
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.

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.

Unwind in the Countryside at Fraser Creek Farm
Unwind in the countryside of South Glengarry. Our location is close to Ottawa, 124 km SE, and Montreal, 81km West, 20km east of Cornwall and 10km south of Williamstown. Embrace the peace and beauty of the orchard during the spring, summer or fall. Breathe in the refreshing winter air. This is our home property, you may see children exploring with one collie, chickens free ranging and waking to a rooster. Ideal for fishermen who want the St. Lawrence River. We start pizza in Spring ‘24.

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.

Le Stonybreck: Modern Wakefield Chalet Getaway
Beautiful, newly built and fully equipped luxury chalet. Located at La Pêche (Edelweiss) just 25 minutes from downtown Ottawa close to the quaint village of Wakefield. This four season chalet is a perfect getaway for any occasion, gathering, or quiet relaxation. Great for outdoor recreational activities. Surrounded by trees and overlooking a large pond. Fire pit to keep you warm on any night. Vegetable garden to pick and eat your own fresh veggies in the summertime.

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!

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.

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.

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

Stonebridge Golf Nest

Relax, fish, boat, BBQ enjoy

Chalet des collines_VDM (Hillside Chalet)

Seaside Bungalow with amazing views

Rideau River Getaway Waterfront 30min to Ottawa

Stunning Home close to Ottawa

St Lawrence River Cottage w/100’ of private beach

Malcolm Cottage House
Destinations to explore
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- Calypso Theme Waterpark
- Mont Cascades
- Camp Fortune
- Carleton University
- University Of Ottawa
- Canadian Museum of Nature
- Edelweiss Ski Resort
- Omega Park
- Ski Vorlage
- Td Place Stadium
- Canadian War Museum
- Ottawa Art Gallery
- Casino Du Lac-Leamy
- Canadian Museum of History
- Dow's Lake Pavilion
- Nigeria High Commission
- The Ottawa Hospital
- Parc Jacques Cartier
- Britannia Park
- Parliament Buildings
- Shaw Centre
- National Gallery of Canada
- Canada Aviation and Space Museum
- Absolute Comedy Ottawa





