Search Lakeside Hotels in Pittsfield

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Pittsfield Lakeside Hotels

Our top choices for Pittsfield hotels on the lake

Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1000)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is 2.667.328 ₫
2.979.405 ₫ total
includes taxes & fees
21 Dec - 22 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Porch
Lakehouse Inn

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (290)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is 4.905.565 ₫
5.753.491 ₫ total
includes taxes & fees
12 Dec - 13 Dec
Lakehouse 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.
View all properties

Top Pittsfield Hotel Reviews

Explore a world of travel with Expedia

Frequently asked questions

How much do lakeside hotels in Pittsfield cost?
The price for lakeside hotels in Pittsfield ranges from 2.979.405 ₫ to 5.753.491 ₫ per night. Whatever your budget, it's a cinch to find a perfect retreat by the water. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Are there any family-friendly lakeside hotels in Pittsfield?
Settle in at The Black Swan Lee - Lenox, Ascend Hotel Collection and make your escape to Pittsfield one to remember. This family-friendly lakeside hotel has a 3-star rating and features including complimentary breakfast and housekeeping services. After checking in and chilling in your comfy new digs, it's time to head out and start exploring. Hancock Shaker Village and Berkshire Museum are just two family-friendly attractions in Pittsfield.
Why book your lakeside hotel in Pittsfield with Expedia?
Finding your ideal lakeside hotel in Pittsfield is a snap with Expedia. Getting away with the kids? Make your way to the filters to search for properties with family-friendly amenities. If you have a budget in mind, select how much you want to spend and your desired hotel star rating. Whatever your needs or travel plans, you'll always get the best deal possible.
How can I find cheap lakeside hotels in Pittsfield?
Use Expedia's handy filters to set your price per night budget. Then, select your preferred hotel star rating — they range from basic (1 star) to luxury (5 star). You can also search based on specific areas you'd like to stay in. Scoring your ideal lakeside hotel in Pittsfield at the perfect price couldn't be easier!
What is there to do in Pittsfield near my lakeside hotel?
Pittsfield has enough activities and sights to keep you entertained for weeks (or months!), starting with Bousquet Ski Area. Pittsfield State Forest, Barrington Stage Company and Berkshire Museum are other renowned attractions. If you're sticking around a while, Colonial Theatre and Arrowhead Museum will put the finishing touches on your itinerary.