Title: Windsor Vacation Home Rentals from CA $231: Search Top Private Vacation Homes for Rent | Expedia.ca [Windsor Travel Guide](https://expedia.ca/Windsor.dx181861)[Hotels in Windsor](https://expedia.ca/Windsor-Hotels.d181861.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.ca/Windsor-Vacation-Rentals.d181861.Travel-Guide-VacationRentals)[Flights to Windsor](https://expedia.ca/Cheap-Flights-To-Windsor.d181861.Travel-Guide-Flights)[Windsor Car Rentals](https://expedia.ca/Car-Rentals-In-Windsor.d181861.Car-Rental-Guide)[Windsor Vacation Packages](https://expedia.ca/Windsor.d181861.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Windsor Vacation Rentals - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=181861&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=181861&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=181861&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=181861&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Windsor vacation homes ![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90020000/90010900/90010852/11f8aa1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90020000/90010900/90010852/837884cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/91000000/90020000/90010900/90010852/56aec8e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90020000/90010900/90010852/88894c31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Leland’s Lakehouse [](https://www.expedia.ca/Sunken-Lake-Hotels-Lelands-Lakehouse.h90010852.Hotel-Information) Kings County 9.6/10 Exceptional (4) "The cabin is in a fantastic location looking over the lake, the interior was very clean and looks great. Convinent location for getting to vineyards and wolfvile. I would highly recommend this place for anyone to stay at. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Max D. [](https://www.expedia.ca/Sunken-Lake-Hotels-Lelands-Lakehouse.h90010852.Hotel-Information) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/87000000/86150000/86147100/86147019/d3081009.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/87000000/86150000/86147100/86147019/7f1bd540.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/87000000/86150000/86147100/86147019/08e8f95f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/87000000/86150000/86147100/86147019/e4edfa16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Oceanfront Home on the Minas Basin [](https://www.expedia.ca/Cheverie-Hotels-Luxury-Oceanfront-Home-On-The-Minas-Basin.h86147019.Hotel-Information) Newport 10/10 Exceptional (44) "A beautiful retreat, the view was incredible. We watched the tide coming in and out, an amazing sight!Our host was superhelpful- highly recommend this place" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) amanda s. CA $180 CA $325 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Cheverie-Hotels-Luxury-Oceanfront-Home-On-The-Minas-Basin.h86147019.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117520000/117518600/117518520/08f0b792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117520000/117518600/117518520/b105e483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/118000000/117520000/117518600/117518520/05987275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117520000/117518600/117518520/c9c0115b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2-bedroom Retreat in the Heart of the Annapolis Valley [](https://www.expedia.ca/New-Minas-Hotels-Charming-2-Bedroom-Retreat-With-AC.h117518520.Hotel-Information) New Minas 9.0/10 Wonderful (2) "Great location, excellent communication with host - exactly what we were hoping for." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Rob F. CA $122 CA $289 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/New-Minas-Hotels-Charming-2-Bedroom-Retreat-With-AC.h117518520.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/70000000/69400000/69399500/69399463/2b935fc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/70000000/69400000/69399500/69399463/81a4f9d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69400000/69399500/69399463/610a096e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/70000000/69400000/69399500/69399463/b71a938e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gaspereau Suite - 2 Seat Jacuzzi, KingBd, Downtown [](https://www.expedia.ca/Wolfville-Hotels-Gaspereau-Suite-Jacuzi.h69399463.Hotel-Information) Wolfville 8.0/10 Very good (14) "Such an amazing place. Quiet and peaceful. Clean and true to pics. Close walk to anything you want to do or see in Wolfville. The bed was as comfortable as can be. The jacuzzi made the relaxing stay that much more relaxing. Wish we could have stayed longer. Thank you so much. Hope to be back. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Stacey M. CA $175 CA $231 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Wolfville-Hotels-Gaspereau-Suite-Jacuzi.h69399463.Hotel-Information) ![3 bedrooms](https://images.trvl-media.com/lodging/95000000/94870000/94865900/94865814/1d45d9f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/95000000/94870000/94865900/94865814/7d13d130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/95000000/94870000/94865900/94865814/43591f3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/95000000/94870000/94865900/94865814/w1167h989x6y0-af79165e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Perfect little house to enjoy [](https://www.expedia.ca/Ellershouse-Hotels-Perfect-Little-House-To-Enjoy.h94865814.Hotel-Information) Ellershouse CA $265 CA $410 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Ellershouse-Hotels-Perfect-Little-House-To-Enjoy.h94865814.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/115000000/114840000/114839900/114839897/w1999h1125x0y0-30b76c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Spa](https://images.trvl-media.com/lodging/115000000/114840000/114839900/114839897/cf44c64b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114840000/114839900/114839897/w1999h1406x0y0-cc35f587.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/115000000/114840000/114839900/114839897/338e03ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Bedroom House- Refined Elegance [](https://www.expedia.ca/Port-Williams-Hotels-3-Bedroom-House-Refined-Elegance.h114839897.Hotel-Information) Port Williams 10/10 Exceptional (3) "Great property " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Shawn R. CA $305 CA $482 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Port-Williams-Hotels-3-Bedroom-House-Refined-Elegance.h114839897.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119140000/119131500/119131441/711ee9a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/120000000/119140000/119131500/119131441/w1338h900x12y0-46a0835e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119140000/119131500/119131441/d0559bd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119140000/119131500/119131441/7e73dfe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Canyon Point Cozy Cottage -Hot tub-Lakefront [](https://www.expedia.ca/Vaughan-Hotels-Canyon-Point-Cozy-Cottage-Hot-Tub-Lakefront.h119131441.Hotel-Information) Windsor 10/10 Exceptional (1) "Beautiful spot, we enjoyed our stay. Thank you!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) tina s. CA $274 CA $488 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Vaughan-Hotels-Canyon-Point-Cozy-Cottage-Hot-Tub-Lakefront.h119131441.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119140000/119131500/119131453/f439c91e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119131500/119131453/w1350h898x0y0-54626b59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, travel crib, WiFi](https://images.trvl-media.com/lodging/120000000/119140000/119131500/119131453/8045535d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119140000/119131500/119131453/10976f47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Destination Lake House - Hot tub [](https://www.expedia.ca/Vaughan-Hotels-Destination-Lake-House-Hot-Tub.h119131453.Hotel-Information) Windsor 10/10 Exceptional (1) "Great spot" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Mark M. CA $419 CA $702 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Vaughan-Hotels-Destination-Lake-House-Hot-Tub.h119131453.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-27&endDate=2025-12-28®ionId=181861&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-Private-Vacation-Homes.d181861-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-Private-Vacation-Homes.d181861-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Windsor Hotel Reviews ![Super 8 by Wyndham Windsor NS](https://images.trvl-media.com/lodging/2000000/1720000/1711000/1710981/dc71ef36_y.jpg) ### Super 8 by Wyndham Windsor NS 10/10 Excellent "Yea" [](https://expedia.ca/Wolfville-Hotels-Super-8-By-Wyndham-Windsor-NS.h1710981.Hotel-Information) ![The August House](https://images.trvl-media.com/lodging/93000000/92030000/92024900/92024852/20fd8b43_y.jpg) ### The August House 10/10 Excellent "Breakfast menu was made with locally sourced products, tons of gluten free options made in house. The room was amazing. Our stay was amazing and the staff were so kind and attentive " [](https://expedia.ca/Windsor-Hotels-The-August-House.h92024852.Hotel-Information) ![Tattingstone Inn](https://images.trvl-media.com/lodging/16000000/15120000/15110300/15110237/b9f447f6_y.jpg) ### Tattingstone Inn 10/10 Excellent "The facilities were spotless and the staff very helpful ad the breakfast was fantastic " [](https://expedia.ca/Wolfville-Hotels-Tattingstone-Inn.h15110237.Hotel-Information) ![The Inn at Grand Pre Winery](https://images.trvl-media.com/lodging/77000000/76980000/76979500/76979462/b35bc36c_y.jpg) ### The Inn at Grand Pre Winery 10/10 Excellent "Lovely updated room and bathroom with a large walk in shower. Quiet location but close to amenities. Breakfast was yogurt and granola with a warm homemade scone. Just enough to start the day. Friendly staff and great winter price. Would definitely recommend and go back. " [](https://expedia.ca/Grand-Pre-Hotels-The-Inn-At-Grand-Pre-Winery.h76979462.Hotel-Information) ![Slumber Inn](https://images.trvl-media.com/lodging/1000000/470000/460600/460541/23cd4e60_y.jpg) ### Slumber Inn 10/10 Excellent "yes " [](https://expedia.ca/Wolfville-Hotels-Slumber-Inn.h460541.Hotel-Information) ![Old Orchard Inn](https://images.trvl-media.com/lodging/1000000/910000/903300/903228/b38dda0d_y.jpg) ### Old Orchard Inn 10/10 Excellent "Stunning" [](https://expedia.ca/Wolfville-Hotels-Old-Orchard-Inn-Spa.h903228.Hotel-Information) ![Micro Boutique Living Wolfville](https://images.trvl-media.com/lodging/10000000/9800000/9796200/9796113/ad45dd5e_y.jpg) ### Micro Boutique Living Wolfville 10/10 Excellent "Very nice stay, will return " [](https://expedia.ca/Wolfville-Hotels-Micro-Boutique-Living-Wolfville.h9796113.Hotel-Information) ![Charming Rustic Farmhouse in NS Wine & Ski Country, The Gaspereau Valley!](https://images.trvl-media.com/lodging/111000000/110900000/110895200/110895101/253e422e_y.jpg) ### Charming Rustic Farmhouse in NS Wine & Ski Country, The Gaspereau Valley! 10/10 Excellent "Great comfortable place" [](https://expedia.ca/Wallbrook-Hotels-Charming-Rustic-Farmhouse-In-The-NS-Wine-Ski-County-The-Gaspereau-Valley.h110895101.Hotel-Information) ![The Breeze Motel ](https://images.trvl-media.com/lodging/97000000/96500000/96496000/96495987/f17445c8_y.jpg) ### The Breeze Motel 10/10 Excellent "It was clean, beautiful and cozy. " [](https://expedia.ca/North-Grand-Pre-Hotels-The-Breeze-Motel.h96495987.Hotel-Information) ## Find out more about Windsor ## Windsor Vacation Homes information | Number of reviews | 66 | | ----------------- | ----------------- | | Accommodation | 34 Vacation Homes | | Lowest Price | CA $231 | | Highest Price | CA $702 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - [3 Star Hotels in Avondale ](https://www.expedia.ca/3Star-Avondale-Hotels.s30-0-d6353718.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Falmouth ](https://www.expedia.ca/4Star-Falmouth-Hotels.s40-0-d6310356.Travel-Guide-Filter-Hotels) - [Hotels near Avon River Heritage Society Museum ](https://www.expedia.ca/Avon-River-Heritage-Society-Museum-Hotels.0-l6309448-0.Travel-Guide-Filter-Hotels) - [Hotels near Avon Valley Golf and Country Club ](https://www.expedia.ca/Avon-Valley-Golf-And-Country-Club-Hotels.0-l6309526-0.Travel-Guide-Filter-Hotels) - [B&B in Avondale ](https://www.expedia.ca/Avondale-Bed-And-Breakfast.d6353718-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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