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.

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Randolph

4.99 out of 5 average rating, 174 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!

Mar 2 – 9

R3,228 ZAR per night

Guest favorite

Cottage in Conewango Valley

5.0 out of 5 average rating, 138 reviews

Romantic Private Cottage/Cabin-Allegany Park20min.

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.

Jun 7 – 14

R3,287 ZAR per night

Guest favorite

Home in Ashville

4.92 out of 5 average rating, 218 reviews

HEART AND SOUL--Secluded setting overlooking Pond

Relax at this Secluded Setting overlooking the centerpiece HEART shaped fish filled Pond. RE-CREATE or Rest your SOUL in Natures Beauty with Woods and Hiking trails to Roam, OR have a BONFIRE. Lots of Parking for reunion/retreats, Sledders, Equine, or Boaters. PEAK & PEAK Ski/Golf Resort,Several Lakes, State Lands with Hiking, Snowmobile, and Horse Trails just minutes away. ONE Main Bedroom and a Queen Sofa Sleeper in the Family Rm/2nd Bedroom. Fastest WIFI Available. Enclosed Deck. ENJOY ENJOY.

Apr 27 – May 4

R2,225 ZAR per night

Guest favorite

Guesthouse in Forestville

4.99 out of 5 average rating, 121 reviews

Forestville Studio Cabin (Rural Guest Home)

Reconnect with nature at our Studio Cabin Guest Home on 5 acres. Nestled along the edge of a creek behind cabin. About 11 miles from Lake Erie and 1hr away from Niagara Falls. 528 yards from Snowmobile trail. 10 mins from Amish Trail and 12 miles to Boutwell Hill State Forest, Hiking, biking, swimming, fishing, tubing, kayaking, snowshoeing, skiing, snowmobiling, state land for hunting, Amish country, wineries. We are currently in the process of logging the property and having it cleaned up.

Sep 22 – 29

R2,456 ZAR per night

Guest favorite

Cottage in Ashville

4.94 out of 5 average rating, 112 reviews

Cozy lake property get away

Small cottage ( app. 400 sq ft ) on large lake front parcel. The rental is the rear cottage with very nice lake front view, quiet neighborhood and large yard. Two miles to Bemus point where there are several restaurants and a grocery store. Chautauqua county voted best small golf town by golf digest. National comedy center in Jamestown. Boat rentals near by. Guests have outdoor dining area and a fire pit. There is a large supply of fire wood also. Chautauqua institution 7 minutes.

Oct 11 – 18

R2,230 ZAR per night

Guest favorite

Home in Frewsburg

4.97 out of 5 average rating, 102 reviews

Private log home located on a private hilltop

Beautiful log home situated on a private wooded hilltop in beautiful Frewsburg NY. This is a real get away for people to experience the peace and solitude of life. 30 acres of private woods with an abundance of wildlife to explore. Walking trails for going back to nature with many species of trees and habitat. Regardless of the season adventure is bound to find you. This is the best of country living. Stores and restaurants are located just minutes away in the historic town of Frewsburg

Dec 15 – 22

R2,451 ZAR per night

Guest favorite

Cabin in Sinclairville

4.94 out of 5 average rating, 193 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.

Aug 6 – 13

R2,982 ZAR per night

Guest favorite

Apartment in Jamestown

4.96 out of 5 average rating, 411 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.

Nov 4 – 11

R2,999 ZAR per night

Guest favorite

Apartment in Randolph

4.91 out of 5 average rating, 137 reviews

The Empty Nest ...2nd floor

Qaintly named "The Empty Nest" ! Freshly renovated 2 bedroom upper apartment with private entrance and driveway. I gladly welcome well behaved pets and offer a large fenced off backyard. 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.

May 1 – 8

R1,667 ZAR per night

Guest favorite

Apartment in Jamestown

4.93 out of 5 average rating, 215 reviews

Fluvanna Grocery, 2 BR Private Apt, Full Kitchen

Our fully furnished, family & pet friendly, lake view apartment is waiting for you. Come enjoy lake views, garden walks, and our open concept, eco living space. The apartment is situated on a quiet street perfect for dog walks & bike rides and conveniently close to restaurants, the highway, and nearby tourist destinations. We will try our best to accommodate reasonable early check ins when requested, dependent on our full-time work schedules.

Aug 17 – 24

R2,339 ZAR per night

Guest favorite

Guest suite in Great Valley

4.93 out of 5 average rating, 324 reviews

Comfy studio nestled in the woods (New Listing)

Nestled in the forest only seven minutes’ drive from Holiday Valley, this contemporary style self-contained studio apartment is the perfect weekend getaway for skiing and nature-loving couples. With every luxury and convenience, you can home cook meals or barbecue on the deck overlooking the creek, with nothing but forest beyond. Relax and watch a movie on our LCD screen or use high speed Starlink internet.

Nov 26 – Dec 3

R2,040 ZAR per night

Guest favorite

Loft in Jamestown

5.0 out of 5 average rating, 215 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.

Sep 24 – Oct 1

R2,636 ZAR per night