Find Romantic Hotels in Pittsfield from S$164

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Check availability on Pittsfield Romantic Hotels

Top Romantic Hotels in Pittsfield

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Dine in style with a long table set for a memorable meal, surrounded by cushioned chairs and large windows offering a view of the outdoors.

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (819)
"Very convenient location, downtown, short drive to local attractions "
The price is S$164
includes taxes & fees
30 Jul - 31 Jul
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Hilton Garden Inn Lenox Pittsfield
Relax on the patio with wicker sofas and armchairs, surrounded by a fire feature and a beautiful garden view.

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 S$308
includes taxes & fees
27 Jul - 28 Jul
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 holiday? Our guests also enjoy Pittsfield for its theatre 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're interested in staying close to a certain attraction, you can sort properties by neighbourhood and proximity to top sights, so you and your partner will get to see everything on your list.
What's the best place to stay for a romantic holiday to Pittsfield?
Hotel On North is a favourite hotel for couples, and features premium bedding and flat-screen TVs.
How many romantic hotels will we be able 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, take a look at these details about year-round temperatures in Pittsfield: The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Pittsfield are January, March, February and November, with each month seeing an average of 18 cm 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 go off without a hitch: The closest major airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 2.5 mi (4 km) from the city centre. To explore the surrounding area, hop aboard a train at Pittsfield Intermodal Transportation Center or Pittsfield Station.