2025 Stockbridge, Massachusetts Hotels

Up To 10% Off Select Hotels With AARP Member Discounts

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The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Free Cancellation
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0.92 km from city center
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Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
Tanglewood Suites

Tanglewood Suites

2.5 out of 5
MA-102, Stockbridge, MA
Free Cancellation
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0.07 km from city center
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Stay at this B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Naumkeag Museum are located ...
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
11.21 km from city center
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Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
13.59 km from city center
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Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
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
Free Cancellation
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16.31 km from city center
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Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
30.95 km from city center
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Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street, South Lee, MA
Free Cancellation
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4.16 km from city center
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Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Free Cancellation
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11.62 km from city center
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Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
The Constance by the Lenox Collection

The Constance by the Lenox Collection

3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
8.13 km from city center
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Stay at this 3.5-star hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
Free Cancellation
18.64 km from city center
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Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Free Cancellation
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14.64 km from city center
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Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in ...
Hotel On North

Hotel On North

3.5 out of 5
297 North Street, Pittsfield, MA
Free Cancellation
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19.18 km from city center
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Stay at this 3.5-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

3 out of 5
435 Laurel St, Lee, MA
6.24 km from city center
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Stay at this 3-star hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular ...
Prospect Berkshires

Prospect Berkshires

2 out of 5
50 Prospect Lake Rd, Egremont, MA
14.64 km from city center
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Stay at this hotel in Great Barrington. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Catamount Aerial Adventure Park and Catamount ...
Quality Inn

Quality Inn

2.5 out of 5
170 Housatonic Street, Lee, MA
6.55 km from city center
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Book a stay at this business-friendly hotel in Lee. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful ...
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
445 Pittsfield Rd, Lenox, MA
Free Cancellation
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13.35 km from city center
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Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
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Stockbridge Hotels

If you're looking for a good rate for when you head to Stockbridge, The AARP Travel Center Powered by Expedia® has plenty of options available for you. We combine members-only benefits with the best rates from Expedia, offering our members the very best price in travel, guaranteed. You can use your membership advantage to book a 5-star resort, or another that's closest to the sights that you want to spend the most time at. Let us help you save money on your upcoming trip to Stockbridge.

Fabulous Accommodations in a Great Location

There are 1,353 accommodations to pick from in Stockbridge, with suggestions to look over so you and your family can see previous guests' vacation tips and ideas for your stay in Stockbridge. Many travelers come to Stockbridge to check out its morning hikes within reach or gorgeous mountain peak views. This city is also known for the chance to experience the great outdoors. You and your fellow travelers will uncover plenty to keep you occupied during your visit. You can always begin by taking a trip into Stockbridge's past. There are 3 historical sites around this city. Start by visiting Naumkeag or Chesterwood, which will provide a detailed look into this city's fascinating history. With us as your travel guide, you will get the rest and relaxation that you deserve on your getaway, and you will travel confidently knowing that we've got your back.

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