4 Night Adventure vacations in The Berkshires

Price found within the past 48 hours. Click for updated prices.

The Red Lion Inn

$753

per person

Nov 23 - Nov 27

found 1 day ago

Roundtrip non-stop flight included

Jacksonville (JAX) to Albany (ALB)

8.8/10 Excellent! (1,010 reviews)

This is a historical hotel and indeed the history is fabulous, everything appears like it did in 1773. Trouble is the rooms are also like this and the beds felt like they were 200 years old - so very uncomfortable. All part of the experience. Our room faced the street and I was surprised how much traffic noise kept me up until late at night, next time I will request a room facing inward. Not enough staff at the bar and dining during peak weekends, took forever just to get a cup of hot chocolate for the kids. But, very quaint, beautiful, that Main Street is just classic.

Reviewed on Oct 21, 2025

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Book a The Berkshires couples adventure vacation for the ultimate in romance and memory-making. Stunning scenery, heart-racing happenings, and the grandeur of the great outdoors—it’s the best way to bond.

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Top Adventure The Berkshires Hotels

Vacation Village in the Berkshires

276 Brodie Mountain Rd, Williamstown, MA

35 min drive from Tanglewood Music Center

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 ...

8.6/10 Excellent! (2,079 reviews)

Front desk was friendly and helpful. Plenty of parking near our specific unit. Our room was clean, spacious, and very comfortable. The pool and hot tub area were clean and had plenty of towels to use. This was our first time here and we will definitely come back.

Reviewed on Oct 19, 2025

Hampton Inn & Suites Berkshires-Lenox

445 Pittsfield Rd, Lenox, MA

8 min drive from Tanglewood Music Center

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)

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Reviewed on Oct 14, 2025

Berkshire Valley Inn

2541 Hancock Rd, Williamstown, MA

42 min drive from Tanglewood Music Center

Stay at this hotel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...

9/10 Wonderful! (563 reviews)

We had a short but pleasant stay.

Reviewed on Sep 30, 2025

See all 1,105 properties in The Berkshires

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.