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Accommodations in Pittsfield (Page 2)

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)
Deluxe Ski On Off 1BR Suite Sleeps 4 on Jiminy Mtn in Hancock, USA

Deluxe Ski On Off 1BR Suite Sleeps 4 on...

Holiday home in Hancock near Pittsfield, Massachusetts , 37 Corey Road
Within 33 km of Tanglewood and 33 km of Cranwell Spa & Golf Club, Deluxe Ski On Off 1BR Suite Sleeps 4 on Jiminy Mtn features free WiFi and a fitness ...
  • Parking
  • Fitness centre

Superb 12 Reviews 9.0

from $183.08 Show details »

Mountain View Suite Sleeps 4 Ski OnOff Jiminy Peak in Hancock, USA

Mountain View Suite Sleeps 4 Ski OnOff J...

Holiday home in Hancock near Pittsfield, Massachusetts , Corey Road 37
Situated about 33 km from Tanglewood, Mountain View Suite Sleeps 4 Ski OnOff Jiminy Peak offers accommodation with an outdoor pool and free WiFi.
  • Parking
  • Fitness centre
  • Indoor pool
  • Outdoor pool
  • Swimming pool

Exceptional 6 Reviews 10.0

from $171.33 Show details »

Gorgeous 1st FL Mtn View Jiminy Suite Sleeps 4 Ski On Off in Hancock, USA

Gorgeous 1st FL Mtn View Jiminy Suite Sl...

Apartment in Hancock near Pittsfield, Massachusetts , Corey Road 37
Set about 33 km from Tanglewood, Gorgeous 1st FL Mtn View Jiminy Suite Sleeps 4 Ski On Off offers accommodation with an outdoor pool and free WiFi.
  • Parking
  • Indoor pool
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $198.67 Show details »

Club Wyndham Bentley Brook in Hancock, USA

Club Wyndham Bentley Brook

Hotel in Hancock near Pittsfield, Massachusetts , 1 Corey Road
Located in Hancock just 35 miles from Norman Rockwell Museum, this hotel features an indoor and outdoor pool.
  • Parking
  • Sauna
  • Fitness centre
  • Family rooms
  • Outdoor pool

Fabulous 331 Reviews 8.7

from $159.64 Show details »

Disney Magic at Jiminy Mountain in Hancock, USA

Disney Magic at Jiminy Mountain

Hotel in Hancock near Pittsfield, Massachusetts , 37 Corey Road 712
Located 33 km from Tanglewood, Disney Magic at Jiminy Mountain offers 4-star accommodation in Hancock and has a shared lounge, a restaurant and a bar.
  • Parking
  • Restaurant
  • Bar
  • Sauna
  • Fitness centre

Fabulous 19 Reviews 8.8

from $206.69 Show details »

Gorgeous New Zen Suite Sleeps 4-Ski On Off Jiminy in Hancock, USA

Gorgeous New Zen Suite Sleeps 4-Ski On O...

Holiday home in Hancock near Pittsfield, Massachusetts , Corey Road 37
Within 33 km of Tanglewood and 33 km of Cranwell Spa & Golf Club, Gorgeous New Zen Suite Sleeps 4-Ski On Off Jiminy provides free WiFi and a fitness c...
  • Parking
  • Fitness centre
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Superb 6 Reviews 9.0

from $162.77 Show details »

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk in Hancock, USA

WOW-New Ski OnOff Suite By Pool Sleeps 4...

Holiday home in Hancock near Pittsfield, Massachusetts , Corey Road 37
Within 33 km of Tanglewood and 33 km of Cranwell Spa & Golf Club, WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk features free WiFi and a fitness ...
  • Parking
  • Fitness centre
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Superb 11 Reviews 9.1

from $171.33 Show details »

Jurassic Dino Suite Jiminy-Must See Sleeps 4 in Hancock, USA

Jurassic Dino Suite Jiminy-Must See Slee...

Apartment in Hancock near Pittsfield, Massachusetts , Corey Road 37
Within 33 km of Tanglewood and 33 km of Cranwell Spa & Golf Club, Jurassic Dino Suite Jiminy-Must See Sleeps 4 features free WiFi and a fitness centre...
  • Fitness centre
  • Indoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $197.67 Show details »

The Cascades in Canaan, USA

The Cascades

Inn in Canaan near Pittsfield, Massachusetts , 40 Cherry Lane
Set in Canaan, 20 km from Tanglewood Musical Center, The Inn at Shaker Mill Falls offers accommodation with a garden, free private parking, a shared l...
  • Parking
  • Pets allowed
  • Family rooms

Good 32 Reviews 7.9

from $175.33 Show details »

Gorgeous Ski On/Off 2 BR Sleeps 8 Jiminy-Must See Luxury in Hancock, USA

Gorgeous Ski On/Off 2 BR Sleeps 8 Jiminy...

Aparthotel in Hancock near Pittsfield, Massachusetts , 8 Corey Road
Located in Hancock in the Massachusetts region, Gorgeous Ski On/Off 2 BR Sleeps 8 Jiminy-Must See Luxury provides accommodation with free WiFi and fre...
  • Parking
  • Sauna
  • Indoor pool
  • Swimming pool
  • Swimming Pool

Fabulous 15 Reviews 9.0

from $346.20 Show details »

Jiminy Peak Mountain Resort in Hancock, USA

Jiminy Peak Mountain Resort

Resort in Hancock near Pittsfield, Massachusetts , 37 Corey Road
Nestled on Hancock, Massachusetts’ ski slopes, Jiminy Peak Mountain Resort offers a restaurant, adventure parks and ski-to-door access.
  • Parking
  • Restaurant
  • Bar
  • Sauna
  • Fitness centre

Good 232 Reviews 7.7

from $169.00 Show details »

Seven Hills Inn in Lenox, USA

Seven Hills Inn

Inn in Lenox near Pittsfield, Massachusetts , 40 Plunkett St
Located in Lenox, 2.2 km from Cranwell Spa & Golf Club, Seven Hills Inn provides accommodation with free bikes, free private parking, a seasonal outdo...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Good 300 Reviews 7.2

from $159.00 Show details »

Vacation Village in the Berkshires in Hancock, USA

Vacation Village in the Berkshires

Holiday park in Hancock near Pittsfield, Massachusetts , 276 Brodie Mountain Road
Nestled in the scenic hills and countryside of the Berkshires in Hancock, Massachusetts, this hotel offers recreational activities.
  • Parking
  • Fitness centre
  • Family rooms
  • Indoor pool
  • Outdoor pool

Very good 1332 Reviews 8.5

from $144.12 Show details »

Picturesque Cottage with Sunroom on Ashmere Lake! in Hinsdale, USA

Picturesque Cottage with Sunroom on Ashm...

Holiday home in Hinsdale near Pittsfield, Massachusetts
Located 32 km from Cranwell Spa & Golf Club, 32 km from Tanglewood Musical Center and 40 km from Norman Rockwell Museum, Picturesque Cottage with Sunr...
  • Parking

Exceptional 1 Reviews 10.0

from $208.00 Show details »

Stockbridge Home Walk to Town Beach! in Stockbridge, USA

Stockbridge Home Walk to Town Beach!

Holiday home in Stockbridge near Pittsfield, Massachusetts
Stockbridge Home - Walk to Lakefront Beach! is situated in Stockbridge, 3.9 km from Tanglewood, 5.7 km from Cranwell Spa & Golf Club, and 6.5 km from ...
  • Parking

no reviews

from $272.33 Show details »

The Ponds at Foxhollow by Capital Vacations in Lenox, USA

The Ponds at Foxhollow by Capital Vacati...

Resort in Lenox near Pittsfield, Massachusetts , 3 Foxhollow Drive
Offering a seasonal outdoor pool and hot tub, The Ponds at Foxhollow is located in Lenox in the Massachusetts Region, 4 km from Tanglewood.
  • Parking
  • Sauna
  • Fitness centre
  • Family rooms
  • Indoor pool

Very good 165 Reviews 8.1

from $399.20 Show details »

The Black Swan Lee - Lenox, Ascend Hotel Collection in Lee, USA

The Black Swan Lee - Lenox, Ascend Hotel...

Hotel in Lee near Pittsfield, Massachusetts , 435 Laurel Street
The Black Swan Lee - Lenox, Ascend Hotel Collection is conveniently located in the foothills of the Berkshire Mountains.
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Fitness centre

Very good 585 Reviews 8.4

from $211.65 Show details »

Hancock Log Cabin Retreat 2 Miles to Jiminy Peak! in Hancock, USA

Hancock Log Cabin Retreat 2 Miles to Jim...

Holiday home in Hancock near Pittsfield, Massachusetts
Situated in Hancock, 34 km from Tanglewood and 34 km from Cranwell Spa & Golf Club, Hancock Log Cabin Retreat 2 Miles to Jiminy Peak! provides accommo...
  • Parking
  • Shower
  • Bath
  • TV
  • Hairdryer

Exceptional 1 Reviews 10.0

from $226.00 Show details »

Cozy Stockbridge Cabin - Walk to Beach and Lake! in Stockbridge, USA

Cozy Stockbridge Cabin - Walk to Beach a...

Holiday home in Stockbridge near Pittsfield, Massachusetts
Set in Stockbridge, 4.7 km from Tanglewood Musical Center and 5.1 km from Norman Rockwell Museum, Cozy Stockbridge Cabin - Walk to Beach and Lake! pro...
  • Parking

Superb 2 Reviews 9.5

from $341.00 Show details »

The Springs Motel in New Ashford, USA

The Springs Motel

Hotel in New Ashford near Pittsfield, Massachusetts , 94 U.S. 7
Located in New Ashford, 30 km from Tanglewood, The Springs Motel provides accommodation with free WiFi and free private parking.
  • Parking
  • Swimming pool
  • Swimming Pool

Very good 65 Reviews 8.2

from $183.33 Show details »

Harbour House Inn B&B in Cheshire, USA

Harbour House Inn B&B

B&B in Cheshire near Pittsfield, Massachusetts , 725 North State Road
Providing accommodation with free WiFi, air conditioning and flat-screen TV, Harbour House Inn B&B is located 32 km from Tanglewood and 32 km from Cra...

Superb 10 Reviews 9.4

from $247.25 Show details »

Shaker Mill Inn in West Stockbridge, USA

Shaker Mill Inn

B&B in West Stockbridge near Pittsfield, Massachusetts , 2 Oak Street
Set 6.3 km from Tanglewood Musical Center in West Stockbridge, Shaker Mill Inn offers accommodation with air conditioning and free WiFi.
  • Parking
  • Pets allowed
  • Breakfast in the room

Superb 85 Reviews 9.3

from $239.00 Show details »

Pilgrim Inn in Lee, USA

Pilgrim Inn

Inn in Lee near Pittsfield, Massachusetts , 165 Housatonic Street
Situated in Lee, between the beautiful Beartown and October Mountain State Forests, Pilgrim Inn is a 20-minute drive from Pitsfield.
  • Parking
  • Pets allowed
  • Family rooms
  • Outdoor pool
  • Kids' outdoor play equipment

Pleasant 633 Reviews 6.7

from $89.00 Show details »

Quality Inn in Lee, USA

Quality Inn

Hotel in Lee near Pittsfield, Massachusetts , 170 Housatonic Street
Featuring 2-star accommodation, Quality Inn is located in Lee, 10 km from Tanglewood and 10 km from Tanglewood Musical Center.
  • Parking
  • Family rooms

Very good 480 Reviews 8.2

from $126.65 Show details »

Devonfield Inn in Lee, USA

Devonfield Inn

B&B in Lee near Pittsfield, Massachusetts , 85 Stockbridge Rd.
Situated on 30 acres, this scenic Berkshires bed and breakfast boasts a heated, seasonal outdoor pool and on-site tennis courts.
  • Parking
  • Fitness centre
  • Family rooms
  • Swimming pool
  • Swimming Pool

Superb 14 Reviews 9.4

from $392.33 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