Find Romantic Hotels in Pittsfield, MA

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Pittsfield Romantic Hotels

Tonight
31 Aug - 1 Sep
Tomorrow
1 Sep - 2 Sep
Next weekend
5 Sep - 7 Sep
In two weeks
12 Sep - 14 Sep

Top Pittsfield Romantic Hotels

Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (702)
"We needed a place to stay in the area Found the place cutely decorated and was happy there was a restaurant on premise "
The price is SAR 603
SAR 673 total
includes taxes & fees
1 Sep - 2 Sep
Berkshires Untold
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 SAR 752
SAR 840 total
includes taxes & fees
7 Sep - 8 Sep
The Williams Inn
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 SAR 563
SAR 855 total
includes taxes & fees
16 Sep - 17 Sep
Berkshire Village Carriage House - Super Private!!
The Dewey
Exterior

The Dewey

3.5 star property
8.6 out of 10, Excellent, (323)
"excellent stay!! The Dewey is a cozy getaway location!"
The price is SAR 705
SAR 788 total
includes taxes & fees
22 Sep - 23 Sep
The Dewey
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (51)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
The price is SAR 886
SAR 936 total
includes taxes & fees
9 Sep - 10 Sep
Harbour House Inn
1896 House Country Inn & Motels
Miscellaneous

1896 House Country Inn & Motels

2.5 star property
6.6 out of 10, (437)
"I've stayed there before when there were different owners. Thy were way more professional and accessible. "
1896 House Country Inn & Motels
The Constance by the Lenox Collection
Front of property

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (532)
"Great place , love it, will return"
The price is SAR 618
SAR 691 total
includes taxes & fees
15 Sep - 16 Sep
The Constance by the Lenox Collection
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Fridge, microwave, oven, stovetop

2 Bed Berkshire Apt minutes to Jiminy Peak Ski

8.4 out of 10, Very Good, (12)
"The apartment is cozy, clean, and perfect for visiting Jiminy Peak."
The price is SAR 512
SAR 1,010 total
includes taxes & fees
1 Sep - 2 Sep
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
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."
The price is SAR 390
SAR 876 total
includes taxes & fees
3 Sep - 4 Sep
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 SAR 650
SAR 727 total
includes taxes & fees
1 Sep - 2 Sep
Whistler's Inn Bed & Breakfast
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

Explore a world of travel with Expedia

Explore a world of travel with Expedia