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Featured Cottages in The Berkshires

Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake

Otis MA
When you stay at this cottage in Otis, you'll be on a lake, within a 5-minute drive of County Beach and Otis Ridge.
Opens in a new windowCozy Cottage-Sunset On The Lake
The Blue Elm - A Historic Berkshire Cottage

The Blue Elm - A Historic Berkshire Cottage

Sheffield MA
Located in Ashley Falls, this cottage is in a rural location, within a 15-minute walk of Ashley Falls Woods and Housatonic River.
Opens in a new windowThe Blue Elm - A Historic Berkshire Cottage
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 MA
Located in Great Barrington, this cottage is on a lake, within a 5-minute drive of Lake Buel and Les Trois Emme Winery.
Opens in a new windowPine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
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2-bedroom cottage close to skiing with gas fireplace

2-bedroom cottage close to skiing with gas fireplace

New Marlborough MA
With a stay at this cottage in New Marlborough, you'll be within a 5-minute walk of New Marlborough Town Library and New Marlborough Town Hall.
Opens in a new window2-bedroom cottage close to skiing with gas fireplace
A-frame Cabin w/ Furnished Deck in Becket!

A-frame Cabin w/ Furnished Deck in Becket!

3 out of 5
Becket MA
Located in Becket, this cottage is a 3-minute drive from Pyramid Lake and 5 minutes from Jacob's Pillow.
Opens in a new windowA-frame Cabin w/ Furnished Deck in Becket!
Private Island - Largest Fresh Water Reservoir in Mass

Private Island - Largest Fresh Water Reservoir in Mass

Otis MA
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.
Opens in a new windowPrivate Island - Largest Fresh Water Reservoir in Mass
Private Lake Cottage on 3 acres w/350 sq. ft. deck

Private Lake Cottage on 3 acres w/350 sq. ft. deck

Becket MA
Located in Becket, this cottage is a 4-minute drive from Iroquis Waterfront and 8 minutes from Becket Quarry.
Opens in a new windowPrivate Lake Cottage on 3 acres w/350 sq. ft. deck
Waterfront Cottage 10 Min From Great Barrington

Waterfront Cottage 10 Min From Great Barrington

New Marlborough MA
With a stay at this cottage in Great Barrington, you'll be steps from Lake Buel and a 4-minute drive from Les Trois Emme Winery.
Opens in a new windowWaterfront Cottage 10 Min From Great Barrington
Charming historic cottage on scenic road to Mt. Greylock

Charming historic cottage on scenic road to Mt. Greylock

Lanesboro MA
Located in Lanesborough, this cottage is in the mountains, a 3-minute drive from Mount Greylock State Reservation and 5 minutes from Mount Greylock State Reservation ...
Opens in a new windowCharming historic cottage on scenic road to Mt. Greylock
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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
81 Cottages
Lowest Price
AU$149
Highest Price
AU$222
Popular accommodation
Cozy Cottage-Sunset On The Lake , The Blue Elm - A Historic Berkshire Cottage, Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly! , 2-bedroom cottage close to skiing with gas fireplace, A-frame Cabin w/ Furnished Deck in Becket!, Private Island - Largest Fresh Water Reservoir in Mass, Private Lake Cottage on 3 acres w/350 sq. ft. deck , Waterfront Cottage 10 Min From Great Barrington, Charming historic cottage on scenic road to Mt. Greylock

Top trending hotels 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
The price is AU$167 per night from 24 May to 25 May
AU$167
24 May - 25 May
includes taxes & fees
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 ...
Opens in a new windowBerkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is AU$166 per night from 21 May to 22 May
AU$166
21 May - 22 May
includes taxes & fees
Located in Lenox, Berkshires Untold is within a 10-minute drive of Shakespeare and Company and The Mount.
Opens in a new windowBerkshires Untold
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
The price is AU$222 per night from 18 May to 19 May
AU$222
18 May - 19 May
includes taxes & fees
A stay at Hotel Downstreet, an Ascend Collection Hotel places you in the heart of North Adams, steps from MCLA Gallery 51 and North Adams City Hall.
Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
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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$149 per night from 17 May to 18 May
AU$149
17 May - 18 May
includes taxes & fees
Located in Williamstown, Vacation Village in the Berkshires is a 3-minute drive from Jiminy Peak Mountain Resort and 5 minutes from Mountain Coaster.
Opens in a new windowVacation Village in the Berkshires
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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.

Top Picks

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^Subject to availability and chosen travel dates.