
Vacation rentals in Berkshire
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Top-rated vacation rentals in Berkshire
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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.
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Lakefront Retreat: Hike, Fish, Campfires, Kayaks
Welcome to Sunset Chalet — your private lakeside escape. Set on peaceful waterfront property, this cozy retreat is perfect for relaxing and enjoying nature. Swim in the private pond, kayak on the lake, explore trails, or unwind around the fire pit under the stars. Enjoy: • Lake access • Private swimming pond • 2 kayaks + canoe • Fire pit • Private setting Close to Greek Peak, Ithaca, waterfalls, hiking, and Finger Lakes wine trails. Reserve early — summer and peak weekends book quickly.
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Riverfront Cottage in Owego, New York
Welcome to our charming 2-bedroom, 1-bathroom riverside retreat in Owego, NY! This home is a haven of comfort with an open-concept kitchen, dining, and living room. Step through sliding glass doors onto a large deck, where the Susquehanna River's beauty unfolds before you. Enjoy Owego's revitalized downtown shops and restaurants, or explore the nearby attractions of the Finger lake wineries, the nature trails/waterfalls of Ithaca and Watkins Glen, or the artistry of the Corning Glassworks
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Farmstay Scottland Yard-Hobbit House dogs welcome!
Scottland Yard farm stay, 'The Hobbit House' Come enjoy our little piece of paradise. We are located 10 easy miles from Ithaca NY in the beautiful Finger lakes region! we are less than 1/2 day trips from NYC, NJ, PA, Rochester and Buffalo. We have consistently been Airbnb super host for 6 years! We have seasonal glamps and cabins, but are now offering our favorite little hideaway year round! Enjoy the gentle peaceful flow of life just breathing the sweet air here at Scottland Yard Farm.
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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).
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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.
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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!
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Cozy cabin with pictureous views
Relax at this unique and tranquil getaway. Sit on the deck and watch the Scottish Highlander cows graze (or even feed them by the fence) to watching the Koi fish by the pond u will enjoy the peacefulness of the country. The position of the cabin is ideal for Sunrises and Sunsets that brighten the sky. State Game Lands 1/2 mile away. Also wine trails and waterfalls around an hour away. 20 minutes to Binghamton area, 30 minutes to a casino, 45 minutes to Ithaca
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1820's Quaint Rustic Farmhouse
Beautiful, spacious, two-bedroom private suite. The Farmhouse is located on 50 acres of farmland in our beautiful river valley. We are directly off the Cortland I-81 exit and are 30 minutes to Cornell, Ithaca and Syracuse. We are conveniently located near Greek Peak and other local ski areas. Great location for professors, parents, students, outdoor enthusiast and anyone exploring the Finger lakes! We hope you enjoy your stay and come back again.
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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*
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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!!
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Waterfront guesthouse with beautiful view
Private guesthouse with 1 king bed and no cleaning fee, in the woods overlooking a 3 acre pond on a 30 acre property with trails and nature all around. Constructed in 2023 with sustainability and views to nature in mind. Conveniently located between Binghamton and Ithaca, and a quick 5-minute drive to historic Owego. A quiet getaway to immerse yourself in nature.
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Popular amenities for Berkshire vacation rentals
Other great vacation rentals in Berkshire

Cozy Cabin in Candor
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Luxurious 3Bdrm with indoor heated Pool year round
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Finch House, Richford, Finger Lakes, EV Charging
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Riverfront Luxury: Hot Tub, Sauna & Gym
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The Barn close to Ithaca, Cornell and I.C.
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Maple Grove Yurt at Finger Lakes Cider House!
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Cottage on Songbird Pond
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Lakefront A-frame near Elk Mountain
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Destinations to explore
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- Cornell University
- Watkins Glen State Park
- Greek Peak Mountain Resort
- Finger Lakes
- Taughannock Falls State Park
- Watkins Glen International
- Chittenango Falls State Park
- Colgate University
- Robert H Treman State park
- Fox Run Vineyards
- Binghamton University
- Cascadilla Gorge Trail
- Buttermilk Falls State Park
- Ithaca College
- Six Mile Creek Vineyard
- Sciencenter
- Wiemer Vineyard Hermann J
- Ithaca Farmers Market
- Song Mountain Resort
- State Theatre of Ithaca
- Salt Springs State Park
- Ithaca Falls Natural Area
- Clark Reservation State Park
- Standing Stone Vineyards





