Holiday rentals in Gerry

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Top-rated holiday rentals in Gerry

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Top guest favourite
A view of the tranquil lake is featured, where several sailboats can be seen on the water. Lush green grass borders the shoreline, with gentle waves in the distance and a clear blue sky dotted with clouds above.
Home in Dunkirk
4.97 out of 5 average rating, 218 reviews

House On Cedar Beach

Walk out of the house and walk on to Cedar Beach! Our house is the only one situated directly on a public beach in the City! It is located on the bicycle path, and is two blocks from the Dunkirk Lighthouse, as well as Point Gratiot Park. There are lake views from the living room, kitchen, sun room porch & 2nd floor master bedroom. There are cathedral ceilings on the entire 2nd floor. The sun porch has a seating area for 4, where you can have your morning coffee and gaze onto the beach & water!

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, 118 reviews

Forest Retreat, ride snowmobiles from the house.

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 cozy bedroom features a spacious bed with a patterned quilt in warm tones. Two bedside lamps provide soft illumination. A window with a wooden frame overlooks outdoor greenery, while floating shelves hold decorative items, enhancing the room’s inviting feel.
Cabin in Mayville
4.99 out of 5 average rating, 139 reviews

Cozy cabin- Snowmobilers/Skiers welcome!

Enjoy a peaceful stay in this cozy cabin on a quiet dead end street. With Snug Harbor Marina just a few minute walk down the street, Chautauqua Lake is right at your fingertips! Enjoy cooking outdoors with the BBQ grill, or make use of the full indoor kitchen. Create memories with the family while roasting s'mores around the gas fire pit and snuggling up with one of the board games provided. Snowmobilers can access the trail a couple miles away by road or by trailering to the Mayville Town Park.

Guest favourite
An old farm house is framed by towering trees, showcasing vintage wooden siding and a welcoming front porch. Lush green grass surrounds the home, reflecting natural beauty during sunrise. The peaceful rural setting is enhanced by gentle sunlight filtering through the branches.
Farm stay in Sugar Grove
4.85 out of 5 average rating, 111 reviews

Patchen Hill Farm House, Tree Farm, & Arboretum

Patchen Hill Farm House, Tree Farm & Arboretum is a wonderful old farm house on 120 acres with a barn, apple orchards, berry bushes, forests, trails, ponds & hardwood trees. The house has four bed rooms with additional sitting room, living room, dining room, laundry room, game room, kitchen with kitchen dinning nook. It's a wonderful old house with charm and vintage appeal. Rent the whole house. There is hiking, fishing, berry/apple picking, and more. Great for families & friends. Pet friendly.

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, 128 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.

Top guest favourite
A cozy living room is presented with soft, natural light filtering through two windows. A striped sofa offers comfortable seating, complemented by two armchairs. A round wooden coffee table sits at the center on a plush area rug, creating an inviting gathering space.
Home in Jamestown
4.94 out of 5 average rating, 137 reviews

Quaint 2 bedroom home overlooking bird sanctuary

2 bedroom house in a quiet neighborhood. just a minute from exit 12 off of I86 , Keybox self checkin arrive as late as you need to.. Beds and bathroom up on the second floor, and it's an old house, stairs are steep.. kitchen, dining and living room on first. Enclosed front porch great for morning coffee, walk out basement has laundry, a flop futon and secure bike storage. Yard overlooks RTPI bird sanctuary and has outdoor seating area with firepit. Driveway parking. Host in neighborhood ,

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 Celoron
4.85 out of 5 average rating, 119 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, 113 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
Guest suite in Youngsville
5 out of 5 average rating, 118 reviews

The Loft, with Hot tub and fire pit.

Kick back and relax in our peaceful, cozy space. We have a wooded area that surrounds the back and side of the house. Come and enjoy a warm fire up in the woods under the beautiful Hemlock trees, as well as the bubbling, steamy hot tub tucked under our pergola behind the house. Don't leave without experiencing the beautiful Allegheny National Forest that surrounds us in Warren County! Summer is so lush and green, with many outdoor activities! We hope to see you!☀️🌿

Top guest favourite
A sitting area is present, featuring a light-colored sofa and two wooden chairs. Natural light enters through a window with light curtains, illuminating the space. Two lamps provide additional lighting. A television is positioned on a cabinet, and decorative items are arranged throughout.
Home in Dunkirk
4.96 out of 5 average rating, 280 reviews

"Close to the Lake" House

The home is located just two blocks from the beach, a short drive to the SUNY Fredonia campus and within the Chautauqua wine trail. You will find it is very clean, well maintained, well stocked and provides a private backyard with covered porch. This is a great location for anyone who wishes to visit the campus, enjoy Lake Erie, explore Chautauqua County or coming into town to visit family. Ideal for couples, solo adventurers, business travelers and families.

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, 134 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.

Guest favourite
An open-concept living area is displayed, featuring a cozy gray sofa and a dining table surrounded by green chairs. White shiplap walls and a high ceiling with exposed beams create a bright atmosphere. Kitchen appliances and decorative elements complement the design.
Guest suite in Bemus Point
4.97 out of 5 average rating, 109 reviews

Luxury Suite at The Cottages - Sauna & Hot Tub

Make some memories at this unique and family-friendly retreat in beautiful Bemus Point! The Luxury Suite at The Cottages is a stylish 3 bedroom 2 bathroom unit featuring an indoor sauna in the master bathroom and a hot tub off the back deck. Our goal is for our guests to feel relaxed and rejuvenated at this four season getaway.

Popular amenities for Gerry holiday rentals

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  2. United States
  3. New York
  4. Chautauqua County
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