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Vacation rentals in Berkshire

Find and book unique accommodations on Airbnb

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, 182 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.

Guest favourite
A rustic cabin with a red metal roof is situated near a tranquil pond surrounded by green foliage. A large wooden deck extends from the front, offering views of the natural landscape. Stone steps lead from the pond's edge to the cabin, enhancing the serene atmosphere.
Cabin in Vestal
4.85 out of 5 average rating, 308 reviews

324 Knight Road, Vestal, NY

This cabin is a rustic getaway with all the comforts of home. Nestled in the woods, the cabin has an abundance of hiking trails with a covered bridge, and small farm that guests are welcome to visit. From APPROXIMATELY December 1 - March 1, the property is home to a full size sheet of ice. The rink and farm are featured in the 2022 Bauer Hockey holiday catalog. Be sure to bring your skates! A travelling massage therapist may be available for private bookings with a few days notice.

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
A rustic vacation cottage is nestled among tall trees, with vibrant pink rhododendrons blooming in front. Grass covers the ground, providing a natural setting. The building features a mix of wood siding and a sloping roof, creating a cozy appearance.
Cottage in Brooktondale
4.98 out of 5 average rating, 131 reviews

Canaan Country Cottage

This is a private, rustic and cozy vacation camp that has been partially modernized with an addition containing two bedrooms. The original part of the building still has that Adirondack camp feel; woodsy and camp-like, but very private. Secluded and also close to Hammond Hill State Forest with many miles of trails for mountain biking, hiking and xc-skiing. The cottage sleeps 4 to 6. We recently upgraded the internet with a fiber connection, and added a propane grill on the back deck.

Top guest favourite
Cabin in Van Etten
4.96 out of 5 average rating, 137 reviews

Gorgeous Hilltop Paradise with epic views and pond

A beautiful slice of nature and unique cabin on 30 acres of land with modern ammenities. Enjoy distant views of hills through huge windows overlooking a swimming pond. It's a retreat for every season, featuring beautiful fall folliage, hiking, cross-country skiing and a lush and picturesque spring and summer. The house features a round kitchen and bedroom with a vaulted ceiling. Enjoy a giant view of the sky, fire pit by the pond, the sound of frogs, meditate, relax, or … work!

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.

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, 325 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
Cottage in Freeville
4.99 out of 5 average rating, 134 reviews

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, grill, and free EV charging. 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.

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, 288 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, 427 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, 307 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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