Holiday rentals in Gerry

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Top-rated holiday rentals in Gerry

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Top guest favourite
The cabin's exterior is illuminated at dusk, reflecting beautifully on the calm surface of the pond. Surrounding tall trees offer a natural backdrop, enhancing the serene atmosphere of the retreat.
Home in Gerry
4.96 out of 5 average rating, 122 reviews

Forest Retreat, 90 miles to Niagara Falls.

Welcome to Forest Retreat! We are nestled in the hills of Western New York, 23 miles to Chautauqua Lake and 14 miles to Lily Dale. This unique home is near several wedding venues and the Earl Cardot Overland Trail, which is surrounded by 2,300 acres of state forest. We are located between 2 local ski resorts, and only 87 miles south of Niagara Falls State park. Relax by the fire, kayak, or fish in the 2 acre pond and just enjoy the scenery. We do require a signed waiver to utilize the pond.

Top guest favourite
A canoe glides across a calm pond, framed by trees showcasing autumn foliage. Two people paddle gently, surrounded by vibrant reflections of fall colors on the water's surface. A clear blue sky enhances the serene atmosphere, inviting exploration of the tranquil landscape.
Home in Randolph
4.99 out of 5 average rating, 254 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!

Top guest favourite
A spacious living area features a comfortable gray sofa with decorative pillows, positioned on a polished floor. A stylish area rug lies beneath, and a modern ceiling fan enhances airflow. A staircase leads to the loft bedroom, while the kitchen and dining area are visible in the background.
Barn in Jamestown
4.97 out of 5 average rating, 110 reviews

Barndominium 132

Welcome to your mini vacation or getaway in this modern, newly constructed apartment! This cozy & stylish space is perfect for up to four people, with 2 bedrooms one being on the 1st floor each featuring a queen bed, ensuring a good nights sleep for everyone. The apartment also features a modern kitchen w/ all the amenities, WIFI & TV's included, you will never miss your favorite shows or miss an email. Off street parking, private patio, bath & laundry conveniently on the main floor.

Guest favourite
A wooden back deck provides seating options, including a glass-topped table and several chairs, with ample space for relaxation. Surrounding greenery and trees offer shade, while a view of the lake is visible in the background, completing the serene outdoor atmosphere.
Home in Jamestown
4.85 out of 5 average rating, 124 reviews

Charming West Ellicott Cottage with Lake View

Nicely decorated with lake theme. Minutes from Lakewood, the Chautauqua Harbor Hotel, Bemus Point and Downtown Jamestown. New kitchen in June 2025. Back deck with spectacular lake views, and campfires in the back yard. National Comedy Center - 3 miles Southern Tier Brewery - 4.2 miles Ellicottville Brewing - 11 miles Lucille Ball House - .25 miles Chautauqua Institute - 14 miles Chautauqua Lake Pops- 18 miles Holiday Valley - 40 miles Peek & Peak - 18 miles Salamanca Casino - 35 miles

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, 120 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 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, 176 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
4.93 out of 5 average rating, 276 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 spacious living area is presented, featuring comfortable seating options including a sofa and two armchairs. A television is mounted on the wall, and a lighted floor lamp adds warmth. Large windows allow natural light to illuminate the space, enhancing the cozy atmosphere.
Flat in Jamestown
4.95 out of 5 average rating, 341 reviews

Chautauqua Lake-View, 2BR Apt w/Full Kitchen

Our fully furnished, family & dog 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.

Top guest favourite
A cozy country home is featured, showcasing a yellow exterior with a front porch and a star decoration. A single-car garage is visible on the right side. Lush green grass surrounds the property, complemented by a backdrop of trees under a clear blue sky.
Home in Falconer
5 out of 5 average rating, 16 reviews

Country home in rural Falconer.

Cozy country home with living room and kitchen open floor plan. One bedroom queen bed and one full bath with washer and dryer. Living room has a queen sleeper sofa. Fully equipped kitchen with microwave. Relax and take in the country or play a round of golf just a stone's throw away. Beautiful hiking and snowmobile trails nearby. Minutes from Falconer and Downtown Jamestown. Our home is in the country but close to all your amenities

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, 329 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
A charming cabin is set in a wooded landscape, featuring a red metal roof and large glass doors that open to a deck area. Two Adirondack chairs surround a fire pit on a gravel base, inviting relaxation amidst nature.
Cabin in Russell
4.98 out of 5 average rating, 126 reviews

Secluded Egypt Hollow Cabin

Escape to a serene cabin near the Allegheny National Forest in Russell NWPA. Perfect for travelers and couples seeking a relaxing getaway surrounded by nature. 1 Bed. 1 Bath. Private Cabin Enjoy a stream, fire pit, and private driveway. Explore hiking, biking, and all types of boating nearby. Enjoy local businesses downtown Warren. Host available for questions and recommendations. Book your getaway now!

Top 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 Gerry holiday rentals

  1. Airbnb
  2. United States
  3. New York
  4. Chautauqua County
  5. Gerry