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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.

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Top guest favorite
A master bedroom features a queen-size bed with a textured white coverlet. Large windows and sliding glass doors allow for natural light and offer views of the waterfront. A small table is positioned near the window for additional functionality.
Cottage in Hammond
4.96 out of 5 average rating, 190 reviews

River Ledge Hideaway

New construction home designed specifically with the thought of guests in mind overlooking the Saint Lawrence River. Enjoy a memorable fall or holiday getaway to this waterfront oasis. Highlighting this home is a large master bedroom overlooking numerous islands speckled throughout the expansive water view. Outdoor fire pit and grilling area will be set up for the fall season. Walk down our path to your own private waterfront. Great place for couples, small families or friends getting together

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, 538 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 cozy guest suite is featured with a spacious bed framed by a delicate canopy. Ambient lighting is provided by two bedside lamps and an electric fireplace, enhancing the serene atmosphere. A small table is positioned nearby, complementing the room's tranquil decor.
Guest suite in Val-des-Monts
4.98 out of 5 average rating, 210 reviews

Niman's rest

Well maintained, unique, cozy, charming, serene & private haven near the lake. Far enough from the big city to leave the bustling day behind but close enough to keep your commute to a minimum. From the suite, downtown Gatineau is 20min away and Ottawa is less than 30min. Designed by us, Airbnb users with the comfort and features we would appreciate ourselves, with all basic commodities. Whether you come for a stopover or a relaxing getaway, it will surely meet your needs and expectations.

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, 304 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.

Top guest favorite
A cozy living area features a sofa adorned with blue and white pillows, complemented by a matching blanket. A wooden shelf holds books and decor, while a lamp provides soft lighting. Natural light enters through a large window, enhancing the inviting space.
Barn in Potsdam
4.99 out of 5 average rating, 237 reviews

The Coop at Laing Family Farm

Set in the heart of our 400 acre certified organic farm, The Coop at Laing Family Farm is a quiet, cozy cottage surrounded by open fields, orchards, and the gentle rhythm of farm life right between Canton and Potsdam. It’s the kind of place where mornings start slowly with coffee on the porch and evenings end under dark, star-filled skies. Perfect for visiting families attending college events, alumni weekends, and campus visits — a quiet place to unwind after a full day.

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, 275 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
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, 104 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 favorite
Home in Morrisburg
4.9 out of 5 average rating, 269 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.

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, 161 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.

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, 192 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.

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, 119 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
The living room features a comfortable seating arrangement, including a blue couch with decorative pillows, a recliner, and a coffee table. A TV is mounted on a wooden shelf, and natural light enters through large windows beside the door, revealing a winter landscape outside.
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.

Popular amenities for Winchester vacation rentals