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Aug 22 - Aug 23
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Compare 1,355 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (584)
"Amazing place to stay. Can’t wait to go again. "
The price is ₩92,059
₩134,090 total
includes taxes & fees
Sep 21 - Sep 22
Berkshire Mountain Lodge
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (863)
"Consistently a clean room with welcoming staff."
The price is ₩152,523
₩170,369 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn & Suites Pittsfield-Berkshires by IHG
FairBridge Inn Express
1 bedroom, desk, iron/ironing board, free WiFi

FairBridge Inn Express

2.5 star property
5.4 out of 10, (767)
"Close to our target event a plus"
The price is ₩99,490
₩111,132 total
includes taxes & fees
Sep 7 - Sep 8
FairBridge Inn Express
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Hypo-allergenic bedding, iron/ironing board, free cribs/infant beds

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (20)
"Really enjoyed my stay here, definitely need a car to get around"
The price is ₩189,114
₩211,241 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Hotel On North
Front of property - evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (758)
"Quite and good location to around towns"
The price is ₩250,473
₩279,774 total
includes taxes & fees
Sep 1 - Sep 2
Hotel On North
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1000)
"Very clean rooms and excellent staff."
The price is ₩148,661
₩166,053 total
includes taxes & fees
Sep 1 - Sep 2
Best Western Plus Berkshire Hills Inn & Suites
The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (307)
"Clean and convenient."
The price is ₩152,523
₩170,364 total
includes taxes & fees
Sep 14 - Sep 15
The Central Downtown Inn & Suites
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (640)
"It’s a three star hotel charging 5 star prices. They should include free breakfast."
The price is ₩202,561
₩226,265 total
includes taxes & fees
Sep 7 - Sep 8
Hilton Garden Inn Lenox Pittsfield
Berkshire Inn
1 bedroom, desk, iron/ironing board, free WiFi

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (799)
"This is a very convenient motel -- it is easy to get to, has a nice pool, quiet area, comfortable room, "
The price is ₩125,922
₩140,657 total
includes taxes & fees
Aug 24 - Aug 25
Berkshire Inn
Comfort Inn & Suites East Greenbush - Albany
Lobby

Comfort Inn & Suites East Greenbush - Albany

2.5 star property
8.4 out of 10, Very Good, (1003)
"Room was great,great breakfast, great place to stay with convenient access to highway"
The price is ₩147,961
₩164,236 total
includes taxes & fees
Sep 2 - Sep 3
Comfort Inn & Suites East Greenbush - Albany
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1966)
"Very relaxing, clean and convenient for a family vacation. Pool area and grills are well kept and also convenient "
The price is ₩151,569
₩184,652 total
includes taxes & fees
Aug 27 - Aug 28
Vacation Village in the Berkshires
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1001)
"Wonderful place to stay"
The price is ₩175,051
₩195,537 total
includes taxes & fees
Sep 21 - Sep 22
The Yankee, Trademark Collection by Wyndham
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is ₩177,220
₩197,955 total
includes taxes & fees
Sep 1 - Sep 2
The Black Swan Lee - Lenox, Ascend Hotel Collection
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (691)
"Great property. Would stay again"
The price is ₩223,713
₩249,888 total
includes taxes & fees
Aug 26 - Aug 27
Berkshires Untold
Hotel Downstreet, Ascend Hotel Collection
Hypo-allergenic bedding, laptop workspace, blackout drapes

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1002)
"Great location!"
The price is ₩201,008
₩224,526 total
includes taxes & fees
Sep 22 - Sep 23
Hotel Downstreet, Ascend Hotel Collection
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1001)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is ₩178,661
₩254,270 total
includes taxes & fees
Sep 1 - Sep 2
The Cornell Inn, Lenox & The Berkshires
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1000)
"Loved our visit"
The price is ₩264,466
₩357,928 total
includes taxes & fees
Aug 26 - Aug 27
The Red Lion Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (701)
"Pleasant stay"
The price is ₩128,049
₩162,569 total
includes taxes & fees
Sep 2 - Sep 3
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Constance by the Lenox Collection
Free WiFi, bed sheets

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (525)
"Great place , love it, will return"
The price is ₩208,830
₩233,262 total
includes taxes & fees
Sep 15 - Sep 16
The Constance by the Lenox Collection
The Brooks Motel
Double Room | 1 bedroom, Egyptian cotton sheets, premium bedding, memory foam beds

The Brooks Motel

2.0 star property
7.8 out of 10, Good, (96)
"Basic, clean and good value for the money."
The price is ₩152,551
₩170,857 total
includes taxes & fees
Aug 24 - Aug 25
The Brooks Motel
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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Check out hotels with a pool in Pittsfield

Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (584)
The price is ₩92,059
₩134,090 total
includes taxes & fees
Sep 21 - Sep 22
Berkshire Mountain Lodge

Pet-friendly hotels in Pittsfield you'll enjoy

Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1000)
The price is ₩148,661
₩166,053 total
includes taxes & fees
Sep 1 - Sep 2
Best Western Plus Berkshire Hills Inn & Suites
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.

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
Pittsfield featuring a city

Top Pittsfield Hotel Reviews

Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

10/10 Excellent
"Great stay. Well balanced, clean, friendly. "
Derek 1-night trip
Posted 3 days ago
Hotel Downstreet, Ascend Hotel Collection

Frequently asked questions

Where is the best place for a stay in Pittsfield?

Hotel On North is a favorite with Expedia customers. This hotel offers free parking and a bar. Other top choices based on traveler reviews include Hilton Garden Inn Lenox Pittsfield and Best Western Plus Berkshire Hills Inn & Suites. See all available top hotels, or vacation rentals in Pittsfield.

If I need to cancel my hotel reservation in Pittsfield, will I receive a refund?

Yes, you'll find most hotel reservations are refundable provided that you cancel before the hotel’s cancellation deadline, which is often 24 or 48 hours before check in. If you have a reservation that's non-refundable, you might be able to cancel it and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Pittsfield.

Where can I learn more about changing or cancelling my trip to Pittsfield?

For more details about changing or cancelling your trip to Pittsfield, head over to our customer service page.

What's the best accommodation for a budget-friendly stay in Pittsfield?

Based on our traveler reviews, Berkshire Inn is a top choice for a less expensive stay. View all budget hotels in Pittsfield.

What's the best hotel for a family vacation in Pittsfield?

Holiday Inn & Suites Pittsfield-Berkshires by IHG is a hotel with an indoor pool and a restaurant, and it's a top choice on Expedia for families. Other good choices for your kid-friendly vacation include Best Western Plus Berkshire Hills Inn & Suites and Holiday Inn Express & Suites Pittsfield - Berkshires by IHG. Attractions like Berkshire Museum and Bousquet Ski Area are also fun for kids of all ages. Find more child-friendly accommodations in Pittsfield.

What's the best LGBTQ-friendly place to stay in Pittsfield?

Holiday Inn & Suites Pittsfield-Berkshires by IHG is a top LGBTQ-friendly hotel, and features free WiFi and free internet. Hilton Garden Inn Lenox Pittsfield is another good option for your stay. See all available hotels listed as LGBTQ-friendly in Pittsfield.

What's the best pet-friendly hotel in Pittsfield?

Holiday Inn & Suites Pittsfield-Berkshires by IHG is a top dog-friendly hotel, and offers a restaurant along with free WiFi for its human guests. Other good choices for you and your pet include Best Western Plus Berkshire Hills Inn & Suites and The Central Downtown Inn & Suites. See more pet-friendly hotel accommodations in Pittsfield.

Where is the best hotel to stay near Hancock Shaker Village?

Best Western Plus Berkshire Hills Inn & Suites is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and free parking. It's located 1.6 mi (2.6 km) from Hancock Shaker Village. Other good options within a few miles include Inn At Richmond and Yankee Inn.

What about the best place to stay close to Bousquet Ski Area?

One of the top choices for your stay is Hilton Garden Inn Lenox Pittsfield, located a short 1 mi (1.5 km) from Bousquet Ski Area, and this 3-star hotel offers a restaurant and an indoor pool. Berkshire Mountain Lodge, located just 0.8 mi (1.4 km) away, is another good choice for your stay.

What are some accommodations with pools in Pittsfield?

Hilton Garden Inn Lenox Pittsfield is a top hotel with a pool, free WiFi, and free parking. View all hotels with pools in Pittsfield.

What is the best accommodation for staying close to Albany International Airport (ALB)?

Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.

What is staying in Pittsfield like?

Visitors to Pittsfield are sure to enjoy the sporting events, entertainment choices, and theaters. Tourists can also enjoy the city's museums, lake views, and ski areas. In Pittsfield, there are 74 hotels and other accommodations to choose from. Find out more about Pittsfield.

What is there to see in Pittsfield?

Cultural venues include Berkshire Museum, Colonial Theater, and Barrington Stage Company. Landmarks like Hancock Shaker Village and Herman Melville's Arrowhead might be worth a visit. A couple of additional sights to add to your agenda are Bousquet Ski Area and Housatonic River. Check out what more to see and do in Expedia's Pittsfield guide.

How can I get around Pittsfield?

To venture out into the surrounding area, ride one of the trains from Pittsfield Intermodal Transportation Center or Pittsfield Station. If you want to venture out around the area, you may want a rental car in Pittsfield for your journey.

What's the seasonal weather like in Pittsfield?

The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.