Romantic Hotels & Resorts in Pittsfield from AU$184

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Pittsfield Romantic Hotels

Best 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, (881)
"Our stay was very pleasant "
The price is AU$184
includes taxes & fees
5 Oct - 6 Oct
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, (646)
"We always stay at the Garden Inn when visiting the Berkshires."
The price is AU$269
includes taxes & fees
28 Sept - 29 Sept
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.
View all properties

Top Pittsfield Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Clean, spacious, well designed room with everything needed gir a great stay …. And so much more. The balcony was a great place to sit, gave coffee etc. can’t say enough about the beautiful grounds and amenities like indoor and outdoor pool areas, etc! Enjoyed staying at Vacation Village in the Berkshire and hope to return next time I am in the area. "
Carol 1-night trip
Posted 1 day ago
Vacation Village in the Berkshires
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"A great place if you appreciate and like history. The lobby is filled with antiques and the porch is great to rock in a chair and sip some wine. Parking is no issue and you can walk to local restaurants and shops. "
Roberta 3-night trip
Posted 9 days ago
The Red Lion Inn

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.
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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia