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Holiday rentals in Berkshire

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Top-rated holiday rentals in Berkshire

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

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Guest favourite
A spacious living area is highlighted by large windows and natural light. A dark sofa with accent pillows faces a wooden coffee table, while a dining table and chairs are visible in the background. Minimalist decor and plants add to the inviting ambiance.
Home in Nichols
4.95 out of 5 average rating, 104 reviews

Modern Susquehanna River Home

Wake up to a serene view of the Susquehanna River and experience the nature of Tioga County in this modern rustic renovated home. Located 3 minutes from Tioga Downs, 4 minutes to a boat launch/fishing site, 15 minutes from the historic town of Owego, and less than an hour to Seneca Lake and the start of the Finger Lakes Wine Trails Whether a relaxing weekend getaway or a trip to watch harness racing, our riverfront house is fully equipped and stocked with the essentials for a comfortable stay.

Guest favourite
A spacious outdoor deck features a large dining table and attached benches for gathering. A grill is positioned nearby, with a natural landscape of trees and a river visible in the background, providing a serene setting for outdoor meals.
Cottage in Whitney Point
4.83 out of 5 average rating, 158 reviews

King size master, high spd internet on the water

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!

Top guest favourite
The interior of the cabin features rustic wooden beams and walls, creating a warm ambiance. A cozy seating area includes a leather couch and a small rug. A kitchen area is visible in the background, with a bar counter and two wooden stools, enhancing the open layout.
Cabin in Lisle
4.95 out of 5 average rating, 307 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.

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
4.84 out of 5 average rating, 293 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
The exterior of the home showcases a two-story white structure with green shutters. Lush greenery and colorful flower beds surround the entrance, highlighting a welcoming atmosphere. A gravel driveway leads up to the house, bordered by neatly trimmed landscaping.
Guest suite in Cortland
4.85 out of 5 average rating, 154 reviews

Conveniently located private suite in Central NY

Clean, comfortable, one-bedroom suite located in one of the best areas of Cortland! Only a 5-min walk to Yaman park where you can sit down for a nice picnic, swim in the beach area, fish, or kayak in the Tioughnioga river. Easy commute to Syracuse 40 mins or Ithaca. Located 40mins to 8 golf courses, and 4 ski resorts. Walking distance to grocery stores, laundromat, coffee shop, restaurants, a fitness center, bus route, and city owned rental bikes all located within just a few minutes.

Top guest favourite
Cabin in Freeville
4.95 out of 5 average rating, 154 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 + HBO, and has satellite wifi (30+ MBPS).

Top guest favourite
A cozy bedroom is highlighted by a queen bed with patterned bedding and colorful accent pillows. Natural light filters through large windows, offering a view of greenery outside. A nightstand beside the bed features a decorative lamp and a small container.
Flat in Ithaca
4.87 out of 5 average rating, 232 reviews

Ithaca Falls View Apartment

Beautiful, private location at the top of Ithaca Falls. A bedroom with a queen bed for 2, a sofa that can sleep 1, a private bathroom, and living room. There is no kitchen or dining room, but there is a a small dining table, two chairs, a microwave, a coffeemaker with coffee, filters, disposable tableware, a toaster, and a mini-fridge (in the closet). It is a 5-minute drive to downtown Ithaca and Cornell University. Ithaca can easily be reached by car, bike, bus, or foot.

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, 320 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, 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
The rustic cabin is nestled amidst lush greenery, with a wraparound deck overlooking the tranquil Cayuta Creek. Steps lead up to the deck, where a shaded picnic table is situated. The natural surroundings enhance the serene atmosphere of this charming retreat.
Cabin in Van Etten
4.98 out of 5 average rating, 106 reviews

Creekside Cabin

A cozy cabin on the banks of Cayuta Creek, immersed in natural beauty. Located on our 75 acre organic orchard and cidery, it is a short drive to Ithaca, Watkins Glen, Finger Lakes wineries, state parks and gorges. Nature surrounds you: water rushing, a tree frog chorus, beavers swimming by, bald eagles fishing trout. Enjoy hanging out and eating meals on a wraparound deck overlooking the water. Easy access, remote feeling.*Composting toilet*

Guest favourite
Flat in Dryden
4.9 out of 5 average rating, 300 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.

Top guest favourite
A bright living area features a spacious blue sofa adorned with patterned throw pillows. A round glass coffee table is centered on a textured rug, while warm wooden beams and large windows allow natural light to fill the space. A flat-screen TV is mounted on the wall.
Home in Brooktondale
5 out of 5 average rating, 214 reviews

The Bar(n)- Cozy chalet with hot tub and campfire

Not your daddy’s barn. This bar(n) is professionally designed with modem flair, beautiful furniture, a hot tub, WFH setup, campfire, and pizza oven. What more could you want? Under 15 minutes to downtown Ithaca, Cornell, and Ithaca College. Level 2 EV charger with NACS (Tesla) and J1772. Dogs welcome (when added to reservation)- sorry no cats or other pets.

Popular amenities for Berkshire holiday rentals

  1. Airbnb
  2. United States
  3. New York
  4. Tioga County
  5. Berkshire