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

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Check availability on Pittsfield Romantic Hotels

Tonight
2 Oct - 3 Oct
Tomorrow
3 Oct - 4 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 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 view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
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.

1. The Yankee Inn

The Yankee Inn
Lenox
United States
William
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.
An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".
A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.
A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.

2. Berkshires Untold

Berkshires Untold
Lenox
United States
Madhavi R
AED 484
AED 540 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 lakeside lodge with a dock, fishing rods, and outdoor seating.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Bob
AED 425
AED 474 total
includes taxes & fees
1 Nov - 2 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 modern living room with a fireplace, comfortable seating, and a large window with curtains.
A dining area with a glass table, red walls, and framed artwork.
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 States
Rosann
AED 564
AED 647 total
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.
A dog lying on a stone wall in a forested area.
A house with a brick exterior, a green roof, and a driveway leading to a garage.
A kitchen with white cabinets, a granite countertop, a stainless steel sink, and a red pendant light.

5. 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
4 Oct - 5 Oct
Berkshire Village Carriage House - Super Private!!
A hotel room with a bed, a desk, and two wall-mounted lamps.
A hotel reception desk with an orange counter, a computer, a beverage cooler, and framed awards on the wall.
Breakfast area
A small kitchenette with a coffee maker, toaster, and cabinets. There is a red and green patterned floor and a plant on the left.

6. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
Lee
United States
Anna
AED 240
AED 269 total
includes taxes & fees
25 Oct - 26 Oct
Econo Lodge Lee - Great Barrington
A patio area with outdoor furniture, a fire pit, and potted plants.
A hotel room with a large bed, a desk, a chair, and a view of the outdoors.
A bar area with stools, a counter displaying fruits and beverages, and a sign reading "Springs".
A poolside area with lounge chairs, umbrellas, and a swimming pool.

7. The Springs Motel

The Springs Motel
New Ashford
United States
Elizabeth
AED 417
AED 458 total
includes taxes & fees
1 Nov - 2 Nov
The Springs Motel
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
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.

8. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Stephan
AED 582
AED 832 total
includes taxes & fees
1 Nov - 2 Nov
The Red Lion Inn
A red building with a sign reading "Shaker Mill Inn."
A covered patio with a round glass table and metal chairs, a wooden deck, and a view of trees and hills.
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 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.

9. Shaker Mill Inn

Shaker Mill Inn
West Stockbridge
United States
Mervin
AED 514
AED 564 total
includes taxes & fees
1 Nov - 2 Nov
Shaker Mill Inn
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.
A white house with a porch, surrounded by a grassy lawn and trees with autumn foliage.
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 375
AED 898 total
includes taxes & fees
27 Oct - 28 Oct
NEW RENO - Historic Loft w/views of the Berkshires
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Top Pittsfield Hotel Reviews

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.