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
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
Sharon K.
The price is ￥26,754
￥64,714 total
includes taxes & fees
Jun 25 - Jun 26
Home in Great Barrington
Home in Great BarringtonGreat Barrington
9.8 out of 10, Exceptional, (33 reviews)
"Perfect space for an overnight stay. Very clean and well appointed. Communication from host was great and check in was a breeze. 2 minute drive from downtown Great Barrington."
Anonymous traveler
The price is ￥43,621
￥66,049 total
includes taxes & fees
Jun 29 - Jun 30
Real Estate: Therapy - Lake, Laundry, Love it
Real Estate: Therapy - Lake, Laundry, Love itSherwood Forest
The price is ￥16,156
￥56,124 total
includes taxes & fees
Jul 16 - Jul 17
Cozy Riverside Berkshires Retreat
Cozy Riverside Berkshires RetreatGreat Barrington
9.4 out of 10, Exceptional, (16 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
Cristine C.
The price is ￥36,206
￥55,241 total
includes taxes & fees
Jul 1 - Jul 2
stylish Berkshires Retreat
stylish Berkshires RetreatLee
10.0 out of 10, Exceptional, (1 review)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
Donna K.
The price is ￥34,752
￥77,438 total
includes taxes & fees
Jul 6 - Jul 7
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, CanoeingSherwood Forest
9.8 out of 10, Exceptional, (15 reviews)
"Great place and welcoming stay!"
Frank M.
The price is ￥32,716
￥71,734 total
includes taxes & fees
Jun 30 - Jul 1
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside ConHancock
9.8 out of 10, Exceptional, (74 reviews)
"Helpful host, lovely condo. Great location. Clean, tons of games and movies in unit. Also plenty of coffee pods included!"
Christy F.
The price is ￥42,825
￥88,913 total
includes taxes & fees
Jun 24 - Jun 25
Comfortable Berkshires retreat on mtn resort, SISO
Comfortable Berkshires retreat on mtn resort, SISOHancock
8.4 out of 10, Very Good, (10 reviews)
"Kind and responsive host."
Javier
The price is ￥26,615
￥88,509 total
includes taxes & fees
Jun 25 - Jun 26
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
Villas
Save an average of 15% on thousands of hotels when you're signed in
Top The Berkshires Hotel Reviews
The Yankee Inn
10/10 Excellent
Find out more about The Berkshires
The Berkshires Vacation Homes information
Number of reviews | 350 |
|---|---|
Accommodation | 349 Vacation Homes |
Lowest Price | ￥55,241 |
Highest Price | ￥214,244 |
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