Holiday rentals in Chautauqua County

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Top-rated holiday rentals in Chautauqua County

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Top guest favourite
A charming cottage is nestled amid lush trees, featuring a welcoming porch with several outdoor chairs. A landscaped yard leads to a well-defined pathway, guiding visitors to the entrance. Natural surroundings enhance the peaceful ambiance of this secluded property.
Guest house in Westfield
5 out of 5 average rating, 117 reviews

Beachfront on Lake Erie * Driftwood Cottage

Come visit us at Steelhead Run offering panoramic views of the sunsets on Lake Erie. You will find this two bedroom cottage to be quite comfortable offering all the utility of a larger home. We also have a one bedroom cottage next door for rent. When you arrive you will find yourself nestled between Lake Erie and Chautauqua Creek on 7 forested acres. Both features can be accessed in less than a 200 foot walk from the cottage. On the beach you can spend time hunting for beach glass and driftwood.

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, 122 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
Home in Cassadaga
5 out of 5 average rating, 118 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!

Top guest favourite
The living area features two sofas and a coffee table with magazines atop it. A wall-mounted television is present alongside a bookshelf filled with books. Windows are adorned with curtains, allowing natural light to enter. A small desk is positioned near a map of the United States.
Flat in Jamestown
4.88 out of 5 average rating, 278 reviews

Cheby Manor - 1 Bedroom Apartment Kitchen/Bath

1 bedroom apartment on 1st floor with full kitchen and bath. Queen bed & sleeper sofa to accommodate up to 4. Walking distance to Downtown Jamestown. Available short term or discounted weekly/monthly rates. Pets welcome with a fee, see 'other notes'. Free street parking. There are residents living in other apartments in the building, all friendly and quiet. The building is over 100 years old so it's not modern or fancy, just comfortable and affordable if that's what you're looking for.

Top guest favourite
A charming cottage is visible by the lake, featuring a stone exterior and a gabled roof. Large windows allow natural light to enter, while a small patio with seating is situated under a red canopy. Surrounding trees enhance the natural setting.
Cottage in Findley Lake
4.98 out of 5 average rating, 118 reviews

Hidden Cove

Beautiful lakefront cottage on Findley Lake. Completely remodeled cozy one-bedroom cottage with two docks, 150 ft. of lake frontage, and boathouse. Tucked away on a quaint woodsy lot, you can enjoy breathtaking sunsets while relaxing around the firepit. Hidden Cove offers a one bedroom with a queen mattress and futon in the living room. The kitchen is fully stocked. Just a few miles from Peak n' Peek resort where you can enjoy skiing, cycling, ziplining, segway tours, and restaurants.

Top guest favourite
A welcoming living space features a large screen TV mounted on a pale wall, surrounded by a black entertainment unit. A cozy couch with patterned throw pillows faces the TV, while warm wood flooring adds a homey touch. A door leads to the entrance.
Home in Asheville
5 out of 5 average rating, 108 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

Top guest favourite
A spacious bedroom features a comfortable bed covered with a light blanket. Two nightstands with lamps stand on either side of the bed. A large mirror reflects the natural light from the window. The wooden floor adds warmth to the neutral-toned room.
Home in Dunkirk
4.95 out of 5 average rating, 136 reviews

Stay & Play

Welcome to your home away from home! Featuring FREE WiFi, Roku TV, electric fireplace, pillow-top mattresses, games, snacks, fresh towels and toiletries, fully equipped Kitchen and complimentary coffee - you'll have all you need for your next get-away! You'll be walking distance to Lake Erie and a short drive to the beach, Chautauqua Lake or Niagara Falls! Your stay comes with an extensive list of local recommendations for places to eat, enjoy and entertain while you Stay & Play!

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, 265 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 favourite
A cozy cabin exterior is surrounded by trees, illuminated by string lights at dusk. A hammock is strung between two trees, offering a comfortable space to relax. Several chairs and a fire pit are visible, inviting outdoor gatherings.
Guest house in Forestville
4.99 out of 5 average rating, 197 reviews

Forestville Studio Cabin (Rural Guest Home)

Reconnect with nature at our secluded studio cabin on 5 acres, nestled beside a creek. Just 11 miles from Lake Erie and an hour from Niagara Falls. Only 528 yards to the snowmobile trail, 10 minutes to the Amish Trail, and 12 miles to Boutwell Hill State Forest. Enjoy hiking, biking, swimming, fishing, tubing, kayaking, skiing, snowmobiling, hunting, and exploring Amish country and local wineries. Located on a quiet dirt road, yet close to main travel routes.

Top guest favourite
A cozy bedroom features a spacious bed with a patterned quilt in warm tones. Two bedside lamps provide soft illumination. A window with a wooden frame overlooks outdoor greenery, while floating shelves hold decorative items, enhancing the room’s inviting feel.
Cabin in Mayville
4.99 out of 5 average rating, 135 reviews

Cozy cabin- walking distance to Chautauqua lake!

Enjoy a peaceful stay in this cozy cabin on a quiet dead end street. With Snug Harbor Marina just a few minute walk down the street, Chautauqua Lake is right at your fingertips! Enjoy cooking outdoors with the BBQ grill, or make use of the full indoor kitchen. Create memories with the family while roasting s'mores around the gas fire pit and snuggling up with one of the board games provided. Snowmobilers and ice fishermen welcome!

Top guest favourite
A charming exterior of a renovated home displays a well-maintained garden with colorful flowers and a pathway leading to the entrance. An American flag is mounted on the side, framed by large windows that allow natural light into the living space.
Home in Westfield
4.99 out of 5 average rating, 624 reviews

Westfield Charmer

Charming 2 Bedroom/1 Bath home that has been totally remodeled. Brand new kitchen, appliances, floors, furniture, and more! Home has an open concept kitchen-living room, large bedrooms, huge deck with dining table and extra seating. There is an additional folding single bed if needed in MBR closet. Gas grill. Almost 1/2 acre backyard. Well behaved pets are welcome as are children.

Top guest favourite
A single-story house is depicted with a light gray exterior and a brown shingled roof. A welcoming front porch features a small set of steps leading to a door. Lush green lawn surrounds the home, accented by trees with autumn leaves.
Home in Dunkirk
4.97 out of 5 average rating, 236 reviews

Cozy 2 BR 1 BA home in a nice quiet neighborhood

This cute little house is just down the road from SUNY Fredonia. It is just a 5 minute drive to the NYS Thruway, shopping, and restaurants. Downtown Fredonia and Lake Erie shoreline are a short drive away.

Popular amenities for Chautauqua County holiday rentals