Pittsfield Family hotels with AARP Discounts

Featured Pittsfield Family Hotels

Hotel On North

Hotel On North

3.5 out of 5
297 North Street, Pittsfield, MA
Fully refundableReserve now, pay when you stay
Hotel On North
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
Fully refundableReserve now, pay when you stay
Best Western Plus Berkshire Hills Inn & Suites
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
Fully refundable
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Save an average of 15% on thousands of hotels when you're signed in
Berkshire Inn

Berkshire Inn

2 out of 5
150 W Housatonic St, Pittsfield, MA
Fully refundableReserve now, pay when you stay
Berkshire Inn
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
FairBridge Inn Express
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

3 out of 5
1032 South Street, Pittsfield, MA
Fully refundableReserve now, pay when you stay
Hilton Garden Inn Lenox Pittsfield
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St., Pittsfield, MA
The Central Downtown Inn & Suites
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.
Pittsfield, Massachusetts, United States of America
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Pittsfield for Families

Looking to plan your next big trip with the whole family? Pittsfield offers some of the best family-friendly activities, hotels, and amenities, so you can rest easy, because your clan is going to love the vacation that you plan. When you book with the AARP Travel Center Powered by Expedia®, traveling to Pittsfield is easier than ever. You'll find that with your member status, you can combine your members-only discount with the best rates from Expedia. Forget stressing over the cost—you'll be getting the best value available.

What Should We See and Do in Pittsfield?

Once you and your clan arrive, you'll need some fun activities that everyone will want to be a part of. If there's other activities you're specifically looking forward to in Pittsfield, we can help you get them scheduled. Remember to check the weather forecast before you pack your bags, so you don't have any surprises along the way. You may experience a longer than usual commute time, so please prepare in advance and double-check your reservation and excursion schedule.

Where to Stay in Pittsfield

If you're looking for quality time at the hotel of your choosing, our family-friendly accommodations feature an array of amenities that will help your trip extra comfortable. From specialty dining, cribs, roll-away beds, and huge family suites, you won't have to lift a finger to make sure your entire crew is satisfied with the accommodations of your choosing.

Your kids and grandkids will be thrilled to stay at one of our Pittsfield kid-friendly hotels. And the adults will love that they are located near attractions, dining options, and activities.

Call the Family, You're Going to Pittsfield

A family that plays together saves together. From seniors to toddlers and everyone in between, you're sure to have an unforgettable Pittsfield trip. Do not miss out on these all-inclusive deals, and make sure you have your member advantage information handy. The best family getaway in Pittsfield is just a click away.