Romantic Hotels in Pittsfield, Massachusetts

    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

Tonight
Jul 4 - Jul 5
Tomorrow
Jul 5 - Jul 6
This weekend
Jul 4 - Jul 6
Next weekend
Jul 11 - Jul 13

Top Pittsfield Romantic Hotels

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (808)
"Staff was welcoming and informative "
The price is P6,919
P7,729 total
includes taxes & fees
Jul 13 - Jul 14
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (49)
"Nice place for a weekend away."
The price is P14,756
P15,597 total
includes taxes & fees
Jul 7 - Jul 8
Harbour House Inn
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Nice place to stay. Good breakfast. "
The price is P9,057
P10,117 total
includes taxes & fees
Jul 13 - Jul 14
The Yankee, Trademark Collection by Wyndham
Gateways Inn & Restaurant
Iron/ironing board, free WiFi, bed sheets

Gateways Inn & Restaurant

3.0 star property
7.8 out of 10, Good, (188)
"Very well kept property, nice restaurant and is in a great area"
The price is P19,414
P22,656 total
includes taxes & fees
Jul 14 - Jul 15
Gateways Inn & Restaurant
The Dewey
Exterior

The Dewey

3.5 star property
8.8 out of 10, Excellent, (314)
"excellent stay!! The Dewey is a cozy getaway location!"
The price is P11,727
P13,099 total
includes taxes & fees
Jul 15 - Jul 16
The Dewey
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (475)
"All was just as advertised and the family/staff was friendly and helpful. "
The price is P9,159
P10,231 total
includes taxes & fees
Jul 10 - Jul 11
Whistler's Inn Bed & Breakfast
The Constance by the Lenox Collection
Free WiFi, bed sheets

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (484)
"Had a fantastic stay, love this property. Cant wsit to go back"
The price is P10,309
P11,516 total
includes taxes & fees
Jul 15 - Jul 16
The Constance by the Lenox Collection
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (152)
"This is a charming and very pleasant place to stay."
Brook Farm Inn
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1000)
"I had excellent stay at the Red Lion Inn "
The price is P12,320
P16,275 total
includes taxes & fees
Aug 4 - Aug 5
The Red Lion Inn
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.