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Featured Cottages in Lenox

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....
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!
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!

4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!

2 out of 5
Richmond
With a stay at this cottage in Richmond, you'll be within a 15-minute drive of Tanglewood Music Center and Nordeen Marsh Natural Heritage Area.
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!
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Private Lake Cottage on 3 acres w/350 sq. ft. deck

Private Lake Cottage on 3 acres w/350 sq. ft. deck

Becket
Located in Becket, this cottage is a 4-minute drive from Iroquis Waterfront and 6 minutes from October Mountain State Forest.
Private Lake Cottage on 3 acres w/350 sq. ft. deck
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.
Welcome to the Red Bridge Cottage!

Welcome to the Red Bridge Cottage!

Valatie
Located in Valatie, this cottage is in a rural location, within a 10-minute drive of Shaker Museum and Library and Valatie Free Library.
Welcome to the Red Bridge Cottage!
The Blue Elm - A Historic Berkshire Cottage

The Blue Elm - A Historic Berkshire Cottage

Sheffield
The price is AU$653 per night from 24 Feb to 25 Feb
AU$653
includes taxes & fees
24 Feb - 25 Feb
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
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
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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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
92 Cottages
Lowest Price
AU$140
Highest Price
AU$653
Popular accommodation
Private Island - Largest Fresh Water Reservoir in Mass...., East Otis Vacation Rental w/ Private Deck & BBQ!, 4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!, Private Lake Cottage on 3 acres w/350 sq. ft. deck , Cozy Berkshire cottage with fireplace., Welcome to the Red Bridge Cottage!, The Blue Elm - A Historic Berkshire Cottage, Charming historic cottage on scenic road to Mt. Greylock, Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

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$187 per night from 8 Mar to 9 Mar
AU$187
includes taxes & fees
8 Mar - 9 Mar
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$140 per night from 2 Mar to 3 Mar
AU$140
includes taxes & fees
2 Mar - 3 Mar
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$183 per night from 25 Feb to 26 Feb
AU$183
includes taxes & fees
25 Feb - 26 Feb
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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Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
445 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AU$208 per night from 2 Mar to 3 Mar
AU$208
includes taxes & fees
2 Mar - 3 Mar
Located in Lenox, Hampton Inn & Suites Berkshires-Lenox is in a rural location, within a 5-minute drive of Guido's Marketplace and Arrowhead Museum.
Hampton Inn & Suites Berkshires-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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^Subject to availability and chosen travel dates.