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

Find Romantic Hotels in Pittsfield, MA from CA $149

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Check availability on Pittsfield Romantic Hotels

Tonight
Oct 24 - Oct 25
Tomorrow
Oct 25 - Oct 26
Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8

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 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.

1. The Yankee Inn

The Yankee Inn
Lenox
United States
Basil
CA $133
CA $149 total
includes taxes & fees
Nov 1 - Nov 2
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 cozy library with bookshelves, a fireplace, and comfortable seating.

2. Berkshires Untold

Berkshires Untold
Lenox
United States
Madhavi R
CA $182
CA $204 total
includes taxes & fees
Nov 1 - Nov 2
Berkshires Untold
A lodge with a large building and a dock by a lake, surrounded by forest.
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.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Gustavo
CA $152
CA $170 total
includes taxes & fees
Nov 22 - Nov 23
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 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.

4. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United Kingdom
judith
CA $215
CA $246 total
includes taxes & fees
Oct 27 - Oct 28
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 covered patio with a round glass table and metal chairs, a wooden deck, and a view of trees and hills.
A stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.

5. Shaker Mill Inn

Shaker Mill Inn
West Stockbridge
United States
Mahadeva
CA $165
CA $181 total
includes taxes & fees
Nov 2 - Nov 3
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 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.

6. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
United States
Mary R.
CA $189
CA $294 total
includes taxes & fees
Oct 26 - Oct 27
Berkshire Village Carriage House - Super Private!!
Dining
Interior
Living area
Room

7. Garden Gables

Garden Gables
Lenox
CA $169
CA $290 total
includes taxes & fees
Nov 4 - Nov 5
Garden Gables
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 cozy living room with a stone fireplace, comfortable seating, and a television.

8. The Springs Motel

The Springs Motel
New Ashford
United States
Elizabeth
CA $148
CA $162 total
includes taxes & fees
Nov 1 - Nov 2
The Springs Motel
A straw hat, sunglasses, and two drinks on a striped towel by a body of water.
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A covered porch with wicker furniture and hanging flower baskets.
A bar with wooden floors and shelves filled with bottles.

9. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Mallory
CA $221
CA $316 total
includes taxes & fees
Nov 4 - Nov 5
The Red Lion Inn
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 kitchen with wooden beams, a dining area with a large table and chairs, and a view of the outdoors through large windows.
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
Linda
CA $258
CA $289 total
includes taxes & fees
Nov 22 - Nov 23
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 1 day ago
The Red Lion Inn
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

8/10 Good
"Nice people, ok and clean room. Too much light from around the window shades and all the gizmos (thermostat, TV etc.) to the point of inhibiting sleep."
Graydon 2-night trip
Posted 6 days ago
Hilton Garden Inn Lenox Pittsfield

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.

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