
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.

Walk 2 OLRT & Hard Rock, mins to airport & EY Ctr
A one-of-a-kind stay; this cozy loft nestled inside a converted airport hangar has rustic charm, curved ceilings, & wide-open views. It offers the perfect blend of character & convenience. Relax on the balcony & watch stunning sunsets, explore the open space, or hit the nearby trails for a walk or bike ride. Enjoy Starlink Wi-Fi, AC, a dedicated workspace, and a stocked pantry. Just 7 minutes from the airport & EY Centre, 2 mins. from the Hard Rock & Casino, golf course, & 20 mins. to downtown.

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.

Les Refuges des Collines - Parc de la Gatineau
Aux abords d'un lac, le Parc de la Gatineau est un superbe chalet en A parfait pour se déconnecter de la ville tout en étant idéalement situé pour vous permettre de bien profiter de tout ce que la région touristique de Gatineau/Ottawa a à offrir. Nos mini-chalets sont équipés pour vous permettre de relaxer avec leur spa ou d'effectuer du télétravail dans leur bureau aménagé à cet effet. Nos chalets seront un endroit où vous vous presserez de revenir puisque vous y sentirez comme chez vous.

Riverside Cabin & Nature Trails
Enjoy our 160 acres in a private natural setting. Owls, trout, heron, osprey, mergansers and the occasional loon will add to your stay. There are over 4 miles of private trails for hiking along the river and in the woods. Kayaks & fishing poles provided. Enjoy a romantic riverside fire-pit, professional massage table & new Finnish wood fired sauna. We sanitize everything 110% before your arrival and offer self check in. We celebrate diversity and welcome people from all communities.

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!

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).

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).

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.

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.

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.

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.

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.
Popular amenities for Winchester holiday rentals
Other great holiday rentals in Winchester

HistoricTrain Depot-Cozy & Centrally Located

1 bedroom furnished suite

Cozy Waterfront Getaway

East Suite - at Abbott Road Suites

Waterfront cottage/boat access/fire pit/BBQ

Prestige home

Stay Above The Village Pantry- Suite 1

Modern Comfort + Private View Very close to Ottawa
Destinations to explore
- Tuckahoe Holiday rentals
- Montreal Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Boston Holiday rentals
- Mississauga Holiday rentals
- Hudson Valley Holiday rentals
- Pocono Mountains Holiday rentals
- Québec City Holiday rentals
- Island of Montreal Holiday rentals
- Capital District, New York Holiday rentals
- Grand River Holiday rentals
- Calypso Theme Waterpark
- Mont Cascades
- Camp Fortune
- Carleton University
- University Of Ottawa
- Canadian Museum of Nature
- Ski Vorlage
- Omega Park
- Edelweiss Ski Resort
- The Ottawa Hospital
- Td Place Stadium
- Canadian War Museum
- Casino Du Lac-Leamy
- Nigeria High Commission
- Ottawa Art Gallery
- Dow's Lake Pavilion
- Canadian Museum of History
- Parc Jacques Cartier
- Parliament Buildings
- Britannia Park
- Absolute Comedy Ottawa
- Canada Aviation and Space Museum
- National Gallery of Canada
- National War Memorial





