Holiday houses in Kennedy

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Top-rated holiday rentals in Kennedy

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Top Guest favourite
The cabin's exterior is illuminated at dusk, reflecting beautifully on the calm surface of the pond. Surrounding tall trees offer a natural backdrop, enhancing the serene atmosphere of the retreat.
Home in Gerry
4.96 out of 5 average rating, 124 reviews

Forest Retreat, 90 miles to Niagara Falls.

Welcome to Forest Retreat! We are nestled in the hills of Western New York, 23 miles to Chautauqua Lake and 14 miles to Lily Dale. This unique home is near several wedding venues and the Earl Cardot Overland Trail, which is surrounded by 2,300 acres of state forest. We are located between 2 local ski resorts, and only 87 miles south of Niagara Falls State park. Relax by the fire, kayak, or fish in the 2 acre pond and just enjoy the scenery. We do require a signed waiver to utilize the pond.

Top Guest favourite
A canoe glides across a calm pond, framed by trees showcasing autumn foliage. Two people paddle gently, surrounded by vibrant reflections of fall colors on the water's surface. A clear blue sky enhances the serene atmosphere, inviting exploration of the tranquil landscape.
Home in Randolph
4.99 out of 5 average rating, 255 reviews

Quiet Convenience

Quiet Convenience 1 mile from I-86 Enjoy the secluded comfort of this rustic retreat close to many area attractions. Nestled in the woods overlooking a large pond with nature at every turn. Enjoy a campfire, fishing, bird watching, snowmobile trails, and skiing. Close to the Amish Trail, and Chautauqua Lake, Allegheny State Park, National Comedy Center, Lucille Ball Museum, Chautauqua Institution, and more! We welcome Sewing/Quilting Retreats, Faith Based Retreats, etc. Come for a visit!

Top Guest favourite
A cabin is nestled among tall pine trees, showcasing a rustic wooden exterior and a welcoming porch. The surrounding landscape reveals vibrant autumn foliage in hues of orange and red, creating a serene and secluded atmosphere.
Cabin in Ellicottville
4.96 out of 5 average rating, 171 reviews

Stylish & Secluded Hideaway, 5 mins to EVL

This private space is quietly tucked away in a stand of pines in the woods alongside Bryant Hill Creek. A wall of windows brings nature and natural light pouring into the space, and a fully-equipped kitchen and European bathroom provide modern comfort. Less than 4 miles outside of E-ville, it comfortably sleeps 2 adults and offers a chic and romantic setting for a couple to hide away with easy access to downtown. 4x4 a must in the snow, or simply park at the foot of the driveway. Tv & wifi.

Top Guest favourite
An open floor plan features a queen bed with light bedding, complemented by a cozy couch and armchair. Large windows allow natural light to brighten the space, while wooden beams add character to the ceiling. A small coffee table and decorative plants enhance the inviting atmosphere.
Cottage in Portland
4.97 out of 5 average rating, 143 reviews

Lake-View Cottage for 4 · Wine Tasting Included

Welcome to Fisherman’s Cottage; a cozy retreat with gorgeous lake views from the enclosed front porch and open-air back deck- perfect for catching a breathtaking sunset. Spend some time enjoying a complimentary wine tasting at nearby 21 Brix and return to comfortable furnishings, a fully equipped kitchen, and an efficient bath complete with a spa tub. Rent alone or pair with our newly renovated Mainstay cottage next door for extra space- ideal for families or groups seeking a peaceful getaway.

Top Guest favourite
Cottage in Cattaraugus
4.94 out of 5 average rating, 119 reviews

Quiet Creekside Escape in the Enchanted Mountains

Enjoy our creekside oasis, nestled in the quaint hills of Amish country, 1 hour from Buffalo + 15 minutes to E-Ville! The Getaway Chalet offers 3 bedrooms, stone hearth & wood-burning fireplace to keep you cozy. Outside, you'll find beautiful waterfalls, creek for exploring, two fire areas, a yoga deck & plenty of space to lounge. Unplug, reconnect + fall asleep to the sounds of the brook or bring your laptops, connect to our hi-speed WiFi and make this cozy cabin your office for the week!

Guest favourite
A wooden back deck provides seating options, including a glass-topped table and several chairs, with ample space for relaxation. Surrounding greenery and trees offer shade, while a view of the lake is visible in the background, completing the serene outdoor atmosphere.
Home in Jamestown
4.86 out of 5 average rating, 125 reviews

Charming West Ellicott Cottage with Lake View

Nicely decorated with lake theme. Minutes from Lakewood, the Chautauqua Harbor Hotel, Bemus Point and Downtown Jamestown. New kitchen in June 2025. Back deck with spectacular lake views, and campfires in the back yard. National Comedy Center - 3 miles Southern Tier Brewery - 4.2 miles Ellicottville Brewing - 11 miles Lucille Ball House - .25 miles Chautauqua Institute - 14 miles Chautauqua Lake Pops- 18 miles Holiday Valley - 40 miles Peek & Peak - 18 miles Salamanca Casino - 35 miles

Top Guest favourite
Three Adirondack chairs face a serene pond surrounded by lush greenery and autumn-colored trees. The grassy area invites relaxation, with natural scenery providing a peaceful atmosphere. Fallen leaves scatter on the ground, adding to the tranquil setting.
Cabin in Sinclairville
4.94 out of 5 average rating, 278 reviews

The A Frame-Cozy cabin, HOT TUB! Nature lovers!

Cabin with great amenities in the forest. There’s a creek flowing and a lovely pond. 4 seat Hot tub! Satellite Tv, WiFi, full size fridge, microwave, apartment size oven/stove, wood stove (primary heat in colder months) and electric baseboard heat 2 double beds, bunk beds. wood stove in garage. Easy access to NY State Land Snowmobile trails! Great location for hunters,Snowmobilers, cross country skiers, hikers, kayakers and all outdoor enthusiasts! Near Cassadaga Lake.

Guest favourite
A charming cottage is nestled among lush greenery alongside a tranquil river. The large building features a combination of wood and glass elements, with expansive windows reflecting the surrounding landscape and a deck visible in the background. Rich foliage enhances the serene setting.
Home in Warren
4.89 out of 5 average rating, 114 reviews

Creekside cottage

Welcome to our Creekside Cottage! I have called this place home for most of my life, playing in the back yard, waving at the steady stream of kayakers or going creeking and exploring the islands. Nowadays, I still adventure out with my kids but you'll also find me kicking back and enjoying the sights from the big picture window or out on the back deck watching the sunset. We are glad you are here. I hope you love it as much as we do.

Top Guest favourite
A calm waterway reflects a red cottage and trees, framed by vibrant green grass. An arched wooden bridge crosses over the water, leading to a deck with colorful chairs. The tranquil setting is enhanced by a slight mist rising from the surface.
Island in Cassadaga
4.99 out of 5 average rating, 333 reviews

Island Cabin - The Paddle Inn

Abundant privacy is yours at this Island paradise on beautiful Cassadaga Lakes. Accessible by an arched bridge or boat, the cottage is brand new inside and out, is environmentally friendly, provides endless outdoor adventure and a charming interior. Fish from the back deck, swim in crystal clear lake water, relax on the covered porch, and enjoy boundless nature literally at your fingertips, in this very unique setting.

Top Guest favourite
A geodesic dome is set in a lush outdoor space, surrounded by trees. A spacious wooden deck features a hot tub and patio furniture, inviting relaxation. The dome's distinctive shape is complemented by large triangular windows that provide ample natural light.
Dome in Youngsville
4.98 out of 5 average rating, 108 reviews

Riverfront Dome with Hot Tub

Welcome to the Downstream Dome! Our newly constructed geodesic dome allows you to wake up to a one of a kind view of the gorgeous Allegheny River, all while feeling nestled in with nature. The Dome includes one Queen bed, one bathroom, dining area, full kitchen, outdoor patio area with a hot tub, grill, and fire pit. For the health and safety of everyone we do have a very strict no animals policy. Thank you.

Top Guest favourite
A charming cabin is set in a wooded landscape, featuring a red metal roof and large glass doors that open to a deck area. Two Adirondack chairs surround a fire pit on a gravel base, inviting relaxation amidst nature.
Cabin in Russell
4.98 out of 5 average rating, 126 reviews

Secluded Egypt Hollow Cabin

Escape to a serene cabin near the Allegheny National Forest in Russell NWPA. Perfect for travelers and couples seeking a relaxing getaway surrounded by nature. 1 Bed. 1 Bath. Private Cabin Enjoy a stream, fire pit, and private driveway. Explore hiking, biking, and all types of boating nearby. Enjoy local businesses downtown Warren. Host available for questions and recommendations. Book your getaway now!

Top Guest favourite
The entryway features a covered porch with a rocking chair and decorative planters. Lush greenery surrounds the steps, leading to the front door. Two hanging ferns and flower pots add a touch of color, creating a welcoming approach to the apartment.
Apartment in Randolph
4.96 out of 5 average rating, 126 reviews

The Empty Nest- 1st Floor

Comfy 1 bedroom first floor apartment. Private drive and entrances. Large side porch to enjoy your morning coffee. Fenced in backyard with seating and fire pit to enjoy. We are conveniently located right off I-86. Just minutes to Amish country, Ellicottville (25 mins), Salamanca (20 mins. , Jamestown (20 mins), Allegheny Park(15 mins) and Reservoir (20 mins.) and Niagara Falls 1:15 hrs).

Popular amenities for Kennedy holiday rentals

  1. Airbnb
  2. United States
  3. New York
  4. Chautauqua County
  5. Kennedy