Holiday rentals in Chautauqua County

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Top-rated holiday rentals in Chautauqua County

Guests agree: these stays are highly rated for location, cleanliness and more.

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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.

Guest favourite
A remodeled camper is positioned on a red wooden deck, showcasing a canopy that provides shade. A picnic table is visible under the awning, surrounded by a grassy area. Trees in the background create a natural setting, while a white fence borders the property.
Camper van/Motorhome in Dewittville
4.87 out of 5 average rating, 191 reviews

29’ camper (Sport). Quiet rural area.

Nice camper in a quiet location. 8 easy miles to the Chautauqua institution. 5 miles to Midway park. 2 miles to Chautauqua lake. 20 mins to the national comedy center. Short drive to Lake Erie wineries. 9 miles to Lily Dale. If you like country living this is the place. The camper is located in our back yard facing the woods with a great view. Hiking is welcomed. Equipped with a fire pit, picnic table. This camper has been remodeled with a new look. Check out our other campers as well.

Top guest favourite
A serene lakeside view showcases the cottage positioned on a rocky shoreline. Two white Adirondack chairs are placed near the water, complemented by a small firepit surrounded by soft landscaping. Bright blue skies and calm water create a peaceful atmosphere.
Cottage in Cassadaga
4.97 out of 5 average rating, 178 reviews

Blue Canoe/Upscale Lake Cottage/Chautauqua

Welcome to Blue Canoe Lake Cottage on Cassadaga Lakes! This small, 2 Queen Bedroom/1 Full Bath, newly renovated, open-concept, light-filled cottage offers 125 ft of private waterfront, a gated covered porch, & thoughtful details throughout. Enjoy 2 kayaks, 2 paddle boards, a pedal boat, 4 adult cruiser bikes, fire pit, & propane grill. Dog-friendly & perfect for up to 4 adults — luxury on the lake awaits! If booked, check out our sister property, Blue Oar (4BR/3BA, lakefront!

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
The exterior of a cozy cottage is depicted, featuring white wood siding and a red door. A small deck leads to the entrance, surrounded by green grass and trees providing shade. Large windows allow for natural light to enter the interior.
Cottage in Dunkirk
4.85 out of 5 average rating, 161 reviews

Cedar Beach Cottage on Lake Erie

Cozy cottage with full lake view from back deck! 1 bedroom w double bed, comfortable living room, full eat-in kitchen (gas stove) updated bathroom, Roku tv, wifi and large windows to let in the sunshine! Easy walking distance Point Gratiot Park. Also listed by me is nearby Cedar Beach House , a separate- but -adjacent lot with larger home suitable for 6 guests, so you can book both houses together for larger family gatherings Price includes all state and local taxes.

Top guest favourite
A historical home is featured with a large, inviting porch framed by lush greenery and blooming flowers. The white railings and steps lead to the entrance, enhancing the welcoming ambiance of the property. Multiple windows allow natural light to brighten the exterior.
Flat in Fredonia
4.94 out of 5 average rating, 488 reviews

Spacious Apartment in Historic Fredonia

This 2-bedroom, 1.5-bath apartment has a fully equipped kitchen; master suite with whirlpool tub; laundry, living, & dining rooms; & study. Attached to an historic home with on-site parking and private entrances, it has a porch overlooking a tree-shaded lot & quiet street. A 5-minute walk from SUNY Fredonia & downtown Fredonia, 3 miles from Lake Erie; a 35-minute drive from the Chautauqua Institute; & 1 hour from Niagara Falls, casinos, & ski resorts.

Superhost
A cozy porch of a tiny off-grid cabin is shown, featuring a small round table with two white folding chairs. A welcome sign and potted flowers add a touch of charm. Surrounded by greenery, the setting offers a peaceful escape into nature.
Cabin in Cassadaga
4.92 out of 5 average rating, 220 reviews

Angie's Good vibes Only. has shared hot tub access

Across road from snowmobile trails. 420 friendly!! nature is one of the greatest healers. bathroom house with flush toilet ! RUSTIC NON ELECTRIC cabin. BioLite solar in the cabin. Near Lily Dale NY. A welcoming haven away from the busy world. hiking trails nearby.perfect spot for road trippers. access to a guest shower & shared Dream Maker hot tub. family friendly. Communal bnb. You cannot park at the cabin and must walk 2 minutes to get to it.

Guest favourite
The exterior of the rustic castle is illuminated at dusk, with warm light spilling from the windows. A tall peak and multiple gables are visible, framed by trees standing against a colorful sky with hues of purple and orange.
Castle in Forestville
4.94 out of 5 average rating, 108 reviews

Cowboy Castle

You won’t forget the peaceful surroundings of this rustic destination. pleasant bungalow styled accommodation 2nd floor main living area with queen bedroom area next to the bathroom and kitchen. 50 inch TV in the spacious living room is wifi and several local..( heated and insulated).**.this is a private apartment styled airbnb, private entrance and not a shared or jointly used space. ** ac * 4th floor roof deck, 2nd floor deck**

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
An open living area features brick walls and tin ceilings, complemented by large windows that allow natural light to fill the space. A cozy sectional sofa and a coffee table sit in the center, while a desk and chairs are positioned nearby, enhancing the welcoming layout.
Flat in Mayville
4.99 out of 5 average rating, 101 reviews

Cozy Loft-Pet Friendly-Spacious

Welcome to the Loft, centrally located in Mayville, NY. Walking in you'll find brick veneer, tin ceiling and natural finished hardwood flooring. The loft has a great view from 8 new windows with darkening shades. There's plenty of room for up to 4 guests with a king bed and a queen murphy bed in the spacious living room. Chautauqua Lake is a .5 mi walk and CHQ Institution main gate is 4 miles away.

Top guest favourite
A comfortable living area features a dark leather sofa adorned with decorative pillows. A glass-top coffee table sits atop a patterned rug, surrounded by wicker chairs. Wooden beams highlight the ceiling, while soft lighting offers a cozy atmosphere. A decorative mirror reflects the room's inviting layout.
Home in Fredonia
4.97 out of 5 average rating, 183 reviews

CASA BELLA. Charming And Spacious.

CASA BELLA is a charming and spacious one bedroom, one bathroom space on the first floor of an unoccupied single family home in a quiet neighborhood. Located 1.7 miles from SUNY Fredonia, 8.1 miles from Lily Dale, 23 miles from Chautauqua and 69 miles from Niagara Falls. Perfect for families or a couple while visiting your college student, attending reunions, or local festivals.

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, 649 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.

Popular amenities for Chautauqua County holiday rentals