Pittsfield Hotels from S$103

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check Pittsfield hotel prices

Tomorrow night
This weekend
Next weekend

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Pittsfield hotels

The Williams Inn
4.0 star property
9.6 out of 10, Exceptional, (371)
"This is the only hotel near Williams College but given that they have no competition it could have been much worse. They messed up our room type reservation (they gave us 2 queen beds instead of a king bed) and didn’t compensate us for that even though they said they would and we had to ask for our complimentary bottle of wine, but despite this, it’s still a nice hotel. Rooms are clean and restaurant is good. Very close to Williams College. I would stay again vs. staying further down the road at...
The price is S$296
includes taxes & fees
2 Dec - 3 Dec
The Williams Inn
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1746)
"The pool/clubhouse was a bit chaotic but the overall experience of this location was fantastic. It was lovely."
The price is S$262
includes taxes & fees
22 Nov - 23 Nov
Vacation Village in the Berkshires
Life House Berkshires
3.5 star property
9.0 out of 10, Wonderful, (442)
"Loved the stay, only two things kept me from saying it was 5 stars. The WiFi connection was spotty so if you were watching tv (because they use Apple TV) it was freezing every 2 mins. Also, you can’t lower the room temp passed 65 and their 65 wasn’t a normal 65. It was still really warm. Besides that I love it. Super clean and quiet. "
The price is S$179
includes taxes & fees
26 Nov - 27 Nov
Life House Berkshires
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1001)
"Staff was very nice, friendly and accommodating. The room was nice, clean, comfortable and spacious. "
The price is S$140
includes taxes & fees
22 Dec - 23 Dec
The Yankee, Trademark Collection by Wyndham
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3.0 star property
8.0 out of 10, Very good, (682)
"We stayed for two weeks and couldn’t have been happier with the service. Such nice people, and so understanding. Six stars if I could!"
The price is S$142
includes taxes & fees
13 Dec - 14 Dec
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is S$219
includes taxes & fees
24 Nov - 25 Nov
Jiminy Peak Mountain Resort
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, (650)
"Beautiful room & exceptional staff. Highly recommend!"
The price is S$217
includes taxes & fees
26 Nov - 27 Nov
Hotel On North
Hotel Downstreet
3.0 star property
8.6 out of 10, Excellent, (1006)
"Great location, wonderful staff, fun pool and cool art. Would definitely stay again! "
The price is S$173
includes taxes & fees
22 Dec - 23 Dec
Hotel Downstreet
Berkshire Mountain Lodge
3.0 star property
8.8 out of 10, Excellent, (411)
"Loved our room. Very clean"
The price is S$273
includes taxes & fees
26 Nov - 27 Nov
Berkshire Mountain Lodge
Hampton Inn & Suites Berkshires-Lenox
2.5 star property
9.2 out of 10, Wonderful, (1002)
"Staff very helpful and friendly "
The price is S$177
includes taxes & fees
2 Dec - 3 Dec
Hampton Inn & Suites Berkshires-Lenox
Berkshire Inn
2.0 star property
7.6 out of 10, Good, (747)
"Good. No highlights."
The price is S$128
includes taxes & fees
26 Nov - 27 Nov
Berkshire Inn
Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
8.4 out of 10, Very good, (1010)
"Room was clean, comfortable, and convenient. Dog Friendly! Will stay again!"
The price is S$135
includes taxes & fees
8 Dec - 9 Dec
Best Western Plus Berkshire Hills Inn & Suites
Courtyard by Marriott Lenox Berkshires
3.0 star property
9.2 out of 10, Wonderful, (533)
"Nice, friendly staff. large lobby area with multiple seating areas. Coffee over priced. "
The price is S$177
includes taxes & fees
11 Dec - 12 Dec
Courtyard by Marriott Lenox Berkshires
FairBridge Inn Express
2.5 star property
5.4 out of 10, (678)
"I don’t know so many complaints. Bed was good, clean. Plenty of park. Provided what we paid for and was expecting. "
The price is S$118
includes taxes & fees
26 Nov - 27 Nov
FairBridge Inn Express
The Porches Inn at Mass MoCA
3.5 star property
9.4 out of 10, Exceptional, (369)
"We had an excellent time and loved all the beautiful details. Will definitely stay here again."
The price is S$262
includes taxes & fees
22 Dec - 23 Dec
The Porches Inn at Mass MoCA
Howard Johnson by Wyndham Lenox
2.0 star property
7.6 out of 10, Good, (701)
"It served our needs"
The price is S$118
includes taxes & fees
24 Nov - 25 Nov
Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Williamstown
2.0 star property
6.4 out of 10, (824)
"Staff was very kind and welcoming!"
The price is S$149
includes taxes & fees
22 Dec - 23 Dec
Howard Johnson by Wyndham Williamstown
Hilton Garden Inn Lenox Pittsfield
3.0 star property
9.2 out of 10, Wonderful, (618)
"Check in and check out where quick and easy. The room was comfortable and clean. The staff were nice and accommodating. Central location to surrounding attractions. "
The price is S$203
includes taxes & fees
22 Dec - 23 Dec
Hilton Garden Inn Lenox Pittsfield
Fairfield Inn & Suites by Marriott Williamstown
2.5 star property
8.8 out of 10, Excellent, (308)
"It was a wonderful stay, the staff was ready to help and it was a quiet clean place to do work and also go enjoy the beautiful town of Williamstown"
The price is S$201
includes taxes & fees
8 Dec - 9 Dec
Fairfield Inn & Suites by Marriott Williamstown
Wagon Wheel Inn
2.0 star property
7.2 out of 10, Good, (597)
"Great location. Pleasant staff."
The price is S$103
includes taxes & fees
23 Nov - 24 Nov
Wagon Wheel Inn
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.
Don't see what you're looking for?
See all available properties in Pittsfield
Save an average of 15% on thousands of hotels when you're signed in
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Where is the best place for a stay in Pittsfield?

Hotel On North is a favourite with Expedia customers. This hotel offers free parking and a fitness centre. Other top choices based on traveller 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 that most hotel room reservations are fully refundable if cancelled before the hotel’s cancellation deadline, which is usually within 24-48 hours of your scheduled arrival. If your reservation is non-refundable, it may still be possible to cancel it and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Pittsfield.

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

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

What's the best family accommodation 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. Other options for your child-friendly holiday include Best Western Plus Berkshire Hills Inn & Suites and Holiday Inn Express Pittsfield Berkshires, an IHG Hotel. Also, attractions such as Berkshire Museum and Bousquet Ski Area are fun for children of all ages. Find more child-friendly accommodations in Pittsfield.

What's the best place to stay for couples in Pittsfield?

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

What is the top LGBTQ-friendly place to stay in Pittsfield?

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel is a top LGBTQ-friendly hotel, and features free Wi-Fi and free Internet. Hilton Garden Inn Lenox Pittsfield is another good option for your trip. See all available hotels listed as LGBTQ-friendly in Pittsfield.

What's the best dog-friendly accommodation option 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's trip include Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield. See more pet-friendly hotel accommodations in Pittsfield.

What's the best high-end hotel in Pittsfield?

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

What's the best boutique accommodation in Pittsfield?

Hotel On North is a favourite 3.5-star hotel with our travellers looking for stylish accommodation, and features 45 guestrooms, a restaurant and a bar.

What's the best hotel for a golf holiday in Pittsfield?

FairBridge Inn Express is one of the top choices for golfers, based on our travel data. You can tee off at Wyndhurst Golf & Club during your trip. See more golf hotels in Pittsfield.

What's the best hotel in Pittsfield to absorb the local history?

Based on our travel expertise, Berkshire Mountain Lodge is a top 3-star lodge for history seekers booking on Expedia, and it offers free parking and in-room kitchens. Other choices near historic sites include Hilton Garden Inn Lenox Pittsfield and Berkshire Inn. Also, Colonial Theater and Hancock Shaker Village are a couple of local landmarks worth a visit.

What's the best accommodation option for a ski holiday in Pittsfield?

Hilton Garden Inn Lenox Pittsfield is a top hotel for hitting the ski slopes, and features free WiFi and free parkingThis hotel is adjacent to Bousquet Ski Area. Other good choices for your stay near the slopes include FairBridge Inn Express and The Central Downtown Inn & Suites.

What are some accommodation options with pools in Pittsfield?

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

What is the best spa hotel in Pittsfield?

Berkshire Mountain Lodge is a top spa hotel featuring a fitness centre and an indoor pool. Spend the afternoon relaxing in the hot tub and sauna. Another popular spa hotel in Pittsfield is Hilton Garden Inn Lenox Pittsfield. See all spa hotels in Pittsfield.

What is staying in Pittsfield like?

Visitors to Pittsfield will definitely enjoy the sporting events, entertainment and theatres. Tourists can also enjoy the city's museums, lake views and ski areas. In Pittsfield, there are 64 hotels and other accommodation options to choose from. Find out more about Pittsfield.

What should I do while I'm visiting Pittsfield?

Cultural venues include Berkshire Museum, Colonial Theater and Hancock Shaker Village. The picturesque setting of Pittsfield State Forest and Housatonic River exemplify the area's natural beauty. A couple of additional sights to add to your itinerary are Bousquet Ski Area and Berkshire Athenaeum. Take a look at what more there is to see and do in Expedia's Pittsfield guide.

How should I get around Pittsfield?

To see more of 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 temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Pittsfield are January, March, February and November, with each month seeing an average of 18 cm of snowfall.