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Accommodations in Pittsfield You’ll Love

Affordable, Top-Rated Places to Stay in Pittsfield – For Every Budget

Looking for accommodation in Pittsfield (Massachusetts)? Discover a wide range of places to stay starting at just $51.00 per night – from hotels and bed & breakfasts to vacation rentals. Whether you're visiting for business or leisure, you'll find the perfect place that fits your budget and travel needs. Book your ideal Pittsfield accommodation today!

We found 30 Accommodations in Pittsfield and the surrounding area (within 20 miles)

Hampton Inn & Suites Berkshires-Lenox in Lenox, USA

Hampton Inn & Suites Berkshires-Lenox

Hotel in Lenox near Pittsfield, Massachusetts , 445 Pittsfield Road
This Lenox, Massachusetts hotel is situated only a short distance from area attractions, including historic downtown Lenox and features a variety of f...
  • Parking
  • Pets allowed
  • Fitness centre
  • Family rooms
  • Indoor pool

Very good 184 Reviews 8.4

from $127.19 Show details »

Holiday Inn & Suites Pittsfield-Berkshires by IHG in Pittsfield, USA

Holiday Inn & Suites Pittsfield-Berkshir...

Hotel in Pittsfield, Massachusetts , 1 West Street
Welcome to the Holiday Inn and Suites Pittsfield-Berkshires Centrally located in downtown Pittsfield Massachusetts.
  • Restaurant
  • Pets allowed
  • Bar
  • Fitness centre
  • Allergy-free room

Good 221 Reviews 7.7

from $87.57 Show details »

Howard Johnson by Wyndham Lenox in Lenox, USA

Howard Johnson by Wyndham Lenox

Hotel in Lenox near Pittsfield, Massachusetts , 462 Pittsfield Road
Featuring a garden, Howard Johnson by Wyndham Lenox is located in Lenox in the Massachusetts region, 4.6 miles from Cranwell Spa & Golf Club and 4.8 m...
  • Parking
  • Family rooms
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Good 291 Reviews 7.0

from $77.07 Show details »

The Yankee, Trademark Collection by Wyndham in Lenox, USA

The Yankee, Trademark Collection by Wynd...

Hotel in Lenox near Pittsfield, Massachusetts , 461 Pittsfield Road
Nestled on a 111-acre wildlife sanctuary and surrounded by the beauty of the Berkshires, The Yankee, Trademark Collection by Wyndham provides a welcom...
  • Parking
  • Bar
  • Fitness centre
  • Indoor pool
  • Outdoor pool

Fabulous 747 Reviews 8.7

from $79.53 Show details »

Best Western Plus Berkshire Hills Inn & Suites in Pittsfield, USA

Best Western Plus Berkshire Hills Inn &...

Hotel in Pittsfield, Massachusetts , 1350 West Housatonic Street
Located off Route 20, this Pittsfield hotel is 3.5 miles from Lichtenstein Center for the Arts.
  • Parking
  • Fitness centre
  • Family rooms
  • Kids' outdoor play equipment

Good 337 Reviews 7.8

from $77.64 Show details »

Wagon Wheel Inn in Lenox, USA

Wagon Wheel Inn

Motel in Lenox near Pittsfield, Massachusetts , 484 Pittsfield Road
This Massachusetts motel offers rooms with free Wi-Fi and a 24-hour front desk.
  • Parking

Pleasant 178 Reviews 6.6

from $77.07 Show details »

Berkshire Inn in Pittsfield, USA

Berkshire Inn

Motel in Pittsfield, Massachusetts , 150 West Housatonic Street
In the heart of the Berkshire Mountains, this family-owned motel features an outdoor pool and free Wi-Fi.
  • Parking
  • Family rooms
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Good 377 Reviews 7.6

from $89.35 Show details »

The Cornell Inn in Lenox, USA

The Cornell Inn

B&B in Lenox near Pittsfield, Massachusetts , 203 Main Street
Located on four acres, this bed and breakfast features traditional exteriors and stunning, updated designer rooms and bathrooms which are all equipped...
  • Parking
  • Bar
  • Family rooms

Fabulous 528 Reviews 8.8

from $148.87 Show details »

Fairbridge Inn Express Pittsfield in Pittsfield, USA

Fairbridge Inn Express Pittsfield

Hotel in Pittsfield, Massachusetts , 16 Cheshire Road
Located in Pittsfield, Fairbridge Inn Express Pittsfield provides air-conditioned rooms with free WiFi.
  • Parking

Disappointing 141 Reviews 4.1

from $77.07 Show details »

The Central Downtown Inn Suites in Pittsfield, USA

The Central Downtown Inn Suites

Hotel in Pittsfield, Massachusetts , 20 West Housatonic Street
Located in Pittsfield, within 7.6 miles of Tanglewood and 7.8 miles of Cranwell Spa & Golf Club, The Central Downtown Inn Suites provides accommodatio...
  • Parking
  • Pets allowed

Good 156 Reviews 7.5

from $94.50 Show details »

Berkshire Mountain Lodge in Pittsfield, USA

Berkshire Mountain Lodge

Lodge in Pittsfield, Massachusetts , 8 Dan Fox Drive
Featuring an indoor swimming pool and a fitness center, Berkshire Mountain Lodge is located in Pittsfield.
  • Parking
  • Sauna
  • Fitness centre
  • Family rooms
  • Indoor pool

Very good 668 Reviews 8.5

from $95.40 Show details »

Hilton Garden Inn Lenox Pittsfield in Pittsfield, USA

Hilton Garden Inn Lenox Pittsfield

Hotel in Pittsfield, Massachusetts , 1032 South Street
Hilton Garden Inn Lenox/Pittsfield/Berkshires offers accommodations in Pittsfield.
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Fitness centre

Very good 115 Reviews 8.4

from $124.21 Show details »

Hotel on North in Pittsfield, USA

Hotel on North

Hotel in Pittsfield, Massachusetts , 297 North Street
Located in Pittsfield and within 8.1 miles of Tanglewood, Hotel on North has a bar, non-smoking rooms, and free WiFi throughout the property.
  • Parking
  • Pets allowed
  • Bar
  • Family rooms
  • Breakfast in the room

Superb 202 Reviews 9.2

from $126.00 Show details »

Courtyard by Marriott Lenox Berkshires in Lenox, USA

Courtyard by Marriott Lenox Berkshires

Hotel in Lenox near Pittsfield, Massachusetts , 70 Pittsfield Road
Located in Lenox, 3 miles from Tanglewood, Courtyard by Marriott Lenox Berkshires provides accommodations with free bikes, free private parking, a fit...
  • Parking
  • Restaurant
  • Bar
  • Fitness centre

Fabulous 104 Reviews 8.9

from $139.63 Show details »

Beautiful Lenox Home, 3 Mi to Shakespeare and Co! in Lenox, USA

Beautiful Lenox Home, 3 Mi to Shakespear...

Holiday home in Lenox near Pittsfield, Massachusetts
Beautiful Lenox Home, 3 Mi to Shakespeare and Co! offers accommodations in Lenox, 3.7 miles from Cranwell Spa & Golf Club and 3.7 miles from Tanglewoo...
  • Parking
  • Spa and wellness centre

Very good 4 Reviews 8.0

from $409.57 Show details »

Restored 1881 Farm House in Lenox, USA

Restored 1881 Farm House

Holiday home in Lenox near Pittsfield, Massachusetts , 76 East Dugway Road
Restored 1881 Farm House offers accommodations in Lenox, 8.6 miles from Norman Rockwell Museum and 26 miles from The Clark Art Institute.
  • Pets allowed
  • Family rooms

Exceptional 5 Reviews 9.8

from $326.15 Show details »

Lakeside Berkshires Home Near Hiking and Skiing! in Lanesborough, USA

Lakeside Berkshires Home Near Hiking and...

Holiday home in Lanesborough near Pittsfield, Massachusetts
Lakeside Berkshires Home Near Hiking and Skiing! is located in Lanesborough, just 12 miles from Tanglewood and 12 miles from Cranwell Spa & Golf Club.
  • Parking
  • Spa and wellness centre

no reviews

from $51.00 Show details »

Life House, Berkshires in Lenox, USA

Life House, Berkshires

Hotel in Lenox near Pittsfield, Massachusetts , 194 Pittsfield Road
Located in Lenox, 3.4 miles from Tanglewood, Life House, Berkshires has accommodations with a shared lounge, free private parking, a restaurant and a ...
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Family rooms

Very good 519 Reviews 8.4

from $109.58 Show details »

Lenox House with Screened Patio and Mountain View in Lenox, USA

Lenox House with Screened Patio and Moun...

Holiday home in Lenox near Pittsfield, Massachusetts
Lenox House with Screened Patio and Mountain View offers accommodations in Lenox, 5.3 miles from Tanglewood and 5.5 miles from Cranwell Spa & Golf Clu...
  • Parking
  • Pets allowed
  • Spa and wellness centre
  • Outdoor pool
  • Swimming pool

no reviews

from $236.17 Show details »

Spacious Historic Home in the Berkshires! in Pittsfield, USA

Spacious Historic Home in the Berkshires...

Holiday home in Pittsfield, Massachusetts
Spacious Historic Home in the Berkshires! is located in Pittsfield, just 7.6 miles from Tanglewood and 7.8 miles from Cranwell Spa & Golf Club.
  • Parking
  • Pets allowed

Fabulous 1 Reviews 9.0

from $399.14 Show details »

Heart of the Berkshires Motel in Pittsfield, USA

Heart of the Berkshires Motel

Motel in Pittsfield, Massachusetts , 970 West Housatonic Street
Located in Pittsfield, within 9.2 miles of Tanglewood Musical Center and 9.3 miles of Tanglewood, Heart of the Berkshires Motel provides accommodation...
  • Parking
  • Pets allowed

Good 220 Reviews 7.3

from $92.68 Show details »

Pittsfield Home with Deck - 12 Mi to Jiminy Peak! in Pittsfield, USA

Pittsfield Home with Deck - 12 Mi to Jim...

Holiday home in Pittsfield, Massachusetts
Pittsfield Home with Deck - 12 Mi to Jiminy Peak! is located in Pittsfield, just 12 miles from Tanglewood and 12 miles from Cranwell Spa & Golf Club.
  • Parking

Fabulous 1 Reviews 9.0

from $299.83 Show details »

Berkshire Vacation Rentals: Chic Pittsfield Home With A View in Pittsfield, USA

Berkshire Vacation Rentals: Chic Pittsfi...

Holiday home in Pittsfield, Massachusetts , Tamarack Road 35
Berkshire Vacation Rentals: Chic Pittsfield Home With A View is located in Pittsfield, just 7.1 miles from Tanglewood and 7.3 miles from Cranwell Spa ...
  • Parking
  • Pets allowed

Good 2 Reviews 7.5

from $344.78 Show details »

Charming Apt in 18th c Berkshire Farmhouse in Lanesborough, USA

Charming Apt in 18th c Berkshire Farmhou...

Apartment in Lanesborough near Pittsfield, Massachusetts , 551 North Main Street
Charming Apt in 18th c Berkshire Farmhouse offers accommodations in Lanesborough, 14 miles from Cranwell Spa & Golf Club and 15 miles from Tanglewood ...
  • Parking

no reviews

from $171.58 Show details »

Cozy Rustic Apt in 18th c Berkshire Farmhouse in Lanesborough, USA

Cozy Rustic Apt in 18th c Berkshire Farm...

Apartment in Lanesborough near Pittsfield, Massachusetts , 545 North Main Street
Cozy Rustic Apt in 18th c Berkshire Farmhouse is located in Lanesborough, just 15 miles from Tanglewood Musical Center and 20 miles from Norman Rockwe...
  • Parking

Exceptional 3 Reviews 9.7

from $148.68 Show details »

Number of Accommodations in Pittsfield 30
Number of guest ratings 2,445
Average price per night $192.00
Lowest price per night $51,00
Highest price per night $1.101,83

Top 10 Most Popular Accommodations in Pittsfield

Explore the Most Popular Accommodations in Pittsfield – Ranked by Average Guest Ratings.

Top 10 Cheapest Accommodations in Pittsfield

Discover the Cheapest Accommodations in Pittsfield – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Accommodations in Pittsfield

Check out the Most Booked Accommodations in Pittsfield – Based on Guest Popularity.

Discover Pittsfield – Your Guide to the Best Places to Stay

Planning a trip to Pittsfield? Choosing the right place to stay is one of the most important parts of making your visit memorable. Whether you are looking for a luxury hotel, a cozy guesthouse, a modern apartment, or a family-friendly vacation rental, Pittsfield offers a wide range of lodging options to suit every travel style and budget.

When deciding where to stay in Pittsfield, consider key factors like location, amenities, reviews, and proximity to attractions or public transport. Do you prefer being in the heart of the city close to restaurants, shops, and nightlife? Or do you want a quiet neighborhood with a more local feel? With so many types of accommodations in Pittsfield, from boutique hotels to spacious homes, you are sure to find something that fits your needs.

Tips for Finding the Perfect Stay in Pittsfield

To find the perfect place to stay in Pittsfield, consider your budget, preferred location, and the amenities you need. Do you want to stay in a hotel or a vacation rental or do your prefer an apartment or house with more space, privacy, and the opportunity to live like a local? Do you need access to a kitchen, laundry facilities, or a gym? Research online reviews and ratings to get an idea of what past guests have experienced. Also, consider the type of trip you're taking. If you're traveling with family, you may need a larger space or a kid-friendly environment. If you're on a romantic getaway, you may want a more intimate setting.

Accommodation data and pictures provided by Booking.com