
Cottage holiday rentals in The Berkshires
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Top-rated cottage rentals in The Berkshires
Guests agree: These cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for The Berkshires cottage rentals
Cottage rentals with a hot tub

Luxury cottage by the sea with hot tub and pool

Cozy Lakefront Cottage w/Swim Spa & Firepit

The King's Cottage- HOT TUB and Pet Friendly!

Litchfield-Hot Tub-Shops & Eats-Vineyards-Hikes

Ye Little Wood | Cozy Forest Cottage with Hot Tub

Country Cottage w/ HOT TUB & Views

Hot Tub & Chic Catskills Woodstock Design Retreat

Stream Come True | Hot Tub, Ski, Hike, Relax
Pet-friendly cottage rentals

Cute Cozy Comfy Cottage in the Berkshires

Columbia County Getaway - Raspberry Ridge Cottage

Foxfire Hill: A Bit of Luxury in the Countryside

Kapitan’s Cottage: Private Retreat with Salt Pool

Be in Nature at this Gorgeous Riverfront Cabin

Pumpkin Pine Cottage: your next adventure awaits!

Cottage on the creek with wonderful waterfall view

Ridgetop 2 Br Cabin- Views, 130acre forest & falls
Private cottage rentals

Kayak, pet a Highland cow, have dinner in Hudson!

Old Mill Cottage - Upstate Mountain Views

Little Cottage Under the Ridge

Vintage Bolton Lake

The Carriage House

Beautiful cottage at the foot of the Birkshires

Catskills Getaway w/AC on 3 Acres near Woodstock

Historic 1810 Farmhouse - Fully Renovated
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