Vacation rentals in Orleans County

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Top-rated vacation rentals in Orleans County

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Guest favorite

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, 105 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!

Superhost

The lakehouse exterior features a spacious wrap-around deck, surrounded by lush greenery. Natural stone stairs lead to the water's edge, enhancing accessibility. The structure is harmoniously integrated with the landscape, offering a serene waterfront view.

Home in Kendall

4.89 out of 5 average rating, 193 reviews

LIC'D N.Y. LakeHouse HotTub-Gameroom-Pets-Lake Ont

WINTER & SUMMER - LIC'D DREAM LAKEHOUSE - PET FRIENDLY - HOT TUB - 3+ BEDROOMS with 100ft WATERFRONT, WATER ACCESS NATURAL STONE STAIRS. 2 mainfloor KING BDRMS & 3RD LOFT BDRM with 2 QUEEN BEDS & BUNKBED. WALKOUT GAMEROOM, LAUNDRY, FIRE PLACE & 3 futon COUCHES. FREE WiFi-TEL. bring screaming devices. 15 MIN DRIVE S/E TO TOWN OF BROCKPORT.. FIND GROCERY, WALMART, RESTAURANTS, BARS, AND LIQUOR STORES. 75 MINS FROM NIAGARA FALLS 5 MINS EAST TO HAMLIN PUBLIC BEACH 30 MINS EAST TO ROCHESTER

Top guest favorite

A historic home is framed by vibrant autumn foliage, featuring a circular porch with multiple arches. Colorful trees surround the property, and fallen leaves blanket the lawn, contributing to a serene outdoor setting that invites exploration.

Guest suite in Albion

4.94 out of 5 average rating, 32 reviews

Historic Homestead

We are very pleased to welcome you to our rental! You enter the rental space from a 10'x10' private deck. The unit is a private bed and bath, and the former formal living room of the house, which has a snack area . You will be staying in a large bedroom, which used to be a ladies parlor, and now has a brand new attached bathroom. The living room is equipped with a microwave, Keurig and mini fridge, and a new air conditioner ! Your area is completely private. Park in front circular driveway.

Guest favorite

Houseboat in Medina

5 out of 5 average rating, 8 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 favorite

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

4.93 out of 5 average rating, 57 reviews

Lake Ontario Nautical Twilight

Take a break and unwind at this peaceful oasis. Early risers enjoy a beautiful sunrise and then lounge on the deck and relax to the sounds of the waves. Enjoy some local wine and read a good book or go kayaking along the shoreline. This cozy cottage is located on a quiet lane. Perfect for a friends weekend or a romantic getaway. End the day with the beautiful sunset over the water and a bonfire on the lakes edge. Please check out guidebook for local recommendation.

Top guest favorite

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, 178 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 on two double beds 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.

Top guest favorite

An inviting dining area features a light wooden table surrounded by four chairs. A cheerful arrangement of yellow flowers is displayed in a central planter. The adjoining living room is visible, with a comfortable seating arrangement and a modern ceiling fan. Natural light enters through the nearby windows.

Apartment in Medina

5 out of 5 average rating, 64 reviews

The Cozy Corner

Welcome to our spacious 1 bedroom first floor apartment in the heart of historic Medina. Totally remodeled, stylish, and cozy. Stay for a weekend or fall in love and stay long term. You’re only blocks away from great downtown restaurants, bars, and boutique shopping. Great place for a couple or a couple of friends. Perfect place to stay for our local wedding venues, traversing the Erie Canal, or one of the numerous community special events.

Top guest favorite

The entrance of the barn features a vibrant red exterior and is framed by large windows. A stone path leads to the front door, which is accentuated by two light fixtures. Fresh flowers and rocks are positioned along the pathway, enhancing the rural appeal.

Farm stay in Kendall

4.9 out of 5 average rating, 125 reviews

Lake View 3 Bedroom Barn

This property is the original barn that was a part of a farm built in the mid 1800's. The 3 bedroom facility is half of the barn, but renters have use of the immediate property surrounding the barn. There are two horses on the property, which is why we cannot accept pets. This is a modern farmhouse where we repurposed many traditional architectural pieces and antiques to maintain the authenticity of the original barn.

Guest favorite

An elegant two-story vintage home features a white exterior with black shutters and ornate porch details. The well-manicured front yard is adorned with various seasonal decorations, while a stone pathway leads to the inviting entrance. Lush greenery and trees create a serene backdrop.

Apartment in Medina

4.89 out of 5 average rating, 182 reviews

Cozy, quaint entire 1 bedroom apartment

Welcome to this quaint vintage upstairs apartment as part of a large 1800's home. Cozy and comfortable with all your basic necessities. Private off street parking in the heart of the village of Medina. You are walking distance from downtown unique shops, boutiques and restaurants. It is less than an hour drive to Niagara Falls, Buffalo and Rochester and about 15 minutes from Lake Ontario (famous for fishermen).

Guest favorite

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, 227 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 favorite

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, 103 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 favorite

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.