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Featured Cottages in The Berkshires

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

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

Otis
Located in Otis, this cottage is on the waterfront, a 1-minute drive from Otis Reservoir and 5 minutes from County Beach.
Private Island - Directly on Largest Fresh Water Reservoir in Mass.
Perfect Vacation Get Away - Historical New Marlborough

Perfect Vacation Get Away - Historical New Marlborough

New Marlborough
The price is AU$414 per night from 7 May to 8 May
AU$414
per night
7 May - 8 May
Located in Great Barrington, this cottage is in a rural location, a 4-minute drive from Dry Hill and 7 minutes from Questing.
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$632 per night from 23 May to 24 May
AU$632
per night
23 May - 24 May
With a stay at this cottage in Sheffield, you'll be within a 5-minute drive of Housatonic River and Ashley House.
The Blue Elm - A Historic Berkshire Cottage
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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.
Charming historic cottage on scenic road to Mt. Greylock

Charming historic cottage on scenic road to Mt. Greylock

Lanesboro
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 ...
Charming historic cottage on scenic road to Mt. Greylock
Charming unique cottage Relax & enjoy the stunning mountains with private views!

Charming unique cottage Relax & enjoy the stunning mountains with private views!

West Stockbridge
Located in West Stockbridge, this cottage is in the mountains, within a 15-minute drive of Ebenezer II Gifts and Antiques and Hotchkiss Mobile Studio.
Charming unique cottage Relax & enjoy the stunning mountains with private views!
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
Located in Otis, this cottage is a 1-minute drive from Otis Reservoir and 8 minutes from County Beach.
East Otis Vacation Rental w/ Private Deck & BBQ!
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$129
Highest Price
AU$632
Popular accommodation
Private Island - Directly on Largest Fresh Water Reservoir in Mass., Perfect Vacation Get Away - Historical New Marlborough, The Blue Elm - A Historic Berkshire Cottage, Cozy Berkshire cottage with fireplace., Charming historic cottage on scenic road to Mt. Greylock, Charming unique cottage Relax & enjoy the stunning mountains with private views!, Quiet rustic cottage with shared lake access, East Otis Vacation Rental w/ Private Deck & BBQ!, Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

Top trending hotels in The 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$266 per night from 14 May to 15 May
AU$266
per night
14 May - 15 May
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
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$167 per night from 8 May to 9 May
AU$167
per night
8 May - 9 May
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 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$185 per night from 12 May to 13 May
AU$185
per night
12 May - 13 May
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 Lenox Collection

The Lenox Collection

3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
The price is AU$129 per night from 12 May to 13 May
AU$129
per night
12 May - 13 May
With a stay at The Lenox Collection in Lenox, you'll be within a 5-minute drive of Tanglewood Music Center and Lenox Library.
The Lenox 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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^Subject to availability and chosen travel dates.