The 10 best romantic hotels in Pittsfield, USA | Booking.com
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Romantic Hotels in Pittsfield

Find the romantic hotels that appeal to you the most

The best romantic hotels in Pittsfield

Check out our pick of great romantic hotels in Pittsfield

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Hotel on North

Hotel in Pittsfield

Situated in Pittsfield and within 13 km of Cranwell Spa & Golf Club, Hotel on North has a bar, non-smoking rooms, and free WiFi throughout the property.

N
Nancy Mac
From
United States
Wonderful stay. Everything exceeded our expectations. The entire staff was so friendly and helpful. I highly recommend this hotel. A particular note. The front desk gentleman we had when checking in was exceptional. Answered any questions we had concerning the hotel, suggested restaurants, activities. He is an asset to you.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 189 reviews
Price from
US$135
1 night, 2 adults

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Hotel in Pittsfield

Welcome to the Holiday Inn and Suites Pittsfield-Berkshires Centrally located in downtown Pittsfield Massachusetts.

A
Andrea
From
United Kingdom
The pool was a real bonus! The on-site restaurant was a delight - excellent food and amusing bartender. The central location was perfect for my needs. Would stay there again without hesitation - lovely hotel.
Scored out of 10, guest rating 7.7
Good - What previous guests thought, 229 reviews
Price from
US$83
1 night, 2 adults

The Yankee, Trademark Collection by Wyndham

Lenox (Near Pittsfield)

Nestled on a 111-acre wildlife sanctuary and surrounded by the beauty of the Berkshires, The Yankee, Trademark Collection by Wyndham provides a welcoming stay by the famous Appalachian Trail in...

F
Frances
From
United Kingdom
The reception staff were so helpful and friendly. Lance kindly found us a lovely room away from the noisy road. The room was comfortable, clean and had a little balcony overlooking trees. The bathroom was large, clean and well appointed. They gave us advice on trails to walk, how to get there and places to eat. We can particularly recommend Frankie's Italian in Lenox. Lenox was beautiful, only a short drive away. The complimentary breakfast was excellent, everything you could possibly want. The muffins and pastries were particularly good.
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 768 reviews
Price from
US$125
1 night, 2 adults

Devonfield Inn

Lee (Near Pittsfield)

Situated just 6.1 km from Cranwell Spa & Golf Club, Devonfield Inn features accommodation in Lee with access to a garden, a shared lounge, as well as a shared kitchen.

L
Lesley- Ann
From
South Africa
We had the most wonderful time at this beautiful inn set in stunning surroundings and gardens. On our holiday this was the only place where we actually met and interacted with the owners , Doug and Jim. Our room was comfortable, clean and had everything we needed. Lovely leather chairs and decor. The bed was comfortable with nice linens. We were invited to the cheese and wine evening and it was great. Lovely wines and cheeses and a great way to meet other guests. We so enjoyed the piano and a few songs from Doug. Breakfast was a feast .. fruit, yogurts , eggs . Delicious and a different menu each morning. Home baked cakes .. yummy. Saturday we sat in the gardens and enjoyed a lovely afternoon of music , it was so nice to see locals join the afternoon too. We wish we could have stayed longer.. Doug and Jim you run a beautiful Inn, your commitment and hard-work tells the story. Thank you!
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 15 reviews
Price from
US$369
1 night, 2 adults

Vacation Village in the Berkshires

Hancock (Near Pittsfield)

Nestled in the scenic hills and countryside of the Berkshires in Hancock, Massachusetts, this hotel offers recreational activities.

B
Barry
From
Australia
Room was excellent very large unfortunately only stayed 1 night
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 1,477 reviews
Price from
US$118.15
1 night, 2 adults

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee (Near Pittsfield)

The Black Swan Lee - Lenox, an Ascend Collection Hotel is conveniently located in the foothills of the Berkshire Mountains.

F
FAUSTINO
From
United States
Very polite and helpful staff. Clean room and good breakfast set up. Great view of the lake.
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 528 reviews
Price from
US$109.65
1 night, 2 adults

The Red Lion Inn

Stockbridge (Near Pittsfield)

Nestled in the heart of central Stockbridge, Massachusetts, this historic hotel offers luxurious accommodations, friendly service and gourmet on-site dining options.

G
Gerry
From
United Kingdom
The hotel is unique. The main building is 18th century and it has worn well. There are interesting things to see in every corner. But the real star of the hotel is the staff, they are lovely.
Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 288 reviews
Price from
US$129
1 night, 2 adults

Chambery Inn

Lee (Near Pittsfield)

This historic Massachusetts bed and breakfast boasts free Wi-Fi access. Cable TV and an en suite bathroom are featured in every uniquely styled room. Ski Butternut is 13 miles away.

L
Lori
From
United States
Beautiful, huge room; stunning 4 poster bed w/ canopy.
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 34 reviews
Price from
US$599.99
1 night, 2 adults

The Little Lion

Great Barrington (Near Pittsfield)

Surrounded by the Berkshires, this motel is 8 km from Ski Butternut and boasts free Wi-Fi access and views of Monument Mountain. The Norman Rockwell Museum is 10 minutes’ drive away.

M
Michael
From
Canada
This is an older motel that was refurbished while retaining its original charm. Our room (#9) was basic but spotless with a very comfortable bed. The continental breakfast had lots of variety and good coffee. For those seeking other options, there are several restaurants within a short drive. I'd also like to mention that due to an unexpected family situation at home, we were almost forced to cancel our stay. We were able to sort things out and keep our reservation but I'd be remiss if I didn't thank Rhonda (innkeeper) for her prompt responses and assistance with late check-in instructions. We'd recommend the Briarcliffe and will be back!
Scored out of 10, guest rating 7.2
Good - What previous guests thought, 206 reviews
Price from
US$249
1 night, 2 adults

Club Wyndham Bentley Brook

Hancock (Near Pittsfield)

Located in Hancock just 35 miles from Norman Rockwell Museum, this hotel features an indoor and outdoor pool. Tennis courts and a hot tub are located on site. A full kitchen is featured in all...

M
Maycon
From
United States
of having a snow rink at my bedroom door
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 296 reviews
All romantic hotels in Pittsfield

Looking for a romantic hotel?

Spoil your other half with a romantic getaway in a hotel that’s designed with lovers in mind. Whether it’s somewhere stylish in the city or a remote countryside retreat, romantic hotels offer couples all the space they need, with luxury touches like champagne room service and private hot tubs.

Romantic hotels that guests love in Pittsfield

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  • Avg. price/night: US$121.53
    Scored out of 10, guest rating 7.7
    Good - What previous guests thought, 229 reviews
    The pool was a real bonus! The on-site restaurant was a delight - excellent food and amusing bartender. The central location was perfect for my needs. Would stay there again without hesitation - lovely hotel.
    Guest review by
    Andrea
    Solo traveller
  • Avg. price/night: US$184
    Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 189 reviews
    The room was a good size, well equipped with lovely wooden floors.The bed and pillows were extremely comfortable. There is secure parking at the rear of the building.
    Guest review by
    Janet
    Young couple
  • Avg. price/night: US$184
    Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 189 reviews
    lovely hotel with friendly staff, great place to stay
    Guest review by
    Raymond
    Solo traveller