We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Winchester Vacation Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    $113 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Don't let other travelers get your favorite Winchester area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 17 Rentals in Winchester
    Sort by:
    Default
    Terrace Green Bed & Breakfast1 / 4
    (1)Excellent
    Winchester
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Winchester
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Winchester
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Winchester
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Offering a barbecue and sun terrace, Terrace Green B&B is located in Winchester in the Ontario Region. Free WiFi is offered throughout the property and free private parking is available on site. Certain rooms feature a seating area to relax in after a busy day. There is a shared kitchen at the...
    View all property information
    Location Information
    Winchester, Ontario K0C 2K0
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Inquiry
    Winchester
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Offering a barbecue and sun terrace, Terrace Green B&B is located in Winchester in the Ontario Region. Free WiFi is offered throughout the property and free private parking is available on site. Certain rooms feature a seating area to relax in after a busy day. There is a shared kitchen at the...
    View all property information
    Location Information
    Winchester, Ontario K0C 2K0
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    The following rentals are within 25 miles of Winchester.
    FAMILY, MATURE ADULTS AND PET FRIENDLY REDBUSH1 / 22
    (4)Excellent
    Morrisburg
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Balcony
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    The house was even better than we expected. It was spotless and had all the amenities of home. The location could not have been better. We were very close to a beautiful park...
    Reviewed June 15, 2019
    We stayed for 3 nights at the Redbush cottage. I'm particular about cleanliness and this met all our needs! Very well equiped newer cottage and Andrea was easy to get in touch...
    See all reviews
    About this property
    REDBUSH is a new two bedroom bungalow situated in the picturesque village of Morrisburg on a dead end lane on a tranquil treed lot. Will sleep 6: 2 double beds and a futon. Enjoy open concept living, a modern kitchen with range, fridge, diswasher and microwave. Small appliances include electric...
    View all property information
    Location Information
    Morrisburg, Ontario K0C 1X0
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    Beautiful 4 bedroom cottage on the Rideau River1 / 15
    (1)Excellent
    Kemptville
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Washer
    • Grill
    • Internet Access
    • Cable/satellite TV
    • Parking
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 17, 2016
    I highly recommend this place for it's great location, amenities and an overall wonderful time.Is very clean and very basic, not fancy but has everything you need,was...
    See all reviews
    About this property
    Beautiful cottage just 40 minutes drive from Ottawa. Close to the village of Burritts Rapids, ten minutes from the picturesque village of Merrickville. The house was built in the 1820s and still retains a lot of the old charm. Recently completely renovated with brand new kitchen and bathrooms....
    View all property information
    Location Information
    Kemptville, North Grenville K0G 1J0
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    Doran Bay Resort Cottages1 / 20
    (2)Average
    Iroquois
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Waterfront
    • Housekeeping Included
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 4, 2018
    We recently visited Doran Bay Resort Cottages and had a really wonderful time. Small group of clean, well kept cottages along the St. Lawrence River near Cornwall. Beds were...
    See all reviews
    About this property
    Doran Bay Resort offers guests the choice of 9 beautiful waterfront cottages on the St. Lawrence River facing westward towards the Iroquois Seaway shipping channel, lock/dam. Cottage 1 is a one bedroom cottage with one full size bed and futon sleeps 3 people. The cottage has an eat-in...
    View all property information
    Location Information
    Iroquois, Ontario K0E1K0
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Inquiry
    Manotick
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Secure Parking
    • Washer
    • DVD Player
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome!! This is a newly renovated basement apartment with common entrance but separate door to the basement. Lots of light. Perfect for a family with or without kids. Located in barrhaven area of ottawa, across from a private golf course. 20 minutes to downtown Ottawa. Close to major...
    View all property information
    Location Information
    Manotick, Ottawa K2J 0E5
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Inquiry
    Iroquois
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Doran Bay Resort Doran Bay Resort is a family owned and operated resort located on the shores of the majestic St. Lawrence River. We offer 9 self-sufficiency, housekeeping cottages situated on 1500' of unspoiled waterfront which faces directly westward into the International Control Dam...
    View all property information
    Location Information
    Iroquois, Ontario K0E 1K0
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Inquiry
    Save time - get the best Winchester rentals sent straight to your email!
    Get the List
    Cardinal
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fully furnished, cute cozy, one bedroom apartment in private residence. Private entrance, private balcony, and lots of parking. Your balcony overlooks the historic 'Galop' canal - popular with fishermen and kayakers. The canal meets the St. Lawrence Seaway a two minute walk away at the end of the...
    View all property information
    Location Information
    Cardinal, Ontario K0E 1E0
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    Waddington, NY
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Parking
    • Air Conditioning
    • Balcony
    • Grill
    • Cable/satellite TV
    • Private Yard
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy an updated 1860's farmhouse 4 miles from the St. Lawrence River. This spacious country home, on 5 acres with a back patio and a quaint enclosed front porch is perfect to enjoy your coffee in the morning or your favorite beverage after dinner. Bring your boat, your passport, and fish the best...
    View all property information
    Location Information
    Waddington, St. Lawrence County 13660
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Inquiry
    Nepean
    4 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to my beautiful, renovated house, centrally located in Ottawa about 10 km to downtown Ottawa, Parliament, and Ottawa airport. This lovely single house has been newly renovated, this includes the modern kitchen and bathrooms, close to public transportation, highways, shopping malls,...
    View all property information
    Location Information
    Nepean, Ottawa K2G 2A6
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 14
    Make Inquiry
    Nepean
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Patio
    • Terrace
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amazing views of the Rideau River. Entire semi detached home has water views from wall to wall. Come and stay for a romantic getaway, business trip or just simply to have some alone time and clear your head. House is 20min to downtown, 10min to Carleton Raceway (future home of the Hardrock...
    View all property information
    Location Information
    Nepean, Ottawa K1V 1H4
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 2
    Make Inquiry
    Nepean
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious, big room in a light and bright townhouse. Situated just steps away from Mooney's Bay beach, the Hog's Back Falls and the Rideau river. 10-15 min drive to downtown Ottawa, ideal location to get to all the summer activities, Bluesfest, CANADA DAY Fireworks to name a few. 10-15 min drive...
    View all property information
    Location Information
    Nepean, Ottawa K2C 0K5
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    Nepean
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Private Yard
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious, big room in a light and bright townhouse. Situated just steps away from Mooney's Bay beach, the Hog's Back Falls and the Rideau river. 10-15 min drive to downtown Ottawa, ideal location to get to all the summer activities, Bluesfest, CANADA DAY Fireworks to name a few. 10-15 min drive...
    View all property information
    Location Information
    Nepean, Ottawa K2C 0K5
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    Nepean
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Yard
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious, big room in a light and bright townhouse. Situated just steps away from Mooney's Bay beach, the Hog's Back Falls and the Rideau river. 10-15 min drive to downtown Ottawa, ideal location to get to all the summer activities, Bluesfest, CANADA DAY Fireworks to name a few. 10-15 min drive...
    View all property information
    Location Information
    Nepean, Ottawa K2C 0K5
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry

    Top-rated Winchester Things to Do

    No photo provided
    Browse all things to do

    Additional Winchester Info

    Go to map view
    • Local time: 05:29 AM (EDT)
    • Exchange rate: 1 Canadian Dollars = 0.76 U.S. Dollars
    List your property
    Owner log in