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

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Check availability on Pittsfield Romantic Hotels

Tonight
17 Oct - 18 Oct
Tomorrow
18 Oct - 19 Oct
Next weekend
23 Oct - 25 Oct
In two weeks
30 Oct - 1 Nov

Our top choices for Pittsfield romantic hotels

A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.
A modern kitchen with white cabinets, a granite countertop, and a central island with stools.
A house with a brick exterior, a green roof, and a driveway leading to a garage.
A dog lying on a stone wall in a forested area.

1. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
United States
Mary R.
AED 496
AED 775 total
includes taxes & fees
19 Oct - 20 Oct
Berkshire Village Carriage House - Super Private!!
A bedroom with a large bed, a nightstand, an air conditioning unit, and a view through the window.
A backyard with a wooden fence, a fire pit, and several Adirondack chairs in blue and white.
A red building with a green door labeled "Apartment 1," a small garden with mulch and plants, and a white car parked in the background.
A modern kitchen with stainless steel appliances, a wooden dining table, and light-colored cabinetry.

2. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
United States
Christine P.
AED 465
AED 1,047 total
includes taxes & fees
18 Oct - 19 Oct
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.
A house with a covered porch and a well-maintained garden.
A green house with a porch, surrounded by a garden with various plants and flowers.
A spacious kitchen with wooden beams, a dining area with a long table, and a living room with a red sofa and a fireplace.

3. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
United States
Ofer C.
AED 1,253
AED 2,372 total
includes taxes & fees
20 Oct - 21 Oct
Secluded Family Home in Serene Stockbridge Woods
A kitchen with white cabinets, a wooden dining table, and pendant lights.
A cozy room with a wooden bench, a small table, and a chair.
A kitchen with white cabinets, wooden dining table, and chairs. There are hanging pendant lights and a window with a view.
A narrow hallway with a wooden floor, a black door at the end, and a wall with floral wallpaper.

4. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
United States
Diane
AED 841
AED 1,781 total
includes taxes & fees
19 Oct - 20 Oct
A roomy remodeled retreat close to MassMoCA
A two-story house with a balcony, a deck, and a view of the surrounding forest.
A kitchen with wooden floors, a central island, a stainless steel refrigerator, and pendant lighting.
A modern kitchen with white cabinets and a built-in knife block.
A spacious living room with a high ceiling, a fireplace, and a staircase leading to an upper level.

5. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
United States
Anne S.
AED 1,008
AED 2,154 total
includes taxes & fees
18 Oct - 19 Oct
Gorgeous Mountain Views Retreat: Family & Nature
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Top Pittsfield Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"This place is a must stay! We loved every bit of it and had a best time!!! Def recommend 100%"
Hope 1-night trip
Posted 13 hours ago
The Red Lion Inn

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.