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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Pittsfield guest houses

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

1. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (436 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
The price is AED 357
AED 399 total
includes taxes & fees
17 Nov - 18 Nov
The Central Downtown Inn & Suites
A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.

2. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (302 reviews)
"Loved the easy Rail Trail access and peace and quite."
United States
Mary R.
The price is AED 551
AED 804 total
includes taxes & fees
24 Nov - 25 Nov
Berkshire Village Carriage House - Super Private!!
A large white house with a prominent tower, surrounded by lush greenery and a well-maintained lawn.

3. Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
8.0 out of 10, Very good, (71 reviews)
"What a unique stay! Wish we could have stayed longer."
United States
Kristina
The price is AED 399
AED 446 total
includes taxes & fees
16 Nov - 17 Nov
Hideaway Inn Lenox
A living room with a fireplace, two sofas, and four black side tables.

4. The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (46 reviews)
"Nice historic, Inn like feeling. Comfy rooms, easy breakfast until 1pm!! Staff responsive via SMS almost 24/7"
United States
Ruby
The price is AED 507
AED 566 total
includes taxes & fees
24 Nov - 25 Nov
The Revival House
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.
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Learn more about Pittsfield

Nestled in the heart of the Berkshires, this cultural hub boasts the renowned Berkshire Museum and historic Colonial Theatre. Outdoor enthusiasts can hike nearby Pittsfield State Forest trails before exploring the vibrant downtown's farm-to-table restaurants and local art galleries.

See all hotels in Pittsfield
A historic building with a clock, a flag, and a street lamp.

Top reviews in Pittsfield

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield

10/10 Excellent

Beautiful room, very conveniently located right next to a main strip of little shops, theaters and restaurants. We brought all of our own food and were able to store it safely, roomy refrigerator provided- and all cooking utensils, pots, pans, plates... Everything provided. There was a dvd player, and we were able to have movie nights, and a back balcony to enjoy coffee on the porch or read a book in a heavily wooded area which provided a nice shady view to block the parking lot. The front desk...
United States
Anonymous traveler
Reviewed June 30, 2015
The Central Downtown Inn & Suites