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Featured Cottages in The Berkshires

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Whitney by Avantstay Private Berkshires Estate

3.0 star property
Whitney by Avantstay Private Berkshires Estate

Luxury Vacation Rental in the Berkshires!

3.0 star property
Luxury Vacation Rental in the Berkshires!

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!

Stockbridge Home: Walk to Town Beach!

3.0 star property
Stockbridge Home: Walk to Town Beach!

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

3.0 star property
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

Skiing & Hiking: Water-view Home in the Berkshires

3.0 star property
Skiing & Hiking: Water-view Home in the Berkshires

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

3.0 star property
8.0 out of 10, Very good, (1)
"Nice location. Spacious with ample bedrooms. Would have been nice if there was a second bathroom on the second floor. It might be time to freshen the furniture in the sitting area."
Ashley Falls Home w/ Fire Pit: Hike & Ski!

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

3.0 star property
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

Picturesque Cottage With Sunroom on Ashmere Lake!

3.0 star property
Picturesque Cottage With Sunroom on Ashmere Lake!

Lakefront Otis Home w/ Stunning Views & Boats!

3.0 star property
Lakefront Otis Home w/ Stunning Views & Boats!

Becket Home w/ 3-season Porch: Walk to Lake Access

3.0 star property
Becket Home w/ 3-season Porch: Walk to Lake Access

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

3.0 star property
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Lakefront Hinsdale Home ~ 10 Mi to Pittsfield!

3.0 star property
Lakefront Hinsdale Home ~ 10 Mi to Pittsfield!

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

3.0 star property
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Cozy Stockbridge Cabin - Walk to Beach & Lake!

3.0 star property
Cozy Stockbridge Cabin - Walk to Beach & Lake!

Forget-me-not by Avantstay Bold Lakefront Escape

3.0 star property
Forget-me-not by Avantstay Bold Lakefront Escape

Walk to Dining: Downtown Lenox Guest House!

3.0 star property
Walk to Dining: Downtown Lenox Guest House!

'the Mill River Cabin w/ Fireplace & River View!

3.0 star property
'the Mill River Cabin w/ Fireplace & River View!

Cozy Great Barrington Home ~ 1 Mi to Ski Resort!

3.0 star property
Cozy Great Barrington Home ~ 1 Mi to Ski Resort!
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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Other property types in The Berkshires

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1799)
"What a beautiful place. Could not be more beautiful and we are so satisfied. We will be back!"
The price is RM453
RM545 total
includes taxes & fees
27 Apr - 28 Apr
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (928)
"Last minute find. Room was tidy/no odors. The kitchen was complete and cute wood art made the place feel cozy. The spare roll away bed was delivered as requested, and surprisingly comfortable. Traveled with hubby and 9 year old between seasons to hit Bash Bish. Will stay here again to visit Naumkeag."
The price is RM586
RM655 total
includes taxes & fees
26 Apr - 27 Apr
Jiminy Peak Mountain Resort

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is RM980
RM1,095 total
includes taxes & fees
9 May - 10 May
The Ponds at Foxhollow
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.