Photo by Photo courtesy of Berkshire Visitors Bureau
Search Vacation Homes in The Berkshires
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for The Berkshires vacation homes
Vacation Home in Great Barrington
Home in Great Barrington9.8 out of 10, Exceptional, (26 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
Cameron M.
The price is ￥23,064
￥39,546 total
includes taxes & fees
Jan 26 - Jan 27
The price is ￥33,853
￥54,777 total
includes taxes & fees
Feb 16 - Feb 17
Vacation Home in Florida
Florida Mountain Log Cabin10.0 out of 10, Exceptional, (4 reviews)
"Place was super clean. Beds were comfortable. Location was great."
Tristan e.
The price is ￥29,067
￥53,792 total
includes taxes & fees
Jan 22 - Jan 23
Vacation Home in Sherwood Forest
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine9.6 out of 10, Exceptional, (10 reviews)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
James D.
The price is ￥25,342
￥59,935 total
includes taxes & fees
Jan 25 - Jan 26
Vacation Home in Hancock
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con9.8 out of 10, Exceptional, (72 reviews)
"Howie was a great host, very responsive and accommodating. If we find ourselves in the area in the future , will def try to stay here again "
jon e.
The price is ￥54,576
￥103,722 total
includes taxes & fees
Feb 12 - Feb 13
Vacation Home in Great Barrington
Family Ski Getaway in the Berkshires9.2 out of 10, Wonderful, (7 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
Cristine C.
The price is ￥32,033
￥47,090 total
includes taxes & fees
Jan 26 - Jan 27
Vacation Home in Lee
Sun Filled Lenox Retreat - Minutes to Tanglewood!9.6 out of 10, Exceptional, (4 reviews)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
Sarah D.
The price is ￥28,474
￥72,799 total
includes taxes & fees
Jan 26 - Jan 27
Vacation Home in Housatonic
Sweet Cozy Victorian in Housatonic. Close to everything.10.0 out of 10, Exceptional, (3 reviews)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
Cheryl F.
The price is ￥21,356
￥42,408 total
includes taxes & fees
Feb 1 - Feb 2
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.
Find vacation rentals that suit your style
Cabins
Aparthotels
Save an average of 15% on thousands of hotels when you're signed in
Top The Berkshires Hotel Reviews
The Yankee, Trademark Collection by Wyndham
10/10 Excellent
Find out more about The Berkshires
The Berkshires Vacation Homes information
Number of reviews | 439 |
|---|---|
Accommodation | 327 Vacation Homes |
Lowest Price | ￥31,825 |
Highest Price | ￥210,112 |
Explore a world of travel with Expedia
- Plainfield Hotels
- Cheap Hotels in Mount Washington
- B&B in Lenox
- Otis Hotels
- Rv Parks in Monterey
- Holyoke Hotels
- Cheap Hotels in Westfield
- Hotels near Mount Greylock
- Cheap Hotels in Southfield
- Aparthotels in Sheffield
- Aparthotels in Otis
- Hotels near Jiminy Peak Mountain Resort
- Villas in Otis
- Sheffield Hotels
- Luxury Hotels in Springfield
- Condo Rentals in Sheffield
- Cheap Hotels in South Lee
- Peru Hotels
- Hotels near MGM Springfield
- Family Hotels in Monterey
- Hotels with Free Parking in East Springfield
- Hotels with Free Parking in Springfield
- Pittsfield Hotels
- Hotels near Mount Holyoke College
- Hotels near Smith College
- South Egremont Hotels
- Resorts in Stockbridge
- Resorts in Washington
- Inns in Sandisfield
- Aparthotels in Lee
- B&B in Sheffield
- Green Hotels in Sheffield
- Hotels near Tanglewood Music Center
- Ashley Falls Hotels
- Business Hotels in Hadley
- Amherst Hotels
- Resorts in Becket
- Hotels near Holyoke Mall
- Resorts in Monterey
- Hotels near Ski Butternut
- Hotels near Colonial Theater
- Cheap Hotels in Stockbridge
- Hinsdale Hotels
- Mount Washington Hotels
- Resorts in Otis
- Luxury Hotels in Peru
- Cheap Hotels in Boston Road
- Rv Parks in Lee
- Luxury Hotels in Lenox
- Guest Houses in Stockbridge
- Cheap Hotels in South Hadley
- Hadley Hotels
- Motels in Monterey
- Springfield Hotels
- Luxury Hotels in East Longmeadow
- Inns in Lenox
- Aparthotels in Chester
- Cheap Hotels in Peru
- Cottages in Washington
- Motels in Otis
- Pet-Friendly Hotels in Pittsfield
- Hotel with a Concierge Hotels in Savoy
- Richmond Hotels
- Resorts in Granville
- Motels in Southfield
- Luxury Hotels in The Berkshires
- Guest Houses in Monterey
- All-Inclusive Hotel Hotels in Becket
- Resorts in Mount Washington
- Cheap Hotels in Lenox
- Business Hotels in Northampton
- Chicopee Hotels
- Housatonic Hotels
- Northampton Hotels
- Farmstay in The Berkshires
- Resorts in The Berkshires
- Cheap Hotels in Metro Center
- Boutique Hotels in The Berkshires
- Historic Hotels in Northampton
- Lenox Hotels
- Luxury Hotels in Monterey
- Luxury Hotels in Chester
- Monterey Hotels
- Hotels near University of Massachusetts Amherst
- Business Hotels in Lenox
- Hotels near Springfield Union Station
- Hatfield Hotels
- Inns in The Berkshires
- Hotels with Free Parking in Boston Road
- Apartments in Sheffield
- B&B in The Berkshires
- Gay friendly Hotels in Northampton
- Boutique Hotels in Cummington
- Pet-Friendly Hotels in Holyoke
- Stockbridge Hotels
- Hotels near Mount Greylock State Reservation Visitor Center