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Featured Cottages in Lenox

The Clearing - Quiet - Close To Nature

The Clearing - Quiet - Close To Nature

Cummington
Located in Cummington, this cottage is in a rural location, a 1-minute drive from Westfield River and 8 minutes from Chesterfield Gorge Reservation.
The Clearing - Quiet - Close To Nature
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!
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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!
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
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
The Blue Elm - A Historic Berkshire Cottage

The Blue Elm - A Historic Berkshire Cottage

Sheffield
The price is AU$665 per night from 11 Apr to 12 Apr
AU$665
includes taxes & fees
11 Apr - 12 Apr
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
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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.

Lenox 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 Lenox 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 Lenox 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 Lenox, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Lenox Cottages essential information

Accommodation
114 Cottages
Lowest Price
AU$133
Highest Price
AU$665
Popular accommodation
The Clearing - Quiet - Close To Nature, 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

Top trending hotels in Lenox

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$172 per night from 15 Apr to 16 Apr
AU$172
includes taxes & fees
15 Apr - 16 Apr
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$157 per night from 10 Apr to 11 Apr
AU$157
includes taxes & fees
10 Apr - 11 Apr
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
The Constance, The Whitlock, & The Dewey By The Lenox Collection

The Constance, The Whitlock, & The Dewey By The Lenox Collection

3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
The price is AU$159 per night from 1 May to 2 May
AU$159
includes taxes & fees
1 May - 2 May
With a stay at The Constance, The Whitlock, & The Dewey By The Lenox Collection in Lenox, you'll be within a 5-minute drive of Tanglewood Music Center and Lenox ...
The Constance, The Whitlock, & The Dewey By The Lenox Collection
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Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2 out of 5
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AU$133 per night from 1 May to 2 May
AU$133
includes taxes & fees
1 May - 2 May
With a stay at Howard Johnson by Wyndham Lenox in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Guido's Marketplace.
Howard Johnson by Wyndham Lenox
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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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