Vacation rentals in Kennedy

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Top-rated vacation rentals in Kennedy

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Top guest favorite
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, 123 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 favorite
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 favorite
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, 170 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 favorite
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, 277 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.

Top guest favorite
Home in Kennedy
5 out of 5 average rating, 37 reviews

Barndominium: Comfort in the Countryside

Nestled in the heart of the countryside, our charming Barndominium offers the perfect retreat for those looking to unwind and recharge. Start your mornings with a fresh cup of coffee as you take in the stunning views surrounding you. Whether you're lounging indoors or stepping out onto the porch, the peaceful ambiance of nature will be right at your doorstep. Located very close to the snowmobile trail. We can’t wait to welcome you to this peaceful getaway!

Top guest favorite
A charming log cabin exterior is showcased, featuring a second-story balcony and a covered porch. Lush greenery and well-maintained landscaping surround the cabin, while a vibrant blue sky filled with clouds adds to the serene atmosphere.
Cabin in Kennedy
5 out of 5 average rating, 34 reviews

Copper Roof Retreat Rustic Log Cabin Country Charm

A little piece of heaven here on Earth! Relax in this beautiful, peaceful log cabin situated on a clear 1 acre pond. Swim, kayak, float or just gaze if you like. View tranquil farm animals in the pasture right outside your window. A covered pavilion for gatherings or quiet reflection is available and an area for bonfires is yours to enjoy. Over 100 acres of forest trails to discover at your leisure are open for non-motorized exploration.

Top guest favorite
A cozy country home is featured, showcasing a yellow exterior with a front porch and a star decoration. A single-car garage is visible on the right side. Lush green grass surrounds the property, complemented by a backdrop of trees under a clear blue sky.
Home in Falconer
5 out of 5 average rating, 17 reviews

Country home in rural Falconer.

Cozy country home with living room and kitchen open floor plan. One bedroom queen bed and one full bath with washer and dryer. Living room has a queen sleeper sofa. Fully equipped kitchen with microwave. Relax and take in the country or play a round of golf just a stone's throw away. Beautiful hiking and snowmobile trails nearby. Minutes from Falconer and Downtown Jamestown. Our home is in the country but close to all your amenities

Top guest favorite
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, 330 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 favorite
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 favorite
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).

Top guest favorite
Loft in Jamestown
5 out of 5 average rating, 266 reviews

Vintage Trolley Station Now Industrial Style Loft

Enjoy a piece of history when you stay in our former trolley station that has been converted into an industrial style loft. Just outside the city limits in a country setting but close to the hospital, local bars/restaurants and the comedy center. The lower portion of the building features a quaint gift shop and across the street is a farm stand with locally grown food.

Top guest favorite
The kitchen features warm wood cabinetry and modern appliances, including a black refrigerator and microwave. A central island with seating for four is highlighted, while decorative plants and a vase of orchids add a touch of elegance to the space.
Apartment in Jamestown
4.96 out of 5 average rating, 170 reviews

A View From Above

Beautiful apartment in the heart of downtown. Great views of the city and within walking distance of all downtown attractions. Within blocks of The National Comedy Center, The Lucy-Desi Musium, the ice arena and The Reg.

Popular amenities for Kennedy vacation rentals

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