Pittsfield Hotels

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Top 10 trending Pittsfield hotels

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (557)
"Amazing place to stay. Can’t wait to go again. "
Berkshire Mountain Lodge

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (855)
"Consistently a clean room with welcoming staff."
The price is €111
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG

FairBridge Inn Express

2.5 star property
5.4 out of 10, (766)
"Close to our target event a plus"
The price is €68
includes taxes & fees
26 Aug - 27 Aug
FairBridge Inn Express

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (14)
"Really enjoyed my stay here, definitely need a car to get around"
The price is €146
includes taxes & fees
14 Aug - 15 Aug
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1008)
"Very clean rooms and excellent staff."
The price is €114
includes taxes & fees
1 Sept - 2 Sept
Best Western Plus Berkshire Hills Inn & Suites

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (752)
"Staff were excellent and welcoming."
Hotel On North

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (300)
"Friendly staff, clean and perfect for a trip with the pups! "
The price is €111
includes taxes & fees
1 Sept - 2 Sept
The Central Downtown Inn & Suites

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (639)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is €150
includes taxes & fees
7 Sept - 8 Sept
Hilton Garden Inn Lenox Pittsfield

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (794)
"good location....easy access to highlight destinations and downtown"
The price is €87
includes taxes & fees
14 Aug - 15 Aug
Berkshire Inn

Comfort Inn & Suites East Greenbush - Albany

2.5 star property
8.4 out of 10, Very good, (1001)
"A great stay in a family friendly hotel."
The price is €105
includes taxes & fees
2 Sept - 3 Sept
Comfort Inn & Suites East Greenbush - Albany

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1944)
"Very relaxing, clean and convenient for a family vacation. Pool area and grills are well kept and also convenient "
The price is €114
includes taxes & fees
27 Aug - 28 Aug
Vacation Village in the Berkshires

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (670)
"Fun place and very clean. Friendly staff and an amazing outdoor area to hang out."
The price is €155
includes taxes & fees
1 Sept - 2 Sept
Berkshires Untold

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1007)
"Wonderful place to stay"
The price is €129
includes taxes & fees
8 Sept - 9 Sept
The Yankee, Trademark Collection by Wyndham

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Had a wonderful time "
The price is €122
includes taxes & fees
1 Sept - 2 Sept
The Black Swan Lee - Lenox, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1010)
"Great location!"
The price is €138
includes taxes & fees
10 Sept - 11 Sept
Hotel Downstreet, Ascend Hotel Collection

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1000)
"Lovely place. Excellent staff, Wonderful breakfast."
The price is €156
includes taxes & fees
1 Sept - 2 Sept
The Cornell Inn, Lenox & The Berkshires

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

3.5 star property
9.0 out of 10, Wonderful, (690)
"This was our third year of two summer weeks at Oak 'n' Spruce. The accommodations are comfortable and convenient, and the staff is wonderful. We hope to be back next summer."
The price is €102
includes taxes & fees
2 Sept - 3 Sept
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (516)
"Great place , love it, will return"
The price is €145
includes taxes & fees
7 Sept - 8 Sept
The Constance by the Lenox Collection

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1003)
"Loved our visit"
The price is €220
includes taxes & fees
18 Aug - 19 Aug
The Red Lion Inn

The Brooks Motel

2.0 star property
7.6 out of 10, Good, (94)
"Basic, clean and good value for the money."
The price is €139
includes taxes & fees
20 Aug - 21 Aug
The Brooks Motel
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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.

Pittsfield featuring a city

Best guest reviews of Pittsfield

Top Pittsfield Hotel Reviews

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 bar. 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.

What are some of the best holiday rentals that Pittsfield has to offer?

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table: This highly rated holiday home rental in Pittsfield is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Another good choice for your trip to Pittsfield is Hancock Village Inn at Jiminy Peak. 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 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 by IHG 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 & Suites Pittsfield - Berkshires. 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 by IHG 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 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's trip include Best Western Plus Berkshire Hills Inn & Suites and The Central Downtown Inn & Suites. 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. See more options for historical stays in Pittsfield.

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. See all ski hotels in Pittsfield.

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. Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more! is an additional hotel with an on-site pool. 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 74 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 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 itinerary are Bousquet Ski Area and Housatonic River. 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.