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

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Check availability on Pittsfield Romantic Hotels

Tonight
23 Oct - 24 Oct
Tomorrow
24 Oct - 25 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for Pittsfield romantic hotels

Two Adirondack chairs facing a river with a forested hill in the background.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
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 modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

1. The Yankee Inn

The Yankee Inn
Lenox
United States
Basil
AED 367
AED 410 total
includes taxes & fees
17 Nov - 18 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.
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
4 Nov - 5 Nov
Berkshires Untold
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
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.
A lakeside dock with kayaks and a covered boat ramp.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Gustavo
AED 400
AED 446 total
includes taxes & fees
22 Nov - 23 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 dining area with a glass table, red walls, and framed artwork.
A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.
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 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.

5. Shaker Mill Inn

Shaker Mill Inn
West Stockbridge
United States
Mahadeva
AED 444
AED 488 total
includes taxes & fees
2 Nov - 3 Nov
Shaker Mill Inn
A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.
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.
A kitchen with white cabinets, a granite countertop, a stainless steel sink, and a red pendant light.

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
26 Oct - 27 Oct
Berkshire Village Carriage House - Super Private!!
Dining
Living area
Interior
Room

7. Garden Gables

Garden Gables
Lenox
AED 480
AED 803 total
includes taxes & fees
26 Oct - 27 Oct
Garden Gables
A patio area with outdoor furniture, a fire pit, and potted plants.
A poolside area with lounge chairs, umbrellas, and a swimming pool.
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.

8. The Springs Motel

The Springs Motel
New Ashford
United States
Elizabeth
AED 388
AED 426 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 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.

9. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Mallory
AED 608
AED 861 total
includes taxes & fees
24 Nov - 25 Nov
The Red Lion Inn
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.

10. Inn at Silver Maple Farm

Inn at Silver Maple Farm
East Chatham
United States
Linda
AED 749
AED 839 total
includes taxes & fees
5 Nov - 6 Nov
Inn at Silver Maple Farm
View all properties

Top Pittsfield Hotel Reviews

The Red Lion Inn

The Red Lion Inn

8/10 Good
"Absolutely great location! An older property- the lobby and hallways seemed dark and aging (yes it’s historic). Our room was surprisingly cheerful! I’d stay here again!!"
carole 1-night trip
Posted 12 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.