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Accommodations in Pittsfield (Page 3)

Enjoy your stay and find the best accommodations in Pittsfield at affordable prices

Searching for an accommodation in Pittsfield (Massachusetts)? You will find a various number of lodgings for your overnight stay in Pittsfield, starting from $45 per bed and night. Whether you are looking for a hotel, a guesthouse or an apartment, you will find an accommodation that meets your needs.

Accommodations in Pittsfield and region (20 miles)
Pleasant Valley Motel West Stockbridge in West Stockbridge, USA

Pleasant Valley Motel West Stockbridge

Motel in West Stockbridge near Pittsfield, Massachusetts , 42 Stockbridge Road
Situated in West Stockbridge, 5.5 km from Norman Rockwell Museum, Pleasant Valley Motel West Stockbridge features accommodation with free WiFi and fre...
  • Parking
  • Shower
  • Bath
  • TV
  • Air conditioning

Okay 126 Reviews 5.8

from $69.52 Show details »

The Inn at Stockbridge in Stockbridge, USA

The Inn at Stockbridge

B&B in Stockbridge near Pittsfield, Massachusetts , 30 East Street
Set on 12 acres of land less than 2 miles from Berkshire Theatre Festival, this bed and breakfast offers stylish rooms with en suite bathrooms.
  • Pets allowed
  • Fitness centre

Superb 25 Reviews 9.4

from $349.40 Show details »

The Cottage in Stockbridge, USA

The Cottage

B&B in Stockbridge near Pittsfield, Massachusetts , 14 Prospect Hill Road
Situated on two acres of hills and forest, this Stockbridge B&B offers free Wi-Fi, free breakfast and stunning views of the surrounding Berkshire moun...
  • Parking
  • Pets allowed
  • Family rooms
  • Breakfast in the room
  • Spa and wellness centre

Pleasant 59 Reviews 6.8

from $289.00 Show details »

Tentrr Signature Site - Hancock Haven in Williamstown, USA

Tentrr Signature Site - Hancock Haven

Luxury tent in Williamstown near Pittsfield, Massachusetts
Tentrr Signature Site - Hancock Haven is set in Williamstown, 37 km from Tanglewood, 37 km from Cranwell Spa & Golf Club, and 37 km from Tanglewood Mu...
  • Parking

Exceptional 1 Reviews 10.0

from $155.00 Show details »

Berkshire Travel Lodge in Canaan, USA

Berkshire Travel Lodge

Motel in Canaan near Pittsfield, Massachusetts , 12703 Route 22
Located off Interstate 90, this hotel is surrounded by the Berkshire Mountains and boasts scenic views and an outdoor pool.
  • Parking
  • Pets allowed
  • Allergy-free room
  • Outdoor pool
  • Swimming pool

Disappointing 242 Reviews 4.5

from $71.99 Show details »

Inn at Silver Maple Farm in East Chatham, USA

Inn at Silver Maple Farm

B&B in East Chatham near Pittsfield, Massachusetts , 1871 State Route 295
Situated in East Chatham, 22 km from Stockbridge, Inn at Silver Maple Farm features air-conditioned rooms and free private parking.
  • Parking
  • Allergy-free room

Superb 56 Reviews 9.4

from $229.00 Show details »

Tranquil 3 BR Stockbridge House with Private Deck! in Stockbridge, USA

Tranquil 3 BR Stockbridge House with Pri...

Holiday home in Stockbridge near Pittsfield, Massachusetts
Tranquil 3BR Stockbridge House with Private Deck! is situated in Stockbridge, 8.5 km from Tanglewood Musical Center, 9.1 km from Tanglewood, and 14 km...
  • Parking
  • Pets allowed
  • Internet facilities
  • Hairdryer
  • Iron

Superb 2 Reviews 9.5

from $416.00 Show details »

Econo Lodge Lee - Great Barrington in Lee, USA

Econo Lodge Lee - Great Barrington

Motel in Lee near Pittsfield, Massachusetts , 980 Pleasant Street
Located 6 miles from October Mountain State Forest, this Massachusetts hotel features guest rooms with balconies and free Wi-Fi.
  • Parking
  • Telephone
  • Air conditioning
  • Hairdryer
  • Iron

Okay 243 Reviews 5.9

from $85.99 Show details »

Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires an IHG Hotel in South Lee, USA

Holiday Inn Club Vacations Oak n Spruce...

Hotel in South Lee near Pittsfield, Massachusetts , 190 Meadow Street
All rooms feature a flat-screen TV with satellite channels and a private bathroom.
  • Parking
  • Bar
  • Fitness centre
  • Family rooms
  • Indoor pool

Very good 463 Reviews 8.4

from $209.66 Show details »

Too Good AKA 2 Goodrich St in Stockbridge, USA

Too Good AKA 2 Goodrich St

Holiday home in Stockbridge near Pittsfield, Massachusetts , 2 Goodrich Street
Within 5.1 km of Norman Rockwell Museum and 10 km of Cranwell Spa & Golf Club, Too Good AKA 2 Goodrich St offers free WiFi and a garden.
  • Family rooms

no reviews

from $449.00 Show details »

Charming Adams Home Near Dtwn, Trails and More! in Adams, USA

Charming Adams Home Near Dtwn, Trails an...

Holiday home in Adams near Pittsfield, Massachusetts
Charming Adams Home Near Dtwn, Trails and More! is situated in Adams, 37 km from Cranwell Spa & Golf Club, 37 km from Tanglewood Musical Center, and 4...
  • Parking

no reviews

from $101.00 Show details »

The Trail in Adams - Berkshires' Art Hotel in Adams, USA

The Trail in Adams - Berkshires' Art Hot...

B&B in Adams near Pittsfield, Massachusetts , 10 Pleasant Street
Located in the heart of the Berkshires, this eco-friendly bed and breakfast offers on-site massage services.
  • Parking
  • Sauna
  • Family rooms
  • Allergy-free room
  • Electric vehicle charging station

Very good 24 Reviews 8.4

from $218.75 Show details »

Berkshires Home on 11 Acres with Pond and 2 Fire Pits! in Becket, USA

Berkshires Home on 11 Acres with Pond an...

Holiday home in Becket near Pittsfield, Massachusetts
Berkshires Home on 11 Acres with Pond and 2 Fire Pits! is located in Becket, 22 km from Cranwell Spa & Golf Club, and provides a patio, garden, and fr...
  • Parking
  • Internet facilities
  • Hairdryer
  • Iron
  • Refrigerator

no reviews

from $383.00 Show details »

The Guest House at Field Farm in Williamstown, USA

The Guest House at Field Farm

B&B in Williamstown near Pittsfield, Massachusetts , 554 Sloan Road
Situated in Williamstown, 34 km from Bennington Battle Monument and 40 km from Tanglewood, The Guest House at Field Farm features accommodation with f...
  • Parking
  • Electric vehicle charging station

Superb 25 Reviews 9.4

from $329.00 Show details »

The Briarcliff Motel in Great Barrington, USA

The Briarcliff Motel

Motel in Great Barrington near Pittsfield, Massachusetts , 506 Stockbridge Road
Surrounded by the Berkshires, this motel is 8 km from Ski Butternut and boasts free Wi-Fi access and views of Monument Mountain.
  • Parking
  • Pets allowed
  • Kids' outdoor play equipment
  • Shower
  • TV

Good 219 Reviews 7.6

from $175.00 Show details »

Berkshires Cabin 2 Mi to Appalachian Trail! in Otis, USA

Berkshires Cabin 2 Mi to Appalachian Tra...

Holiday home in Otis near Pittsfield, Massachusetts
Berkshires Cabin 2 Mi to Appalachian Trail! is located in Otis, 21 km from Cranwell Spa & Golf Club, 25 km from Tanglewood, as well as 26 km from Tang...
  • Parking

no reviews

from $259.00 Show details »

Lakefront Berkshires Retreat with Deck, Dock and Boat! in Great Barrington, USA

Lakefront Berkshires Retreat with Deck,...

Holiday home in Great Barrington near Pittsfield, Massachusetts
Offering lake views, Lakefront Berkshires Retreat with Deck, Dock and Boat! is an accommodation set in Great Barrington, 8.3 km from Norman Rockwell M...
  • Parking
  • Pets allowed
  • Internet facilities
  • Hairdryer
  • Iron

Good 4 Reviews 7.7

from $329.00 Show details »

Haddock Hill House in Old Chatham, USA

Haddock Hill House

B&B in Old Chatham near Pittsfield, Massachusetts , 20 Haddock Hill Road
Haddock Hill House offers accommodation in Old Chatham.
  • Parking

Fabulous 14 Reviews 8.9

from $140.00 Show details »

Thornewood Inn in Great Barrington, USA

Thornewood Inn

Inn in Great Barrington near Pittsfield, Massachusetts , 453 Stockbridge Road
Great Barrington’s Thornewood Inn is a bed and breakfast that features antique furniture throughout the property.
  • Parking
  • Pets allowed
  • Bar
  • Family rooms
  • Outdoor pool

Good 18 Reviews 8.0

from $249.00 Show details »

Stay Berkshires in Williamstown, USA

Stay Berkshires

Hotel in Williamstown near Pittsfield, Massachusetts , 1146 Cold Spring Road
Located in Williamstown, Massachusetts, this motel is surrounded by the Berkshire Mountains and boasts rooms with an outdoor seating area and free Wi-...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Pleasant 65 Reviews 6.6

from $198.00 Show details »

Granville House in Great Barrington, USA

Granville House

B&B in Great Barrington near Pittsfield, Massachusetts , 98 Division Street
Situated in Great Barrington in the Massachusetts region, Granville House features accommodation with free private parking.
  • Parking
  • Pets allowed
  • Family rooms

Exceptional 131 Reviews 9.9

from $275.00 Show details »

The 1896 House Country Inn - Brookside & Pondside in Williamstown, USA

The 1896 House Country Inn - Brookside &...

Inn in Williamstown near Pittsfield, Massachusetts , 910 Cold Spring Road
Surrounded by gardens and lush landscaping, this 17-acre accommodation boasts an outdoor heated pool and an on-site restaurant and bar.
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Family rooms

Pleasant 371 Reviews 6.1

from $119.20 Show details »

1896 House Country Inn - Barnside Inn in Williamstown, USA

1896 House Country Inn - Barnside Inn

Inn in Williamstown near Pittsfield, Massachusetts , 910 Cold Spring Road
Located in Williamstown, the 1896 House Luxury Inn Williamstown is 5 minutes drive from Williams College.
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Family rooms

Good 137 Reviews 7.5

from $193.44 Show details »

Holiday Inn Express Great Barrington, an IHG Hotel in Great Barrington, USA

Holiday Inn Express Great Barrington, an...

Hotel in Great Barrington near Pittsfield, Massachusetts , 415 Stockbridge Road
Located in the Southern Berkshire Mountains, this hotel boasts an indoor pool and hot tub, as well as a daily continental breakfast.
  • Parking
  • Fitness centre
  • Allergy-free room
  • Indoor pool
  • Swimming pool

Very good 287 Reviews 8.2

from $185.57 Show details »

Travelodge by Wyndham Great Barrington Berkshires in Great Barrington, USA

Travelodge by Wyndham Great Barrington B...

Motel in Great Barrington near Pittsfield, Massachusetts , 400 Stockbridge Road
Situated only 5 miles from Stockbridge & Norman Rockwell, this hotel is set in a convenient location in Great Barrington.
  • Parking
  • Family rooms
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Pleasant 196 Reviews 6.9

from $100.50 Show details »

Number of Accommodations in Pittsfield 90
Number of guest ratings 1907
Average price per night $210.98
Lowest price per night $45.00
Highest price per night $995.00

Most popular accommodations in Pittsfield

The most popular accommodations in Pittsfield based on average guest rating (Top 10).

Cheapest accommodations in Pittsfield

The cheapest accommodations in Pittsfield based on room rate per night (Top 10).

Most booked accommodations in Pittsfield

The most booked accommodations in Pittsfield based on popularity with guests (Top 10).

Sleep & Travel in Pittsfield (Massachusetts)

Getting the best travel and overnight stay experience requires careful planning and attention to detail. Start by researching your destination and choosing the right accommodations for your needs and budget. Consider factors such as location, amenities, and reviews from other travelers. To make the most of your trip, take the time to explore Pittsfield and immerse yourself in the local culture. This might include trying new foods, visiting historic sites, or attending cultural events.

When booking your accommodation in Pittsfield, be sure to communicate any special requests or preferences you may have, such as a specific room type or dietary restrictions. This will help ensure that your stay is comfortable and enjoyable. Also don't forget to pack wisely and bring along any necessary travel essentials, such as comfortable shoes, sunscreen, and a camera to capture all of your memories. With careful planning and a spirit of adventure, you can have an unforgettable travel and overnight stay experience.

How to find the best accommodation 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