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 favorite
A charming cottage is framed by vibrant pink rhododendron blooms, creating a striking entrance. A pathway of circular stepping stones leads from the grassy area to the front door, surrounded by lush greenery.
Tiny home in Oxford
4.96 out of 5 average rating, 363 reviews

⭐Wildflower Country Cottage

🏡 Cozy cottage in the countryside. Gardens galore to explore! 🏘 Less than 5 minutes from town 🎟 Many local attractions including: 🦒 Animal Adventure 🏎 Northeast Classic Car Museum 🥾 State Parks, and hiking trails 🚶‍♂️Enjoy an afternoon in the gazebo or take a stroll around any of the many garden paths. 📕 See our guidebook for our favorite local attractions and eateries. ℹ️ Please check out our other listing: Lakeside Reflections https://airbnb.com/h/lakesidereflections

Top guest favorite
The cozy brick bungalow is surrounded by trees, showcasing a snow-covered exterior. Two warm lights illuminate the entrance, which features glass doors. A small patio with a table and chairs sits nearby, creating a peaceful outdoor space amidst the winter landscape.
Guesthouse in Ithaca
4.97 out of 5 average rating, 841 reviews

Secluded Free-Standing Cabin in Bucolic Setting

Cozy, comfortable, brick bungalow nestled in a stand of trees offers convenience & seclusion just off the beaten-path. Knotty pine, radiant heating, cathedral ceiling & loft are warm & inviting. Minutes away from 3 state parks, Cayuga & Seneca lakes, wine trails, Cornell, Ithaca College & the renowned Ithaca Commons. **Sorry, Airbnb prohibits booking for another person including "gift bookings." Booking that are gifts must be done so in the name of the guest who will be staying at the property.

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
4.96 out of 5 average rating, 99 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 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, 294 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.

Top guest favorite
Cabin in Montrose
4.99 out of 5 average rating, 134 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 late fall 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 alpacas, 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, 303 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, 288 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
The exterior of a rustic cottage is framed by a large tree and vibrant blooming rhododendrons. The building features a sloped roof and multiple windows, blending harmoniously with the surrounding nature.
Cottage in Brooktondale
4.98 out of 5 average rating, 125 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 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
4.94 out of 5 average rating, 143 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 rustic cabin features a screened porch and circular turret adorned with large windows. Two red adirondack chairs are positioned on the grassy area in front of the cabin, inviting relaxation amidst the surrounding autumn foliage.
Cabin in Van Etten
4.95 out of 5 average rating, 122 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 favorite
The exterior of the farmhouse showcases a classic design with white siding and dark green shutters. A spacious front porch provides ample seating, framed by lush green grass and mature trees. The background features rolling hills, hinting at the surrounding countryside.
Farm stay in Newark Valley
4.97 out of 5 average rating, 117 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 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, 315 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!

Popular amenities for Berkshire vacation rentals

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