Holiday houses in Urbana

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Top-rated holiday rentals in Urbana

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Guest favourite
An outdoor seating area is presented with a circular antique wine barrel fire pit surrounded by modern bar stools. The deck features wooden flooring and offers a view of the lake, with a dining set visible in the background and trees lining the perimeter.
Barn in Hammondsport
4.95 out of 5 average rating, 91 reviews

The Barn On Keuka-HotTub-LakeView-WineTrail

Experience a picturesque lakeside retreat at our newly built modern barn on the Keuka Lake. Restored wood from the original barn accent the home, adding a touch of rustic charm to the modern design. Nestled in the heart of wine country, this stunning property offers the perfect blend of luxury and relaxation. Not only can you enjoy the tranquility of a lakeview home, but a HOT TUB, antique barrel firepit, SHUFFLEBOARD, and grill are provided to offer you the type of stay you've been dreaming of!

Guest favourite
A spacious outdoor seating area features comfortable furniture, surrounded by greenery. Sunlight filters through trees, highlighting panoramic lake views. An inviting atmosphere is created with a soft rug underfoot and decorative lanterns placed on the table.
Cabin in Hammondsport
4.89 out of 5 average rating, 61 reviews

Lake View with Balcony- Private 2 bedroom chalet

Hidden and what a view! Private 1900' drive leads to custom built private chalet overlooking Keuka Lake. Forget your worries in this serene space while enjoying the indoor great rooms' panoramic views or outdoor wrap around balcony. Paths meander the acreage for you to explore. Located in the heart of wine country. Keuka boat/jet ski rentals within minutes. Bristol mountain and Watkins Glen State Park 35 minutes away. 8 min drive to town for restaurants & shopping. Keuka State Park 22 min away

Top Guest favourite
A deck area is shown, featuring several outdoor chairs arranged around a small table. Natural light is visible through large windows of the cottage, while a serene view of trees and sky enhances the space.
Guesthouse in Hammondsport
4.95 out of 5 average rating, 123 reviews

Waterfront Cottage with moorage on Keuka Lake

Charming cottage on the waterfront with a beautiful view of the lake. Direct access that’s mere steps to the water with large dock/mooring for swimming/watersport fun. Fully furnished with a great kitchen, outdoor grill and a comfy queen sized bed. It's only 5 miles to the town square with lots of cute shops & quaint restaurants. Close to a variety of wineries, craft breweries & hiking/biking trails. A short drive to the Glenn H. Curtiss Museum and just over the hill from Watkins Glenn raceway!

Top Guest favourite
A single-story lake house is pictured, featuring a light yellow exterior with large windows and a spacious deck. The deck extends toward the water with a railing and seating area visible. Surrounding greenery enhances the natural ambiance of the lakeside setting.
Guesthouse in Keuka Park
4.99 out of 5 average rating, 382 reviews

Keuka Beach House - Glamping at its best!

My place is right on the lake and great for summer activities. The deck hangs out over the water overlooking the beach and dock. Outdoor opportunities include your own hiking trail on five acres of land behind the house, cycling, swimming, kayaking and canoeing. It's a great place for couples, solo adventurers, and pets who like to swim. Currently, New York State charges 8% sales tax and Yates County charges 4% Occupancy Tax which is added to the amount you pay when booking the space. Sorry.

Top Guest favourite
A hilltop retreat is depicted from an elevated view, showcasing a contemporary two-story home with a dark roof. Lush green fields surround the property, leading to distant hills and the shimmering waters of Keuka Lake, creating a scenic backdrop.
Home in Hammondsport
4.97 out of 5 average rating, 289 reviews

Heard It View The Grapevine

Walking distance to Dr. Frank's Winery, Barrelhouse 6 Distillery, & Divided Sky Winery. A 6 minute or less drive to Point of the Bluff Winery & Concert venue, Keuka Brewing, Krooked Tusker Distillery, Steuben Brewing, Heron Hill Winery & Bully Hill Winery. Panoramic clear views boast from this hilltop hideaway. Perfect family vacation or couples getaway spot for the ultimate Finger Lakes retreat. Fiber Optic internet at the house. Rare for this area - better speeds and more reliable service.

Superhost
The tiny cabin features a rustic wooden porch with two black chairs positioned beside the entrance. A white door with glass paneling provides a welcoming entry. Surrounding gravel creates a natural setting, with outdoor seating and a campfire area visible nearby, framed by trees.
Tiny home in Hammondsport
4.87 out of 5 average rating, 30 reviews

40 Acre Silsbee Falls Tiny Cabin

Peaceful and private tiny cabin on 40 beautiful acres filled with wild life, waterfalls, and lake views. The property does have various trails/two-track "roads" that guests are welcome (and encouraged) to hike. The main trail-way ends at a spectacularly unique late 1700's cemetery, situated at the top of the southern waterfall-filled ravine - lost to the woods for hundreds of years. Guests can observe graves of the early settlers in the area, including numerous members of the Silsbee family.

Top Guest favourite
The estate is surrounded by lush greenery, with expansive landscaped grounds leading towards a charming two-story structure. A spacious deck can be seen at the back, offering views of the rolling hills and trees in the distance under a clear blue sky.
Home in Hammondsport
4.96 out of 5 average rating, 114 reviews

The Manor House Estate

The Manor House Estate is a premier 5,000 sf lake-view estate located directly on the Keuka Lake Wine Trail within proximity of over 100 Finger Lakes wineries, breweries and distilleries and a few miles from some amazing dining establishments, retail shops, museums and more. Nowhere can you find an affordable place this large and amazing! Boat, kayak and other rentals available within two miles! Perfect for weddings and other events! Inquire within for more details. 16 person maximum

Guest favourite
Two wooden Adirondack chairs are positioned on a dock, facing a vast, calm lake. The water reflects the clear blue sky, with gentle ripples created by a soft breeze. In the distance, sloping hills are visible, accented by patches of colorful foliage.
Home in Hammondsport
4.74 out of 5 average rating, 125 reviews

Keuka Lake Getaway

Secluded getaway for a stay/work-cation. Travel & stay as a group or separate! Winterized house has 4 br, 2 kitchs , 2 living rms & 2 baths. 2nd floor closes off for two separate living areas w/ 2 br each, or keep it open as a 4 br house. Cozy sunroom- enjoy the sunrise. Huge deck & fireplace at house, or enjoy a fire on the private 80ft lakefront across the street & down stairs. Boat whips on dock. Kayaks, SUPs & canoe for use! Docks/deck to spread out.

Guest favourite
A modest blue cabin is set amid a lush green lawn, surrounded by tall oak trees. A wooden deck extends from the front, furnished with several outdoor chairs, inviting relaxation in the serene natural setting.
Cabin in Bath
4.95 out of 5 average rating, 102 reviews

The Cabin

Experience true relaxation at this updated cabin just up the hill from the beautiful small town of Hammondsport, NY and the head of Keuka Lake. Explore the countless wineries nearby making up the Keuka lake wine trail, along with several breweries and distilleries. Surrounded by picturesque wooded landscape and open fields, enjoy cooking on the grill, over a campfire, or chose one of the unique restaurants in downtown Hammondsport or others nearby.

Top Guest favourite
Home in Watkins Glen
4.91 out of 5 average rating, 151 reviews

Watkins Glen Country Living

Kick back and relax in this calm, stylish space located in the country setting of Watkins Glen, NY. The whole house is dedicated to your enjoyable guest experience with 3 king bedrooms and 2 full bathrooms, of which the master bath has both a shower and jetted tub. Come enjoy the peaceful setting surrounded by fields and beautiful views. The interior of the house was completely remodeled and painted in 2024.

Top Guest favourite
The tiny house features charming architecture with a combination of wooden accents and white siding. A cozy front porch is accessible from the exterior, surrounded by greenery, while a decorative American flag adds a touch of character.
Tiny home in Hammondsport
4.97 out of 5 average rating, 221 reviews

Shalestone Landing (Lakeside Tiny House)

As the name suggests, Shalestone Landing sits nestled in at the bottom of our home vineyard, atop layers and layers of hidden shale.....perfect for growing grapes! This quaint and comfortable tiny house is located on the west side of Keuka Lake offering lakeside views of gorgeous Keuka Lake. Shalestone Landing is perfect for a couple or small family (up to 4) looking to get away!

Top Guest favourite
A spacious loft-style living area features vaulted wood-paneled ceilings and ample natural light. Comfortable seating is arranged around a central coffee table, complemented by a large area rug. A kitchenette is visible in the background, along with a dining space, enhancing the open layout.
Barn in Hammondsport
5 out of 5 average rating, 121 reviews

The Barn at Graystones

The Barn at Graystones is a private spacious loft-style rental with a tennis-pickleball court and brand new amenities. Enjoy a relaxing stay with lake views, conveniently located in the heart of the Finger Lakes region. A perfect getaway for two.

Popular amenities for Urbana holiday rentals

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