The Best Adventure Hotels in Stockbridge, MA from AED 451 in 2026

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Our top choices for Stockbridge adventure hotels

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

charles

AED 451 total

includes taxes & fees

28 May - 29 May

NEW RENO - Chalet-style farm loft near Tanglewood

New Lebanon

Joanna P.

AED 752 total

includes taxes & fees

27 May - 28 May

Courtyard by Marriott Lenox Berkshires

Lenox

Jairo

AED 686 total

includes taxes & fees

2 Jun - 3 Jun

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

Sharon K.

AED 1,370 total

includes taxes & fees

28 May - 29 May

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Hancock

Jen B.

AED 907 total

includes taxes & fees

27 May - 28 May

Cozy Riverside Berkshires Retreat

Great Barrington

Jennifer L.

AED 1,163 total

includes taxes & fees

27 May - 28 May

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

Hancock

Thomas S.

AED 898 total

includes taxes & fees

27 May - 28 May

Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby

Hancock

Marc F.

AED 907 total

includes taxes & fees

27 May - 28 May

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Top Stockbridge Hotel Reviews

Hotel On North

10/10 Excellent

"Delighted by my experience. Staff was mega friendly, room was immaculate, impeccable vibe all around : )"

The Yankee Inn

10/10 Excellent

"Had a great stay at the Yankee Inn. I would definitely stay here again. Check in was great and super helpful for what to do and eat in the area. Carl at the bar was the best! Only complaint is that the fitted sheet kept coming up from our king mattress I had the fix them multiple times. Nice indoor pool and hot tub. Close to a lot."

The Red Lion Inn

10/10 Excellent

"Every year my sisters and I go to the Red Lion to celebrate our mom’s birthday. It was one of her favorite places! We love the charm, the history and the “old fashioned” feel. Every guest room is different and they kindly upgraded me to a suite the last two times. The food at the restaurant is really good and we always love hearing the Jazz in the Lion’s Den on Sunday night. Can’t wait to return next year."

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good

"I was a bit distressed by the parking lot situation and with the garage and lot all dug up and torn apart it looked horrible. But the staff was super kind and helpful and the room was really nice and I liked everything else about it. I was a bit anxious when I pulled up. It would have been nice to know in advance. But our stay went great. (My dog and me). I would stay there again if I have another dog trial out in that area."

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"The Cornell Inn completely won us over from the moment we walked in. The staff are genuinely warm and welcoming — the kind of friendly that feels real, not scripted — and they go out of their way to make you feel at home. We arrived after hours and the check-in process couldn't have been smoother — they left clear, easy-to-follow instructions that made the whole thing stress-free. Breakfast is a nice touch — solid and satisfying. The pastries pair nicely with your morning coffee and are a pleasant way to start the day. The rooms themselves are clean, comfortable, and well-appointed. Everything felt well-maintained and thoughtfully put together — no complaints whatsoever. And it's worth calling out that the Cornell Inn is proudly LGBTQIA+ friendly. It's a welcoming space for everyone, and that inclusivity is genuinely felt throughout the property, not just a line on a website. Highly recommend. This place has the hospitality, the atmosphere, and the little details that make any stay memorable."

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Our top choices for Stockbridge adventure hotels

Best Western Plus Berkshire Hills Inn & Suites