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Featured Cottages in Lanesborough

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
Cozy cottage with pool, walking distance to lake

Cozy cottage with pool, walking distance to lake

Averill Park
When you stay at this cottage in Averill Park, you'll be on a lake and 14 minutes by car from Pineridge Cross Country Ski Center.
Cozy cottage with pool, walking distance to lake
Cozy Berkshire cottage with fireplace.

Cozy Berkshire cottage with fireplace.

Pittsfield
Located in Pittsfield, this cottage is in the mountains, within a 5-minute drive of Guido's Marketplace and Berkshire Museum.
Cozy Berkshire cottage with fireplace.
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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
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
Morgan House Ski Lodge on Crooked Lake

Morgan House Ski Lodge on Crooked Lake

Averill Park
A stay at this cottage places you in the heart of Averill Park, and within a 15-minute drive of Pineridge Cross Country Ski Center.
Morgan House Ski Lodge on Crooked Lake
Beachwood Cottage

Beachwood Cottage

Stockbridge
Located in West Stockbridge, this cottage is on a lake, a 5-minute drive from Frelinghuysen Morris House and Studio and 6 minutes from Tanglewood Music ...
Beachwood Cottage
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

3 out of 5
Great Barrington
Located in Great Barrington, this cottage is within a 10-minute drive of Art et Industrie and Housatonic River.
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

3 out of 5
Charlemont
With a stay at this cottage in Charlemont, you'll be within a 10-minute drive of Deerfield River and Mohawk Trail State Forest.
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
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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.

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

Lanesborough Cottages essential information

Accommodation
57 Cottages
Lowest Price
AU$158
Highest Price
AU$361
Popular accommodation
Charming historic cottage on scenic road to Mt. Greylock, Cozy cottage with pool, walking distance to lake, Cozy Berkshire cottage with fireplace., Private Lake Cottage on 3 acres w/350 sq. ft. deck , The Clearing - Quiet - Close To Nature, Morgan House Ski Lodge on Crooked Lake, Beachwood Cottage, Lakefront Berkshires Retreat w/ Deck, Dock & Boat!, Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

Top trending hotels in Lanesborough

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough
The price is AU$361 per night from 30 Dec to 31 Dec
AU$361
includes taxes & fees
30 Dec - 31 Dec
Located in Lanesborough, this vacation home is in the mountains, within a 15-minute drive of Crane Museum of Papermaking and Berkshire Athenaeum.
Berkshire Village Carriage House - Super Private!!
Hotel Downstreet

Hotel Downstreet

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is AU$207 per night from 5 Jan to 6 Jan
AU$207
includes taxes & fees
5 Jan - 6 Jan 2025
A stay at Hotel Downstreet places you in the heart of North Adams, steps from Western Gateway Heritage State Park and 3 minutes by foot from Massachusetts Museum ...
Hotel Downstreet
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$173 per night from 30 Dec to 31 Dec
AU$173
includes taxes & fees
30 Dec - 31 Dec
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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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$158 per night from 1 Jan to 2 Jan
AU$158
includes taxes & fees
1 Jan - 2 Jan 2025
Located in Lenox, Life House Berkshires is within a 15-minute walk of Kennedy Park and Pleasant Valley Wilderness Sanctuary.
Life House Berkshires
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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.