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
13 Oct - 14 Oct
Tomorrow
14 Oct - 15 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Pittsfield romantic hotels

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

1. The Yankee Inn

The Yankee Inn
Lenox
United States
Basil
AED 389
AED 435 total
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.
A cozy library with bookshelves, a fireplace, and comfortable seating.
An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

2. Berkshires Untold

Berkshires Untold
Lenox
United States
Madhavi R
AED 478
AED 534 total
includes taxes & fees
1 Nov - 2 Nov
Berkshires Untold
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A lakeside dock with kayaks and a covered boat ramp.
A lodge with a large building and a dock by a lake, surrounded by forest.
A dining area with large windows, wooden furniture, and a view of a lake.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Gustavo
AED 421
AED 471 total
includes taxes & fees
8 Nov - 9 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A snow-covered outdoor area with a patio, seating, and a covered dining area.
A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.
A modern living room with a fireplace, comfortable seating, and a large window with curtains.
A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.

4. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United Kingdom
judith
AED 564
AED 647 total
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
A red building with a sign reading "Shaker Mill Inn."
A cozy room with a bed, a sofa, a small table, and a desk. There are two lamps on the bed and a window with curtains.
A cozy living room with a sofa, a small table, and a bookshelf. There is a window with curtains, and a painting on the wall.
A covered patio with a round glass table and metal chairs, a wooden deck, and a view of trees and hills.

5. Shaker Mill Inn

Shaker Mill Inn
West Stockbridge
United States
Steven
AED 481
AED 528 total
includes taxes & fees
9 Nov - 10 Nov
Shaker Mill Inn
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 kitchen with white cabinets, a granite countertop, a stainless steel sink, and a red pendant light.
A house with a brick exterior, a green roof, and a driveway leading to a garage.

6. 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 large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A bar with wooden floors and shelves filled with bottles.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A covered porch with wicker furniture and hanging flower baskets.

7. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Stephan
AED 579
AED 829 total
includes taxes & fees
3 Nov - 4 Nov
The Red Lion Inn
A patio area with outdoor furniture, a fire pit, and potted plants.
A poolside area with lounge chairs, umbrellas, and a swimming pool.
A hotel room with a large bed, a desk, a chair, and a view of the outdoors.
A cozy living room with a stone fireplace, comfortable seating, and a television.

8. The Springs Motel

The Springs Motel
New Ashford
AED 388
AED 426 total
includes taxes & fees
1 Nov - 2 Nov
The Springs Motel
An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.
A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.
A spacious living room with a high ceiling, wooden beams, a fireplace, and a bookshelf filled with books.
A spacious kitchen with wooden beams, a dining area with a large table and chairs, and a view of the outdoors through large windows.

9. Inn at Silver Maple Farm

Inn at Silver Maple Farm
East Chatham
United States
Linda
AED 639
AED 716 total
includes taxes & fees
8 Nov - 9 Nov
Inn at Silver Maple Farm
A large tree with a bench in a grassy area.
A spacious kitchen with wooden flooring, a dining area with a table and chairs, a black sofa, and a television mounted on the wall.
A compact kitchen with white cabinetry, a stove, a microwave, and a dishwasher.
Outdoor dining

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 356
AED 880 total
includes taxes & fees
2 Nov - 3 Nov
NEW RENO - Historic Loft w/views of the Berkshires
View all properties

Top Pittsfield Hotel Reviews

The Red Lion Inn

The Red Lion Inn

8/10 Good
"We had a nice stay at the Red Lion Inn. Our room was clean and had a fireplace, but did not have a mini-refrigerator and the TV was placed to the side of the bed. The restaurant charged a lot ($65 for a filet mignon entree) and the food was not up to that price. The bread and salad were a la carte. The whole place seemed in need of a refresh."
Patricia 1-night trip
Posted 1 day 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.