Hot The Berkshires Cottage Rates

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Cottages in The Berkshires

Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location

Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location

Pittsfield
With a stay at this vacation home in Pittsfield, you'll be within a 10-minute drive of Pittsfield Dog Park and Crane Museum of Papermaking.
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Charming historic cottage on scenic road to Mt. Greylock

Charming historic cottage on scenic road to Mt. Greylock

Lanesboro
With a stay at this cottage in Lanesborough, you'll be in the mountains, within a 10-minute drive of Jiminy Peak Mountain Resort and Mount Greylock State ...
Charming historic cottage on scenic road to Mt. Greylock
Perfect Vacation Get Away - Historical New Marlborough

Perfect Vacation Get Away - Historical New Marlborough

New Marlborough
Located in Great Barrington, this cottage is in a rural location, a 4-minute drive from Dry Hill and 5 minutes from New Marlborough Town Hall.
Perfect Vacation Get Away - Historical New Marlborough
Save an average of 15% on thousands of hotels when you're signed in
East Otis Vacation Rental w/ Private Deck & BBQ!

East Otis Vacation Rental w/ Private Deck & BBQ!

East Otis
With a stay at this cottage in Otis, you'll be on the waterfront, just steps from Otis Reservoir and a 3-minute drive from Larkum Pond.
East Otis Vacation Rental w/ Private Deck & BBQ!
Cozy Berkshire cottage with fireplace.

Cozy Berkshire cottage with fireplace.

Pittsfield
With a stay at this cottage in Pittsfield, you'll be in the mountains, within a 15-minute drive of Tanglewood Music Center and Guido's Marketplace.
Cozy Berkshire cottage with fireplace.
The Blue Elm - A Historic Berkshire Cottage

The Blue Elm - A Historic Berkshire Cottage

Sheffield
Located in Ashley Falls, this cottage is in a rural location, within a 15-minute walk of Ashley Falls Woods and Housatonic River.
The Blue Elm - A Historic Berkshire Cottage
Lake Views & Dock Access - Pittsfield Cottage!

Lake Views & Dock Access - Pittsfield Cottage!

Pittsfield
Located in Pittsfield, this cottage is on the waterfront, within a 10-minute drive of Pittsfield Dog Park and Crane Museum of Papermaking.
Lake Views & Dock Access - Pittsfield Cottage!
Beachwood Cottage

Beachwood Cottage

Stockbridge
With a stay at this cottage in West Stockbridge, you'll be on a lake, within a 10-minute drive of Tanglewood Music Center and Stockbridge Bowl.
Beachwood Cottage
Private Island - Largest Fresh Water Reservoir in Mass....

Private Island - Largest Fresh Water Reservoir in Mass....

Otis
With a stay at this cottage in Otis, you'll be on the waterfront, just steps from Otis Reservoir and a 4-minute drive from Larkum Pond.
Private Island - Largest Fresh Water Reservoir in Mass....
Don't see what you're looking for?
See all available properties in The Berkshires
View all properties
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.

The Berkshires Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in The Berkshires will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to The Berkshires definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in The Berkshires, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

The Berkshires Cottages essential information

Accommodation
84 Cottages
Lowest Price
Highest Price
Popular accommodation
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location, Charming historic cottage on scenic road to Mt. Greylock, Perfect Vacation Get Away - Historical New Marlborough, East Otis Vacation Rental w/ Private Deck & BBQ!, Cozy Berkshire cottage with fireplace., The Blue Elm - A Historic Berkshire Cottage, Lake Views & Dock Access - Pittsfield Cottage!, Beachwood Cottage, Private Island - Largest Fresh Water Reservoir in Mass....

Top trending hotels in The Berkshires

Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
With a stay at Quality Inn in Great Barrington, you'll be near ski lifts, just a 4-minute walk from Mahaiwe Performing Arts Center and 7 minutes by foot from ...
Quality Inn
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
Located in Lenox, The Yankee, Trademark Collection by Wyndham is on the Strip, a 4-minute drive from Bousquet Ski Area and 7 minutes from Shakespeare and ...
The Yankee, Trademark Collection by Wyndham
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
Fully refundableReserve now, pay when you stay
Located in Pittsfield, Best Western Plus Berkshire Hills Inn & Suites is a 2-minute drive from Hancock Shaker Village and 5 minutes from Bousquet Ski Area.
Best Western Plus Berkshire Hills Inn & Suites
Save an average of 15% on thousands of hotels when you're signed in
Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
A stay at Hotel Downstreet, Ascend Hotel Collection places you in the heart of North Adams, steps from MCLA Gallery 51 and North Adams City Hall.
Hotel Downstreet, Ascend Hotel Collection
Don't see what you're looking for?
See all available properties in The Berkshires
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.