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!

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

4.92 out of 5 average rating, 25 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.

Top guest favorite

The image presents a historic Victorian manor, showcasing its charming architectural details. A sparkling in-ground pool is visible in the bottom right corner, framed by a pristine patio area. Tall trees surround the property, contributing to a peaceful and serene environment.

Guest suite in Albion

5 out of 5 average rating, 66 reviews

Meli's Home Suite - 1st floor Victorian & Pool!

You and your family will love this peaceful 1880's Victorian Manor, mixed with luxuries of the modern day. The pool is open May - October for paid guests & includes access to the patio and yard as well! Nestled in the rural Lake Ontario Community, featuring Farmers Markets, the Erie Canal, and Unique Local Shops, take a trip back into the 19th Century! You'll enjoy your own private floor with private entrance, and many amenities to offer you a fun and pleasant stay! Contact us today!

Guest favorite

A modern kitchen area features custom butcher block countertops and sleek white cabinetry. An island with seating for four is positioned next to a contemporary stove and microwave. Natural light filters through several windows, illuminating the spacious layout.

Cabin in Albion

4.94 out of 5 average rating, 17 reviews

The Pinewoods Cabin near Oak Orchard Creek fishing

Kick back and relax in this newly remodeled calm, stylish space. The cabin boasts all new appliances, custom butcher block counter tops, flooring, beds, bathrooms. It has a 65" flat screen TV. The cabin is located in the heart of a fishing town. It is minutes from the Waterport Dam, Oak Orchard Creek, Lake Ontario, boat launches, and many charters. Perfect for fishing enthusiasts who want to be close to the action. Between Buffalo Niagara falls and Rochester. Close to State parks.

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, 173 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, 59 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, 121 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, 180 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, 224 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

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, 137 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 favorite

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, 196 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.

Guest favorite

The living room features a comfortable sofa and a wooden dining table with chairs, illuminated by natural light from a large window. A neutral color palette is complemented by sliding barn-style wood accents on one wall. A television is mounted on the opposite wall.

Home in Kendall

4.82 out of 5 average rating, 71 reviews

Ontario Vista Countryside Home

Welcome to the Ontario Vista - a countryside home located in Kendall, NY! This 1878 farm house is a side-by-side duplex, with the host family living on one side. You will have full access to the other side, with a private parking area and entry door. From the upper story, you can see Lake Ontario, which is only a mile north of the home.