Pittsfield Hotel Guide - Romantic Hotels in Pittsfield, Massachusetts

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Check availability on Pittsfield Romantic Hotels

Top Pittsfield Romantic Hotels

Our top choices for Pittsfield romantic hotels

Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (256)
"Host was very friendly and helpful. House was absolutely adorable and decorated well. Plenty of parking. Beautiful, well-maintained property. Great for hikes. Lovely fire pit area and lots of wood. Very convenient location to recreation in The Berkshires. I would stay here again. "
The price is €200
includes taxes & fees
16 Sept - 17 Sept
Berkshire Village Carriage House - Super Private!!
The Dewey
Exterior

The Dewey

3.5 star property
8.8 out of 10, Excellent, (322)
"excellent stay!! The Dewey is a cozy getaway location!"
The price is €161
includes taxes & fees
22 Sept - 23 Sept
The Dewey
The Williams Inn
Front of property – evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (491)
"Great hotel, staff and restaurant!"
The price is €224
includes taxes & fees
14 Sept - 15 Sept
The Williams Inn
1896 House Country Inn & Motels
Miscellaneous

1896 House Country Inn & Motels

2.5 star property
6.6 out of 10, (435)
"Near hiking for Mt. Greylock and the Appalachian Trail. Nice walking area close by at Lamb's Hill. Clean Older mattress, was OK, but could feel springs a little. If you like a tub, it is tiny. The shower is OK"
1896 House Country Inn & Motels
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Exterior

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

9.8 out of 10, Exceptional, (19)
"The condo was clean and well located for easy access to the mountain. We were there for tri-state races and having easy acass to the mountain was exactly what we needed for a fun weekend. We would stay here again."
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (482)
"Nice quaint out of the ordinary vacation experience. "
The price is €164
includes taxes & fees
29 Aug - 30 Aug
Whistler's Inn Bed & Breakfast
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business centre

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

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is €322
includes taxes & fees
10 Sept - 11 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Gateways Inn & Restaurant
Room (King Room)

Gateways Inn & Restaurant

3.0 star property
7.8 out of 10, Good, (189)
"Very well kept property, nice restaurant and is in a great area"
The price is €286
includes taxes & fees
2 Sept - 3 Sept
Gateways Inn & Restaurant
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Pittsfield Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Wonderful old inn; chock full of charm."
Karen 1-night trip
Posted 3 days ago
The Red Lion Inn

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