Downtown Stockbridge, Massachusetts
Discover shopping, dining, and accommodation in downtown Stockbridge.

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Hotels
The Red Lion Inn
30 Main Street
Stockbridge, Massachusetts
1862 Seasons on Main B and B
47 Main Street
Stockbridge, Massachusetts
Stockbridge Country Inn
26 Glendale Road
Stockbridge, Massachusetts
Hotel Tips
Elevators are notorious for being a nuisance so ask to be roomed on the top floor and as far away as possible. Most hotels book nearby rooms last so hopefully they have availability elsewhere.
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.
Always tip staff when you feel the service was great and don't forget the housekeeping staff which you may never see. You should tip every day if you are staying multiple days as the staff may rotate out and miss the bounty at the end.
Things To Do
Stockbridge 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.
Stockbridge shopping is better than online shopping so that you can touch, feel, smell and taste as an experience with an item before deciding to purchase it for yourself or as a gift. Local merchants have hand selected their inventory to provide a unique selection for your downtown.
Stockbridge can warm you up on a cloudy day or simply offer your daily perk by visiting your local coffee shop. Quality, purity and punch are targeted with coffee beans curated globally and locally roasted while being served fresh as it is made right in front of you. Order up!
Why Do You Love Downtown?
Rita
Maureen is there
Jennifer Wagner
First time downtown!
Judy Dechent
My daughter and her fiance are relocating from PA to Ashland. They leave next week. I've heard nothing but great things from them and look forward to visiting.
Robby
High quality group of restaurants and wonderful shops! Authentic old fashioned down-town atmosphere brings it all together very well.
Caren Murphy
Cute shops, great crab cakes, friendly.
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