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Featured Cottages in The Berkshires

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!
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!
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Family-Friendly Richmond Cottage w/ Private Yard

Family-Friendly Richmond Cottage w/ Private Yard

2 out of 5
Pittsfield
With a stay at this cottage in Richmond, you'll be on the waterfront, within a 15-minute drive of Tanglewood Music Center and Nordeen Marsh Natural Heritage ...
Family-Friendly Richmond Cottage w/ Private Yard
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 Bidwell House Museum and Ashintully Gardens.
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
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....
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
The Blue Elm - A Historic Berkshire Cottage

The Blue Elm - A Historic Berkshire Cottage

Sheffield
The price is AU$650 per night from 13 May to 14 May
AU$650
includes taxes & fees
13 May - 14 May
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 Frelinghuysen Morris House and ...
Beachwood Cottage
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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
84 Cottages
Lowest Price
AU$179
Highest Price
AU$650
Popular accommodation
Quiet rustic cottage with shared lake access, Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly! , East Otis Vacation Rental w/ Private Deck & BBQ!, Family-Friendly Richmond Cottage w/ Private Yard, Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks, Private Island - Largest Fresh Water Reservoir in Mass...., Charming historic cottage on scenic road to Mt. Greylock, The Blue Elm - A Historic Berkshire Cottage, Beachwood Cottage

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$180 per night from 5 May to 6 May
AU$180
includes taxes & fees
5 May - 6 May
With a stay at Berkshires Untold in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Kennedy Park.
Life House Berkshires
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street, South Lee, MA
Fully refundableReserve now, pay when you stay
The price is AU$209 per night from 14 May to 15 May
AU$209
includes taxes & fees
14 May - 15 May
With a stay at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG in South Lee, you'll be near ski lifts, within a 15-minute drive of Tanglewood ...
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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$179 per night from 30 Apr to 1 May
AU$179
includes taxes & fees
30 Apr - 1 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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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
The price is AU$221 per night from 30 Apr to 1 May
AU$221
includes taxes & fees
30 Apr - 1 May
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
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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.