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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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Guest favorite
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, 102 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.

Top guest favorite
The image captures a serene lakeside view at sunset, with sunlight reflecting on calm waters. The cottage's exterior and a small dock are visible, framed by wildflowers and trees. The tranquil atmosphere presents an ideal setting for relaxation and enjoyment of nature.
Cottage in Oxford
4.92 out of 5 average rating, 145 reviews

✨Lakeside Reflections

🚣‍♂️ Lakeside Reflections is a year-round lakeside cottage in the quiet upstate NY countryside with pristine views of Lake Gerry. 🌻 Come enjoy a peaceful nook of historic Oxford complete with gardens, decks, docks, boats, and modern amenities. ♨️ Grill out on the lakefront deck, or fish directly off the deck! 🛶 Jump in the lake, or take a kayak, paddle boat, or walk around the lake. 🔥 Have a campfire (BYO wood) 🎟️ Enjoy one of the many local attractions (see our Airbnb guidebook for ideas)

Top guest favorite
The exterior of the uniquely designed guesthouse features a combination of dark siding and large windows, highlighted by colorful fall foliage. A spacious deck with seating is visible, surrounded by potted plants, creating a peaceful outdoor space.
Cabin in Erin
4.99 out of 5 average rating, 295 reviews

Unique Country GuestHouse

Unique country GuestHouse artistically renovated from a repurposed insulated tractor trailer. Private, quiet woodland setting under starry night skies. 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. The spacious sunny deck, shady patio, & fire pit bring your experience more outside. 1.6mi woodland trail. Turkeys, chickens, herb farm. Wifi. 10% discount for repeat guests.

Guest favorite
A well-appointed bedroom features a spacious bed with soft linens and a decorative blanket. Warm yellow lamps provide light on either side of the bed, and a chandelier enhances the ambiance. A soft area rug lays beneath the bed, adding comfort to the wooden flooring.
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 favorite
Cabin in Montrose
4.99 out of 5 average rating, 137 reviews

Cozy Cabin with Mini Goats & Hot tub Starlink WiFi

Here you can relax with the whole family or it’s a perfect getaway for 2. From Spring to early winter we’ll have mini goats and free range rabbits & chickens. The creek is perfect for tubing on a hot summer day.Have a picnic in the trees next to the water.Just a mile away is an ice cream/petting zoo and greenhouse with amish gifts. Next door is our operating hobby farm with donkeys, sheep, goats and chickens.If you’re looking for a nice relaxing retreat, we have what you’re looking for.

Top guest favorite
A gravel driveway leads to a secluded cabin nestled among tall pine trees. Sunlight filters through the branches, casting a warm glow on the landscape. The natural surroundings feature a blend of greenery and autumn foliage, creating a tranquil setting.
Cabin in Lisle
4.95 out of 5 average rating, 305 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 favorite
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, 291 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 favorite
A charming wooden cabin features a large screened-in porch and multiple windows. A stone fire pit is surrounded by rustic stools, creating a cozy outdoor gathering space. Lush greenery and trees provide a natural backdrop, evoking a serene atmosphere for relaxation.
Cabin in Freeville
4.95 out of 5 average rating, 148 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 favorite
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.
Apartment in Ithaca
4.87 out of 5 average rating, 224 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 favorite
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, 317 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 favorite
The entrance to a timber frame cottage is framed by tall trees, featuring a wooden door with a simple black handle. Cozy seating is provided on the porch, adorned with colorful decorative bunting and string lights for a cheerful touch.
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!

Guest favorite
A cozy living area features wooden walls, a sofa bed adorned with multicolored patterns, and a leather couch. A round dining table is positioned nearby. Natural light streams in through large windows, enhancing the inviting atmosphere, while decorative lamps provide additional lighting.
Apartment 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.

Popular amenities for Berkshire vacation rentals

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