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.

0 of 0 items showing

1 of 3 pages

Guest favorite

Guesthouse in Newington

4.92 out of 5 average rating, 353 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.

May 7 – 14

$57 per night

Guest favorite

Treehouse in Chesterville, Canada

4.93 out of 5 average rating, 241 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)

Jun 16 – 23

$125 per night

Guest favorite

Cabin in Rockland , Canada

4.91 out of 5 average rating, 107 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.

Sep 5 – 12

$129 per night

Guest favorite

Home in Morrisburg, Canada

4.92 out of 5 average rating, 199 reviews

StoneCropAcres Winery and Vineyard Guest Home

Our home is located at our StoneCropAcres Winery and Vineyard. Please check the Winery's website stonecropacres.ca 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, the llama ranch across the road 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.

Aug 15 – 22

$187 per night

Guest favorite

Cabin in Merrickville, Canada

4.99 out of 5 average rating, 112 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!

Mar 25 – Apr 1

$240 per night

Guest favorite

Home in Winchester

4.95 out of 5 average rating, 104 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.

Oct 8 – 15

$104 per night

Guest favorite

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.

Oct 9 – 16

$100 per night

Superhost

Cottage in Iroquois

4.83 out of 5 average rating, 117 reviews

✨CLUB HOUSE on the PENINSULA✨

Welcome to Clubhouse 10930, a unique heritage accommodation in Iroquois that offers the perfect blend of modern amenities and old-world charm from the 1800s. Our 7-bedroom home sits on its own private peninsula surrounded by the majestic St. Lawrence River, affording guests unparalleled panoramic views - an ideal getaway for discerning travellers! Follow us on I nstagram @clubhouse10930 for more pictures and videos!

Dec 24 – 31

$920 per night

Guest favorite

Cabin in Wakefield, Canada

4.93 out of 5 average rating, 630 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

Sep 20 – 27

$122 per night

Guest favorite

Barn in Potsdam, New York

4.99 out of 5 average rating, 140 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.

Jun 11 – 18

$72 per night

Guest favorite

Loft in Merrickville, Canada

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.

Feb 11 – 18

$116 per night

Guest favorite

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.

Jan 11 – 18

$115 per night