Holiday houses in Oak Orchard

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Top-rated holiday rentals in Oak Orchard

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Guest favourite
The spacious kitchen features modern stainless-steel appliances, including a refrigerator and oven. Ample cabinetry and a large countertop provide plenty of space for meal preparation. A window allows natural light to brighten the area, highlighting the rich wood flooring.
Home in Waterport
4.97 out of 5 average rating, 105 reviews

Beautiful Home Minutes From Lake Ontario fishing

Freshly remodeled, fully furnished, four bedroom home in a country setting close to Lake Ontario's famed fishing locations. Two story, open floor plan. First floor Kitchen, living room, dining room, bathroom, three bedrooms. One bedroom upstairs. Private large country yard. Only minutes away from Lake Ontario, Lake Alice, and the Oak Orchard River. Great for fishing, boating, kayaking, leisure. Ring video security sys. We are located half way between Rochester and Buffalo/Niagara Falls.

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, 110 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!

Top Guest favourite
Home in Waterport
4.95 out of 5 average rating, 39 reviews

Quiet cottage

Unwind in this calm, stylish home. Perfect for solo travelers, couples, and small families. Cozy, modern, functional spaces for all to enjoy. This cottage is newly renovated and upgraded with numerous amenities. Tucked away property with a number of interior accommodations. Located in a private, tranquil area with lots of outdoor space and privacy. Close proximity to Lakeside State Park and local fishing marinas. Reasonable distance from prime locations including Lake Ontario and Point Breeze.

Guest favourite
A charming house with a large front porch is displayed, featuring multiple windows that allow ample natural light. The exterior is complemented by colorful autumn foliage, and an American flag is proudly displayed near the entrance.
Home in Waterport
4.93 out of 5 average rating, 14 reviews

Entire home on Lake Alice.

Escape to our newly renovated home on Lake Alice. Unwind and enjoy the lake view. Fish off the dock or bring your boat to enjoy Lake Alice. Great place for kayaking, fishing and swimming. Sit out back and enjoy a fire in the spacious yard. Explore the area and enjoy the local farm markets, visit Lake Ontario, Point Breeze is less than 10 minutes away where there is award winning salmon fishing, charter boats. Cook in our fully equipped kitchen or just relax and enjoy friends and family.

Top Guest favourite
Houseboat in Medina
5.0 out of 5 average rating, 18 reviews

Erie Canal Houseboat!

Venice, Amsterdam, and.... Medina, New York? Live like a European this side of the pond aboard the Erie Floatel - the first-of-its-kind houseboat rental on the Erie Canal. Docked in the wide waters of Medina's Canal Basin, the Erie Floatel offers a unique overnight experience immersed among downtown's shops, bars and eateries. Thoughtfully designed, this floating bungalow sleeps two on a full-size bed. A kitchenette, full bath, and TV/wifi are on board, with private covered deck outside.

Guest favourite
A serene view of a cottage nestled among trees along a calm shoreline. The still water mirrors the blue sky and lush greenery, creating a peaceful atmosphere. The stone waterfront leads to vibrant landscaping surrounding the home.
Home in Lyndonville
4.86 out of 5 average rating, 28 reviews

North Star Cottage

Immerse yourself in nature at this rustic getaway just steps from Lake Ontario. Centrally located between Buffalo, NF, and Rochester, this beautiful cottage offers panoramic views of sunrises and sunsets! Enjoy the spectacular night skies with no light pollution and breathtaking views of Lake Ontario’s stunning blue waters! Gourmet kitchen, newly renovated bathroom, and open floor plan! Master bedroom has panoramic views of the lake! Cottage was featured in Buffalo Spree Magazine Nov. 2023

Top Guest favourite
A serene sunset view is captured over the lake, with the sun casting a golden glow on the water. The image features the edge of a spa tub in the foreground, with gentle ripples of water visible. A blue chair is positioned nearby, inviting relaxation.
Cottage in Barker
4.95 out of 5 average rating, 111 reviews

Lake Front Vista & HotTub

Enjoy Spectacular Lakefront views. Relax at your own pace. Take a dip in the spa tub or just enjoy the scenery Very quiet road Speedy internet Fire-pit Enjoy the Niagara Wine Trail 2 Bdrm 6 min to Golden Hill Park 12 min to White Birch Golf course 15 min to Olcott/Burt (fishing charters) 20 min to Waterport/Kent (fishing charters) 50 min to Niagara Falls *Promo: 3rd night or more, will be discounted ~25% (no discount on cleaning and fees, excl 06/23-09/10)

Guest favourite
A cozy living area features a sofa adorned with floral-patterned cushions and a vibrant yellow throw. A wooden coffee table sits in front, with a decorative plant placed on it. A floor lamp and side table with a small vase enhance the welcoming space.
Home in Medina
4.84 out of 5 average rating, 103 reviews

Cozy Village Flat Nestled in the heart of Medina

Adorable Flat in the heart of Medina just blocks away from the Erie Canal. This cozy flat has one bedroom and sleeps 3 people. The bedroom has a queen bed and there is a futon/sleeper in the living room. Be your own chef in this newly renovated kitchen or enjoy close by restaurants! Enjoy the sounds of nature from the yard while also taking in the peaceful neighborhood. Up to two dogs allowed $75 per stay. Please let us know if you are bringing a dog.

Guest favourite
A cozy cottage is set along the shoreline, featuring a covered porch with a selection of outdoor chairs and a small table. Lush grass leads to the water’s edge, with a few potted plants adding a touch of greenery. The cottage's exterior showcases light-colored siding and large windows.
Cottage in Lyndonville
4.92 out of 5 average rating, 64 reviews

Lake Ontario Nautical Twilight

Escape to this peaceful lakeside cottage, perfect for a romantic getaway or relaxing weekend with friends. Start your mornings with stunning sunrises, coffee on the deck, and the soothing sound of the waves. Spend the day kayaking along the shoreline, enjoying local wine, or curling up with a good book. In the evening, unwind with breathtaking sunsets and a bonfire by the water. Be sure to check out the guidebook for local favorites and recommendations.

Guest favourite
The kitchen features exposed brick walls complemented by dark cabinetry and a spacious island. A chandelier illuminates the area, highlighting stainless steel appliances and a sink. Two large windows allow natural light to fill the space, creating a warm ambiance.
Apartment in Albion
4.93 out of 5 average rating, 184 reviews

Bunked on Bank

Welcome to Bunked on Bank! This second story loft style apartment is centrally located between Rochester and Buffalo. Conveniently located near Niagara Falls, Letchworth State Park and Lake Ontario for plenty of day trips during your stay. This apartment offers two queen size beds and two twin beds. The bathroom includes a large soaking tub along with a stand-up shower. Full kitchen with all the amenities. Free parking on site. WiFi included.

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, 245 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
A cozy living area features gray sofas facing a mounted television on the wall. Dark wooden shelving units hold decorative items. A round wooden coffee table sits in the center, accompanied by two comfortable chairs, creating a welcoming space for relaxation.
Apartment in Middleport
4.96 out of 5 average rating, 80 reviews

A vintage diamond in the rough

This 1 BR/1BA downtown apartment is perfect for a quaint getaway that is newly renovated. Within walking distant to coffee shop, pub and Erie Canal tow path. A short drive to downtown Medina, Albion, Lockport, Lake Ontario, Becker Farms/Vizcarra Vineyards & Becker Brewing Co, Niagara Wine Trail.

Popular amenities for Oak Orchard holiday rentals