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, 119 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, 249 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, 100 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, 121 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
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, 270 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 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.
Flat in Jamestown
4.96 out of 5 average rating, 473 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 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, 333 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.

Guest favourite
A charming ranch-style house is set against a bright blue sky, surrounded by well-maintained greenery and landscaped shrubs. A welcoming front porch features rocking chairs, and an American flag hangs proudly from the front. A gravel pathway leads to the entrance.
Home in Bemus Point
4.88 out of 5 average rating, 194 reviews

Chautauqua Lakehouse with a picturesque view

Tastefully decorated with lake charm. Minutes from Bemus Point and Downtown Jamestown. Across the lake from Lakewood and the new Chautauqua Harbor Hotel. A short drive to the Chautauqua Institute. Enjoy morning coffee and evening drinks on the front porch. Also a nice winter getaway. On the snowmobile trail. Holiday Valley Ski Resort -40 miles Peak &Peak Ski Resort - 30 miles Cockaigne Ski Resort - 18 miles Salamanca Casino - 35 miles

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, 323 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
The entryway features a covered porch with a rocking chair and decorative planters. Lush greenery surrounds the steps, leading to the front door. Two hanging ferns and flower pots add a touch of color, creating a welcoming approach to the apartment.
Flat in Randolph
4.96 out of 5 average rating, 122 reviews

The Empty Nest- 1st Floor

Comfy 1 bedroom first floor apartment. Private drive and entrances. Large side porch to enjoy your morning coffee. Fenced in backyard with seating and fire pit to enjoy. We are conveniently located right off I-86. Just minutes to Amish country, Ellicottville (25 mins), Salamanca (20 mins. , Jamestown (20 mins), Allegheny Park(15 mins) and Reservoir (20 mins.) and Niagara Falls 1:15 hrs).

Top guest favourite
A light-filled living area showcases large windows with lake views. A cozy, elegant loveseat and two tufted armchairs frame a wooden coffee table, positioned on a soft area rug. A potted plant adds a touch of greenery near the open door leading to the outdoor space.
Home in Jamestown
4.99 out of 5 average rating, 135 reviews

Cozy Lakefront Cottage

Enjoy and relax with the whole family at this peaceful place to stay. The Chautauqua lake is just a few steps from the backyard. Enjoy fishing, (ice fishing in the winter!) boating, bonfire, bbq, canoeing and breathtaking sunsets are not to be missed! This home is newly renovated and is located near all major shops and amenities. Free parking.

Top guest favourite
A tranquil lakefront scene is captured at sunset, showcasing soft pastel hues reflecting on the water's surface. A fluffy white dog sits on a wooden dock, framed by the serene backdrop of the lake and distant tree line.
Guest suite in Bemus Point
4.96 out of 5 average rating, 210 reviews

Lakefront Apt & boat slip, walk/boat/bike to Bemus

Lake Pines Loft private apartment was new in 2021. 1 Min. walk to private lakefront. Walk, or ride our included well-tuned classic bikes to Bemus. Take a quiet paddle in the canoe. Read, sunbathe, fish, or cocktail on a private dock, with mooring provided for your boat up to 25 ft. Private parking for 2 cars and a trailer.

Popular amenities for Gerry holiday rentals

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