Vacation rentals in Winchester

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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 secluded guesthouse is shown, featuring a rustic exterior with grey wood siding and a vibrant red door. A path leads to the entrance, complemented by a welcome mat and a recycling bin. Flowering plants add a touch of color to the outdoor space.
Guesthouse in Newington
4.92 out of 5 average rating, 545 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.

Top guest favorite
A wooden cabin is nestled among trees, featuring a spacious outdoor deck with a large table surrounded by several chairs. The structure is designed with large windows, allowing natural light to fill the interior. Lush greenery surrounds the cabin, enhancing the natural setting.
Farm stay in Alexandria
4.97 out of 5 average rating, 143 reviews

3 Quiet Forest Retreat | Treehouse Near Montreal

Wake up to birdsong, fresh forest air, and the quiet of a true off-grid retreat. Welcome to **Anastasia’s Domain**, a peaceful forest sanctuary where guests slow down and reconnect with nature. Set on woodland with walking trails, a pond, and open skies, our cabins offer a rare escape from busy life. Enjoy morning coffee outside, explore the forest, and end the day around a campfire under the stars. An easy drive from **Montreal and Ottawa**, the Domain is a favourite nature escape.

Top guest favorite
A collection of vintage items is displayed against a bright yellow wall. Notable elements include a retro Pepsi-Cola sign, a vibrant red popcorn container, and various decorative mugs. A small toy car, a Polaroid-style camera, and an assortment of playful signs add character to the arrangement.
Apartment in Prescott
4.96 out of 5 average rating, 308 reviews

2 Bedroom Vintage Suite (mid-term available)

The 2 bedroom apartment is located on the 2nd floor and can accommodate 4 guests. The suite is in the Mechanic Block and dates back to 1874. The apartment was restored while keeping the historical integrity in check. With vintage sink, clawfoot tub and 7' interior walls (not reaching ceiling as shown on photos) There is private parking and separate entrance. You get the entire apartment. The main level of this historical commercial building is operated by the building owner.

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
Home in Morrisburg
4.9 out of 5 average rating, 272 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.

Top guest favorite
The exterior of the home features a welcoming porch framed by wooden beams. A white railing surrounds the area, with a small seating arrangement positioned beneath it. The light grey siding complements the blue sky, creating a serene first impression.
Home in Winchester
4.96 out of 5 average rating, 197 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.

Guest favorite
A modern A-frame chalet is nestled among tall trees, featuring a unique sloped roof and large windows that allow natural light to filter in. Soft illumination from inside enhances the cozy atmosphere, while the natural surroundings create a sense of tranquility.
Chalet in Val-des-Monts
4.96 out of 5 average rating, 135 reviews

Haven at the Hills - Lac McGregor

Near a lake, the McGregor is a superb A frame cottage, perfect for disconnecting from the city while being ideally located to allow you to fully enjoy everything the Gatineau/Ottawa tourist region has to offer. Our mini-chalets are equipped to allow you to relax with our spa or to work remotely in our office, according to your needs. They will be a place you'll be eager to return to since you'll feel right at home there.

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, 123 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.

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.

Guest favorite
An aerial view of the treehouse reveals its unique design, elevated on sturdy log pillars. The exterior features a modern metal roof and a green wood panel accent. Surrounding trees enhance the natural setting, creating a serene retreat atmosphere.
Cabin in Wakefield
4.93 out of 5 average rating, 844 reviews

The Wakefield Treehouse

We hope to fulfill your treehouse fantasy. The treehouse is a unique minimalist experience for those seeking quiet solitude in the Gatineau hills. Includes all the amenities of home to offer the most comfort in all seasons. Walking distance from Le Belvedere wedding reception centre. One of a kind hand hewn log treehouse is an inspiring and tranquil nature retreat. Establishment CITQ number: #295678

Popular amenities for Winchester vacation rentals