Some info has been automatically translated. Show original language

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.

1 of 1 pages1 / 1
Guest favorite
A modern two-story home features a large covered porch supported by wooden pillars. Expansive glass windows invite natural light, while a well-maintained lawn extends around the property. The exterior showcases a blend of stone and contemporary design, providing an appealing entrance.
Home in Nepean
4.93 out of 5 average rating, 106 reviews

Stonebridge Golf Nest

Welcome to our beautifully appointed 4-bedroom, 2.5-bathroom detached home in Ottawa, located just moments from the prestigious Stonebridge Golf Course. Offer perfect blend of modern design and luxurious comfort, ideal for both relaxation and exploration. Take advantage of nearby parks, walking trails, and the serene environment around you, or simply unwind in the private backyard of this quiet corner lot. Perfect for families, groups, or anyone seeking a luxurious and convenient Ottawa getaway

Top guest favorite
A bright dining area is surrounded by large windows offering views of the waterfront. A round table is surrounded by six upholstered chairs, while natural light fills the space, highlighting the wooden ceiling and flooring.
Home in Manotick
4.95 out of 5 average rating, 107 reviews

The River Retreat on the Rideau

Discover the charm of The River Retreat on the Rideau River, just outside of the quaint town of Manotick, Ontario and 30 minutes from downtown Ottawa, the Capital of Canada. It is the perfect blend of organic design, modern features and breathtaking views. Enjoy the beautiful and colourful sunsets at this unique waterfront property. This vacation home has everything you need and more for an incredible getaway with a group of friends, family gatherings, a business trip or corporate retreats.

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
4.91 out of 5 average rating, 556 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
The living area features a dark sectional couch positioned near a wall-mounted TV, with shelves holding decorative plants. A wooden dining table with four upholstered chairs occupies the space, complemented by a small plant centerpiece. Natural light enters through a nearby window.
Bungalow in Mountain
4.84 out of 5 average rating, 70 reviews

Cozy Country Bungalow

Our cozy bungalow is easily accessible from the city. You will immerse yourself in a natural setting with woods, ponds and trails. The bedroom has a double bed, plus a Roku TV and dresser. The couch pulls out to a queen sized bed. There is another TV in the living room area. You can access your own accounts for Netflix, Prime or whatever subscriptions you have as well as regular TV channels. The bathroom also contains a washer and dryer for your convenience. Laundry soap is provided.

Top guest favorite
Home in Kemptville
5 out of 5 average rating, 16 reviews

Cozy 3 bedroom home with backyard oasis.

This bright and cozy home is designed for comfort and relaxation. The king-size primary bedroom features a private ensuite for a peaceful retreat. Enjoy the backyard dining and seating area, perfect for outdoor meals or evening stargazing. Conveniently located just 30 minutes south of Ottawa and minutes from Kemptville’s charming downtown, you’ll find local shops, restaurants, cafés, and a scenic waterfront nearby. **Please note: the hot tub is unavailable during July and August**

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
4.91 out of 5 average rating, 100 reviews

Rideau Getaway: Waterfront 3BR Cottage

Wake up to the Rideau right in your backyard and unwind in this peaceful, year-round cottage getaway. Tucked away on a quiet private road with a boat launch, this is the perfect place to slow down and enjoy cottage life. Whether you're sipping morning coffee on the dock, spending the day on the water, or winding down by the fire table in the evening, this is the perfect place to relax, recharge, and make memories with family and friends while enjoying beautiful waterfront views.

Top guest favorite
A bright living room is shown, featuring a leather couch and a cozy red armchair. A wooden coffee table rests on a light-colored rug, while a decorative piece hangs on the wall. Large windows allow natural light to fill the space, offering views of the outside.
Guest suite in Nepean
4.9 out of 5 average rating, 175 reviews

Forest Suite in the City: 1bd/1bth + parking

Take it easy at this unique and tranquil getaway. Located 12 mins from the airport and 18 mins from downtown, this private guest suite is attached to our family home nestled in Pinhey Forest, with access to over 5km of year-round trails. You will have the use of your own private entrance leading to a full suite, including a fully-stocked, eat-in kitchen; 4-piece bath, queen bedroom with closet space, and a bright and cozy living room with smart TV. On-site parking is included.

Top guest favorite
The exterior showcases a contemporary cabin with a spacious wooden deck and large glass walls. Comfortable outdoor seating is positioned on the deck, surrounded by a well-maintained lawn and lush greenery in the background. The structure is illuminated by natural light under a partly cloudy sky.
Cottage in Wakefield
4.97 out of 5 average rating, 642 reviews

The Meadow

Welcome to our modern countryside cabin located on a 2 acre lot in Wakefield, Quebec. Come relax and recharge for a few days while taking advantage of nature and the cozy interior with fireplace. There is plenty to do nearby: discover the Wakefield village, its restaurants, boutiques, farms, the Gatineau Park, the Nordik Spa, Eco-Odyssee, the nearby golf courses and ski hills, etc. (CITQ Permit #298430. We pay all Sales and Income taxes to the prov/fed governments).

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
4.85 out of 5 average rating, 110 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).

Guest favorite
Home in Morrisburg
4.9 out of 5 average rating, 282 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
Apartment in Winchester
4.98 out of 5 average rating, 42 reviews

Bright Modern Apartment Backing onto Golf Course

Bright, modern lower-level apartment with stunning golf course views. Perfect for couples or remote workers, this private suite offers peace, luxury, and comfort with large windows, natural light, in-floor heating, AC, advanced air filtration, and pure remineralized water. Features include a modern open layout, dedicated desk, ample parking, and thoughtful design—your ideal retreat to relax, recharge, or work in quiet comfort near Winchester.

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, 181 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.

Popular amenities for Winchester vacation rentals