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A historic building with a clock, a flag, and a street lamp.

Pittsfield
Massachusetts
United States of America
North America
Hotwire.com

Pittsfield Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

Berkshire Mountain Lodge

3 out of 5

Price was $583, price is now $414 per person

$414

per person

Oct 15 - Oct 18

found 5 hours ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.

The room kitchen & bath were very clean.

Reviewed on Jul 29, 2026

Lodges At Cresthaven

4 out of 5

Save 100% on your flight

Price was $2,341, price is now $1,489 per person

$1,489

per person

Sep 4 - Sep 8

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Albany (ALB)

Book a stay at this beach lodge in Lake George. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Lake George Steamboat Company and Fort William Henry Museum are located nearby.

Loved the room and the view was absolutely amazing. Not far from everything we wanted to do. Staff were nice and friendly.

Reviewed on Jul 29, 2026

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5

Save 100% on your flight

Price was $1,291, price is now $831 per person

$831

per person

Oct 15 - Oct 18

found 5 hours ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Stay at this B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Tanglewood Music Center and The Bookstore are located nearby.

Studio 6 Lake George, NY - Adirondacks

2 out of 5

Price was $906, price is now $629 per person

$629

per person

Sep 4 - Sep 8

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Albany (ALB)

Stay at this hotel in Lake George. Enjoy free parking, an outdoor pool, and a fitness center. Popular attractions Six Flags Great Escape and Outlets at Lake George are located nearby.

The owners are super friendly, the rooms we surprisingly wonderful. Indoor and outdoor pool, loved the picnic table and grill out our back sliding doors!

Reviewed on Jul 29, 2026

Prospect Berkshires

3 out of 5

Save 100% on your flight

Price was $1,324, price is now $933 per person

$933

per person

Oct 15 - Oct 18

found 5 hours ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Stay at this hotel in Great Barrington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Catamount Aerial Adventure Park and Catamount Ski Area are located nearby.

Sundowner on Lake George

2.5 out of 5

Save 100% on your flight

Price was $1,435, price is now $1,012 per person

$1,012

per person

Sep 4 - Sep 8

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Albany (ALB)

Book a stay at this beach motel in Lake George. Enjoy free parking, an outdoor pool, and a private beach. Popular attractions Six Flags Great Escape and Lake George Steamboat Company are located nearby.

Nothing like the pictures. No staffs to receive you, you have to call a phone number. The place is old and outdated.

Reviewed on May 3, 2026

The Perch Hotel

2 out of 5

Price was $1,673, price is now $1,239 per person

$1,239

per person

Sep 12 - Sep 19

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Albany (ALB)

Stay at this hotel in Cornwallville. Enjoy free WiFi, free parking, and a garden. Popular attractions Elm Ridge Wild Forest and Zoom Flume are located nearby.

It was a wonderful stay the room was very clean and spacious. The common area downstairs was my favorite part of my whole stay. Wide variety of games to play with other guest that are also staying.

Reviewed on Jul 16, 2026

The Whitlock

2 out of 5

Price was $720, price is now $543 per person

$543

per person

Oct 15 - Oct 18

found 5 hours ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Stay at this hotel in Lenox. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and The Bookstore are located nearby.

a great choice if you want to stay in the heart of Lenox. It's a quiet place and had everything you needed. The people who worked there are kind. It's no frills, comfortable and affordable.

Reviewed on Jul 30, 2026

Pittsfield Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.

Studio 6 Lake George, NY - Adirondacks

2 out of 5

Price was $906, price is now $629 per person

$629

per person

Sep 4 - Sep 8

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Albany (ALB)