
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.

LoveNestChalet | Romantic with Private Hot Tub
☞ Welcome to the enchanting LoveNest Chalet, your perfect haven for a romantic getaway in the heart of nature in the Laurentians near Ontario province ☞ With generous windows that frame breathtaking views of the majestic mountain and lake is designed to provide an intimate escape for those seeking tranquility ☞ LoveNest Chalet offers the ideal retreat for those looking to reconnect and create lasting memories in a secluded setting ☞ Perched at the top of a mountainous land of over 50,000 sq. ft.

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.

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.

3 Quiet Forest Retreat | Treehouse Near Montreal
Wake up to birdsong, fresh forest air, and the quiet of a true off-grid retreat. Welcome to **Anastasia’s Domain**, a peaceful forest sanctuary where guests slow down and reconnect with nature. Set on woodland with walking trails, a pond, and open skies, our cabins offer a rare escape from busy life. Enjoy morning coffee outside, explore the forest, and end the day around a campfire under the stars. An easy drive from **Montreal and Ottawa**, the Domain is a favourite nature escape.

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.

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!

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.

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.

Haven at the Hills - Lac McGregor
Near a lake, the McGregor is a superb A frame cottage, perfect for disconnecting from the city while being ideally located to allow you to fully enjoy everything the Gatineau/Ottawa tourist region has to offer. Our mini-chalets are equipped to allow you to relax with our spa or to work remotely in our office, according to your needs. They will be a place you'll be eager to return to since you'll feel right at home there.

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.

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.

The Wakefield Treehouse
We hope to fulfill your treehouse fantasy. The treehouse is a unique minimalist experience for those seeking quiet solitude in the Gatineau hills. Includes all the amenities of home to offer the most comfort in all seasons. Walking distance from Le Belvedere wedding reception centre. One of a kind hand hewn log treehouse is an inspiring and tranquil nature retreat. Establishment CITQ number: #295678
Popular amenities for Winchester vacation rentals
Other great vacation rentals in Winchester

Deluxe Water View Loft - Free on-site EV Charging

1 bedroom furnished suite

Best of modern country living

Bright 1-BR Suite | Kitchen • Work Area • River

Linden Leaf Gausthaus Inn

Cozy unit near airport with free parking in Ottawa

The Haven on Halton

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





