
Jul 27 - Jul 28
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.

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 Barrington Stage Company. 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.
What's the best place to stay for a couple going to Pittsfield?
Hotel On North is a favorite hotel for couples, and features premium bedding and flat-screen TVs.
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 Barrington Stage Company.
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.