Downtown Pittsfield, Massachusetts

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Hotels

BEST WESTERN BERKSHIRE HILLS

1350 West Housatonic Street

Pittsfield, Massachusetts

White Horse Inn

378 South St

Pittsfield, Massachusetts

Quality Inn

16 Cheshire Road

Pittsfield, Massachusetts

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St

Pittsfield, Massachusetts

Crowne Plaza Pittsfield-Berkshires

1 West St

Pittsfield, Massachusetts

Berkshire Inn

150 W Housatonic St

Pittsfield, Massachusetts

Comfort Inn Pittsfield

1055 South St

Pittsfield, Massachusetts

Hotel Tips

Upon check-in, slip the desk agent a tip and ask for the best room they can find at your current booked rate. Often times a quick $10 or $20 bill can go a long way towards the mood of the person who directly decides where you lay your head for the night.

Always find a reason to email the front desk manager in hotels that you plan to visit again. Tell them what they did right and express your plans to stay again and ask what opportunities there might be for frequent discounts or upgrades on your next visits. If you become friends with the manager, you just might get the friends and family rate some day.

Policies vary on the availability of pet friendly rooms to it is wise to be open, honest and upfront during the booking process. You may find yourself kicked out or even paying a large deposit if you are not in a pet-friendly hotel and bring one anyway. New ADA laws are fuzzy though as service animals are not required to be documented and proprietors are legally not allowed to ask if the animal is a pet vs. a service animal.

Things To Do

Pittsfield helps you expand your skills and learn some new ways to expand your artisan flare? Sign up for classes at your kitchen supply store, yarn shop, art and craft shop and photo gallery. You'll be having great fun with your new friends as you you take on that next project.

Pittsfield micro breweries have popped up in downtown corridors to quench the thirst of local or traveller whos is looking for a one-of-a-kind experience for suds brewed on site. If you are looking for a light beer or something randy and dark, you are sure to find a wide assortment of options to choose from.

Pittsfield visitors are always welcome and you will receive exceptional service from local merchant-owners as opposed to staff at the big box retailers. We take the extra time to make sure that you how to make best use of your purchase and that you get exactly what you need.

Why Do You Love Downtown?

BOB BLACKMAN

Just a fun place to visit.

Kristin Miller

Things you can't find anywhere else

Angela Shields

I will be visiting Ashland for the first time this coming weekend! I have heard from numerous people what a great town it is and how much I will like it. Very excited to check it out and do some shopping!

Alison Barlow

Charming, lovely downtown. Love the antique shops!

Terri Simon

I love to dine at the Inn and to shop at specialty shops.

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