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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....
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
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 steps from Otis Reservoir and a 3-minute drive from Larkum Pond.
East Otis Vacation Rental w/ Private Deck & BBQ!
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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
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.
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 steps from Lake Buel and a 4-minute drive from Les Trois Emme Winery.
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
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
The Blue Elm - A Historic Berkshire Cottage

The Blue Elm - A Historic Berkshire Cottage

Sheffield
The price is AU$735 per night from 3 Dec to 4 Dec
AU$735
includes taxes & fees
3 Dec - 4 Dec
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
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

Monterey
With a stay at this cottage in Monterey, you'll be within a 10-minute drive of Beartown State Forest and Bidwell House Museum.
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
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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
71 Cottages
Lowest Price
AU$175
Highest Price
AU$735
Popular accommodation
Private Island - Largest Fresh Water Reservoir in Mass...., Quiet rustic cottage with shared lake access, East Otis Vacation Rental w/ Private Deck & BBQ!, Charming historic cottage on scenic road to Mt. Greylock, Cozy Berkshire cottage with fireplace., Rustic Berkshires Cottage at Lake Buel w/ Kayaks!, Perfect Vacation Get Away - Historical New Marlborough, The Blue Elm - A Historic Berkshire Cottage, Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

Top trending hotels in The Berkshires

Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AU$183 per night from 4 Nov to 5 Nov
AU$183
includes taxes & fees
4 Nov - 5 Nov
With a stay at Life House Berkshires in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Kennedy Park.
Life House Berkshires
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is AU$300 per night from 14 Nov to 15 Nov
AU$300
includes taxes & fees
14 Nov - 15 Nov
With a stay at The Red Lion Inn in Stockbridge, you'll be in the historical district, within a 15-minute drive of Tanglewood Music Center and Housatonic ...
The Red Lion 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
The price is AU$180 per night from 11 Nov to 12 Nov
AU$180
includes taxes & fees
11 Nov - 12 Nov
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
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The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

3 out of 5
435 Laurel St, Lee, MA
Fully refundableReserve now, pay when you stay
The price is AU$175 per night from 17 Nov to 18 Nov
AU$175
includes taxes & fees
17 Nov - 18 Nov
With a stay at The Black Swan Lee - Lenox, Ascend Hotel Collection in Lee, you'll be on the waterfront, within a 10-minute drive of Tanglewood Music Center and ...
The Black Swan Lee - Lenox, Ascend Hotel Collection
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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.

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