Photo by Photo courtesy of Berkshire Visitors Bureau
Open Photo by Photo courtesy of Berkshire Visitors Bureau
The Berkshires long stay rentals
Stay a week, a month or longer in a comfortable place all your own
Relax—Stayz takes the hassle out of booking monthly rentals in The Berkshires. The wide selection available and useful search filters make finding your home away from home a breeze. Whether you’re looking for fast Wi-Fi for remote working, a fully equipped kitchen for home cooking or a pool where you can relax with a good book, you’re sure to find it on Stayz. Many long-term rentals in The Berkshires are great for kids and welcome four-legged friends, too. What's more, some offer monthly discounts on extended-stay homes and weekly discounts on shorter-term rentals.
Featured long stay living spaces - The Berkshires
Properties highly-rated for stays of 28 nights or longer, with space to feel right at home
Showing deals for:29 June - 27 July
Image gallery for InTown Victorian Front House 5 Bd 3.5 Ba Back House 6 Bd 4 Ba Both 11 Bd 7.5 Ba
9.89.8 out of 10, Exceptional, (59 reviews)
Exceptional
(59 reviews)
InTown Victorian Front House 5 Bd 3.5 Ba Back House 6 Bd 4 Ba Both 11 Bd 7.5 Ba
Stockbridge
9% off
Price is AU$33,577
AU$33,577
for 28 nights, 1 home
AU$1,199 per night
includes taxes & fees
Image gallery for Beautiful cabin in the woods close to skiing, hiking and shopping with hot tub.
8.08.0 out of 10, Very good, (1 review)
Very good
(1 review)
Beautiful cabin in the woods close to skiing, hiking and shopping with hot tub.
Austerlitz
17% off
Price is AU$17,855
AU$17,855
for 28 nights, 1 cabin
AU$638 per night
includes taxes & fees
Image gallery for Cozy escape in the trees of the Berkshires
1010 out of 10, Exceptional, (4 reviews)
Exceptional
(4 reviews)
Cozy escape in the trees of the Berkshires
Great Barrington
13% off
Price is AU$24,970
AU$24,970
for 28 nights, 1 home
AU$892 per night
includes taxes & fees
Image gallery for Stylish remodeled 2 bedroom property in enchanting Shelburne Falls Village.
1010 out of 10, Exceptional, (23 reviews)
Exceptional
(23 reviews)
Stylish remodeled 2 bedroom property in enchanting Shelburne Falls Village.
Shelburne Falls
12% off
Price is AU$8,031
AU$8,031
for 28 nights, 1 home
AU$287 per night
includes taxes & fees
Image gallery for Beautiful Timber Frame Home in the Berkshires /Available for Long Term
1010 out of 10, Exceptional, (19 reviews)
Exceptional
(19 reviews)
Beautiful Timber Frame Home in the Berkshires /Available for Long Term
Washington
16% off
Price is AU$19,623
AU$19,623
for 28 nights, 1 home
AU$701 per night
includes taxes & fees
Image gallery for Magical yurt in the woods, full kitchen! Haydenville, Massechusettes
1010 out of 10, Exceptional, (3 reviews)
Exceptional
(3 reviews)
Magical yurt in the woods, full kitchen! Haydenville, Massechusettes
Williamsburg
13% off
Price is AU$4,330
AU$4,330
for 28 nights, 1 cabin
AU$155 per night
includes taxes & fees
Image gallery for Cozy Cabin with HOT TUB in Copake Lake - near winter activities!
1010 out of 10, Exceptional, (2 reviews)
Exceptional
(2 reviews)
Cozy Cabin with HOT TUB in Copake Lake - near winter activities!
Copake Lake
8% off
Price is AU$10,583
AU$10,583
for 28 nights, 1 cabin
AU$378 per night
includes taxes & fees
Image gallery for Traveler Dream Space in the Center of Downtown Bennington Steps From Everything!
9.69.6 out of 10, Exceptional, (20 reviews)
Exceptional
(20 reviews)
Traveler Dream Space in the Center of Downtown Bennington Steps From Everything!
Bennington
26% off
Price is AU$8,362
AU$8,362
for 28 nights, 1 apartment
AU$299 per night
includes taxes & fees
Image gallery for Secluded large country home for big groups with giant open yard for outdoor fun.
9.49.4 out of 10, Exceptional, (31 reviews)
Exceptional
(31 reviews)
Secluded large country home for big groups with giant open yard for outdoor fun.
Whitingham
30% off
Price is AU$11,779
AU$11,779
for 28 nights, 1 home
AU$421 per night
includes taxes & fees
Image gallery for Spacious Home nestled along the Blackberry River in Northwest CT
1010 out of 10, Exceptional, (92 reviews)
Exceptional
(92 reviews)
Spacious Home nestled along the Blackberry River in Northwest CT
East Canaan
8% off
Price is AU$13,240
AU$13,240
for 28 nights, 1 home
AU$473 per night
includes taxes & fees
Image gallery for Spacious/Elegant 3 level house on Spruce Lake- swim or fish, short drive to Mt.
9.49.4 out of 10, Exceptional, (25 reviews)
Exceptional
(25 reviews)
Spacious/Elegant 3 level house on Spruce Lake- swim or fish, short drive to Mt.
Wilmington
37% off
Price is AU$21,379
AU$21,379
for 28 nights, 1 home
AU$764 per night
includes taxes & fees
Image gallery for Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
1010 out of 10, Exceptional, (15 reviews)
Exceptional
(15 reviews)
Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
Sheffield
17% off
Price is AU$20,510
AU$20,510
for 28 nights, 1 home
AU$733 per night
includes taxes & fees
Image gallery for Enjoy all Four Seasons in Beautiful Wilmington, VT; 15 min from Mt. Snow
1010 out of 10, Exceptional, (46 reviews)
Exceptional
(46 reviews)
Enjoy all Four Seasons in Beautiful Wilmington, VT; 15 min from Mt. Snow
Wilmington
8% off
Price is AU$10,187
AU$10,187
for 28 nights, 1 home
AU$364 per night
includes taxes & fees
Image gallery for Getaway Near Mass MoCA, Great Hiking, Scenic Views
1010 out of 10, Exceptional, (29 reviews)
Exceptional
(29 reviews)
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
13% off
Price is AU$5,710
AU$5,710
for 28 nights, 1 apartment
AU$204 per night
includes taxes & fees
Image gallery for SKIING, PARTY SAFELY IN THE SNOW! NO NEED TO DRINK & DRIVE.
1010 out of 10, Exceptional, (52 reviews)
Exceptional
(52 reviews)
SKIING, PARTY SAFELY IN THE SNOW! NO NEED TO DRINK & DRIVE.
Wilmington
13% off
Price is AU$39,986
AU$39,986
for 28 nights, 1 home
AU$1,428 per night
includes taxes & fees
Image gallery for Romantic 1-Bedroom Retreat in Downtown Shelburne Falls—Walk to Everything
1010 out of 10, Exceptional, (2 reviews)
Exceptional
(2 reviews)
Romantic 1-Bedroom Retreat in Downtown Shelburne Falls—Walk to Everything
Shelburne Falls
13% off
Price is AU$12,300
AU$12,300
for 28 nights, 1 apartment
AU$439 per night
includes taxes & fees
Image gallery for Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
1010 out of 10, Exceptional, (45 reviews)
Exceptional
(45 reviews)
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
Hancock
13% off
Price is AU$30,241
AU$30,241
for 28 nights, 1 home
AU$1,080 per night
includes taxes & fees
Image gallery for 19th Century Farm House on 300 Acre Farm
1010 out of 10, Exceptional, (1 review)
Exceptional
(1 review)
19th Century Farm House on 300 Acre Farm
Ghent
18% off
Price is AU$44,075
AU$44,075
for 28 nights, 1 home
AU$1,574 per night
includes taxes & fees
Image gallery for Tutti Farmhouse - 6 bedroom 3 bath 1847 Farmhouse Upstate NY
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Tutti Farmhouse - 6 bedroom 3 bath 1847 Farmhouse Upstate NY
Petersburg
23% off
Price is AU$41,313
AU$41,313
for 28 nights, 1 home
AU$1,475 per night
includes taxes & fees
Image gallery for Modern Log Chalet - 10 acres, views, and a pond!
1010 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Modern Log Chalet - 10 acres, views, and a pond!
Chatham
9% off
Price is AU$33,968
AU$33,968
for 28 nights, 1 home
AU$1,213 per night
includes taxes & fees
Image gallery for Cozy Condo Near MASS MoCA
1010 out of 10, Exceptional, (17 reviews)
Exceptional
(17 reviews)
Cozy Condo Near MASS MoCA
North Adams
17% off
Price is AU$11,650
AU$11,650
for 28 nights, 1 home
AU$416 per night
includes taxes & fees
Image gallery for La Petite Maison, Chatham, NY
9.89.8 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
La Petite Maison, Chatham, NY
Chatham
25% off
Price is AU$6,794
AU$6,794
for 28 nights, 1 home
AU$243 per night
includes taxes & fees
Image gallery for Light, Airy And Fabulous
9.09.0 out of 10, Wonderful, (6 reviews)
Wonderful
(6 reviews)
Light, Airy And Fabulous
Monterey
7% off
Price is AU$24,479
AU$24,479
for 28 nights, 1 home
AU$874 per night
includes taxes & fees
Image gallery for 3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
9.69.6 out of 10, Exceptional, (17 reviews)
Exceptional
(17 reviews)
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Hancock
44% off
Price is AU$14,017
AU$14,017
for 28 nights, 1 apartment
AU$501 per night
includes taxes & fees
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Great discounts on monthly rentals in The Berkshires
You’ll often find discounted rates for long stays of over 28 days on Stayz, making stays of a month or more excellent value.
Entire homes, maximum privacy
Looking for your own place to retreat to? On Stayz, you'll enjoy secluded stays with entire monthly rental homes just for you.
Pet-friendly monthly rentals
Many homes welcome guests with animal companions, so you don’t have to leave your pet at home.
The Berkshires Furnished monthly rentals for remote workers
Find your perfect home office set up. There are plenty of stays on Stayz with dedicated workspaces and fast Wi-Fi so that you can take your work with you.
Monthly stays with practical kitchens
Most furnished extended-stay rentals in The Berkshires come with well-equipped kitchens ideal for home cooking, so you can enjoy healthy meals in or even host your own dinner parties.
Long-term rentals with parking in The Berkshires
Take advantage of the ‘amenities’ filter to find monthly stays with their very own parking spot for the ultimate in convenience.
Wheelchair-accessible holiday rentals
Stayz offers a range of monthly rental homes designed to accommodate everyone for a comfortable and inclusive extended stay.
Holiday rentals in The Berkshires with pool
Stayz's handy search filters will help you find monthly holiday homes with swimming pools so that you can relax in your very own pool.
Rentals with free cancellation in The Berkshires
Plans change. We get that. With Stayz, you can search, select 'free cancellation,' and see all rentals in The Berkshires with flexible cancellation policies.