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Featured Cottages in The Berkshires

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!
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
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
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Ashley Falls Home w/ Fire Pit: Hike & Ski!

Ashley Falls Home w/ Fire Pit: Hike & Ski!

3 out of 5
Ashley Falls MA
Located in Ashley Falls, this cottage is within a 5-minute drive of Ashley Falls Woods and Bartholomew's Cobble.
Opens in a new windowAshley Falls Home w/ Fire Pit: Hike & Ski!
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
Charming historic cottage on scenic road to Mt. Greylock

Charming historic cottage on scenic road to Mt. Greylock

Lanesboro MA
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 ...
Opens in a new windowCharming historic cottage on scenic road to Mt. Greylock
Massachusetts Vacation Rental w/ Deck & Grill

Massachusetts Vacation Rental w/ Deck & Grill

3 out of 5
Windsor MA
With a stay at this cottage in Windsor, you'll be 8.1 mi (13 km) from Susan B. Anthony Birthplace Museum and 8.2 mi (13.2 km) from Tannery Falls.
Opens in a new windowMassachusetts Vacation Rental w/ Deck & Grill
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

3 out of 5
325 Long Pond Road Great Barrington MA
Located in Great Barrington, this cottage is within a 10-minute drive of Art et Industrie and Housatonic River.
Opens in a new windowLakefront Berkshires Retreat w/ Deck, Dock & Boat!
Light-filled cottage

Light-filled cottage

New Marlborough MA
Located in New Marlborough, this cottage is on a lake, within a 15-minute drive of Cookson State Forest and Dry Hill.
Opens in a new windowLight-filled 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$128
Highest Price
AU$333
Popular accommodation
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly! , The Blue Elm - A Historic Berkshire Cottage, Waterfront Cottage 10 Min From Great Barrington, Ashley Falls Home w/ Fire Pit: Hike & Ski!, Private Island - Largest Fresh Water Reservoir in Mass, Charming historic cottage on scenic road to Mt. Greylock, Massachusetts Vacation Rental w/ Deck & Grill, Lakefront Berkshires Retreat w/ Deck, Dock & Boat!, Light-filled cottage

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
The price is AU$191 per night from 13 Jan to 14 Jan
AU$191
13 Jan - 14 Jan 2026
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 ...
Opens in a new windowVacation Village in the Berkshires
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$211 per night from 22 Jan to 23 Jan
AU$211
22 Jan - 23 Jan 2026
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 3 minutes by foot from Mohawk ...
Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
The price is AU$333 per night from 24 Dec to 25 Dec
AU$333
24 Dec - 25 Dec
includes taxes & fees
Located in Williamstown, The Williams Inn is just steps from Williams College and 11 minutes by foot from The Clark Art Institute.
Opens in a new windowThe Williams Inn
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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$128 per night from 4 Jan to 5 Jan
AU$128
4 Jan - 5 Jan 2026
includes taxes & fees
Located in Lenox, The Yankee, Trademark Collection by Wyndham is a 4-minute drive from Bousquet Ski Area and 8 minutes from The Mount.
Opens in a new windowThe Yankee, Trademark Collection by Wyndham
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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.