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

Find Hotel Wedding Venues in Pittsfield, MA

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Check availability on Pittsfield Hotel Wedding Venues

Tonight
Sep 4 - Sep 5
Tomorrow
Sep 5 - Sep 6
This weekend
Sep 4 - Sep 6
Next weekend
Sep 11 - Sep 13

Our top choices for Pittsfield wedding hotels

A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.
A multi-story hotel with a brick facade and a flat roof.
A pool area with a glass ceiling, multiple levels, and outdoor seating.

1. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
United States
Debra
NT$3,746
NT$4,184 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 spacious living room with a grand piano, a red armchair, and a chandelier.
A house surrounded by trees with autumn foliage.

2. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
Lenox
United States
Mary Anna
NT$5,628
NT$6,287 total
includes taxes & fees
Sep 8 - Sep 9
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 spacious living room with a large window, a sofa, a chair, and a dining area.
A gazebo in a lush garden with flowering plants and a large tree.
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.

3. Harbour House Inn

Harbour House Inn
Cheshire
United States
Gregory
NT$8,053
NT$8,512 total
includes taxes & fees
Sep 17 - Sep 18
Harbour House Inn
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 bar with wooden floors and shelves filled with bottles.
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$5,033
NT$7,200 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 pool area with a white building, a fence, and trees in the background.
A white two-story house with a sloped roof, large windows, and a small porch.
A covered porch with white furniture and green chairs, surrounded by lush greenery.

5. 1896 House Country Inn & Motels

1896 House Country Inn & Motels
Williamstown
United States
William
NT$3,373
NT$3,767 total
includes taxes & fees
Sep 6 - Sep 7
1896 House Country Inn & Motels
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 well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.
A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.

6. 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$10,491
NT$12,691 total
includes taxes & fees
Sep 28 - Sep 29
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A large, multi-story building with a prominent stone facade and a metal roof, surrounded by landscaped gardens and a pedestrian bridge.
An outdoor seating area with stone fire pit, chairs, and a red building in the background.
A bar area with wooden beams, red chairs, and a long wooden table.
A spacious interior with a wooden staircase, a seating area with patterned cushions, and large windows allowing natural light.

7. The Williams Inn

The Williams Inn
Williamstown
United States
John
NT$7,356
NT$8,217 total
includes taxes & fees
Sep 21 - Sep 22
The Williams Inn
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.
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.
A bed with a white lace bedspread, a tray with cookies and a bottle, and two glasses of red wine.
A cozy living room with a fireplace, a blue sofa, a red armchair, and a coffee table with books and a teapot.

8. Brook Farm Inn

Brook Farm Inn
Lenox
United States
Carrie
NT$7,985
NT$9,173 total
includes taxes & fees
Sep 17 - Sep 18
Brook Farm Inn
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Top Pittsfield Hotel Reviews

The Yankee Inn

The Yankee Inn

8/10 Good
"The lounge was closed on Thursday. We went to a concert at Tanglewood and it would have been nice to have a nightcap. Might I suggest that you pole yiur guests and see if they are in town for a concert and if they would patronize the lounge if it was open."
Kenneth 1-night trip
Posted 11 hours ago
The Yankee Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Excellent customer service from front desk staff! Very nice decor everywhere. Fun little balcony! Quiet in the suite. All good!"
Leslieann H 1-night trip
Posted 11 hours ago
Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Hotel was clean and stag was helpful and friendly."
Basil 2-night trip
Posted 1 day ago
Hotel Downstreet, an Ascend Collection Hotel
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"this grand old hotel is warm and welcoming — a real hub of Bershires life and history"
James 2-night trip
Posted 2 days ago
The Red Lion Inn

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