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
The elevated treehouse is illuminated by soft lighting along the wrap-around deck, surrounded by trees in a nighttime setting. A gentle slope leads up to the entrance, providing accessibility. The structure features warm wood tones that complement the natural surroundings.
Treehouse in Horseheads
5 out of 5 average rating, 275 reviews

Falcon Nest - Treehouse Secluded in Private Forest

A Treehouse. Reconnect with nature at this unforgettable escape. Nestled in 28 acres of woods with hiking trails. This unique newly constructed all electric 525 sq foot elevated structure offers a wrap around deck for an ever changing view. King size bed & new technology foam offers complete comfort in separate climate controlled bedroom. Heated bathroom floor is a “warm” surprise. Optional seasonal outdoor shower for the adventurous. Kitchen lacks nothing tucked conveniently in the great room.

Guest favorite
Chalet in Willet
4.94 out of 5 average rating, 156 reviews

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.

Top guest favorite
Cabin in Candor
5 out of 5 average rating, 72 reviews

Cozy Cabin in Candor

600 square foot, 1 bedroom, 1 bathroom efficient and cozy cabin on a beautiful hilltop location in Candor, NY. Built in 2022. The cabin is easily accessible through a shared driveway in a quiet and private setting. Watch beautiful sunrises from one direction and gorgeous sunsets from the other direction, and the occasional wildlife passing by. Many outdoor recreation opportunities at nearby State Forests/Parks. Pets are welcome! Portable mattresses can be provided for additional guests.

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, 167 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 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, 132 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
Cabin in Van Etten
4.96 out of 5 average rating, 141 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
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, 328 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 rustic cabin features a wooden exterior with large windows, allowing natural light to fill the interior. A covered porch with steps leads to the entrance. Firewood is neatly stacked beside the cabin, surrounded by lush greenery and a gravel pathway.
Cabin in Berkshire
4.97 out of 5 average rating, 94 reviews

"Sled Shack", secluded cabin in woods.

Private cabin on 115 acres. Has large pond to walk to. Several miles of trails. Cabin has kitchen and full bath. Bath is entered from outside. Electric is supplied by electric start generator. Queen bed with 2 cots and all linens. Wood stove for heat. Fire pit. Firewood is available for small fee. This cabin is very secluded, you can drive up a 1/2 mile driveway to the front door. Come and enjoy the peace and Quiet. {No motorized vehicles allowed on trails}

Top guest favorite
The cabin is positioned on a grassy area, with a serene pond visible nearby. The structure features a sloped roof and wooden siding, surrounded by lush green hills. A clear sky at dusk displays the moon, creating a peaceful ambiance.
Cabin in Newark Valley
4.94 out of 5 average rating, 18 reviews

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

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, 291 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 favorite
A wooden staircase leads down to a tranquil pond, surrounded by lush greenery. The water reflects the sky and nearby trees, creating a serene outdoor setting. Vibrant plants frame the view, enhancing the natural surroundings.
Guesthouse in Spencer
4.92 out of 5 average rating, 164 reviews

Tree house in Ithaca

Tree house inspired, located in the town of Danby, this one bedroom apartment is both peaceful and centrally-located: 8 miles from Cornell University, 6 miles from Ithaca College, and accessible to the Finger Lakes Wine Trails, and the Finger Lakes Trail system. Featuring a private deck that overlooks a park-like setting, well stocked kitchen, and a beautiful indoor space that is perfect for year round adventures.

Top guest favorite
The guesthouse, constructed in wood, is nestled beside a serene pond surrounded by trees in autumn colors. A kayak is seen docked nearby, while a small seating area on the porch invites relaxation. The modern design blends with the natural surroundings.
Guesthouse in Owego
5 out of 5 average rating, 100 reviews

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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