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Compare 1,250 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, 1,005 reviews
"We were upgraded by the wonderful front desk staff to a third floor room. very nice. however, the breakfast was pretty bad. bad eggs, terrible bacon and bad sausage patties. the sausage links were good. "
The price is $160
includes taxes & fees
$144 per night
Aug 7 - Aug 8
The Yankee, Trademark Collection by Wyndham
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, 1,689 reviews
"We had a great stay! "
The price is $195
includes taxes & fees
$178 per night
Jul 28 - Jul 29
Vacation Village in the Berkshires
Berkshire Mountain Lodge
3.0 star property
8.8 out of 10, Excellent, 339 reviews
"We arrived after dark on Tuesday and checked out Wednesday morning; so we didn't get to experience much. Compared to some we've seen the rooms are modern, enormous, and comfortable. Staffing is efficient (no overnight front desk; guests strip beds and put out trash when leaving). The full kitchen was impressive; but we didn't bring food, so had to look elsewhere for breakfast."
The price is $227
includes taxes & fees
$205 per night
Jul 28 - Jul 29
Berkshire Mountain Lodge
Life House Berkshires
3.5 star property
9.0 out of 10, Wonderful, 330 reviews
"Felt luxurious. Modern. Also very clean. A step above other inns in the area."
The price is $182
includes taxes & fees
$163 per night
Aug 12 - Aug 13
Life House Berkshires
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, 609 reviews
"The hotel was beautiful and staff very nice, but it was not in the nicest area. There were a couple of good places you could walk to to eat or have a drink. No restaurant or bar at the hotel. "
The price is $222
includes taxes & fees
$199 per night
Aug 4 - Aug 5
Hotel On North
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, 879 reviews
"Only stayed a night but kids liked the pool and it was close to the adventure park "
The price is $159
includes taxes & fees
$144 per night
Jul 29 - Jul 30
Jiminy Peak Mountain Resort
Courtyard by Marriott Lenox Berkshires
3.0 star property
9.2 out of 10, Wonderful, 516 reviews
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The price is $278
includes taxes & fees
$249 per night
Aug 22 - Aug 23
Courtyard by Marriott Lenox Berkshires
The Williams Inn
4.0 star property
9.6 out of 10, Exceptional, 315 reviews
"Beautiful stay in a lovely property. Very serene, with understated elegant decor. Well appointed room & bath. Wonderful evening at the Barn restaurant. "
The price is $311
includes taxes & fees
$278 per night
Jul 29 - Jul 30
The Williams Inn
Hampton Inn & Suites Berkshires-Lenox
2.5 star property
9.2 out of 10, Wonderful, 1,000 reviews
"It was clean, comfortable and convenient. "
The price is $227
includes taxes & fees
$203 per night
Aug 27 - Aug 28
Hampton Inn & Suites Berkshires-Lenox
Hotel Downstreet
3.0 star property
8.6 out of 10, Excellent, 949 reviews
"This such a wonderful hotel! Everything seems clean and new. There is a comfortable lounge area to work or read and interesting art galleries on the main floor. Our room was spacious and clean. The staff was incredible. The evening and morning staff were so friendly and accommodating. It made the stay so much more relaxing. The only complaint is that there was no breakfast. I wish they would have a continental breakfast. The coffee was delicious."
The price is $142
includes taxes & fees
$127 per night
Jul 28 - Jul 29
Hotel Downstreet
Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
8.4 out of 10, Very Good, 976 reviews
"The property is pretty much standard for these class of inns. They did have a good breakfast. "
The price is $173
includes taxes & fees
$155 per night
Aug 7 - Aug 8
Best Western Plus Berkshire Hills Inn & Suites
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3.0 star property
7.8 out of 10, Good, 612 reviews
"I had a quiet stay & everything was clean and tidy. The only thing I didn’t like was that I had to park down the street at the bank. But besides that I was satisfied with my room. "
The price is $147
includes taxes & fees
$131 per night
Aug 25 - Aug 26
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Fairfield Inn & Suites by Marriott Williamstown
2.5 star property
8.8 out of 10, Excellent, 283 reviews
"Excellent stay."
The price is $210
includes taxes & fees
$188 per night
Jul 30 - Jul 31
Fairfield Inn & Suites by Marriott Williamstown
The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
8.8 out of 10, Excellent, 113 reviews
"We spent a splendid night at The Trail. People were very friendly and extremely helpful when my son forgot his watch in the room. The place is very clean and beautifully renovated. Excellent for hiking Mt. Greylock or the Appalachian Trail."
The price is $202
includes taxes & fees
$181 per night
Jul 29 - Jul 30
The Trail in Adams - Berkshires’ Art Hotel
Berkshire Inn
2.0 star property
7.6 out of 10, Good, 692 reviews
"A bargain, given how close the hotel is to all the great Berkshire venues."
The price is $101
includes taxes & fees
$90 per night
Jul 29 - Jul 30
Berkshire Inn
Berkshire Valley Inn
2.5 star property
9.0 out of 10, Wonderful, 515 reviews
"The owners are great. It’s like staying in Schitt’s Creek. It’s worn down but with all the sweet details to added for warmth and charm."
The price is $169
includes taxes & fees
$154 per night
Jul 28 - Jul 29
Berkshire Valley Inn
FairBridge Inn Express
2.5 star property
5.2 out of 10, 603 reviews
"We had a peaceful night's rest and felt secure. Our room was clean, beds comfy, and bathroom updated. The outside appearance and the room doors could use some help. "
The price is $88
includes taxes & fees
$79 per night
Jul 28 - Jul 29
FairBridge Inn Express
Wagon Wheel Inn
2.0 star property
7.2 out of 10, Good, 571 reviews
"I always enjoy my stays at the Wagon Wheel. They've recently painted the outside of the motel and the appearance is improved. "
The price is $111
includes taxes & fees
$99 per night
Jul 28 - Jul 29
Wagon Wheel Inn
Howard Johnson by Wyndham Lenox
2.0 star property
7.6 out of 10, Good, 647 reviews
"Tough to get a room in Berkshires in July on short notice. Found this and location smack dab in middle of everything worked. Main thing the place is QUIET. Staff deeply committed to guest comfort "
The price is $122
includes taxes & fees
$109 per night
Jul 29 - Jul 30
Howard Johnson by Wyndham Lenox
Stay Berkshires
2.0 star property
8.4 out of 10, Very Good, 340 reviews
"Creek/river sound outside room"
The price is $179
includes taxes & fees
$160 per night
Jul 28 - Jul 29
Stay Berkshires
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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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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 fitness center. 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.

What are some of the best vacation home rentals in Pittsfield?

Berkshire Village Carriage House - Super Private!!: You might want to consider this vacation home rental near Pittsfield, which is located in the mountains and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books in this rental home to help you unwind. See all 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, an IHG Hotel is a hotel with an indoor pool and a restaurant, and it's a top choice on Expedia for families. Best Western Plus Berkshire Hills Inn & Suites is another good option for your family trip. 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 place to stay for a couple visiting Pittsfield?

Hotel On North is a favorite hotel for couples, and features premium bedding and flat-screen TVs. See all romantic hotels in Pittsfield.

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

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel 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, an IHG Hotel 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 Hilton Garden Inn Lenox Pittsfield. 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's the best high-end hotel in Pittsfield?

Yankee Suites Extended Stay is a 4-star guesthouse with a terrace, and a popular choice for Expedia travelers looking for a luxurious stay. Find more luxury hotels in Pittsfield.

Recent reviews of Pittsfield hotels
Expedia verified reviews

Pittsfield Travel Info

Number of reviews
4,827
Accommodation
1,250 hotels
Highest price
$311
Lowest price
$88
Reasons to visit
Bousquet Ski Area, Colonial Theater and Barrington Stage Company
Hotels with skiing
28
Hotels with nearby historical attractions
5