Holiday houses in Winchester

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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 suite features a comfortable bed with a striped blanket, paired with a stylish seating area. A desk and chair are positioned near the window, providing a workspace. Soft lighting complements the warm wall tones, leading to a modern bathroom visible through an open doorway.
Bungalow in Kemptville
4.91 out of 5 average rating, 45 reviews

East Suite - at Abbott Road Suites

Spacious, very private suite with no shared areas. Modern bathroom with slate and glass shower, separate powder room and bedroom, with a walk-in closet, towels, linen and toiletries. Coffee, tea, cream, juice, water. Fridge, freezer, microwave, toaster oven, cooktop, Keurig, kettle, iron/board, pots, pans and dishes. Beautiful property, just 5 minutes from the quaint downtown core and 30 minutes from Ottawa. Fast wifi, and cold AC. Access to washer/dryer, barbecue grill & backyard bonfire pit.

Guest favourite
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, 102 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 favourite
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
4.96 out of 5 average rating, 104 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 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
4.91 out of 5 average rating, 554 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
Apartment in Kemptville
4.97 out of 5 average rating, 65 reviews

Road trip Luxury Private Entrance Suite near 416

A clean, bright, new, private entrance above-ground main floor suite designed for peaceful stays with 10 foot ceilings, natural light and no overhead noise. Not a basement suite! Very accessible for seniors. This modern suite has driveway parking and is just off the 416 in the quaint small town of Kemptville (25 min fr Ottawa). Separated from the rest of the house by a locked door, no shared spaces. The self contained suite has a queen bed, 2 TVs, couch, desk, coffee station and microwave.

Guest favourite
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
4.85 out of 5 average rating, 66 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.

Guest favourite
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, 98 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 favourite
Home in Kemptville
5 out of 5 average rating, 14 reviews

Cozy 3 bedroom home with backyard oasis.

This bright and cozy home is designed for comfort, relaxation, and effortless living. The king-size primary bedroom features a private ensuite, giving you a peaceful retreat at the end of the day. The backyard boasts a comfortable dining spot and seating area, ideal for al fresco meals or stargazing. This home is conveniently located 30 minutes south of Ottawa and minutes from Kemptville’s walkable downtown, with local shops, restaurants, cafes, and scenic waterfront.

Guest favourite
The cabin is set amidst tall trees, illuminated by warm interior lighting that highlights its log construction. The night sky sparkles with stars above, while the surrounding foliage creates a natural, secluded ambiance.
Cabin in Plantagenet
4.92 out of 5 average rating, 429 reviews

PERCHED CABIN at Mariposa Farm

The Perched cabin is one of our three cabins. We also have the Apple Tree and the Poplar cabin. This is glamping at its best. Window walls letting light into every side. A sleeping loft. Built with logs. Well equipped for cooking. Heated with woodstove - firewood included. In the middle of the forest. A lot of trails to enjoy. No neighbours. The perfect spot to unwind. We are farmers, a precise time of arrival is important. You are welcome to visit the farm.

Top Guest favourite
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, 109 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 favourite
Home in Morrisburg
4.9 out of 5 average rating, 277 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
Apartment in Winchester
4.97 out of 5 average rating, 37 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.

Popular amenities for Winchester holiday rentals