
Vacation rentals in Kennedy
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Kennedy
Guests agree: these stays are highly rated for location, cleanliness, and more.

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!
4.99 out of 5 average rating, 265 reviews
The Empty Nest ...2nd floor
Qaintly named "The Empty Nest" ! Comfortable 2 bedroom upper apartment with private entrance and driveway. I gladly welcome well behaved pets (2 pet max) and offer a large partially fenced off backyard ( Tree limb damage). Come visit Randolph for a couple of days or an extended stay. Conveniently located close to Ellicottville, Jamestown and the Chautauqua Lake Region, Seneca Allegany Casino, Allegany State Park and the Amish trail. Popular wedding venues and golf courses right near by as well
4.91 out of 5 average rating, 200 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.
4.96 out of 5 average rating, 130 reviews
Private Romantic-cottage/cabin-Allegany St Park.
Comfy, cozy, romantic; Modern country cottage/cabin. 1 acre of lawn and wooded area. Seasonal outdoor deck/dinning, fire pit. Nestled amongst a quaint Old Order Amish community . Private secluded driveway. Allegany State park, Amish Shops, Jamestown's National Comedy Center, Lucy Desi Museum, Seneca/Allegany Casino, State land hiking trails, Ellicottville-30min. Public creeks, Lake Erie-Wineries, Chautauqua Institution, Chautauqua Lake. No city lights to obscure night skies. Seasonally decorated
4.99 out of 5 average rating, 207 reviews
Blue Oar/Luxe Lakehouse/Chautauqua
Welcome to Blue Oar Lakehouse on Cassadaga Lakes! Luxe 4 Bed / 3 full Bath, with stunning views, private dock, and 75 ft beach. Spacious and light-filled, renovated 1925 Craftsman home, perfect for family or group getaways. Located in a quiet, year-round neighborhood just minutes from Lily Dale and The Red House. Dog-friendly. Kayaks, paddle boards, pedal boat, bikes, yard games, grill, firepit on lakefront. If booked, check out our sister property, Blue Canoe (2BR/1BA, right on the water!
5.0 out of 5 average rating, 144 reviews
Barndominium 132
Welcome to your mini vacation or getaway in this modern, newly constructed apartment! This cozy & stylish space is perfect for up to four people, with 2 bedrooms one being on the 1st floor each featuring a queen bed, ensuring a good nights sleep for everyone. The apartment also features a modern kitchen w/ all the amenities, WIFI & TV's included, you will never miss your favorite shows or miss an email. Off street parking, private patio, bath & laundry conveniently on the main floor.
4.97 out of 5 average rating, 125 reviews
Lovely 2 bedroom 1 bath country cottage on 5 acres
LOCATION LOCATION LOCATION... This cozy home is close to everything. Located just 2.5 miles from Chautauqua Lake, 10 miles from The Chautauqua Institution, 19 miles from skiing this is the perfect place. THE SPACE... First floor laundry, full kitchen, large screen tv featuring YouTube TV, gas grill and much more. Everything you need to feel at home. NOTE: THERE IS ROOM FOR 4 TO SLEEP, FEATURING TWO QUEEN BEDS AND A LARGE STANDARD (non pullout) COUCH TO SLEEP ON. NO GARAGE ACCESS
5.0 out of 5 average rating, 135 reviews
Thurston Terrace Apartment in Downtown Jamestown
Our 19th-century row house apartment has been thoughtfully designed to provide a comfortable stay and authentic local experience on your next visit to Jamestown. Perfectly located in the heart of downtown Jamestown, you can easily walk to excellent restaurants, pubs, and boutique shops, including a café and beer + wine lounge right downstairs. Explore the National Comedy Center, visit the Lucille Ball Desi Arnaz Museum, and head to Chautauqua Lake for scenic walks.
4.97 out of 5 average rating, 486 reviews
Chautauqua Lakehouse with a picturesque view
Tastefully decorated with lake charm. Minutes from Bemus Point and Downtown Jamestown. Across the lake from Lakewood and the new Chautauqua Harbor Hotel. A short drive to the Chautauqua Institute. Enjoy morning coffee and evening drinks on the front porch. Also a nice winter getaway. On the snowmobile trail. Holiday Valley Ski Resort -40 miles Peak &Peak Ski Resort - 30 miles Cockaigne Ski Resort - 18 miles Salamanca Casino - 35 miles
4.88 out of 5 average rating, 206 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.
4.9 out of 5 average rating, 125 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.
5.0 out of 5 average rating, 276 reviews
Cozy Lakefront Cottage
Enjoy and relax with the whole family at this peaceful place to stay. The Chautauqua lake is just a few steps from the backyard. Enjoy fishing, (ice fishing in the winter!) boating, bonfire, bbq, canoeing and breathtaking sunsets are not to be missed! This home is newly renovated and is located near all major shops and amenities. Free parking.
4.99 out of 5 average rating, 149 reviewsPopular amenities for Kennedy vacation rentals
Other great vacation rentals in Kennedy

Island Cabin - The Paddle Inn
4.98 out of 5 average rating, 353 reviews
Secluded Egypt Hollow Cabin
4.99 out of 5 average rating, 139 reviews
Quaint 2 bedroom home overlooking bird sanctuary
4.94 out of 5 average rating, 160 reviews
Riverside Villa -King Suite
4.95 out of 5 average rating, 262 reviews
The Carriage House (Apt 2)
4.95 out of 5 average rating, 96 reviews
Copper Roof Retreat Rustic Log Cabin Country Charm
5.0 out of 5 average rating, 45 reviews
Barndominium: Comfort in the Countryside
5.0 out of 5 average rating, 63 reviews
Country home in rural Falconer.
5.0 out of 5 average rating, 27 reviewsDestinations to explore
- New York Vacation rentals
- Philadelphia Vacation rentals
- Washington Vacation rentals
- Pittsburgh Vacation rentals
- Columbus Vacation rentals
- Cleveland Vacation rentals
- Niagara Falls Vacation rentals
- Detroit Vacation rentals
- Jersey City Vacation rentals
- Mississauga Vacation rentals
- Newark Vacation rentals
- Baltimore Vacation rentals
- Holiday Valley Ski Resort
- Allegheny National Forest
- Peek'n Peak Resort
- Allegany State Park
- Kinzua Bridge State Park
- Kissing Bridge
- Buffalo and Erie County Botanical Gardens
- Knox Farm State Park
- Highmark Stadium
- Ellicottville Brewing Company
- Eternal Flame Falls
- Holimont Ski Club
- Lucille Ball Desi Arnaz Museum
- Chestnut Ridge Park
- National Comedy Center
- Midway State Park
- Woodlawn Beach State Park
- Lake Erie State Park
- Zippo & Case Museum/Visitor Center
- Evangola State Park





