Stockbridge Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €185 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Stockbridge
The Red Lion Inn
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
The price is €181 per night from 14 Jan to 15 Jan
€181
14 Jan - 15 Jan 2026
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Old time charm and hot tub under the stars
Reviewed on 15 Dec 2025
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183 Stockbridge MA
The price is €395 per night from 5 Jan to 6 Jan
€395
5 Jan - 6 Jan 2026
includes taxes & fees
9.2/10 Wonderful! (85 reviews)
It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!
Reviewed on 27 Oct 2025
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
The price is €109 per night from 4 Jan to 5 Jan
€109
4 Jan - 5 Jan 2026
includes taxes & fees
8.6/10 Excellent! (2,170 reviews)
Awesome for ski
Reviewed on 14 Dec 2025
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.
Popular places to visit
National Shrine of the Divine Mercy
Learn about the local history of Stockbridge when you spend time at National Shrine of the Divine Mercy. While you're in the area, stroll along the lakeside.
Naumkeag Museum
You can spend time studying the exhibits at Naumkeag Museum in Stockbridge. While you're in the area, stroll along the lakeside.
Berkshire Botanical Garden
Explore the great outdoors at Berkshire Botanical Garden, a lovely green space in Stockbridge. While you're in the area, stroll along the lakeside.
Explore a world of travel with Expedia
- 4 Star Hotels in Chester
- 4 Star Hotels in Granville
- 4 Star Hotels in Western Massachusetts
- Alford Hotels
- Becket Hotels
- Cabin Rentals in Cheshire
- Cheshire Hotels
- Apartments in Chesterfield
- Dalton Hotels
- Drury Hotels
- Apartments in Granville
- Cheap Hotels in Great Barrington
- Hotels with Spa in Great Barrington
- Great Barrington Hotels
- Hotels with Spa in Hancock
- Hancock Hotels
- Hotels near Jacob's Pillow
- Hotels near Jiminy Peak Mountain Resort
- Hotels near Kennedy Park
- Apartments in Lee
- Historic Hotels in Lee
- Lee Hotels
- Cheap Hotels in Lenox
- Lenox Hotels
- Hotels near National Shrine of the Divine Mercy
- Cabin Rentals in October Mountain State Forest
- Otis Hotels
- Luxury Hotels in Pittsfield
- Hotels with Spa in Pittsfield
- Pittsfield Hotels
- Plainfield Hotels
- Richmond Hotels
- Russell Hotels
- Savoy Hotels
- Cabin Rentals in Sheffield
- Southfield Hotels
- Stockbridge Hotels
- Hotels near Tanglewood Music Center
- Cabin Rentals in The Berkshires
- Cottages in The Berkshires
- Boutique Hotels in The Berkshires
- Cheap Hotels in The Berkshires
- Hotels with Spa in The Berkshires
- West Stockbridge Hotels
- Cabin Rentals in Western Massachusetts
- Castles in Western Massachusetts
- Luxury Hotels in Western Massachusetts
- Williamstown Hotels
- Windsor Hotels
- Becket Land Trust Historic Quarry
- Visit Sherwood Forest
- Visit Becket
- Berkshire Botanical Garden
- Charlemont Federated Church
- Charlemont Holidays
- Charles H. Baldwin & Sons
- Visit Cheshire
- Chesterfield Holidays
- Chesterwood
- Visit Great Barrington
- Visit Hancock
- Lee Holidays
- Visit Lee
- Romantic Holiday Packages The Berkshires
- Mclennan Reservation
- Visit Middlefield
- National Shrine of the Divine Mercy
- Naumkeag Museum
- Otis Holidays
- Visit Pittsfield
- Rowe Holidays
- Visit South Lee
- Visit Southampton
- Springfield Holidays
- Studio 21 South
- Tanglewood Music Center
- Visit Western Massachusetts
- White Barn Studio
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
