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Vacation rentals in Winchester

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A spacious, freestanding bathtub is set by large windows that reveal a serene view of the surrounding trees. Natural light bathes the scene, highlighting tranquil water and a few decorative candles on the edge of the tub.
Chalet in Argenteuil
4.98 out of 5 average rating, 121 reviews

LoveNestChalet | Romantic with Private Hot Tub

☞ Welcome to the enchanting LoveNest Chalet, your perfect haven for a romantic getaway in the heart of nature in the Laurentians near Ontario province ☞ With generous windows that frame breathtaking views of the majestic mountain and lake is designed to provide an intimate escape for those seeking tranquility ☞ LoveNest Chalet offers the ideal retreat for those looking to reconnect and create lasting memories in a secluded setting ☞ Perched at the top of a mountainous land of over 50,000 sq. ft.

Top guest favorite
A silhouette of a dog is framed by a window, showcasing a stunning sunset that bathes the landscape in warm hues. The scene captures a serene rural setting with an expansive field in the background, emphasizing a peaceful connection with nature.
Apartment in Greely
4.97 out of 5 average rating, 217 reviews

Walk 2 OLRT & Hard Rock, mins to airport & EY Ctr

A one-of-a-kind stay; this cozy loft nestled inside a converted airport hangar has rustic charm, curved ceilings, & wide-open views. It offers the perfect blend of character & convenience. Relax on the balcony & watch stunning sunsets, explore the open space, or hit the nearby trails for a walk or bike ride. Enjoy Starlink Wi-Fi, AC, a dedicated workspace, and a stocked pantry. Just 7 minutes from the airport & EY Centre, 2 mins. from the Hard Rock & Casino, golf course, & 20 mins. to downtown.

Top guest favorite
A welcoming entrance to the studio guesthouse is framed by vibrant yellow chrysanthemums in a large terracotta pot, alongside decorative pumpkins, one orange and one white. A small blue birdhouse adds a charming touch near the steps leading to the door.
Guesthouse in Newington
4.92 out of 5 average rating, 543 reviews

Trees, open spaces, and the milky way at night

8 min. from 401 & St Lawrence River, at Ingleside, pet friendly, secluded studio guesthouse, tranquil, safe location for those seeking a road break or destination traveler's seeking the St Lawrence and its environs. Sit by a fire, listen to wind and birds or watch the sky. $50 cleaning fee per pet through extra fee request if necessary before arrival. There is no reliable internet but good cell coverage available; the smart tv can tether to your own device and streaming service provider.

Top guest favorite
A cabin features large green windows that reflect the surrounding trees and the calm river, creating a serene connection with nature. The sloped metal roof enhances the rustic charm of the structure, which is framed by lush greenery.
Cabin in Potsdam
4.97 out of 5 average rating, 262 reviews

Riverside Cabin & Nature Trails

Enjoy our 160 acres in a private natural setting. Owls, trout, heron, osprey, mergansers and the occasional loon will add to your stay. There are over 4 miles of private trails for hiking along the river and in the woods. Kayaks & fishing poles provided. Enjoy a romantic riverside fire-pit, professional massage table & new Finnish wood fired sauna. We sanitize everything 110% before your arrival and offer self check in. We celebrate diversity and welcome people from all communities.

Guest favorite
A rustic log cabin is set among greenery, featuring a sloped roof with metal panels and a welcoming front porch. Large windows provide natural light, while a gravel pathway leads to the entrance. Surrounding grass and dandelions complete the peaceful rural setting.
Cabin in Merrickville-Wolford
4.95 out of 5 average rating, 278 reviews

Cottontail Cabin with Hot Tub and wood fired Sauna

Cottontail Cabin, nestled on 22 acres of serene woods! This is the perfect retreat for those seeking a relaxing and rejuvenating getaway in the heart of nature. The cabin is fully equipped with all the amenities you need to make your stay comfortable and enjoyable. With 2 bedrooms and a pull out couch, the cabin can accommodate up to 6 guests. The cabin features infloor heating and a woodstove to keep you warm and cozy. We have a full-size hot tub and a wood fired sauna!

Top guest favorite
A wooden dock extends into the water, featuring two Adirondack chairs facing the river. Behind, a modern home with a large window displays a Canadian flag and a unique barrel sauna. Lush greenery surrounds the setting, providing a peaceful atmosphere.
Cottage in Kemptville
4.84 out of 5 average rating, 106 reviews

Rideau River Retreat - Waterfront Home

Relax with the whole family at this peaceful all-season home on the Rideau River, only 30 minutes from the heart of Ottawa and 5 mins to Kemptville. Take in the river view while relaxing inside our Cedar Barrel Sauna or sipping morning coffee on the dock. Easily explore the neighbouring towns of Manotick and Merrickville or boat, fish, kayak, or canoe in the middle of the largest stretch of the Rideau River (46km of open water from Manotick to Burritts Rapids).

Top guest favorite
Home in Morrisburg
4.9 out of 5 average rating, 271 reviews

StoneCropAcres Winery and Vineyard Guest Home

Our home is located at our StoneCropAcres Winery and Vineyard. Please check the Winery's website stonecropacres for Winery hours of operation. Our Guest Home is a country style, spacious, bright and clean home with wonderful views of the rural surroundings including our vineyard, farm fields, and the apple farm just around the corner. Both the Guest Home and the Winery are wheelchair accessible and there is an electric medical bed available for use.

Guest favorite
The A-frame chalet is set against a backdrop of vibrant autumn foliage. Its striking black exterior contrasts with warm wooden accents. A large glass front showcases an inviting interior, while a stone terrace framed by fallen leaves adds to the natural ambiance.
Chalet in Val-des-Monts
4.96 out of 5 average rating, 166 reviews

Les Refuges des Collines – Gatineau Park

On the shores of a lake, Parc de la Gatineau is a superb A-frame chalet perfect for disconnecting from the city while being ideally located to allow you to enjoy all that the Gatineau/Ottawa tourist region has to offer. Our mini-chalets are equipped to allow you to relax with their hot tub or to telecommute in their office equipped for this purpose. Our chalets will be a place you'll be eager to return to, as you'll feel at home here.

Top guest favorite
A modern living area features a gray sectional sofa and a stylish coffee table on a soft area rug. A wall-mounted TV is positioned above a sleek electric fireplace. Natural light filters through the window, enhancing the open concept that connects to the kitchen.
Home in Winchester
4.96 out of 5 average rating, 193 reviews

RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa

Welcome to The Lofty Nest! Located 30 minutes south of Ottawa (Canada's Capital City) in the intimate village of Winchester. This 2-bed Century home was gutted and lovingly restored, using reclaimed materials, sweat and love. Visiting for work, play or just the experience of living in a tiny house, the Lofty Nest will charm you with its 'Instaworthy' decor and hotel standards. Perfect for 1 or 2 guests; can accommodate up to 4.

Top guest favorite
An inviting exterior view of the property features a wooden deck adorned with soft lighting. A covered seating area includes a small table and chairs, enhancing the outdoor space. Lush greenery surrounds the home, creating a tranquil setting for relaxation.
Place to stay in Spencerville
5 out of 5 average rating, 121 reviews

Honeybee Haven - Dog Friendly, Free Parking

Escape to a cozy, dog friendly haven, perfect for embracing the magic of the spring season. Nestled in a picturesque landscape, our property offers all the comforts you need for a memorable stay. Whether you’re here for adventure, romance or relaxation, Honeybee Haven is your ultimate getaway. Located minutes off of Hwy 401 and the US border crossing, an hour from both Kingston and Ottawa and two hours from Montreal.

Top guest favorite
An open-concept living area is highlighted by a kitchen with a wooden countertop and white cabinetry. A cozy seating area features a light gray couch and decorative pillows. Large glass doors allow natural light to fill the space and provide views of the outdoors.
Vacation home in Kemptville
4.91 out of 5 average rating, 134 reviews

Boathouse Café Airbnb

Getaway at our stylish and open concept airbnb just steps from the Rideau River. Our Airbnb boasts views of the Rideau locks from the front, and of our 6 acre property from the back. Take our canoe or paddle boards out on the river, enjoy a campfire under the stars, hike the nearby trails, or go exploring in the nearby town of Merrickville. Enjoy your own private courtyard with dining table, BBQ, and lots of privacy.

Guest favorite
A serene view of the river at sunset, with vibrant colors reflected on the water's surface. Several kayaks in various colors are lined up on the grassy bank, surrounded by lush trees that frame the scene.
Cottage in Chase Mills
4.92 out of 5 average rating, 156 reviews

Lazy River Cottage

This well loved family-friendly river cottage is ready for you. The river is just steps from the house with breath taking views and sunsets to remember. Great fishing from the waterfront and dock. Enjoy a fire in the fire pit near the shore. The water is wonderful for those swimmers in your family. There are paddle boats and kayaks in season. Conveniently located close to St. Lawrence University and Clarkson.

Popular amenities for Winchester vacation rentals