Cottage vacation rentals in Berkshire County

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Top-rated cottage rentals in Berkshire County

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

Guest favorite
Cottage in Great Barrington
Artist Cottage
Enchanting, private, romantic, retro style, artsy, cottage & lodge building with fireplaces and outdoor hot tub and shower area in a quaint, quiet, neighborhood nested at the base of Flag Rock and near nature trails and downtown Great Barrington. Perfect for a romantic get-away. Open retro style kitchen with wood stove and TV is stocked with utensils and pans for cooking with gas oven and retro appliances. Upstairs bedroom with ensuite large bathroom with soaking tub and message chair.
Jun 13 – 20
$181 per night
4.93 out of 5 average rating, 231 reviews
Guest favorite
Cottage in Williamstown
Cute Cozy Comfy Cottage in the Berkshires
A cute cozy cottage sleeps 4 comfortably. One queensize bed and 1 full futon. Dog friendly for up to 2 dogs .More than two dogs will have to be an additional fee of 50.00 each pet. My cottage sits on 13 privately owned acres. Partially fenced in.3 miles down the road from Jiminy Peak ski resort & summer activities and a short drive to Ramblewild adventure park. Hiking, boating, museums, shopping, restaurants- all sorts of activities in the Berkshires. Two minute ride to Bloom Meadows!
Jan 15 – 22
$140 per night
4.9 out of 5 average rating, 164 reviews
Guest favorite
Cottage in New Lebanon
The Writer's Cottage
The Writer's Cottage is a tiny white house on a country road; vintage, complete, and inspiring. Built in the nineteenth century, it's perfect for a solo traveler or a pair of travelers exploring the Berkshires and the Hudson Valley. If you like rustic buildings, you'll be a fan of the cottage; it's an incredibly cozy time warp. Queen bed and living quarters downstairs; airy loft up a narrow set of enclosed stairs. There's an orchard and lawn with grill, hammock and table.
Aug 20 – 27
$100 per night
4.94 out of 5 average rating, 173 reviews

Popular amenities for Berkshire County cottage rentals

Cottage rentals with a hot tub

Superhost
Cottage in Great Barrington
THE GREAT ESCAPE BERKSHIRE SKI COTTAGE w/HOT TUB!
Apr 10 – 17
$931 per night
4.84 out of 5 average rating, 25 reviews
Cottage in Becket
A Magical Spot on Little Robin Lake
Jun 10 – 17
$212 per night
4.6 out of 5 average rating, 143 reviews
Guest favorite
Cottage in Otis
Berkshire lakefront cabin with modern luxuries
May 20 – 27
$458 per night
4.96 out of 5 average rating, 28 reviews
Cottage in Monterey
mountain refuge
Apr 13 – 20
$98 per night
4.88 out of 5 average rating, 8 reviews
Cottage in Becket
Berkshires Cottage Retreat - Private Hot Tub
May 12 – 19
$144 per night
4.67 out of 5 average rating, 333 reviews
Guest favorite
Cottage in Lanesborough
Norte Maison 2 beds 2 Baths Minutes to Jiminy Peak
Jan 31 – Feb 7
$287 per night
5.0 out of 5 average rating, 11 reviews

Pet-friendly cottage rentals

Superhost
Cottage in Canaan
Plan your Berkshires by the lake
Apr 1 – 8
$194 per night
4.9 out of 5 average rating, 125 reviews
Superhost
Cottage in Florida
Peaceful Cottage near Berkshire East Ski Resort
Jan 13 – 20
$131 per night
4.83 out of 5 average rating, 87 reviews
Superhost
Cottage in Great Barrington
Carriage house with Chef's Kitchen, close to town
Sep 11 – 18
$219 per night
4.86 out of 5 average rating, 35 reviews
Guest favorite
Cottage in Sheffield, The Berkshires
Cheerful 3-bedroom cottage with woodstove.
Feb 12 – 19
$217 per night
4.93 out of 5 average rating, 99 reviews
Superhost
Cottage in Becket
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Oct 9 – 16
$187 per night
4.76 out of 5 average rating, 136 reviews
Guest favorite
Cottage in Austerlitz
Harvey Mountain Lodge by State Forest
Jun 6 – 13
$261 per night
4.94 out of 5 average rating, 50 reviews
Guest favorite
Cottage in Williamstown
Pet friendly, cozy, modest cape, two bedrooms
Jul 23 – 30
$134 per night
4.73 out of 5 average rating, 55 reviews
Guest favorite
Cottage in Monterey
Historic Berkshires Cottage with a View
May 2 – 9
$315 per night
5.0 out of 5 average rating, 18 reviews
Guest favorite
Cottage in Becket
Cheerful 3+ bedroom cottage with lake views
May 4 – 11
$233 per night
5.0 out of 5 average rating, 13 reviews
Guest favorite
Cottage in Austerlitz
Cozy Berkshire Cottage
Oct 10 – 17
$198 per night
5.0 out of 5 average rating, 6 reviews
Guest favorite
Cottage in Spencertown
Rock Haven Cottage
Mar 3 – 10
$197 per night
5.0 out of 5 average rating, 25 reviews
Guest favorite
Cottage in Hancock
Berkshire Cottage Queen Bd-Jiminy Peak 3 mi
Dec 14 – 21
$133 per night
4.86 out of 5 average rating, 64 reviews

Private cottage rentals

Guest favorite
Cottage in Lanesborough
Stone School Cottage
Jul 18 – 25
$165 per night
4.93 out of 5 average rating, 219 reviews
Guest favorite
Cottage in West Stockbridge
Historic 1810 Farmhouse - Fully Renovated
Apr 18 – 25
$215 per night
4.98 out of 5 average rating, 104 reviews
Guest favorite
Cottage in Great Barrington
Newly built cottage on working farm
Dec 23 – 30
$100 per night
4.98 out of 5 average rating, 123 reviews
Guest favorite
Cottage in Hinsdale
Cozy Cottage in the Berkshires
Mar 25 – Apr 1
$175 per night
4.99 out of 5 average rating, 138 reviews
Superhost
Cottage in Great Barrington
Ski Cottage with fireplace in the Berkshires
Apr 13 – 20
$190 per night
4.71 out of 5 average rating, 52 reviews
Guest favorite
Cottage in Stockbridge
Quiet 2 BR cottage in the heart of the Berkshires
Jun 16 – 23
$255 per night
5.0 out of 5 average rating, 21 reviews
Guest favorite
Cottage in Lanesborough
Amazing 2 bedroom lake front cottage, large patio
Sep 9 – 16
$363 per night
4.98 out of 5 average rating, 46 reviews
Guest favorite
Cottage in Becket
Stylish Shales Brook Cottage-Cozy up to happiness
Feb 5 – 12
$299 per night
4.86 out of 5 average rating, 71 reviews
Guest favorite
Cottage in Sheffield
The Blue Elm - A Historic Country Cottage
May 7 – 14
$200 per night
5.0 out of 5 average rating, 17 reviews
Guest favorite
Cottage in Williamstown
Artistic Nature Cottage
Feb 15 – 22
$214 per night
4.97 out of 5 average rating, 72 reviews
Guest favorite
Cottage in Monterey
Beaver Lodge
Jan 19 – 26
$172 per night
5.0 out of 5 average rating, 33 reviews
Guest favorite
Cottage in Clarksburg
Hilltop Heights Cottage 3 Minutes from Mass MoCA
Mar 27 – Apr 3
$96 per night
4.84 out of 5 average rating, 95 reviews

Destinations to explore