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Apartment vacation rentals in Berkshire County

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Top-rated apartment rentals in Berkshire County

Guests agree: these apartments are highly rated for location, cleanliness, and more.

Guest favorite
Apartment in Copake Falls
Modern Copake Falls Getaway - 8 Mins to Catamount
Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!
May 31 – Jun 7
$125 per night
Guest favorite
Apartment in Sheffield
Hideaway with Spectacular Berkshire Views
Located on the border of Massachusetts and Connecticut with spectacular views of the Berkshire Hills and fifteen minutes drive from Great Barrington, MA, this apartment is located on a secluded seven-acre property. Owners live on the property. Above an artist studio this renovated one bedroom apartment with private entrance, full kitchen, fast internet is stylish, light and airy with a contemporary and eclectic decor. Please note During winter all-wheel drive vehicle is strongly advised.
May 20 – 27
$140 per night
Guest favorite
Apartment in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
Soak up the Berkshires in a renovated 3rd floor apartment (private entrance, 2 flights up) that is well-appointed & homey w/ great views! Culture, skiing, nature, shopping, food & drinks just minutes away! But ALSO the urban amenities of Pittsfield: shops, dining, drinks...all in the Heart of the Berkshires! Located just off Hwy 7 (but very quiet!). 15 min=>Kripalu, Lenox & Tanglewood. 30 min=>Lee Outlets. 40 min=>Gr Barrington. 35 min=>MassMoca.
Mar 15 – 22
$60 per night

Popular amenities for Berkshire County apartment rentals

Weekly apartment rentals

Guest favorite
Apartment in Sheffield
Private Berkshire Barn Apartment
Oct 17 – 24
$116 per night
Guest favorite
Apartment in Williamstown
New Studio In Town, By the Water
Mar 9 – 16
$122 per night
Guest favorite
Apartment in Lenox
Lovely Downtown Lenox apt, walk to everything!
Oct 26 – Nov 2
$275 per night
Guest favorite
Apartment in North Adams
The Bear’s Den @ America's Switzerland
Sep 24 – Oct 1
$173 per night
Guest favorite
Apartment in North Adams
River Apartment, walk to MassMOCA and downtown
Aug 2 – 9
$88 per night
Guest favorite
Apartment in Williamstown
COLD SPRING
May 7 – 14
$125 per night
Guest favorite
Apartment in Pittsfield
Marie's Place
Dec 10 – 17
$122 per night
Guest favorite
Apartment in North Adams
#7 Downtown Historic Flatiron building getaway.
Apr 2 – 9
$130 per night
Superhost
Apartment in Lee
Cozy Berkshire Cottage Style Apartment
Sep 4 – 11
$175 per night
Guest favorite
Apartment in North Adams
Whiteley Hideaway- walk to Mass MoCA and Downtown
May 1 – 8
$145 per night
Guest favorite
Apartment in North Adams
Private guest apartment. One block from downtown.
Sep 25 – Oct 2
$169 per night
Guest favorite
Apartment in North Adams
Sunny Suite with Mountain Views, Steps from MoCA
Mar 1 – 8
$110 per night

Private apartment rentals

Guest favorite
Apartment in Lenox
Main Street Delight - One Bedroom Apartment
Apr 28 – May 5
$214 per night
Guest favorite
Apartment in Lenox
The Penthouse, Downtown Lenox by Evergreen Home
Nov 9 – 14
$478 per night
Guest favorite
Apartment in Great Barrington
Walk Everywhere! | Relax in Easy Elegance!
Jun 14 – 21
$255 per night
Guest favorite
Apartment in Great Barrington
Lush Setting, Private Deck, Queen Bed in GB
Mar 8 – 15
$101 per night
Guest favorite
Apartment in Great Barrington
King Bed|2mi Ski Resort|Fast Wi-Fi|Studio|
Apr 18 – 25
$167 per night
Superhost
Apartment in Pittsfield
Cozy Studio Apt in Downtown Victorian
May 13 – 20
$96 per night
Guest favorite
Apartment in Pittsfield
Simply off North
Apr 10 – 17
$72 per night
Guest favorite
Apartment in Stockbridge
Historic,Famous,Iconic, Unforgettable Berks Escape
Apr 7 – 14
$186 per night
Guest favorite
Apartment in Lee
Lovely Berkshire apartment with beautiful views
Dec 6 – 13
$214 per night
Superhost
Apartment in Pittsfield
The Sunset Sanctuary - King Bed with Kitchen
Oct 26 – Nov 2
$59 per night
Guest favorite
Apartment in Stephentown
Cozy 2-Bedroom Vacation Apartment
May 20 – 27
$106 per night
Superhost
Apartment in Stockbridge
Historic Retreat
Oct 10 – 17
$251 per night

Apartment rentals with a hot tub

Guest favorite
Apartment in Adams
Mountain Living, 1-bedroom unit, outdoor hot-tub
Jul 12 – 19
$86 per night
Guest favorite
Apartment in Hancock
Ski-in, Ski-out, Recently Renovated 2BR Condo
Oct 26 – Nov 2
$305 per night
Guest favorite
Apartment in Sandisfield
Sweet Dreams Retreat
Jan 16 – 23
$189 per night
Guest favorite
Apartment in Hancock
Ski on Ski Off - Jiminy Peak
Jun 11 – 18
$155 per night
Guest favorite
Apartment in Hancock
Ski-InSki-Out Loft Lift&MT.Views
Dec 11 – 18
$569 per night
Guest favorite
Apartment in Pittsfield
*Berkshire's Sweet Spot 2-Close to Ski Resorts/Spa
Apr 12 – 19
$270 per night
Superhost
Apartment in Lenox
Welcome to Your Retreat @Ponds at Foxhollow Resort
Dec 18 – 25
$129 per night
Superhost
Apartment in Hancock
1 Bedroom Deluxe @ Wyndham Bentley Brook
Apr 18 – 25
$155 per night
Guest favorite
Apartment in Hancock
Mountainside Condo Ski on/off
Jun 6 – 13
$134 per night
Guest favorite
Apartment in Hancock
All-Season Condo at Jiminy Peak (Berkshires)
Mar 6 – 13
$260 per night
Apartment in Lee
Lee time-share near ski hiking music
Mar 4 – 9
$195 per night
Apartment in North Adams
The Crystal Loft
Mar 30 – Apr 6
$150 per night

Destinations to explore