Hotels in Pittsfield

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Next weekend
May 22 - May 24
In two weeks
May 29 - May 31

Where to stay in Pittsfield?

Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (855 reviews)
Enjoy a serene retreat in Pittsfield with a seasonal outdoor pool and proximity to Colonial Theater and Berkshire Museum. This motel offers clean rooms, free WiFi, and parking. Just a 2-minute drive from the transportation hub for your Tanglewood adventures.
The price is $80
$89 total
includes taxes & fees
May 25 - May 26
Berkshire Inn
Property entrance

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (854 reviews)
This boutique hotel combines business-friendly amenities with cozy accommodations near Barrington Stage Company. Enjoy thoughtful perks including complimentary WiFi, free parking, and convenient room service, all while exploring nearby cultural attractions.
The price is $159
$178 total
includes taxes & fees
Jun 16 - Jun 17
Hotel On North
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (936 reviews)
The price is $93
$126 total
includes taxes & fees
May 24 - May 25
Berkshire Mountain Lodge
Exterior

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (365 reviews)
The price is $114
$127 total
includes taxes & fees
Jun 1 - Jun 2
The Central Downtown Inn & Suites
Exterior

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1,000 reviews)
Unwind at this centrally located Pittsfield hotel with an indoor pool and health club. Just 15 minutes from Tanglewood Music Center and a quick 6-minute walk to transportation. Enjoy quiet rooms with microwaves, refrigerators, and a bar on-site.
The price is $118
$132 total
includes taxes & fees
May 25 - May 26
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,003 reviews)
Escape to this Pittsfield hotel near the train station, with Tanglewood Music Center nearby. After enjoying the complimentary breakfast, explore local skiing trails or workout in the fitness center. Clean rooms and attentive staff create a welcoming mountain getaway.
The price is $110
$123 total
includes taxes & fees
May 20 - May 21
Best Western Plus Berkshire Hills Inn & Suites
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (94 reviews)
Escape to the heart of Pittsfield where this hotel offers an indoor pool and relaxing hot tub after exploring Tanglewood. Free breakfast, WiFi, and parking enhance your stay while nearby Guido's Marketplace awaits your discovery.
The price is $127
$142 total
includes taxes & fees
May 28 - May 29
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Breakfast, lunch and dinner served

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (677 reviews)
Embrace comfort at this Pittsfield retreat with an indoor pool and fitness center. Jae's Asian Fusion restaurant serves three daily meals, while rooms offer convenient refrigerators and microwaves. Guido's Marketplace and literary landmarks await nearby.
The price is $127
$141 total
includes taxes & fees
May 28 - May 29
Hilton Garden Inn Lenox Pittsfield
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (819 reviews)
Tucked away in a peaceful corner of Pittsfield, this quiet motel offers free WiFi and parking with a 24-hour front desk. Nearby Crane Museum of Papermaking awaits exploration, while winter enthusiasts will love the downhill skiing options just moments away.
The price is $79
$88 total
includes taxes & fees
May 18 - May 19
FairBridge Inn Express
Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
Discover this Lenox retreat with stunning mountain views, year-round swimming options, and fireplaces in select rooms. Just minutes from Bousquet Ski Area and local attractions, enjoy free breakfast and helpful staff after a day exploring.
The price is $109
$122 total
includes taxes & fees
May 18 - May 19
The Yankee Inn
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (853 reviews)
Dive into Berkshires charm at this centrally located Lenox motel, where you'll enjoy the refreshing outdoor pool and free parking. Near Guido's Marketplace and Bousquet Ski Area, with clean rooms and exceptionally helpful staff to enhance your stay.
The price is $79
$88 total
includes taxes & fees
May 18 - May 19
Howard Johnson by Wyndham Lenox
Free daily buffet breakfast

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,005 reviews)
Dive into the indoor pool at this Lenox hotel, just 10 minutes from Tanglewood Music Center. Enjoy a complimentary breakfast before exploring nearby attractions like Guido's Marketplace and Bousquet Ski Area. Free WiFi and parking complete your comfortable stay.
The price is $119
$133 total
includes taxes & fees
May 25 - May 26
Hampton Inn & Suites Berkshires-Lenox
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (948 reviews)
Nestled in Lenox, this lodge offers easy access to Kennedy Park and Pleasant Valley Wilderness Sanctuary. The Club Room serves American cuisine, while the terrace provides a perfect spot to unwind after exploring local attractions.
The price is $111
$124 total
includes taxes & fees
May 25 - May 26
Berkshires Untold
Lobby lounge

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
Embrace mountain charm at this Lenox hotel with free breakfast and parking. Take a refreshing dip in the indoor pool before heading to nearby Tanglewood or Kennedy Park. Grab a drink at the bar after exploring the scenic Berkshires.
The price is $159
$178 total
includes taxes & fees
May 28 - May 29
Element by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (625 reviews)
Immerse yourself in the Berkshires at this centrally located hotel with an indoor pool and fitness center. Rooms feature microwaves and refrigerators, while the café and bar provide dining options. Free WiFi, parking, and proximity to Kennedy Park enhance your stay.
The price is $155
$173 total
includes taxes & fees
May 28 - May 29
Courtyard by Marriott Lenox Berkshires
Lobby sitting area

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
8.0 out of 10, Very Good, (2 reviews)
The price is $134
$150 total
includes taxes & fees
May 31 - Jun 1
Hideaway Inn Lenox
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
Wake up to free breakfast at this cozy Berkshires inn where a garden terrace offers peaceful moments. The coffee shop/cafe and bar provide refreshments after exploring nearby attractions like The Bookstore and Lenox Library.
The price is $144
$166 total
includes taxes & fees
May 19 - May 20
The Cornell Inn, Lenox & The Berkshires
Exterior

The Whitlock

The Whitlock
2.0 star property
Lenox
8.6 out of 10, Excellent, (299 reviews)
Immerse yourself in the Berkshires at this charming hotel just 5 minutes from Tanglewood Music Center. Enjoy hiking trails nearby, plus free WiFi and parking. A terrace, garden and helpful staff create a welcoming atmosphere for music lovers and nature enthusiasts alike.
The price is $122
$137 total
includes taxes & fees
May 18 - May 19
The Whitlock
Exterior detail

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (44 reviews)
Tucked in Lenox, this charming hotel offers easy access to Tanglewood Music Center and local museums. Unwind by the seasonal pool or enjoy a cocktail at the bar after exploring nearby Ventfort Hall. Free WiFi and parking enhance your Berkshires getaway.
The price is $274
$306 total
includes taxes & fees
May 25 - May 26
Hampton Terrace Inn
Property grounds

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very Good, (501 reviews)
Tucked into the Berkshires, this cozy B&B serves complimentary breakfast and provides free WiFi and parking. Explore nearby hiking trails, go kayaking, or visit local attractions like The Bookstore, all within easy reach of this charming retreat.
The price is $266
$297 total
includes taxes & fees
May 25 - May 26
Whistler's Inn Bed & Breakfast
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 pet-friendly hotels in Pittsfield

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1003)
The price is $110
$123 total
includes taxes & fees
May 20 - May 21
Best Western Plus Berkshire Hills Inn & Suites
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You may also like hotels with pools in Pittsfield

Lobby
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (936)
The price is $93
$126 total
includes taxes & fees
May 24 - May 25
Berkshire Mountain Lodge
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.
View all properties

When is the best time to visit Pittsfield?

Our prices for hotels in Pittsfield are cheapest in January
Price trends for hotels in Pittsfield
Pricing is based on two traveler single night rates
View properties in May
Currently viewing crowd sizes and weather for May.
Typical weather for Pittsfield
May
High 19°C / low 8°C. Sunny most days.
View properties in May
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May, no crowd data, average high temperature 19 degrees Celsius, average low temperature 8 degrees Celsius. Sunny most days.
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23°
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June, no crowd data, average high temperature 23 degrees Celsius, average low temperature 13 degrees Celsius. Sunny most days.
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July, no crowd data, average high temperature 27 degrees Celsius, average low temperature 16 degrees Celsius. Sunny most days.
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26°
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August, no crowd data, average high temperature 26 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
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September, no crowd data, average high temperature 22 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
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October, no crowd data, average high temperature 14 degrees Celsius, average low temperature 6 degrees Celsius. Sunny most days.
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November, no crowd data, average high temperature 7 degrees Celsius, average low temperature -1 degrees Celsius. Partly sunny.
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December, no crowd data, average high temperature 2 degrees Celsius, average low temperature -5 degrees Celsius. Snow likely.
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January, no crowd data, average high temperature -2 degrees Celsius, average low temperature -9 degrees Celsius. Snow likely.
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February, no crowd data, average high temperature 0 degrees Celsius, average low temperature -9 degrees Celsius. Snow likely.
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March, no crowd data, average high temperature 5 degrees Celsius, average low temperature -4 degrees Celsius. Snow likely.
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April, no crowd data, average high temperature 12 degrees Celsius, average low temperature 2 degrees Celsius. Cloudy most days.
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Monthly weather averages (˚C)

Top landmarks in Pittsfield

Historic Shaker village

Hancock Shaker Village

4.6/5 (101 reviews)
If seeing the sights is on your list of things to do, head to Hancock Shaker Village— just one of the landmarks located 4.7 mi (7.6 km) from central Pittsfield. You could also start your cultural experience by heading over to the museums in the area.
See properties

Learn more about Pittsfield

Tucked into the heart of the Berkshires, this cultural powerhouse punches well above its weight. The Berkshire Museum offers an eclectic mix of art, history, and aquarium exhibits that somehow work perfectly together. At the gloriously restored Colonial Theater, performances unfold in a space where the acoustics haven't changed since 1903. Herman Melville wrote 'Moby-Dick' at his home Arrowhead, now open for tours that reveal the author's mountain view that reminded him of a whale's back. The Hancock Shaker Village presents a fascinating glimpse into America's most successful utopian community. Come winter, locals hit the slopes at Bousquet Ski Area, while summer brings outdoor theater at Barrington Stage Company where Broadway shows often premiere before heading to New York.

See all hotels in Pittsfield

Check out reviews of Pittsfield hotels guests love

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Loved our stay. This property is very clean, well-maintained, and had everything we needed for a comfortable stay."
Brianna 1-night trip
Posted 1 hour ago
Hotel Downstreet, an Ascend Collection Hotel

Frequently asked questions

What accommodations do travelers like in Pittsfield?
Guests like Berkshire Mountain Lodge, Hotel On North and Holiday Inn & Suites Pittsfield-Berkshires by IHG.
Where can I find free parking at my hotel in Pittsfield?
Park your car for free at Holiday Inn & Suites Pittsfield-Berkshires by IHG.
Can I book a refundable hotel in Pittsfield?
If you need the flexibility to change your travel plans to Pittsfield, most properties provide refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
Where should I stay in Pittsfield if I'm looking for a reasonably priced accommodation?
An inexpensive option worth considering is Holiday Inn Express & Suites Pittsfield - Berkshires by IHG.
Where can I stay in Pittsfield if I want a vacation rental instead of a hotel?
If you want to find a good alternative to a hotel, browse our selection of 39 vacation homes. You can also consider one of the 8 apartments or 7 cottages.
What will the weather in Pittsfield be like during my vacation?
July and August are typically the warmest months in Pittsfield when the average temp is 66°F. January and February are the coldest months when the average temperature is 27°F. October and August are the months with the most rain.
Why should I book my Pittsfield hotel with Hotels.com?
There are lots of reasons to book your Pittsfield trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.