Vacation rentals in Chautauqua County

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Top-rated vacation rentals in Chautauqua County

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

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Top guest favorite

The exterior of the lodge is captured, showcasing a covered porch with a swing and two Adirondack chairs. Surrounding greenery and vibrant autumn foliage frame the scene. A gravel driveway leads to the entrance, enhancing the inviting ambiance of the lodge.

Guesthouse in Fredonia

5 out of 5 average rating, 25 reviews

Bear Lake Lodge

Kick back and relax at the Bear Lake Lodge. Wake up to the sound of birds and view of the pond to the west & peaceful woodlot to the northeast. You will find over a mile of trails on the property, boulder fire pit and covered porch. 1.5 miles from Bear Lake, 10 minutes from downtown Fredonia, 13 minutes from SUNY Fredonia, just minutes away from Lake Erie Wine Trail, nearby access to the Chautauqua Rails to Trails, and direct access to 500+ miles of snowmobile trails by way of Old Chautauqua Rd.

Top guest favorite

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.

Cabin in Portland

4.98 out of 5 average rating, 106 reviews

The Fisherman's Cottage - a Lakeside Loft

A cozy retreat in the heart of the Lake Erie Wine Trail that comes with a complimentary wine tasting. This newly renovated 1950's fishing cabin boasts modern amenities to ensure your comfort while retaining hints of it's former purpose. Wake up each morning to take in the panoramic view of Lake Erie from the back deck. Enjoy sunset from the screened in porch while you listen to the waves below. The Fisherman's Cottage is perfect for a girl's weekend at the wineries or a romantic getaway.

Top guest favorite

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

4.99 out of 5 average rating, 119 reviews

Blue Canoe/Upscale Lake Cottage/Chautauqua

Welcome to Blue Canoe Lake Cottage on Cassadaga Lakes! Brand new EVERYTHING!!! This upscale cottage oasis sits right on the waters edge with 125ft of private waterfront and a gated covered deck overlooking the lake. This incredible renovated space is light filled and very bright with lots of high-end details and amenities. Luxury on the Lake! 2 adult kayaks, 2 child kayak, 2 paddle boards, 4 cruiser bikes, pedal boat, fire pit, propane grill. Recommended for 4 Adults MAX. Dog Friendly!

Guest favorite

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, 133 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.

Guest favorite

Three adirondack chairs are positioned on a grassy area overlooking a peaceful creek. Lush green trees surround the space, creating a serene ambiance. The sunlight filters through the foliage, enhancing the natural beauty of the setting.

Cabin in Sinclairville

4.93 out of 5 average rating, 246 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 favorite

A cozy living room features two grey sofas adorned with colorful cushions, complemented by a wooden coffee table. A decorative fireplace is centrally positioned against a green wall, while shelves holding books and art pieces are mounted beside it. Natural light is welcomed through large windows with patterned curtains.

Apartment in Jamestown

4.96 out of 5 average rating, 458 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.

Top guest favorite

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.

Guesthouse in Forestville

4.99 out of 5 average rating, 182 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 favorite

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, 303 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 favorite

A new 7-person hot tub is positioned amidst tall trees, illuminated by warm string lights. Two charming tiny cabins are visible in the background, their warm glow suggesting welcoming interiors. The tranquil setting offers a relaxing atmosphere for evening enjoyment.

Cabin in Portland

4.95 out of 5 average rating, 40 reviews

Luxe Cabin/Hot Tub/EV Charger/Modern/Tranquil

Welcome to The Scandinavian Escape Tucked into the woods like a hidden gem, The Scandinavian Escape is your own private resort—where luxury meets warmth and modern comfort blends with natural beauty. Thoughtfully designed for relaxation, this peaceful retreat offers your group complete privacy, serene surroundings, and fun for all ages. **You will have the entire property exclusively to your group.**

Top guest favorite

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

4.98 out of 5 average rating, 166 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 favorite

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, 591 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.