The 10 best luxury hotels in Pittsfield, USA | Booking.com
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Luxury Hotels in Pittsfield

Find the luxury hotels that appeal to you the most

The best luxury hotels in Pittsfield

Check out our pick of great luxury hotels in Pittsfield

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Doctor Sax House

Lenox (Near Pittsfield)

Situated in Lenox, 2.4 km from Tanglewood Musical Center, Doctor Sax House features accommodation with a shared lounge, free private parking, a terrace and a restaurant.

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 22 reviews
Price from
US$316.58
1 night, 2 adults

Shaker Mill Inn

West Stockbridge (Near Pittsfield)

Set within 6.3 km of Tanglewood Musical Center and 6.6 km of Tanglewood, Shaker Mill Inn offers rooms with air conditioning and a private bathroom in West Stockbridge.

R
Roy
From
Australia
Breakfast was great. Lovely location in quiet town.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 88 reviews
Price from
US$132
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.

a
amir
From
Israel
Great place for vacation and relaxation
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 1,473 reviews
Price from
US$118.15
1 night, 2 adults

Gorgeous Ski On/Off 2 BR Sleeps 8 Jiminy-Must See Luxury

Hancock (Near Pittsfield)

Located in Hancock and only 33 km from Cranwell Spa & Golf Club, Gorgeous Ski On/Off 2 BR Sleeps 8 Jiminy-Must See Luxury provides accommodation with mountain views, free WiFi and free private...

E
Emma
From
United States
This place was a godsend. After the nearby Wyndham Resort canceled our booking last minute due to overbooking, my family was scrambling to find local accommodation. After the recent, sudden loss of my mother, my family was looking forward to our annual trip to Jiminy Peak, which was one of her favorite places. This place appeared at just the right time and was a great, even better, alternative to Wydham. Howie was a wonderful host and the accommodations were clean, comfortable, and cute. The place felt like home and had all of the amenities we needed. There were many comfortable beds and a copious number of fluffy blankets. It also had 2 bedrooms, unlike many of the other hotels in the area. Howie was very responsive to our questions and provided helpful recommendations. They even left a cute stuffed bear that we could take home as a souvenir! What a thoughtful touch. All in all, it was a wonderful stay and we would definitely stay again.
Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 28 reviews
All luxury hotels in Pittsfield

Looking for a luxury hotel?

If you’re looking to treat yourself, a high-end hotel will provide that extra something special to make your trip even more memorable. These five-star properties feature lavish luxuries such as on-site restaurants with sweeping city views, in-room massage and spacious private terraces. They often have a central location which makes exploring the main sights a breeze.