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, 195 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, 35 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

Houseboat in Medina

5 out of 5 average rating, 12 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.

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

4.82 out of 5 average rating, 22 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

Superhost

Home in Medina

5 out of 5 average rating, 4 reviews

The Worthy Escsape 2BR, Porch & Pet Friendly

This charming 2BR, 1BA home in the historic village of Medina is perfect for a relaxing getaway. All on one level, it sleeps 4 with two queen beds, fresh linens, and thoughtful touches. The cozy living room has a sofa, dining area, and smart TV, while the updated kitchen is stocked with essentials. Relax on the covered porch with your morning coffee or evening drink. Pet friendly, up to 2 dogs ($75 fee). Just minutes to Main Street shops, dining, the Erie Canal, and local trails.

Top guest favorite

A welcoming entrance is highlighted by blooming flower beds filled with vibrant colors. The staircase leads to a black front door, flanked by windows that allow natural light to enhance the entrance. A simple wreath adorns the door, adding a touch of charm.

Apartment in Medina

5 out of 5 average rating, 51 reviews

Spacious One-Bedroom Retreat with Modern Comforts

Make yourself at home in this bright and comfortable upstairs apartment — the perfect spot for a relaxing getaway, family visit, or extended stay. Thoughtfully furnished and fully equipped, it’s designed to give you both comfort and convenience. Fully stocked kitchen with everything you need to cook meals at home. In-unit full-size washer and dryer to make longer stays easy. Private off street parking. All in the heart of downtown just blocks from the Erie Canal.

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, 179 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

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

4.91 out of 5 average rating, 127 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

4.88 out of 5 average rating, 183 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, 229 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, 104 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!