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

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....
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

New Marlborough
With a stay at this cottage in Great Barrington, you'll be on the waterfront, just steps from Lake Buel and a 4-minute drive from Les Trois Emme Winery.
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
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
Save an average of 15% on thousands of hotels when you're signed in
Entire cottage in Berkshire Villiage

Entire cottage in Berkshire Villiage

3 out of 5
Lanesborough
Located in Lanesborough, this cottage is on a lake, within a 10-minute drive of St Mary's of the Assumption Church and Crane Museum of Papermaking.
Entire cottage in Berkshire Villiage
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!
The Blue Elm - A Historic Berkshire Cottage

The Blue Elm - A Historic Berkshire Cottage

Sheffield
The price is AU$636 per night from 25 Aug to 26 Aug
AU$636
25 Aug - 26 Aug
includes taxes & fees
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
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
Quiet rustic cottage with shared lake access

Quiet rustic cottage with shared lake access

New Marlborough
With a stay at this cottage in Great Barrington, you'll be on a lake, just steps from Lake Buel and a 4-minute drive from Les Trois Emme Winery.
Quiet rustic cottage with shared lake access
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

New Marlborough
Located in Great Barrington, this cottage is on a lake, within a 5-minute drive of Lake Buel and Les Trois Emme Winery.
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
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
95 Cottages
Lowest Price
AU$121
Highest Price
AU$636
Popular accommodation
Private Island - Largest Fresh Water Reservoir in Mass...., Rustic Berkshires Cottage at Lake Buel w/ Kayaks!, Charming historic cottage on scenic road to Mt. Greylock, Entire cottage in Berkshire Villiage, East Otis Vacation Rental w/ Private Deck & BBQ!, The Blue Elm - A Historic Berkshire Cottage, Beachwood Cottage, Quiet rustic cottage with shared lake access, Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

Top trending hotels in The Berkshires

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is AU$202 per night from 27 Aug to 28 Aug
AU$202
27 Aug - 28 Aug
includes taxes & fees
With a stay at Vacation Village in the Berkshires in Williamstown, you'll be a 3-minute drive from Jiminy Peak Mountain Resort and 5 minutes from Mountain ...
Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
With a stay at Berkshire Mountain Lodge in Pittsfield, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Guido's ...
Berkshire Mountain Lodge
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is AU$121 per night from 28 Aug to 29 Aug
AU$121
28 Aug - 29 Aug
includes taxes & fees
Located in Pittsfield, FairBridge Inn Express is in the suburbs, a 4-minute drive from Crane Museum of Papermaking and 6 minutes from Berkshire Athenaeum.
FairBridge Inn Express
Save an average of 15% on thousands of hotels when you're signed in
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is AU$158 per night from 1 Sept to 2 Sept
AU$158
1 Sept - 2 Sept
includes taxes & fees
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
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.