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Wilder House Berkshires

Wilder House Berkshires

2 out of 5
48 S Main Street Sheffield MA
  • 8 min drive from Ashley House
Stay at this B&B in Sheffield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife ...
9.6/10 Exceptional! (38 reviews)
Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you!

Reviewed on Nov 10, 2025

Wilder House Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
  • 59 min drive from Ashley House
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (776 reviews)
Friendly staff, room was very clean. Pool area well maintained. Overall a great place to stay

Reviewed on Nov 30, 2025

Berkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
  • 55 min drive from Ashley House
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
9/10 Wonderful! (804 reviews)
Enjoyed the Clubhouse before retiring in for the evening. Cozy, comfortable, and relaxing atmosphere.

Reviewed on Nov 10, 2025

Berkshires Untold
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
  • 37 min drive from Ashley House
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
8.8/10 Excellent! (1,003 reviews)
Quaint Inn located in the Berkshire. Dinner in the tavern was delish. The main inn lobby has plenty of seating to lounge around and people watch. We enjoyed our stay.

Reviewed on Nov 20, 2025

The Red Lion Inn
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
  • 36 min drive from Ashley House
Book a stay at this family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in ...
9/10 Wonderful! (791 reviews)
We stayed over Thanksgiving and it did not disappoint. The customer service was great, the indoor pools were clean, there were tons of activities for kids even over the holiday. We will be back!

Reviewed on Nov 29, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
  • 57 min drive from Ashley House
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 ...
9/10 Wonderful! (1,011 reviews)
Everything was a great experience

Reviewed on Nov 28, 2025

The Yankee, Trademark Collection by Wyndham
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St Lee MA
  • 44 min drive from Ashley House
Stay at this hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions ...
9/10 Wonderful! (1,006 reviews)
Great service. Attentive staff. Great location. Rooms clean and comfortable. Thanks for another great stay!

Reviewed on Nov 29, 2025

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
445 Pittsfield Rd Lenox MA
  • 57 min drive from Ashley House
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 ...
9/10 Wonderful! (1,002 reviews)
Yes

Reviewed on Nov 24, 2025

Hampton Inn & Suites Berkshires-Lenox
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 out of 5
415 Stockbridge Rd Great Barrington MA
  • 26 min drive from Ashley House
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
8.8/10 Excellent! (702 reviews)
Everyone was Curtieus and very helpful !!! Room was very clean and nice!!!! Would be glad to stay again !!!! Thank You for making our stay pleasant and welcoming !!!! To all of the staff, Have A Great. Holiday Season !!!!!

Reviewed on Dec 1, 2025

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3 out of 5
70 Pittsfield Rd Lenox MA
  • 53 min drive from Ashley House
Book a stay at this business-friendly hotel in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (588 reviews)
Clean room. Very nice staff. Quiet.

Reviewed on Nov 29, 2025

Courtyard by Marriott Lenox Berkshires
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
  • 58 min drive from Ashley House
Stay at this hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Guido's Marketplace and Herman Melville's Arrowhead ...
9.2/10 Wonderful! (63 reviews)
I visited Berkshire area for Thanksgiving and stayed at the brand new Holiday Inn Express. It was fantastic! The hotel is beautiful and pet friendly but also in a great location. The staff were amazing and professional. Over all 10/10 stay. Will definitely stay there again

Reviewed on Nov 28, 2025

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street Great Barrington MA
  • 22 min drive from Ashley House
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 ...
8.4/10 Very Good! (1,004 reviews)
Room was extremely clean, beds very comfortable, staff friendly. The only problem was the noisy heating system which loudly switched on and off at night preventing us from getting a good nights sleep. I would also suggest getting a room in the front of the hotel, rather than the back, since a train ...

Reviewed on Nov 22, 2025

Quality Inn
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.

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