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Holiday houses in Winchester

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Winchester

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

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Guest favourite
The exterior of a charming two-story building is illuminated by a warm glow from the interior. A fire pit with a crackling fire is positioned in front, surrounded by wooden Adirondack chairs. Tall trees frame the scene under a twilight sky.
Cabin in Ingleside
4.89 out of 5 average rating, 145 reviews

Lost Village Guest House 1860s Renovated Barn

Original 1860 Building Moved From The Lost Villages During The St Lawrence Seaway Project. Lots of Character & Charm❤💕 Whether You’re Looking To Soak Up The Sun At The Beaches, Have Fun On The Water, Bike Around The Parkway, or Enjoy The Sledding Trails and Ice Fishing In The Winter Months. Enjoy The Natural Light Offered In Every Area of The Home. This Home is Dedicated Exclusively To Airbnb Guests And Sleeps Upto (2) Adults Comfortably Ideal For Any Vacation, Renovation or Work Stay!

Guest favourite
A cozy bedroom is highlighted by a plush queen-sized bed, adorned with soft linens and a decorative throw pillow. Two bedside lamps provide warm light, while floral artwork hangs above the headboard, enhancing the serene feel of the space.
Apartment in Kemptville
4.94 out of 5 average rating, 33 reviews

Road trip Luxury Private Guest Suite off 416

Our super clean cozy private entrance guest suite just off the 416 in the quaint small town of Kemptville (20 min from Ottawa) can often host last minute bookings. The suite is separated from the rest of the house by a locked door and there are no shared spaces. The self contained suite has a queen-sized bed, 2 TVs, couch, chair, desk, mini-fridge, microwave, coffee-maker. On the main level of a bungalow. Not in a basement! 10 foot ceilings, tons of light! Must have car, no uber, no transit.

Top Guest favourite
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, 519 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 favourite
A well-lit entrance features a decorative front door with a glass pattern, complemented by a small bench and shoe rack. The tile floor extends throughout, while beige walls provide a neutral backdrop. Natural light filters in, enhancing the welcoming atmosphere of the entryway.
Guesthouse in St-Albert
4.97 out of 5 average rating, 30 reviews

1 Bedroom Furnished Guest House

Discover the perfect blend of comfort and convenience in our smoke-free guest house attached to our home. This furnished space features: - Free Parking - Internet Access - Cable TV: For your entertainment. - Washer/Dryer: In-unit laundry. - Complete Kitchen: fridge, stove, and microwave - Queen Size Bed - Private Entrance - Patio: Extend your living space outdoors with access from both the bedroom and living room. - Generac Generator: Peace of mind with a reliable backup power source

Superhost
The off-grid mushroom house features a unique architectural design with a grassy rooftop and vibrant greenery surrounding the entrance. Rustic stonework and wooden accents are complemented by the soft glow of sunset, creating a serene atmosphere within a naturally integrated environment.
Tiny home in Chesterville
4.93 out of 5 average rating, 349 reviews

The Mushroom Cabin ~ it’s a real trip

Get away from the hustle at the OFF-GRID MUSHROOM HOUSE! Cozy up in the cabin, take a walk on the trails, heat up in our wood burning sauna, or just sit outside and listen to the frogs and birds sing. Get rustic by cooking with our wood fire earth oven or grill over a campfire! You’ll have all the cooking tools you need for a fabulous meal. IMPORTANT! ***No running hot water or shower available from October 1st to May 10th*** Regardless, our place is a retreat you’ll love!

Top Guest favourite
A welcoming living area is observed with a sectional gray sofa and an accent chair in turquoise. A small coffee table is situated in front of the sofa, and a decorative area rug adds warmth to the space. Natural light is provided by large windows.
Home in Winchester
4.96 out of 5 average rating, 186 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. Check us out at theloftynest dot ca.

Top Guest favourite
Home in Morrisburg
4.9 out of 5 average rating, 259 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 favourite
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, 103 reviews

Honeybee Haven - Dog Friendly, Free Parking

Escape to a cozy, dog friendly haven, perfect for embracing the magic of the winter 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 winter 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 favourite
A modern living area showcases a light-colored sofa positioned near a cozy bean bag. Natural wood accents are visible in the dining area, featuring a round table surrounded by dark chairs. Soft lighting highlights the open space, contributing to a bright and airy feel.
Apartment in Ottawa
4.98 out of 5 average rating, 123 reviews

Whispering Timber Suite

Enjoy the peaceful calm of being surrounded by nature in Whispering Timber suite. You'll have exclusive access to the in-law suite of our home, complete with a bedroom (queen size bed), a sofa bed, a full bathroom and a small kitchen. The suite is located at the back of the home with it's own exterior entrance. Extra towels, sheets and comforters are provided, along with dishes and cookware in case you want to make a meal.

Guest favourite
A modern kitchen features white cabinetry and a wood countertop. Stainless steel appliances include a refrigerator and a range with an oven. Subway tiles provide a clean backsplash. Open shelving displays small kitchen items, contributing to the organized appearance.
Holiday home in Kemptville
4.9 out of 5 average rating, 116 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.

Top Guest favourite
Cottage in Ottawa
4.9 out of 5 average rating, 192 reviews

Beautiful Waterfront Home | 30 Minutes from Ottawa

Escape to a serene 3-acre waterfront retreat on the beautiful Rideau River, just 30 minutes from Ottawa. Modern home with 400 feet of shoreline, situated next to Baxter Beach and the scenic trails of the Rideau Valley Conservation Area, it’s the perfect spot for outdoor enthusiasts. Riverside patio, complete with a fire pit and BBQ, as you take in stunning sunsets and the peaceful surroundings. A heavenly getaway!

Top Guest favourite
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, 808 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 holiday rentals