Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Guest favorite
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, 142 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!

Superhost
A spacious living area is shown, featuring light-colored walls and wooden flooring. A sectional couch is positioned against one wall, while a dining table with four chairs stands nearby. Soft lighting is provided by recessed ceiling lights. Decorative plants and artwork enhance the space.
Home in Russell
4.75 out of 5 average rating, 60 reviews

2Bedroom Basement Suite near Calypso Private Entry

Enjoy the serenity this spacious 2-bedroom basement suit with private entrace has to offer you and your family. Located in the Embrun, East of Ottawa, this is an amazing great location for you and family with lots of room. The spacious living room has a sectional, a TV with various apps, Netflix, dining section and kitchenette with a microwave, refrigerator, coffee maker and toaster. Close to central stores and restaurants, The suite has central air conditioning and heat and Free WIFI internet

Top guest favorite
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
4.97 out of 5 average rating, 31 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.

Guest favorite
The image captures the early morning light filtering through trees, illuminating a misty Rideau River. Gentle waves can be seen near the shore, with a lamppost providing a nostalgic touch amidst the natural scenery.
Cottage in Kemptville
4.9 out of 5 average rating, 80 reviews

Open Concept 3 Bedroom Cottage on the Rideau

Enjoy a weekend getaway with the Rideau River located right in your backyard. Located on a quiet private road with a boat launch at the end of the street. Year round cottage with stunning sunrises. The Rideau River in this section is one of the widest sections and the longest sections of the World Heritage, Rideau Canal system. Equipped with a beautiful deck, outdoor seating area, BBQ, and fireplace. Dock your boat and enjoy. Don't have a boat? Check out Long Island Marina for boat rentals.

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, 513 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.

Guest favorite
A newly constructed home is featured alongside other residential buildings in a serene neighborhood setting. The house showcases modern architectural elements with a distinct facade, large windows, and a double garage. A well-maintained lawn stretches to the foreground under a partly cloudy sky.
Home in Embrun
4.96 out of 5 average rating, 51 reviews

4 bedroom luxury home in the heart of Embrun

Relax with the whole family at this peaceful place to stay. Newly built home in a family oriented neighborhood. Comes with all appliances, stove, fridge, microwave, and laundry. Downtown Embrun is 5-7min drive bars, and a lot of restaurants in the shopping center and downtown ottawa is 25min. The Calypso water park is just 7 min drive with lots of attractions for extended stays, please reach out to me even if the dates are not available online as i may be able to make them available

Top guest favorite
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

Top guest favorite
A vibrant sunset illuminates the sky with shades of orange and pink, reflecting on the calm water. A boat is docked at the edge of the water, with the serene landscape framed by trees in the background.
Cottage in Kemptville
5 out of 5 average rating, 37 reviews

Rideau River Getaway Waterfront 30min to Ottawa

Welcome to the Rideau River Getaway! A serene 4-season retreat just 30 minutes from Ottawa. With breathtaking sunset views, a 70-foot dock, outdoor kitchen, and Starlink WiFi, it’s the perfect escape for families, couples, and friends. Enjoy kayaking, paddleboarding, fires by the water, and hikes right across the river. Inside, relax in a newly renovated home with luxurious touches, top-tier appliances, and space for up to 8 guests. Peaceful, private, and packed with charm.

Guest favorite
A two-story house is illuminated softly in the evening light, highlighting its brick facade. A well-maintained lawn with potted flowers frames the entrance. A vehicle is parked in the driveway, with large windows allowing a view of the home's interior.
Apartment in Manotick
4.9 out of 5 average rating, 73 reviews

Apartment with Big Lounge

Welcome to our stylish 1-bedroom apartment , featuring a spacious living room perfect for relaxation or entertaining. The open layout includes a cozy kitchenette equipped with all the essentials. A dedicated office desk is perfect for remote work or study. Located in a quiet neighborhood, this bright and modern space is ideal for couples, solo travelers, or business stays. Enjoy comfort and convenience while staying close to local attractions, restaurants, and sightseeing!

Top guest favorite
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, 181 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.

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
4.82 out of 5 average rating, 95 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. Easily explore the neighbouring towns of Manotick and Merrickville or spend your time on the water from our 60ft dock in the middle of the largest stretch of the Rideau River (46km of open water from Manotick to Burritts Rapids).

Guest favorite
A well-maintained garden path is surrounded by lush greenery and flowering plants. A gazebo with seating is visible in the background, providing a shaded area for relaxation. A trellis adorned with climbing vines leads towards the gazebo, enhancing the peaceful outdoor setting.
Apartment in Williamsburg
4.72 out of 5 average rating, 121 reviews

Kim's Country Retreat

Come and stay in this cozy cottage-like century home/apartment complete with pine wood flooring accented with country antique decor. Clean, bright and quiet. Perfect for travelers, long and short term temporary workers or students. 10 minutes south to Morrisburg amenities, and Hwy 401. 10 minutes north to Winchester amenities, and Hwy 43. Kemptville and 416 is only another 20 minutes. Easy commute to Ottawa, Brockville or Cornwall.

Popular amenities for Winchester vacation rentals