Holiday houses in Oak Orchard

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Top-rated holiday rentals in Oak Orchard

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Guest favourite
A charming cottage showcases a combination of white siding and a metal roof, accented by a red brick chimney. A wrap-around deck is visible, bordered by green grass and flowering planters, creating a tranquil outdoor space surrounded by trees.
Cottage in Waterport
4.95 out of 5 average rating, 107 reviews

Oak Orchard Bliss: Angler’s Haven & Family Oasis

Welcome to Crooked Creek Property! There is so much to love about this cozy cottage right on Oak Orchard River. Let yourself in with the high-tech Nest keypad and get to enjoying the huge wrap-around deck that overlooks the Oak Orchard River. The property provides privacy and offers direct access to the River via a private walking path down the river bank. Enjoy your time on the creek fishing, kayaking, canoeing, swimming, or just enjoying the beauty of nature. We have Kayaks available to rent!

Guest favourite
A one-story cottage is set near Lake Ontario, framed by lush greenery. Wooden decking leads to the entrance, while a grassy area extends towards the water's edge. The structure features large windows and a simple exterior. A vehicle is parked nearby, highlighting the accessible location.
Home in Kendall
4.76 out of 5 average rating, 100 reviews

The Love Shack

Nice & cozy Winter get a way with lower rates! Lake front 2 bedroom plus pull out couch with hot tub overlooking beautiful Lake Ontario. This recently remodeled 2 bedrooms on Lake Ontario is 20 miles west of Rochester, NY. 2 king beds, pull out couch,6 man hot tub, cable TV, Netflix, HBO, HULU, TVs in both bedrooms and living room, stereo, full kitchen all the pans and silver, all fresh clean bedding, outdoor shower (full bath too) towels, paper goods, books, bikes, board games, ro ck painting,

Guest favourite
A spacious loft area features a cozy sleeping space with a large bed, complemented by a decorative light fixture overhead. A television is positioned for viewing, and natural light fills the area through multiple windows. A comfortable seating area and soft textures contribute to the serene environment.
Loft in Niagara-on-the-Lake
4.9 out of 5 average rating, 512 reviews

Luxury In The Heart Of Wine Country

Hidden along the shores of the Niagara River, Grayden Estate is nestled on a quiet dead end street in beautiful Queenston/Niagara on the Lake. A short drive to Old Town and within a few minute walk or bike to world class wineries, art galleries, farmers markets, hiking trails, parks and the waterfront, Grayden Estate is the ideal location for a peaceful quiet getaway for anyone looking to surrender to the simple living quiet life. Complimentary tour bikes are available for use. Lic # 112-2023

Top Guest favourite
A light-filled living area features a comfortable sofa and two armchairs arranged around a coffee table. Large windows offer views of the lawn and nearby lake, while a ceiling fan adds to the airy ambiance. A subtle area rug defines the space.
Cottage in Wilson
5 out of 5 average rating, 113 reviews

Cozy Lakefront Home 30 minutes from Niagara Falls

We are a lake front property located directly on Lake Ontario in Wilson NY that offers you beautiful views, stunning sunsets and a peaceful place to relax. We offer a comfortable 2 bedroom 2 bath home with 2 living areas, a fully equipped kitchen & a beautiful front porch that invites you to relax and unwind. There is so much to enjoy in our Niagara Region and our home is in the middle of it all! Close to wineries, restaurants, shopping, biking & hiking trails, swimming, kayaking & fishing.

Top Guest favourite
Castle in Elmwood Village
4.89 out of 5 average rating, 302 reviews

King Fireplace Luxury Rooftop Loft Gym Bball EV+

Experience the unique luxury! Perfect for family, business, or romantics. With high end finishes, 16' ceilings, a stunning 6' fireplace, this space exudes comfort & elegance. Unwind in the 5' round tub, or enjoy a movie on the 85' smart tv, while appreciating the building's history. For the active guests, an indoor basketball court and gym. Office area for business travellers. Seasonal rooftop area for sunsets or enjoying the weather. Additional bedrooms can be added for larger groups.

Top Guest favourite
A welcoming exterior view of a remodeled country home is showcased, featuring a screened porch with dark trim and a white door. Lush greenery surrounds the property, complemented by freshly landscaped flower beds and a gravel pathway leading to the entrance.
Home in Perry
4.97 out of 5 average rating, 157 reviews

Peaceful Country Home

A peaceful clean home for you to enjoy!! We have a very nice size yard for camp fires and just relax in without any neighbors.Welcome to a peaceful country home in the middle of several very large ponds. Relax on the covered screened porch or the back deck for peaceful meals or just some bird watching. Not super far off the road but you feel like it. Road is pretty quiet and lots of wild life. Ponds and woods not our property so please stay in yard/ grass only

Top Guest favourite
The exterior of the timber-frame home is shown, featuring large two-story windows and wood accents. A covered veranda extends from the structure, offering seating. Surrounding greenery and manicured grass enhance the natural setting, inviting a peaceful retreat in the countryside.
Home in East Aurora
4.98 out of 5 average rating, 123 reviews

Timber-frame home on 12 wooded acres

Featured in Buffalo Spree and Artvoice, this timber-frame home features stunning hickory and black walnut interiors illuminated by two-story windows that face the morning sun. Radiant floor heating and earthen-plaster climate design. Wake up in queen and king beds, lounge under covered verandas, and shop right next door at Thorpe’s organic farm store. • 7 minutes from the Village of East Aurora • 24 minutes from Bills stadium • 1 hour from Niagara Falls

Top Guest favourite
A cozy living area is featured, showcasing a plush sectional sofa and a wooden coffee table. Two vintage oars are mounted on the wall, enhancing the rustic charm. A stand lamp and a small wooden chair complement the space, which is illuminated by natural light through nearby windows.
Apartment in Albion
4.98 out of 5 average rating, 181 reviews

Lagom Living Not too little ~ Not too Much

Our Airbnb is an entire two-bedroom apartment in an 1800s home in Albion, NY. You’ll have plenty of room to settle in and stretch out here. We can sleep five people in one queen, one double bed and a couch. The comfortable living room is stocked with board games and our full kitchen has all the appliances and kitchenware you need to make your own meals. With onsite parking, a private entrance, and washer and dryer, you can really make yourself at home.

Guest favourite
The exterior of a vibrant blue house is framed by lush green trees, with a well-maintained lawn leading towards the lake. A spacious deck is visible, adjacent to the water, providing a serene setting for relaxation and outdoor activities.
Cottage in Albion
4.95 out of 5 average rating, 233 reviews

Lake Front: Beautiful Cottage on Lake Alice

Lake front designer gem has Main House, Boat House and Bath House. Boat House is an additional fee and offered seasonally : see details below. Gourmet kitchen, rock fireplace, expansive deck, stairs to lake with dock, swim platform, fire ring, beach chairs, 4 kayaks and a canoe for your use. Just a day trip away to Niagra Falls or Toronto and 5 min to Oak Orchard River which hosts World Class Fishing.

Guest favourite
Two Adirondack chairs in contrasting colors of red and teal are positioned on a green lawn facing a calm lake. A small firepit is located between the chairs, surrounded by a clear view of the water and a cloudless sky.
Cottage in Kent
4.94 out of 5 average rating, 105 reviews

Lakefront 2BR between Rochester and Niagara Falls

Point Breeze Lake Ontario, NY Q Bed, 2 twins and a couch sleep 4-5 fully equipped kitchen, WiFi, TV BBQ steps to marinas, restaurants, historic lighthouse Minutes from wineries, antiques, Amish crafts and markets hour to Niagara Falls,Buffalo,Rochester WE WELCOME SMALL TO MEDIUM SIZED DOGS FOR AN ADDITIONAL FEE OF $30. PER NIGHT. PLEASE ADD AS ADDITIONAL GUEST (3 GUEST MINIMUM W/ PET). Thanks!

Guest favourite
A charming cottage exterior is presented, featuring blue shingle siding and white trim. An American flag hangs from the porch, which is bordered by two green chairs. Sunlight illuminates the well-maintained lawn, enhancing the inviting appearance of the home.
Cottage in Kent
4.94 out of 5 average rating, 139 reviews

Captain Dan's Lake Ontario Cottage

Lake Ontario cottage with a large deck right on the water. Walking distance from some of the best Salmon fishing in the world with your boat or our charter fleet. Great restaurants and the Oak Orchard river and Lake Ontario to fish or boat on. Listen to the waves from your bedroom and watch lake freighters pass by day and night. Enjoy beautiful sunrises and sunsets over the water.

Guest favourite
A compact living space features a cozy sleeping area with a spacious bed. A kitchenette with wooden cabinetry is visible, alongside a dining area. Light streams in through multiple windows, illuminating the neutral color palette and natural wood accents.
Cottage in Kent
4.89 out of 5 average rating, 217 reviews

Newly Renovated Cottage on Oak Orchard Creek

Whether you are coming to the Oak the fish, relax or meet up with family and old friends, our cottages are a great place to call home during your stay. There is a kitchen with stove, microwave and fridge as well as a newly renovated bathroom and access to Oak Orchard Creek. Need fishing advice, stop next door at Narby's for tips as well as great prices on tackle.

Popular amenities for Oak Orchard holiday rentals

  1. Airbnb
  2. United States
  3. New York
  4. Orleans County
  5. Oak Orchard