Photo by Photo courtesy of Berkshire Visitors Bureau
Holiday 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 holiday homes
Florida Mountain Log Cabin
Florida Mountain Log CabinFlorida
10.0 out of 10, Exceptional, (4 reviews)
"Place was super clean. Beds were comfortable. Location was great."
Tristan e.
The price is NZ$555
includes taxes & fees
24 Feb - 25 Feb
Home in Great Barrington
Home in Great BarringtonGreat Barrington
9.8 out of 10, Exceptional, (27 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 NZ$445
includes taxes & fees
25 Feb - 26 Feb
3-bedroom house in beautiful Berkshires, close to amenities!
3-bedroom house in beautiful Berkshires, close to amenities!Pittsfield
The price is NZ$505
includes taxes & fees
2 Mar - 3 Mar
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, DineSherwood Forest
9.8 out of 10, Exceptional, (13 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
Matthew F.
The price is NZ$649
includes taxes & fees
24 Feb - 25 Feb
North Getaway Cottage
North Getaway CottageWilliamstown
9.2 out of 10, Wonderful, (24 reviews)
"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"
Carole S.
The price is NZ$734
includes taxes & fees
24 Feb - 25 Feb
Family Ski Getaway in the Berkshires
Family Ski Getaway in the BerkshiresGreat Barrington
9.0 out of 10, Wonderful, (11 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
Cristine C.
The price is NZ$521
includes taxes & fees
26 Feb - 27 Feb
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, (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 NZ$912
includes taxes & fees
2 Mar - 3 Mar
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
Liz V.
The price is NZ$809
includes taxes & fees
25 Feb - 26 Feb
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 holiday 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
Berkshire Mountain Lodge
10/10 Excellent
Find out more about The Berkshires
The Berkshires Holiday Homes information
Number of reviews | 279 |
|---|---|
Accommodation | 328 Holiday Homes |
Lowest Price | NZ$441 |
Highest Price | NZ$2,128 |
Explore a world of travel with Expedia
- Lenox Hotels
- Great Barrington Hotels
- Stockbridge Hotels
- Peru Hotels
- Washington Hotels
- Becket Hotels
- Hotels near Berkshire Museum
- Hotels near Magnolia Bluffs Casino
- Chesterfield Hotels
- Chester Hotels
- Mount Washington Hotels
- Blandford Hotels
- Hotels near Tanglewood Music Center
- Pittsfield Hotels
- Hotels near Walter J. Koladza
- Sheffield Hotels
- Granville Hotels
- Hotels near Lake Mansfield Park
- New Marlborough Hotels
- South Egremont Hotels
- Russell Hotels
- Alford Hotels
- Tyringham Hotels
- Richmond Hotels
- Lee Hotels
- Huntington Hotels
- Monterey Hotels
- Otis Hotels
- Dalton Hotels
- Berkshire County Hotels
- West Stockbridge Hotels
- Hotels near Guido's Marketplace
- Westfield Hotels
- Hotels near Ashintully Gardens
- Beach Hotels in Lee
- Lgbt Welcoming Hotels in Lee
- Cheap Hotels in Lenox
- Golf Hotels in The Berkshires
- Luxury Hotels in The Berkshires
- Hotels with Pool in Sheffield
- Resort in Hinsdale
- Motels in New Ashford
- Motels in Northampton
- Motels in South Hadley
- B&B in Great Barrington
- B&B in Ashuwillticook Rail Trail
- B&B in The Berkshires
- Resort in The Berkshires
- Cabin Rentals in The Berkshires
- Apartments in Southwick
- Country House in Western Massachusetts
- B&B in Western Massachusetts
- Apartments in Westfield
- Apartments in Holyoke
- Cottages in Mill River
- B&B in Adams
- Motels in Becket
- Condo Rentals in Otis
- Apartments in Granville
- B&B in Granville
- Resort in Granville
- B&B in Lenox
- Cottages in Lenox
- Cabin Rentals in Cheshire
- Lodges in Cheshire
- Apartments in Lanesborough
- Cottages in Southfield
- B&B in Springfield
- Motels in Springfield
- Accor Hotels in Russell
- Visit Western Massachusetts
- Visit The Berkshires
- Visit Great Barrington
- Visit West Stockbridge
- Visit Middlefield
- Visit Tyringham
- Visit Otis
- Beach Holiday Packages Western Massachusetts
- All inclusive Holiday Packages Western Massachusetts
- Goose Pond Reservation
- Otis Holidays
- Pittsfield Holidays
- Ski Butternut
- National Shrine of the Divine Mercy
- Norman Rockwell Museum