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

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Check availability on Pittsfield Romantic Hotels

Tonight
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 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 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.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

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.
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.
A cozy library with bookshelves, a fireplace, and comfortable seating.
A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

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 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.
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
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 snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.
A dining area with a glass table, red walls, and framed artwork.
A modern living room with a fireplace, comfortable seating, and a large window with curtains.

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 red building with a sign reading "Shaker Mill Inn."
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.
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.

5. Shaker Mill Inn

Shaker Mill Inn
West Stockbridge
United States
Mervin
AED 507
AED 556 total
includes taxes & fees
1 Nov - 2 Nov
Shaker Mill Inn
A hotel room with a bed, a desk, and two wall-mounted lamps.
A hotel room with a bed, two bedside tables, a desk, two chairs, and a large window with a view of greenery.
A building with a parking lot, a flag, and several parked cars.
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
26 Oct - 27 Oct
Econo Lodge Lee - Great Barrington
A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.
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.
A modern kitchen with white cabinets, a granite countertop, and a central island with stools.

7. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
United States
Mary R.
AED 551
AED 845 total
includes taxes & fees
4 Nov - 5 Nov
Berkshire Village Carriage House - Super Private!!
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A bar with wooden floors and shelves filled with bottles.

8. 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 bar area with stools, a counter displaying fruits and beverages, and a sign reading "Springs".
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.

9. The Springs Motel

The Springs Motel
New Ashford
United States
Elizabeth
AED 409
AED 449 total
includes taxes & fees
4 Nov - 5 Nov
The Springs Motel
An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.
A wooden interior with a table, chair, and a view of a red barn through an open door.
A spacious living room with a high ceiling, wooden beams, a fireplace, and a bookshelf filled with books.
A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

10. Inn at Silver Maple Farm

Inn at Silver Maple Farm
East Chatham
United States
Erdem
AED 713
AED 798 total
includes taxes & fees
4 Nov - 5 Nov
Inn at Silver Maple Farm
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Top Pittsfield Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Great staff, heated bathroom floors."
Ellen 3-night trip
Posted 5 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.