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 outdoor seating area is presented, featuring a wooden swing with cushions, surrounded by lush greenery. A fire pit sits nearby, with a set of chairs and ambient lighting. The scene conveys a peaceful retreat among nature, ideal for relaxation and evening gatherings.
Cottage in Conewango Valley
5 out of 5 average rating, 199 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

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 charming cottage is depicted with a metal roof and an American flag waving at the front. Two blue chairs are positioned on the patio, overlooking a grassy area leading to the lake, where an orange kayak is secured at the dock.
Cottage in Cassadaga
4.95 out of 5 average rating, 142 reviews

Lakefront Sunset Getaway on Cassadaga Lake

Welcome to the Cottage! This cottage sits directly on Cassadaga Lake where you can enjoy beautiful sunsets every night from the concrete patio or from the couch. Feel free to go kayaking, fishing, or swimming directly from the dock or shoreline. Perfect for anyone who wants to enjoy lake life for the weekend, week, or month! *NEW* 2 kayaks are available for free use during your stay. No gatherings, events, and/or parties larger than your reservation. Free parking up to 2 cars.

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, 180 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!

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
4.93 out of 5 average rating, 279 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 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, 489 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.

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, 335 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, 184 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
Loft in Jamestown
5 out of 5 average rating, 267 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 favourite
A charming house is illuminated at night, showcasing its architectural features and lush landscaping. Soft lighting highlights the front porch and garden, while large trees provide shade around the property. The expansive yard is visible, creating a welcoming outdoor setting.
Flat in Fredonia
4.95 out of 5 average rating, 139 reviews

Elegant 2 bedroom apt 1 block from SUNY Fredonia

Kick back and relax in this calm, stylish space—perfectly located in the heart of Fredonia. Just steps away from SUNY Fredonia, and a short drive to Lake Erie, local vineyards, Lily Dale, several scenic lakes, and the renowned Chautauqua Institution.

Guest favourite
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.
Flat 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 Chautauqua County holiday rentals