Berkshire vacation rentals

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Top-rated vacation rentals in Berkshire

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

Superhost

Cottage in Freeville

Country retreat near Ithaca

Your own comfy, private, immaculately clean 2-story cottage with A/C, full kitchen, dishwasher, full bath, wifi, TV+Roku, washer/dryer, deck, couch, desk, fire pit, charcoal grill. Ideal for relaxing, remote work, or as base to explore the area's restaurants, trails, wineries, and more. Nestled against a wooded hillside, surrounded by trees, meadows, and marshes. Tons of birds and animals. 20-mins east of the Ithaca Commons and college campuses. We follow AirBnB's enhanced cleaning protocol.

$141 per night

Superhost

Home in Newark Valley

Private Scenic Retreat

The entire place is yours to enjoy! Our guest house is located on a dead-end road five minutes from the town of Newark Valley and only 30 minutes from Binghamton, Cortland, and Ithaca Included is a kitchen with open common area, two bedrooms, full bath and washer/dryer within living area. A farm setting is viewable from the common area and attached deck. There is a 2 acre pond and miles of scenic trails spread over 250+ acres, with sights as far as Pennsylvania!

$96 per night

Superhost

Cottage in Ithaca

The Timber Garden Cottage

This entire stunning home is waiting for you! It has classic timber frame construction boasting large beautiful wood beams, lots of light, and a rustic feel. Both spacious and cozy at the same time! Located centrally to all things Ithaca, 7-10 mins drive to downtown, 15 mins to both Cornell and Ithaca College, and a few miles to Taughannock State Park, the beginning of the Cayuga Wine trail, and Trumansburg. This cottage puts you close to all things Ithaca!

$144 per night