Vacation rentals in Berkshire

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Top-rated vacation rentals in Berkshire

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

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Top guest favourite
Tiny homes in Burdett
4.99 out of 5 average rating, 183 reviews

FLX 3- Lake View Wine Country Tiny Cabin

Nestled up on a hill overlooking Seneca Lake, watch the sunset while laying in bed or from your own patio with a fire crackling. We are local hosts and will make sure you have an unforgettable stay! Everything you could want to do in the Finger Lakes will be at your fingertips. Wineries galore, two even just next door, multiple breweries nearby, minutes to the lake, 15 minutes to downtown Watkins Glen, 10 minutes to hiking trails at the national forest, or stay in, relax, and enjoy the view!!

Top guest favourite
A hot tub is situated on a wooden deck, surrounded by privacy curtains. A small table and padded seating are nearby, with natural greenery visible in the background, creating a secluded outdoor relaxation space.
Chalet in Ithaca
4.97 out of 5 average rating, 490 reviews

Naturalists' Retreat

Retreat to paradise at this cozy cottage in the heart of the Finger Lakes. Charming custom woodwork offers a unique, rustic aesthetic while modern amenities provide the comfort of home. Minutes from famous naturalist attractions in all directions. Enjoy the entire peaceful cottage and surrounding yard with outdoor seating, fire pit, and hot tub to yourself. Three acres of adjoining trails and creek shared with neighboring host family, who are fun-loving and approachable but respect your privacy.

Top guest favourite
The elevated treehouse is illuminated by soft lighting along the wrap-around deck, surrounded by trees in a nighttime setting. A gentle slope leads up to the entrance, providing accessibility. The structure features warm wood tones that complement the natural surroundings.
Treehouse in Horseheads
5 out of 5 average rating, 270 reviews

Falcon Nest - Treehouse Secluded in Private Forest

A Treehouse. Reconnect with nature at this unforgettable escape. Nestled in 28 acres of woods with hiking trails. This unique newly constructed all electric 525 sq foot elevated structure offers a wrap around deck for an ever changing view. King size bed & new technology foam offers complete comfort in separate climate controlled bedroom. Heated bathroom floor is a “warm” surprise. Optional seasonal outdoor shower for the adventurous. Kitchen lacks nothing tucked conveniently in the great room.

Top guest favourite
Guest suite in Brooktondale
4.86 out of 5 average rating, 128 reviews

Modern Country Retreat! 15min to Cornell & IC

Private apartment in a country setting, attached to main house with beautiful views. Separate Entrance. Peaceful location and proximity to gorgeous hiking/waterfalls or winter skiing. Enjoy wildlife, the sunrise over the valley and the vast farmland that surrounds the home. Driveway parking. Contactless Check-in. Conveniently located. 15min to downtown Ithaca, Treman and Buttermilk Falls. 6 miles to Shindagin State Forest and Six Mile Creek Winery. 4min to the famous Brookton Market Cafe.

Top guest favourite
An outdoor seating area is arranged with picnic tables and chairs, surrounded by trees. A fire pit with a grill stands nearby, and soft lighting is visible on the cabin's exterior. The gravel driveway is seen in the background, leading to the cabin.
Tiny homes in Newfield
4.94 out of 5 average rating, 180 reviews

Cabin @Sanctuary in the Woods in the Finger Lakes

Enjoy our forest in cabin w/queen bed near creek w/electricity, lights, portable heater, hammock, picnic table, fire pit w/grill, BBQ& chairs. A short walk uphill 2 outdoor hot water on demand private shower & porta potty. Well water from sink & spiquot. No firewood can come in b/c of invasive species so we sell bundles on porch. Park next to cabin. Near Ithaca, Watkins Glen, State Parks- Treman, Buttermilk, Taughannock & Watkins Glen & 60 wineries/breweries around Lakes Seneca & Cayuga.

Top guest favourite
Cabin in Freeville
4.94 out of 5 average rating, 163 reviews

Hot tub under the stars at cozy cabin in the FLX

Nestled in a grove of Norway spruce, your peaceful cabin getaway rests in the heart of the Finger Lakes. Built by a local carpenter (with help from his dog Indiana), the cabin has enough coziness and charm to make any stay special. Hike down to Mill Creek (on the property), grill up some burgers on the gas grill, or lounge in a hot tub beneath the stars. The cabin is 15 minutes to Ithaca / Cornell, has a living room with a Switch + BluRay + Netflix, and has satellite wifi (30+ MBPS).

Top guest favourite
Home in Ithaca
4.96 out of 5 average rating, 229 reviews

Ithaca Music-lovers Barn

The barn is a cozy and unique space, situated on 27 acres of meadow and forest with a pond for swimming, fishing, and ice skating, depending on the season. There is no highway noise on the dirt road, and the stars shine brightly on clear nights, giving the place a true country feel, yet it’s still only a five minute drive from downtown Ithaca, Ithaca College, and Cornell University. Feel free to enjoy and play our piano, any stringed instruments, and extensive record collection!

Top guest favourite
Farm stay in Newark Valley
4.97 out of 5 average rating, 123 reviews

Howland Farm

The John Howland Farm is an iconic 1840s family farm. We follow strict cleaning protocols and only accept whole house reservations. Your party will be the only guests in the farmhouse with suites. The "Butterfly Suite" includes three bedrooms, sitting room with board games, books, and private bath. The "Garden Suite" is fully ADA accessible with bedroom, bath, and sitting room. The "Pine Cone Suite" is also ADA accessible with bedroom, bath, and adjacent laundry room.

Top guest favourite
A serene landscape features a calm pond reflecting a colorful sunset sky. A small guest house is visible on the opposite shore, surrounded by lush greenery and trees. The tranquil scene captures the natural beauty of the area.
Home in Newark Valley
4.96 out of 5 average rating, 326 reviews

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!

Top guest favourite
A rustic porch area, featuring a weathered wooden floor and a sturdy chair with a turquoise finish. A white basin sits on the ground, amidst a backdrop of trees and gentle sunlight filtering through the leaves.
Cottage in Candor
4.97 out of 5 average rating, 289 reviews

Tiny, romantic, timber frame

Unplugged (no WiFi) and peaceful. We provide breakfast foods. Unfortunately we cannot provide fresh breakfasts at this time, to keep our prices the same, with inflation. We hope to again in the future, if the current costs go down. A family built, tiny, timber frame. We are in a farming community, and several Amish farms dot our road. Please drive slow for children and animals. Please book both weekend nights during weekend stays, May-Oct. Thank you!

Top guest favourite
Cabin in Binghamton
4.93 out of 5 average rating, 430 reviews

Cozy/Chic Cabin Binghamton NY

Retreat, isolated get-away but nearby town. This cozy cabin is rustic with some chic flair, decor & recent updates. Privately set on 2 wooded acres & near town. 2 stone fireplaces, indoor Jacuzzi tub, 2 1/2 BA, 3-4 BR & 7 person outdoor hot tub. Excellent WIFI, kitchen & dining. Picnic, grill & fire pit. Great fall foliage, near skiing, near hiking, boat launch. Fully outfitted, just bring yourself!! Willing to accommodate guests—ask!!

Guest favourite
A hot tub is situated on a wooden deck, featuring a light-colored surface and multiple water jets. The water appears clear and calm, reflecting the surroundings. Nearby, wooden panels and natural elements provide a rustic backdrop.
Apartment in Dryden
4.9 out of 5 average rating, 309 reviews

Spacious apartment in the heart of the FingerLakes

Private spacious apartment with all amenities, located 15 minutes drive from Ithaca, NY. To relax during your stay, you can pour yourself a hot bath, unwind in the living-room or enjoy the outdoor deck with view on the 1 acre property. Other tenants include our poodle (Angélique) and Trouble, our outdoor cat. If you feel butch, you can start a fire and relax around our bonfire area or strip in your swimsuit and hop in our hot tub.

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