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 favourite
A cozy interior features warm wooden walls and a view of the lake through a large window. A spacious bed is positioned near the window, complemented by a small seating area with a leather couch and a round table for meals or activities.
Tiny homes in Burdett
4.99 out of 5 average rating, 182 reviews

FLX 3- Lake View Wine Country Tiny Cabin

Nestled up on a hill overlooking Seneca Lake, watch the sunset while laying in bed or from your own patio with a fire crackling. We are local hosts and will make sure you have an unforgettable stay! Everything you could want to do in the Finger Lakes will be at your fingertips. Wineries galore, two even just next door, multiple breweries nearby, minutes to the lake, 15 minutes to downtown Watkins Glen, 10 minutes to hiking trails at the national forest, or stay in, relax, and enjoy the view!!

Top guest favourite
A charming bedroom features a wooden bed topped with a floral-patterned blanket. An antique dresser with a marble top stands adjacent to the bed, accompanied by a vintage mirror and decorative items. Natural light filters through the room, enhancing the rustic ambiance.
Barn in Ithaca
4.88 out of 5 average rating, 101 reviews

Beautiful barn home in Danby

The house is built into a barn. It has rustic charm and modern comforts. It's situated in a beautiful valley with a lovely view. The back porch and yard are nice places for relaxing. There is a basketball hoop in driveway side. Dwelling is 7 miles from Ithaca , which is about a 15 minute drive. There is is no real public transportation, except for a bus that runs to Ithaca at 8am and 5pm on weekdays. To catch it, walk the half mile to the highway and flag it down. Welcome to the country.

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
4.85 out of 5 average rating, 308 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
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, 163 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 favourite
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
4.96 out of 5 average rating, 138 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 favourite
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, 123 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.

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, 326 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 spacious living area features a leather couch with decorative pillows and a wooden coffee table centered on a plush area rug. Large windows provide natural light and views of the surrounding trees. A dining table is visible to the right, enhancing the inviting atmosphere.
Cottage in Freeville
4.99 out of 5 average rating, 134 reviews

Country retreat near Ithaca

Your own comfy, private, immaculately clean 2-story cottage with A/C, full kitchen, dishwasher, full bath, wifi, TV+Roku, washer/dryer, deck, couch, desk, fire pit, grill, and free EV charging. Ideal for relaxing, remote work, or as base to explore the area's restaurants, trails, wineries, and more. Nestled against a wooded hillside, surrounded by trees, meadows, and marshes. Tons of birds and animals. 20-mins east of the Ithaca Commons and college campuses.

Top guest favourite
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, 289 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 favourite
Apartment in Dryden
4.9 out of 5 average rating, 308 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
An open living area features high ceilings and large windows, allowing natural light to fill the space. A modern kitchen with sleek cabinetry is paired with a dining table surrounded by four chairs. A spacious blue sofa invites comfort, complemented by stylish decorative elements.
Home in Brooktondale
5 out of 5 average rating, 222 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.

Top guest favourite
A charming cabin is set on an elevated platform, surrounded by lush greenery. Stairs lead to the entrance, where warm light spills from the windows, illuminating the welcoming structure. Two benches are positioned nearby, adding to the serene outdoor setting.
Farm stay in Brooktondale
4.98 out of 5 average rating, 146 reviews

Glamping with a gorgeous view

Enjoy private fancy camping in this light-filled, fully furnished cabin on a platform overlooking a pond, pastures, and the valley beyond. Situated on a working farm just 15 min. southeast of Ithaca, NY, this is perfect for a family or romantic get-away. Unplug, relax, and visit the local trails, wineries, and waterfalls, or just hang out and enjoy the view!

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