Berkshire vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Berkshire

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

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Guest favorite

Guesthouse in Ithaca

4.97 out of 5 average rating, 702 reviews

Secluded Free-Standing Cabin in Bucolic Setting

Cozy, comfortable, brick bungalow nestled in a stand of trees offers convenience & seclusion just off the beaten-path. Knotty pine, radiant heating, cathedral ceiling & loft are warm & inviting. Minutes away from 3 state parks, Cayuga & Seneca lakes, wine trails, Cornell, Ithaca College & the renowned Ithaca Commons. **Sorry, Airbnb prohibits booking for another person including "gift bookings." Booking that are gifts must be done so in the name of the guest who will be staying at the property.

Nov 4 – 11

ﺩ.ﺇ510 per night

Guest favorite

Cabin in Erin

4.99 out of 5 average rating, 208 reviews

Unique Country GuestHouse

A unique country GuestHouse artistically renovated from a repurposed insulated tractor trailer. Brilliantly designed to maximize space for a bedroom- queen bed, desk area. Full bathroom, fully equipped kitchen, eating and lounging area, comfy loft with a sleeper sofa. Private, quiet woodland setting under dark night skies. The spacious sunny deck, shady patio, & firepit bring your experience more outside. Wifi. 1.6mi woodland trail. Turkeys, chickens, herb farm. 10% discount for repeat guests.

Apr 9 – 16

ﺩ.ﺇ601 per night

Guest favorite

Guesthouse in Ithaca

4.94 out of 5 average rating, 303 reviews

Ithaca Ski Country Great Escape Mins to Cornell U

Enjoy this beautiful, green guest house mins to Cornell University,(5 Min) & downtown Ithaca(12 Min). A short drive to Greek Peak Ski Resort, this newly built, one bedroom cottage features a separate entrance, deck, green bamboo floors, solar electric heat & air conditioning. It is surrounded by 22 acres of beautiful woods and rolling lawns. Inside enjoy the open floor plan including a kitchen with quartz/recycled glass countertop and the ceramic tiled bath featuring a rain shower. Sleeps four.

Oct 3 – 10

ﺩ.ﺇ436 per night

Guest favorite

Home in Newfield

4.97 out of 5 average rating, 129 reviews

Camp S’mores- An A-Frame for the modern traveler

Welcome to Camp S’mores- this revitalized luxury A-frame has all the modern amenities you need for your Finger Lakes adventure. We just brought new life into this house from top to bottom. The home features three bedrooms and a Murphy bed in the game room on the lower level. EV charger. It wouldn't be camp without a pool so our home has a large HEATED in-ground pool is open May 15th - Oct 1st. The house is located outside of town on 2+ private acres. Dog friendly, sorry no cats or other pets

May 14 – 21

ﺩ.ﺇ2,913 per night

Guest favorite

Apartment in Van Etten

4.97 out of 5 average rating, 166 reviews

Finger Lakes Sunset View near Ithaca and Watkins

Escape to our charming, country-chic space, an ideal retreat for two. This private haven has all the essentials for a perfect getaway. Nestled in the beauty of NY’s Finger Lakes, our location is 30-40 mins from diverse attractions: the lively college town of Ithaca, Cornell University, thrilling NASCAR events in Watkins Glen, renowned wineries, & state parks. For those seeking tranquility, step onto the private deck and enjoy a fire as the sun sets. Welcome to your peaceful escape in upstate NY!

Oct 12 – 19

ﺩ.ﺇ455 per night

Guest favorite

Apartment in Hector

4.96 out of 5 average rating, 255 reviews

Private Lakefront on Seneca Wine Trail

You’ll enter a Large, Luxurious, Private studio apartment in beautiful Arts & Crafts style. *Located on a Town Maintained secluded lake-side road on the shores of the east side of Seneca Lake. *Ten-foot Coffered Ceilings *On the Seneca Lake Wine Trail. *We welcome visitors all year round. A wonderful option for couples looking for a private, quiet place to get away. *Many custom-crafted details. *2 additional guests can be accommodated with a fold-out sofa bed (an additional fee. )

Feb 24 – Mar 3

ﺩ.ﺇ513 per night

Guest favorite

Chalet in Willet

4.96 out of 5 average rating, 117 reviews

Lakefront Home; private, with kayaks and canoe

Welcome to the Sunset Chalet - your serene, lakeside getaway! Gorgeous lakefront with lake access, over an acre of private land, and trails to explore! A private swimming pond & fire pits. Free use of 2 kayaks- 2 adult life jackets; and a canoe (Summer time). Rejuvenate with amazing views and hikes. We are conveniently located near Greek Peak Resort Ski Area, and Labrador Mountain. Not far from wine trails, Ithaca, and great hiking. Lots of open space. Relax, and savor the tranquility!

Aug 15 – 22

ﺩ.ﺇ618 per night

Guest favorite

Home in Spencer

4.96 out of 5 average rating, 179 reviews

Cozy new 2 bedroom house near Ithaca

Looking for value and a nice property? Our updated quiet and cozy house is close to Ithaca, Cornell Univ., Ithaca College, Fingerlakes, Watkins Glen, Wineries and State Forests. You’ll love our place because of it's proximity to many areas and the price is very reasonable & NO cleaning fee. Washer & Dryer, flat SMART TV, WIFI, large yard. Perfect place for your next stay in the Southern Tier/ Fingerlakes of NY. Owners on adjacent property to assist you in making your stay a memorable one.

Oct 3 – 10

ﺩ.ﺇ367 per night

Superhost

Home in Whitney Point

4.83 out of 5 average rating, 132 reviews

River Cottage in Village high-speed internet

Located between Ithaca, Binghamton and Cortland great for college visits, tours of wine/breweries and skiing. The house is set up for sound, enjoy tunes on the deck, back porch and inside. It's clean, comfortable and close to so many things! Kid/dog friendly too. (NO cats) Walk to restaurants, ice cream, grocery, liquor store, playgrounds, BC fairground and village amenities. Close to Dorchester Park, close to kayak/canoe launch and quick highway access. Wired/ethernet speed 300 down 10 up!

Jan 12 – 19

ﺩ.ﺇ457 per night

Guest favorite

Cabin in Lisle

4.94 out of 5 average rating, 251 reviews

Private Cabin and Pond Property

Enjoy our secluded cabin, pond, and picnic area with many acres to roam. Rest comes easy with the privacy and peaceful woodlands that is the setting of our family's newly refurbished vacation space. Up to two Cots available upon request (must bring your own bedding.) Comfortable space for up to 4 guests. Our cozy cabin is the perfect chance to unplug from the busyness of life, equipped with WiFi but very sparse cell reception. WiFi calling feature can be used for important connections.

Feb 16 – 23

ﺩ.ﺇ693 per night

Guest favorite

Home in Warren Center

5.0 out of 5 average rating, 148 reviews

Country Tucked Inn, with pond Sauna woods hunting.

Tucked Inn is a totally remodeled house in a quiet country setting. The pond offers swimming, a dock, pedal boat and fishing. The sunroom has a sauna for 2. The owners are next door and have a 500 acre family farm with beef cattle and a maple syrup operation. Sit on the front porch or grill on the back porch and enjoy the propane fire ring. Kids can run and play. Hunting available a mile away on a State Game Lands 219. Enjoy hiking in the large woods just out your back door.

Apr 1 – 8

ﺩ.ﺇ519 per night

Guest favorite

Home in Cortland

4.96 out of 5 average rating, 131 reviews

Privacy at the heart of Cortland. Block from SUNY!

Peaceful and centrally-located 2 bedroom private and stand alone house. Walking distance to SUNY Cortland. (1block) Natural hardwood throughout. Comfy cozy and simple. Has full kitchen with separate dining area. Features a full basement with laundry. Free Wi-Fi with Roku tv in both bedrooms and common area. Front porch seating and side yard for play! Minutes from Dining, Bar-grill, club, shopping. Sports field and parks. 10 minutes to Greek Peak Mountain Resort.

Apr 5 – 12

ﺩ.ﺇ445 per night