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.

0 of 0 items showing

1 of 3 pages

Guest favourite

Guesthouse in Newington

4.92 out of 5 average rating, 355 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 and safe location for those seeking a road break or destination traveler's seeking the St Lawrence and its environs. Sit by a fire, take a hammock ride, listen to wind and and birds or watch the sky. Multi day guest have free use of kayaks and equipment. $50 cleaning fee per pet through extra fee request if necessary before arrival. Multi day guests have free access to kayaks and carrier.

15 – 22 Sept

$877 AUD total

Guest favourite

Guest suite in South Glengarry

4.96 out of 5 average rating, 223 reviews

River Retreat

This is a 1,000 square foot apartment in an architecturally designed home. Walking upstairs to the apartment, guests will be in awe of the panoramic views of the St Lawrence River through the floor-to-ceiling windows. The kitchen is equipped with everything that you need for cooking and entertaining. The apartment has in-floor heating and AC throughout. Guests will enjoy a private waterfront backyard with a BBQ, fire pit and dock. Boat docking is sometimes possible to accommodate upon request.

25 Nov – 2 Dec

$1,711 AUD total

Guest favourite

Treehouse in Chesterville, Canada

4.93 out of 5 average rating, 243 reviews

Tiny House Off-Grid Cabin & Wood Burning Sauna

Get away from the hustle at our off-grid oasis. A unique structure with a living roof. Pick your own veggies in our seasonal garden and cook outdoors with our wood fire earth oven or use the grill over a camp fire! Includes all cooking tools needed for a good meal. Cozy up in the cabin with your favourite book, take a walk on the trails, or heat up in our wood burning sauna. Hot water and Shower are seasonally in service from May 10th through to October 1st (depending on freezing temperatures)

7 – 14 Dec

$1,661 AUD total

Guest favourite

Cabin in Lanark, Canada

4.93 out of 5 average rating, 125 reviews

The Owl's Nest Cabin, a peaceful retreat

Welcome to The Owl's Nest, a brand new woody pine cabin overlooking beautiful fields and forests. This completely private cabin offers a cozy, clean, open concept design with large bright windows designed to let the natural beauty of the land inside. Spend days unwinding at the cabin, walking our nature trail, or explore nearby attractions. Hike to the lookout at Blueberry Mountain, or visit local boutique shops, restaurants & beaches around historic Perth. Come Be in nature, explore & relax!

11 – 18 Dec

$908 AUD total

Guest favourite

Cabin in Rockland , Canada

4.91 out of 5 average rating, 108 reviews

The Nest - Nordic style tiny cabin

All booked up? Check out our other listings in the same area! Discover serenity in our 10x10 off grid wood cabin, nestled amidst the forest. Reconnect with the your partner cozying up by the fireplace or sip on coffee with a friend for a retreat. Savour the beauty from our hammock chairs on the porch or recline and relax on our loft net. Enjoy the glow of the campfire and wake up in our king size bed overlooking the trees. It's time to slow down and do less. Let moments become memories.

19 – 26 Sept

$1,694 AUD total

Guest favourite

Guesthouse in Perth, Canada

4.98 out of 5 average rating, 179 reviews

Lakefront Cozy Cabin, Perth, On

Come and enjoy sunsets, stargazing, wildlife and our beautiful lake! A private, picturesque getaway suitable for a couple or solo travellers. 20 min SW of Perth/Westport,50 min. to Kingston, 1 hr to Ottawa. Our cozy guest cabin offers you a place to relax, rejuvenate, and explore. We want your stay to be a special one so please read the complete listing details. We are located in a natural lakefront setting in cottage country, so you must be comfortable with wildlife.

6 – 13 Feb

$1,384 AUD total

Guest favourite

Home in Winchester

4.95 out of 5 average rating, 106 reviews

CUTE Tiny House + 2 BR + 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-bedroom 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. Check us out at theloftynest dot ca.

31 Oct – 7 Nov

$1,524 AUD total

Guest favourite

Cabin in Plantagenet

4.91 out of 5 average rating, 374 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.

25 Feb – 4 Mar

$1,333 AUD total

Guest favourite

Cabin in Wakefield, Canada

4.93 out of 5 average rating, 631 reviews

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

11 – 18 Sept

$1,676 AUD total

Guest favourite

Barn in Potsdam, New York, US

4.99 out of 5 average rating, 141 reviews

The Coop at Laing Family Farm

The Coop at LFF is a small and cozy cottage that sits on our 220 acre certified organic farm. It has a kitchen and living area, bedroom and full bath. There is Roku TV and Free WIFI. Enjoy hiking, snowshoeing or cross country skiing the trails around our farm. Relax in the rocking chairs on the porch. The fire pit in the front yard is perfect for s’mores or to stay warm while star gazing.

7 – 14 Aug

$1,156 AUD total

Guest favourite

Cottage in Clarence-Rockland

4.99 out of 5 average rating, 130 reviews

Dawsons Landing-Waterfront retreat 30min to Ottawa

Hello, Welcome to Dawson’s Landing, a waterfront cottage retreat located 30 minutes from Ottawa and a little less than 2 hours from Montreal. The home offers a fully equipped kitchen, two bedrooms with queen size beds, and lots of open space for watching TV, reading a book or just surfing the web while enjoying the beautiful sunrises and sunsets.

21 – 28 Feb

$1,727 AUD total

Guest favourite

Loft in Merrickville

4.95 out of 5 average rating, 152 reviews

The Gallery Loft

This 1500 square foot , two storey classic-contemporary guest suite is located in the downtown business district. Steps from Galleries, shops, and fabulous restaurants. Perfect for a girls night out, families or romantic get-a-ways. Welcoming all brands of adventurer. Beautiful hiking trails, canoeing and kayaking. Quiet secondary roads for cycling.

17 – 24 Mar

$1,524 AUD total