A historic building with classical architecture, a traffic light, and a yellow taxi.

Find Romantic Hotels in Pittsfield, MA

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check availability on Pittsfield Romantic Hotels

Tonight
27 Sep - 28 Sep
Tomorrow
28 Sep - 29 Sep
Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct

Our top choices for Pittsfield romantic hotels

Superior Room, 1 King Bed, Jetted Tub | Jetted tub
Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, sun loungers
42-inch flat-screen TV with cable channels, TV
View from room

1. The Yankee Inn

The Yankee Inn
Lenox
United States
William
AED 397
AED 443 total
includes taxes & fees
27 Oct - 28 Oct
The Yankee Inn
Lobby lounge
Terrace/patio
Lobby
Lobby

2. Berkshires Untold

Berkshires Untold
Lenox
United States
Drue
AED 544
AED 608 total
includes taxes & fees
29 Sep - 30 Sep
Berkshires Untold
Lake
Lake
Lake
Exterior

3. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Ann M
AED 496
AED 555 total
includes taxes & fees
29 Oct - 30 Oct
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Terrace/patio
Property grounds
Exterior
Coffee/tea maker, fridge, microwave, oven

4. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
United States
Maya H.
AED 496
AED 759 total
includes taxes & fees
30 Sep - 1 Oct
Berkshire Village Carriage House - Super Private!!
Courtyard
Cabin, 3 Bedrooms, Mountainside | Living area | Smart TV
Breakfast meal
Honeymoon Suite, 1 King Bed, Patio | Laptop workspace, WiFi (free), individually decorated

5. The Springs Motel

The Springs Motel
New Ashford
United States
Elizabeth
AED 417
AED 458 total
includes taxes & fees
30 Sep - 1 Oct
The Springs Motel
In-room dining
Free continental breakfast
Lobby
Room, 1 Queen Bed | Desk, iron/ironing board, cribs (free), rollaway beds (surcharge)

6. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
Lee
United States
Anna
AED 244
AED 273 total
includes taxes & fees
26 Oct - 27 Oct
Econo Lodge Lee - Great Barrington
Garden
Standard Apartment, Private Bathroom (Greylock - No Pets)
Superior Suite, Private Bathroom (Honeymoon - Pets Allowed)
Deluxe Suite, Private Bathroom (Clark - Pets Allowed)

7. Shaker Mill Inn

Shaker Mill Inn
West Stockbridge
United States
Mervin
AED 657
AED 721 total
includes taxes & fees
1 Oct - 2 Oct
Shaker Mill Inn
Exterior
Lobby
Exterior
Bar (on property)

8. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United States
Rosann
AED 564
AED 647 total
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
Property grounds
Outdoor pool, sun loungers
Exterior
Pub

9. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Stephan
AED 562
AED 810 total
includes taxes & fees
29 Sep - 30 Sep
The Red Lion Inn
TV
Exterior
Outdoor dining
Coffee/tea maker, fridge, microwave, oven

10. NEW RENO - Historic Loft w/views of the Berkshires

NEW RENO - Historic Loft w/views of the Berkshires
New Lebanon
United States
John
AED 342
AED 828 total
includes taxes & fees
29 Sep - 30 Sep
NEW RENO - Historic Loft w/views of the Berkshires
View all properties

Top Pittsfield Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Another unforgettable experience at the Red Lion. My family has been coming up for 50 years, we’re happy to continue the tradition. Wether Fall, Spring, Summer or Winter, the 4 seasons at the Red Lion are always a favorite!"
Nelson 1-night trip
Posted 13 hours ago
The Red Lion Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"Nice place, would stay again"
kaitlyn 1-night trip
Posted 13 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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.
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.