Beginning of main content

Get 24/7 travel help, thanks to our Customer First Guarantee

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Featured Cottages in Winchester

Doran Bay Resort C$160
Doran Bay Resort

Doran Bay Resort

11128 County Road 2, South Dundas, ON
     
    2.5 out of 5.0 Stars

    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 mi (20 km).

    Map

    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
    Winchester B&B Get Rates
    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 mi (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 mi (40 km).

      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 mi (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 mi (40 km).

        Tourist Inn C$120
        Tourist Inn

        Tourist Inn

        4022 County Road 43, North Grenville, ON
           
          2.5 out of 5.0 Stars

          Located in Ottawa Division, this motel is 5.4 mi (8.8 km) from Rideau River Provincial Park and within 25 mi (40 km) of Watson's Mill and Chapman Mills Marketplace. Rideau Carleton Raceway and Walter Baker Sports Centre are also within 25 mi (40 km).

          Microtel Inn & Suites Casselman C$118
          Microtel Inn & Suites Casselman

          Microtel Inn & Suites 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 mi (32 km). Casselman Station is 14 minutes by foot.