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Featured Cottages in Winchester

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Doran Bay Resort

Doran Bay Resort

2.5 out of 5.0 11128 County Road 2, South Dundas, ON
Located in South Dundas, this beachfront cottage is next to a golf course, 1.3 mi (2 km) from Iroquois Golf Club, and 2.1 mi (3.3 km) from Iroquois Beach. Crysler Park Marina and Upper Canada Playhouse are also within 12 miles (20 km).

Winchester Cottages For Rent

Dreaming of a getaway that’s reminiscent of a fairytale? Travelocity doesn’t have magic wands or talking animals in our inventory—at least, none that we can find—but we do have holiday cottages in Winchester that will make you feel like you’ve stepped inside your vacation dreams.

The word “cottage” may make you think of whitewashed walls, flower print curtains, and sprawling views of rolling green hills—lucky for you, we do offer tons of country cottages that were furnished with a rustic feel in mind. Appreciate the vase of daffodils on your dining room table, and peek out the window onto the private patio that surrounds yours and other rustic cottages in the area.

These charming “home away from homes” have long been a beacon for those who love the outdoors, so pick a spot peppered with hiking trails and spend lazy afternoons meandering through the gorgeous scenery Winchester is known for. Snap some pictures while you’re at it—you’ll want to remember sunset over this waterfall for the rest of your life. When the sun goes down, cuddle up in front of a cheerful fire, or head into town to explore the shops, restaurants, and art galleries that have sprung up over the years. Ah, it’s nice to return to civilization every once in a while, isn’t it?

Whether you select cottages minutes away from the bustling city center, or coastal cottages that are footsteps from the sand and surf, you’ll find the accommodation you’re looking for here on Travelocity. Just because you’re booking a place that reminds you of a fairytale doesn’t mean you need a fairy godmother to find the best deal around! Just a gnome…

Top Trending Hotels in Winchester

See all 14 properties in Winchester
Terrace Green Bed & Breakfast C$95
Terrace Green Bed & Breakfast

Terrace Green Bed & Breakfast

11952 County Road 43, North Dundas, ON
    3.0 out of 5.0 Stars

    Located in Ottawa Division, this bed & breakfast is within 25 miles (40 km) of Upper Canada Playhouse, Rideau River Provincial Park and Rideau Carleton Raceway. Crysler Park Marina and Upper Canada Village are also within 25 miles (40 km).

    Winchester B&B C$120
    Winchester B&B

    Winchester B&B

    528 St Lawrence St, North Dundas, ON
      3.0 out of 5.0 Stars

      Located in Ottawa Division, this bed & breakfast is within 25 miles (40 km) of Upper Canada Playhouse, Calypso Theme Waterpark and Rideau River Provincial Park. Crysler Park Marina and Rideau Carleton Raceway are also within 25 miles (40 km).

      Microtel by Wyndham Casselman C$110
      Microtel by Wyndham Casselman

      Microtel by Wyndham Casselman

      17 Rue Industriel, Casselman, ON
        3.0 out of 5.0 Stars

        Situated in Casselman, this golf hotel is 1.3 mi (2.2 km) from Casselview Golf and Country Club and 10.2 mi (16.4 km) from Calypso Theme Waterpark. Glengarry Sports Hall of Fame and Sacred Heart Parish are also within 20 miles (32 km). Casselman Station is 15 minutes by foot.

        *Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.