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

Find Hotel Wedding Venues 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 Hotel Wedding Venues

Tonight
Sep 5 - Sep 6
Tomorrow
Sep 6 - Sep 7
Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20

Our top choices for Pittsfield wedding hotels

A round dining table set for a formal event, with white tablecloth, silverware, and purple napkins.
A buffet area with a counter, food items, and a beverage station.
A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.

1. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
United States
Debra
NT$3,749
NT$4,188 total
includes taxes & fees
Sep 9 - Sep 10
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A garden with a white gazebo, a brick pathway, and various plants and flowers.
A courtyard with stone steps, potted plants, and a small wooden structure.
A house surrounded by trees with autumn foliage.
A breakfast buffet with various dishes and beverages.

2. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
Lenox
United States
Mary Anna
NT$5,610
NT$6,266 total
includes taxes & fees
Sep 7 - Sep 8
Whistler's Inn Bed & Breakfast
A large, two-story building with a symmetrical facade, multiple windows, and a central entrance with a covered porch.
A room with a large sliding glass door leading to a garden. Inside, there is a table with chairs and a small table with a vase.
A gazebo in a lush garden with flowering plants and a large tree.
A spacious living room with a large window, a sofa, a chair, and a dining area.

3. Harbour House Inn

Harbour House Inn
Cheshire
United States
Gregory
NT$8,027
NT$8,485 total
includes taxes & fees
Sep 7 - Sep 8
Harbour House Inn
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 brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A backyard with a swimming pool, lounge chairs, and a hot tub.

4. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
James
NT$5,012
NT$7,170 total
includes taxes & fees
Sep 30 - Oct 1
The Red Lion Inn
A sign for 'The 1896 House' with a logo for Brookside Accommodations.
A covered porch with white furniture and green chairs, surrounded by lush greenery.
A room with plaid wallpaper, a lamp on a table, and a chair.
A white two-story house with a sloped roof, large windows, and a small porch.

5. 1896 House Country Inn & Motels

1896 House Country Inn & Motels
Williamstown
United States
William
NT$3,362
NT$3,755 total
includes taxes & fees
Sep 14 - Sep 15
1896 House Country Inn & Motels
A large, multi-story building with a prominent stone facade and a metal roof, surrounded by landscaped gardens and a pedestrian bridge.
A spacious living area with a fireplace, wooden beams, and a large window.
A bar area with wooden beams, red chairs, and a long wooden table.
An outdoor seating area with stone fire pit, chairs, and a red building in the background.

6. The Williams Inn

The Williams Inn
Williamstown
United States
John
NT$6,146
NT$6,865 total
includes taxes & fees
Sep 13 - Sep 14
The Williams Inn
A two-story house with a brick entrance and a white facade.
A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.
A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.

7. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Stockbridge
United States
Philippe
NT$10,447
NT$12,637 total
includes taxes & fees
Sep 28 - Sep 29
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.
A dining table set with a vase of flowers, a book, and cutlery.
A bed with a white lace bedspread, a tray with cookies and a bottle, and two glasses of red wine.
A loft bedroom with a sloped ceiling, a ceiling fan, a floor lamp, a bed with a patterned bedspread, a chair, and a small table.

8. Brook Farm Inn

Brook Farm Inn
Lenox
United States
Carrie
NT$7,993
NT$9,182 total
includes taxes & fees
Sep 17 - Sep 18
Brook Farm Inn
View all properties

Top Pittsfield Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Everything was clean, the unit was well stocked, and the front desk staff member was excellent."
Elizabeth 1-night trip
Posted 3 hours ago
Vacation Village in the Berkshires
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good
"Staff was helpful. Location close to Tanglewood. Bed and pillows were awesome. One elevator was not working so that was inconvenient"
April 1-night trip
Posted 17 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Charming, updated throughout. Extremely clean and well appointed. Extremely delightful stay."
Colleen And mark 2-night trip
Posted 21 hours ago
The Red Lion Inn

Explore a world of travel with Expedia