Make like a snowbird and escape from the Cape! Go West, young man, to The Berkshires. Located across the Commonwealth, the mountainy region is a year-round destination with something for everyone. Wait, we're starting to sound like a tourism board, or worse, a chamber of commerce. Let's start over - if you're having withdrawal from the New York summer tourists and want to visit, we've located them in The Berkshires. Hike with them on the Appalachian Trail, spend some BerkShares, stretch with them at Kripalu, sit next to them at The Mahaiwe, or just chill in one of the seasonal rentals we picked out and avoid them altogether.
Read More:format(webp)/cdn.vox-cdn.com/uploads/chorus_image/image/48740115/curbed_placeholder.54.0.jpg)
Escape From the Cape With These Berkshire Vacation Rentals
View as Map
1. Egremont
Blunt Rd & Baldwin Hill Rd W
Egremont, MA 01230
Egremont, MA 01230
Located 10 minutes from Great Barrington, this 1700s farmhouse is available for $5,000 per week. The three bedroom, three and a half bath features a chef's kitchen, a spring fed swimming pool, and a barn with a sleeping loft and yoga studio (Bikram, we hope).
2. Alford
Alford Rd
Alford, MA 01230
Alford, MA 01230
We chose this $20,000 per month summer rental just for its name, "Tofu's Retreat." We have no idea whether that means it's the perfect place for wealthy vegans to hide from the carnivorous masses or some other inside joke, but the pool looks nice.
3. Great Barrington
Long Pond Rd
Great Barrington, MA 01230
Great Barrington, MA 01230
This one-of-a-kind modern home in the mountains is available from $3060 per night or $45,000 per month. The nine bedroom accommodates 16+ and features a 25 meter lap pool (sorry, we're too lazy to convert), jacuzzi, private ski/sleding hill, art studio, media room, and more.
4. West Stockbridge
Great Barrington Rd
West Stockbridge, MA
West Stockbridge, MA
This 1850s farmhouse on four acres rents nightly and weekly. Rates vary depending on the season and number of guests - it sleeps up to 12 - starting at $290 per night or $1,375 per week. The five bedroom, two bath features original details, a fully equipped country kitchen and a screened in porch.
5. Housatonic
Park St
Housatonic, MA
Housatonic, MA
Here's a two bedroom apartment, or as the listing calls it, an "artist's flat." The conveniently located property (it's even close to public transportation) accommodates up to four and rents for $145 per night with a two night minimum stay.
6. Stockbridge
Rattlesnake Mountain Rd
Stockbridge, MA
Stockbridge, MA
Listed as a $2,000 per week summer rental, this "super cool contemporary with drop dead views" is close to the centers of both Lenox and Stockbridge. The 2,130 sq. ft. three bedroom, two and a half bath features a wood burning fireplace, a new kitchen and a master suite.
7. Sheffield
Hickey Hill Rd
Sheffield, MA
Sheffield, MA
Located on the border of Sheffield and New Marlborough, this $3,000 per month three bedroom offers "stylish and modern country living" on 14.21 acres. Amenities include an open chef's kitchen, screened porch and a media room. Plus, there are westerly views over the Housatonic Valley to the Taconic Range from every room.
8. New Marlborough
Hayes Hill Rd
New Marlborough, MA
New Marlborough, MA
Brook Haus is a three bedroom, three bath renting for $3,000 per week. The "magical, hip renovation" features a cook's kitchen, original fireplace and two separate areas for dining and living. Outside, there's a wood fired hot tub on the master deck and a far out enameled fireplace on the front deck.
9. Mill River
Hartsville Mill River Rd
Great Barrington, MA 01230
Great Barrington, MA 01230
Across from the Konkopot River is this "sweet turn of the century cottage." The two bedroom accommodates five and is available for $250 per night with a two night minimum. There's a spring and summer veggie/herb garden "for the ultimate in locavore harvesting." Take that, Tofu's Retreat!
10. Monterey
Fairview Rd
Monterey, MA 01245
Monterey, MA 01245
This contemporary on a county road across from Beartown State Forest is available as a three month winter rental for $18,000. The 3-4 bedroom with views from most rooms sleeps 8 and includes winter-friendly amenities such as a heated mudroom and an attached two-car garage.
© 2021 Vox Media, Inc. All rights reserved.