Title: Holiday Rentals Windsor from £101: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk [Hotels in Windsor](https://expedia.co.uk/Windsor-Hotels.d180667.Travel-Guide-Hotels)[Windsor Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Windsor.d180667.Car-Hire-Guide)[Windsor Holidays](https://expedia.co.uk/Windsor.d180667.Holidays-City-Breaks) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 In two weeks [20 Feb - 22 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=180667&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [3 Apr - 5 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=180667&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [1 May - 3 May](https://www.expedia.co.uk/Hotel-Search?regionId=180667&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [29 May - 31 May](https://www.expedia.co.uk/Hotel-Search?regionId=180667&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Windsor holiday rentals ![Reception](https://images.trvl-media.com/lodging/111000000/110850000/110849800/110849795/b591d86e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/111000000/110850000/110849800/110849795/8d8391e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite | Living area](https://images.trvl-media.com/lodging/111000000/110850000/110849800/110849795/a67fadd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Two Bedroom Suite - Queen/Queen | Dining room](https://images.trvl-media.com/lodging/111000000/110850000/110849800/110849795/593ef7f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Dylin [](https://www.expedia.co.uk/Madison-Hotels-The-Dylin-By-Locale.h110849795.Hotel-Information) Tenney-Lapham 9.4/10 Exceptional (123 reviews) "Check in was easy, the room was super clean and cute, great amenities, close to the Sylvee and other bars/restaurants and the lake. Would stay again!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caitlin £101 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Madison-Hotels-The-Dylin-By-Locale.h110849795.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/84000000/83140000/83137300/83137225/48c40e67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83140000/83137300/83137225/ef80e055.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/84000000/83140000/83137300/83137225/070b417b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83140000/83137300/83137225/b273577f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pool with Slide. Great for Business Travelers! [](https://www.expedia.co.uk/Madison-Hotels-Pool-With-Slide-Great-For-Business-Travelers.h83137225.Hotel-Information) Fitchburg £109 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Madison-Hotels-Pool-With-Slide-Great-For-Business-Travelers.h83137225.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/112000000/111999300/111999285/915f9e15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/112000000/111999300/111999285/94b7dd7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/112000000/111999300/111999285/f90b098b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/112000000/112000000/111999300/111999285/923928f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 3-bedroom Duplex unit with WiFi in Cottage Grove [](https://www.expedia.co.uk/Cottage-Grove-Hotels-Charming-3-Bedroom-Duplex-Unit-With-WiFi-In-Cottage-Grove.h111999285.Hotel-Information) Village of Cottage Grove 10/10 Exceptional (9 reviews) "Stayed with friends for the weekend and really enjoyed the home. It was comfortable and had great amenities for our group!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anakin F. £329 includes taxes & fees 16 Feb - 17 Feb [](https://www.expedia.co.uk/Cottage-Grove-Hotels-Charming-3-Bedroom-Duplex-Unit-With-WiFi-In-Cottage-Grove.h111999285.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/70000000/69720000/69715700/69715655/04b276b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/70000000/69720000/69715700/69715655/ea0ca1e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69720000/69715700/69715655/36645ce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69720000/69715700/69715655/3a2053bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cannery Square Short Term Rentals -104 by Patriot [](https://www.expedia.co.uk/Madison-Hotels-Cannery-Square-Short-Term-Rentals-104-By-Patriot.h69715655.Hotel-Information) Sun Prairie 9.6/10 Exceptional (47 reviews) "Roomy. Kitchen had basics. Good beds and pillows. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan £238 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Madison-Hotels-Cannery-Square-Short-Term-Rentals-104-By-Patriot.h69715655.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/116000000/115340000/115333200/115333182/cf9e642a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115340000/115333200/115333182/98b4110c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/116000000/115340000/115333200/115333182/79d75eff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/116000000/115340000/115333200/115333182/9e5dccce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens! [](https://www.expedia.co.uk/Madison-Hotels-King-Suite-Free-Breakfast-Pool-With-A-Slide-Close-To-Olbrich-Botanical-Gardens.h115333182.Hotel-Information) Fitchburg £119 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Madison-Hotels-King-Suite-Free-Breakfast-Pool-With-A-Slide-Close-To-Olbrich-Botanical-Gardens.h115333182.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/75000000/74640000/74637500/74637492/7369ac14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/75000000/74640000/74637500/74637492/12bdd8b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/75000000/74640000/74637500/74637492/aa0e675c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74640000/74637500/74637492/3efd103e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Enjoy Nature with Full Comfort! [](https://www.expedia.co.uk/Verona-Hotels-Enjoy-Nature-With-Full-Comfort.h74637492.Hotel-Information) Verona 9.2/10 Wonderful (39 reviews) "Clean very friendly nice spot" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Oliver H. £97 includes taxes & fees 15 Feb - 16 Feb [](https://www.expedia.co.uk/Verona-Hotels-Enjoy-Nature-With-Full-Comfort.h74637492.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/86000000/85540000/85537300/85537244/a2858593.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/86000000/85540000/85537300/85537244/39556d41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/86000000/85540000/85537300/85537244/eed91014.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/86000000/85540000/85537300/85537244/15c7e503.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### King Suite | Free Breakfast. Pool and Hot Tub [](https://www.expedia.co.uk/Madison-Hotels-King-Suite-Free-Breakfast-Pool-And-Hot-Tub.h85537244.Hotel-Information) Middleton 8.0/10 Very good (5 reviews) "Great place for a stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andy D. £106 includes taxes & fees 15 Feb - 16 Feb [](https://www.expedia.co.uk/Madison-Hotels-King-Suite-Free-Breakfast-Pool-And-Hot-Tub.h85537244.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/79000000/78120000/78111100/78111089/83622a62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78120000/78111100/78111089/b9f70f6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78120000/78111100/78111089/d3d01fda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/79000000/78120000/78111100/78111089/6d5da384.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cannery Square Short Term Rentals -102 by Patriot [](https://www.expedia.co.uk/Madison-Hotels-Cannery-Square-Short-Term-Rentals-102-By-Patriot.h78111089.Hotel-Information) Sun Prairie 8.0/10 Very good (12 reviews) "Was cute neighborhood and everything was very clean and close by" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bri £205 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Madison-Hotels-Cannery-Square-Short-Term-Rentals-102-By-Patriot.h78111089.Hotel-Information) ![Smart TV, computer monitors](https://images.trvl-media.com/lodging/121000000/120680000/120679100/120679093/2f2d26f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120680000/120679100/120679093/f9754302.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/121000000/120680000/120679100/120679093/4906c5d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120680000/120679100/120679093/d446c4db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat [](https://www.expedia.co.uk/Middleton-Hotels-Chic-Apartment-In-Amazing-Middleton-With-Fitness-Equipment.h120679093.Hotel-Information) Middleton 10/10 Exceptional (2 reviews) "We had a fantastic stay at this property, and it truly exceeded our expectations. The location is excellent—perfectly situated with convenient access to both the east and west sides of Madison, making it easy to get wherever we needed to go. The owners were incredibly helpful and responsive, answering the few questions we had quickly and kindly, which made the entire experience even smoother.One of the biggest highlights for us was the private fenced-in area, which was absolutely perfect for our... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessi P. £257 includes taxes & fees 28 Feb - 1 Mar [](https://www.expedia.co.uk/Middleton-Hotels-Chic-Apartment-In-Amazing-Middleton-With-Fitness-Equipment.h120679093.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/75000000/74130000/74124600/74124541/e901e932.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, travel cot, free WiFi](https://images.trvl-media.com/lodging/75000000/74130000/74124600/74124541/f8090f44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/75000000/74130000/74124600/74124541/199c30da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74130000/74124600/74124541/621d9da3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Doty ★ Walk to Everything -Hotel Quality- Downtown [](https://www.expedia.co.uk/Madison-Hotels-Doty-Walk-To-Everything-Hotel-Quality-Downtown.h74124541.Hotel-Information) Downtown Madison 9.8/10 Exceptional (37 reviews) "Very convenient" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joe R. £215 includes taxes & fees 10 Feb - 11 Feb [](https://www.expedia.co.uk/Madison-Hotels-Doty-Walk-To-Everything-Hotel-Quality-Downtown.h74124541.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/110000000/109150000/109141700/109141636/fbab5046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![WiFi](https://images.trvl-media.com/lodging/110000000/109150000/109141700/109141636/506de11e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109150000/109141700/109141636/1b348406.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/110000000/109150000/109141700/109141636/13ba8e83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Studio Queen in the heart of downtown. [](https://www.expedia.co.uk/Madison-Hotels-Studio-Queen-In-The-Heart-Of-Downtown.h109141636.Hotel-Information) Downtown Madison 10/10 Exceptional (1 review) "Convenient location for events on the Capital Square, State Street and UW-Madison Campus." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey W. £146 includes taxes & fees 15 Feb - 16 Feb [](https://www.expedia.co.uk/Madison-Hotels-Studio-Queen-In-The-Heart-Of-Downtown.h109141636.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88420000/88410700/88410689/ec91cc9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/89000000/88420000/88410700/88410689/24cf5025.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/89000000/88420000/88410700/88410689/cd9099b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/89000000/88420000/88410700/88410689/0f817c46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 Bedroom - Main Street Sun Prairie WI [](https://www.expedia.co.uk/Madison-Hotels-2-Bedroom-Main-Street-Sun-Prairie-WI.h88410689.Hotel-Information) Sun Prairie 9.6/10 Exceptional (38 reviews) "Clean and quiet. Nice neighborhood amenities. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark L. £300 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Madison-Hotels-2-Bedroom-Main-Street-Sun-Prairie-WI.h88410689.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89790000/89783700/89783692/4270c7c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89790000/89783700/89783692/0743063b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/90000000/89790000/89783700/89783692/10858971.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89790000/89783700/89783692/2f8cdff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown! [](https://www.expedia.co.uk/Madison-Hotels-NEW-OWNER-SPECIALMadison-Lakefront-Home.h89783692.Hotel-Information) Monona 9.8/10 Exceptional (47 reviews) "It was lovely to be by the lake and have the view from the living room along with gas fireplace. So relaxing even in the off season." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Justine K. £369 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Madison-Hotels-NEW-OWNER-SPECIALMadison-Lakefront-Home.h89783692.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/28000000/27140000/27131100/27131051/w1024h682x0y1-669a016c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27140000/27131100/27131051/f7402a8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/28000000/27140000/27131100/27131051/w1023h682x1y1-1324bcc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel cot, free WiFi](https://images.trvl-media.com/lodging/28000000/27140000/27131100/27131051/w1023h682x1y1-375fab3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A Pleasant Retreat- No Cleaning Fee & New Discounts [](https://www.expedia.co.uk/Madison-Hotels-A-Pleasant-Retreat-For-1.h27131051.Hotel-Information) Sun Prairie 10/10 Exceptional (269 reviews) "Great place and the hosts were great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Drew M. £259 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Madison-Hotels-A-Pleasant-Retreat-For-1.h27131051.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83300000/83295200/83295120/e73435fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/84000000/83300000/83295200/83295120/w2998h1998x2y2-cbbfc1a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83300000/83295200/83295120/876ac21e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/84000000/83300000/83295200/83295120/0675f8d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Free Breakfast Pool & Hot Tub. Near UW-Madison [](https://www.expedia.co.uk/Madison-Hotels-Free-Breakfast-Pool-Hot-Tub-Near-UW-Madison.h83295120.Hotel-Information) Madison 10/10 Exceptional (1 review) "It was comfortable and clean and the staff was so nice. It was well located and the pool and hot tub were lovely as well." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joy E. £216 includes taxes & fees 12 Feb - 13 Feb [](https://www.expedia.co.uk/Madison-Hotels-Free-Breakfast-Pool-Hot-Tub-Near-UW-Madison.h83295120.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/92000000/91680000/91678600/91678589/de864266.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table football, books](https://images.trvl-media.com/lodging/92000000/91680000/91678600/91678589/w2041h1365x3y0-d97a9b21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table football, books](https://images.trvl-media.com/lodging/92000000/91680000/91678600/91678589/w2048h1362x0y0-069c1a49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/92000000/91680000/91678600/91678589/3f652e1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakeview Cabin > Unique Mid-Century Tucked in Bluff [](https://www.expedia.co.uk/Merrimac-Hotels-NEW-OWNER-SPECIAL-Mid-Century-Cabin-W-Lakeview.h91678589.Hotel-Information) Merrimac 9.8/10 Exceptional (25 reviews) "Beautiful property with a perfect view for fall color. Very comfortable and great space for both couples and family. We enjoyed a very relaxing stay. Host was very prompt with responses and easy to work with." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jenel S. £269 includes taxes & fees 17 Feb - 18 Feb [](https://www.expedia.co.uk/Merrimac-Hotels-NEW-OWNER-SPECIAL-Mid-Century-Cabin-W-Lakeview.h91678589.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/113000000/112250000/112243000/112243000/8a317c5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112250000/112243000/112243000/511923cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/113000000/112250000/112243000/112243000/c87e9887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/113000000/112250000/112243000/112243000/71c1dc76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown [](https://www.expedia.co.uk/Madison-Hotels-Citys-EDGE-Of-Madison-6-Miles-To-Downtown.h112243000.Hotel-Information) Sun Prairie 10/10 Exceptional (13 reviews) "Beautiful spacious property, extremely clean and excellent host!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jen F. £424 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Madison-Hotels-Citys-EDGE-Of-Madison-6-Miles-To-Downtown.h112243000.Hotel-Information) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/85000000/84050000/84049300/84049281/3c6616e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/85000000/84050000/84049300/84049281/f4c4e83a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/85000000/84050000/84049300/84049281/w506h683x259y0-0748895f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/85000000/84050000/84049300/84049281/82e34e45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Entire 3 Bedroom with Fireplace - sleeps 12 [](https://www.expedia.co.uk/Madison-Hotels-Entire-3-Bedroom-With-Fireplace-Sleeps-12.h84049281.Hotel-Information) Sun Prairie 9.8/10 Exceptional (16 reviews) "The beds were super comfortable and the house had a lot of space. Tami was very helpful and communicative with the check in and check out process." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Noah D. £442 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Madison-Hotels-Entire-3-Bedroom-With-Fireplace-Sleeps-12.h84049281.Hotel-Information) ![Smart TV, fireplace, stereo, printers](https://images.trvl-media.com/lodging/104000000/103060000/103055100/103055012/5f06971e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo, printers](https://images.trvl-media.com/lodging/104000000/103060000/103055100/103055012/0a59d24f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103060000/103055100/103055012/2d3f3f82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103060000/103055100/103055012/72c8c4c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Winter Trail Access | Cozy Fireplace Haven [](https://www.expedia.co.uk/Madison-Hotels-3-BR-Executive-Home-Near-Madison-W-Nature-Trails-Madisons-Best-Nearby.h103055012.Hotel-Information) Fitchburg 10/10 Exceptional (20 reviews) "Property was generally clean, spacious and had all the amenities that our family needed.An enjoyable stay at a nice property!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim & Jeff T. £536 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Madison-Hotels-3-BR-Executive-Home-Near-Madison-W-Nature-Trails-Madisons-Best-Nearby.h103055012.Hotel-Information) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101620000/101617200/101617146/b69df2cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101620000/101617200/101617146/99f10351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101620000/101617200/101617146/255de9c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101620000/101617200/101617146/2b886a71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Capital PrimeTime - 6 Miles from Madison w/ fireplace [](https://www.expedia.co.uk/Madison-Hotels-Capital-PrimeTime-6-Miles-From-Madison-W-Fireplace.h101617146.Hotel-Information) Sun Prairie 9.8/10 Exceptional (36 reviews) "Very clean and very spacious house. Great neighborhood and location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharon M. £465 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Madison-Hotels-Capital-PrimeTime-6-Miles-From-Madison-W-Fireplace.h101617146.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.co.uk/Hotel-Search?startDate=2026-02-22&endDate=2026-02-23®ionId=180667&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find holiday rentals that suit your style Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Windsor%2C+Wisconsin%2C+United+States+of+America®ionId=180667&latLong=43.218327%2C-89.341507&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=APARTMENT) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Windsor%2C+Wisconsin%2C+United+States+of+America®ionId=180667&latLong=43.218327%2C-89.341507&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=VACATION_HOME) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=Windsor%2C+Wisconsin%2C+United+States+of+America®ionId=180667&latLong=43.218327%2C-89.341507&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=CONDO) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Windsor%2C+Wisconsin%2C+United+States+of+America®ionId=180667&latLong=43.218327%2C-89.341507&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=COTTAGE) ![](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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-Holiday-Rentals.d180667.Travel-Guide-HolidayRentals)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-Holiday-Rentals.d180667.Travel-Guide-HolidayRentals) ## Top Windsor Hotel Reviews ![Moxy Madison Downtown](https://images.trvl-media.com/lodging/104000000/103390000/103384000/103383944/d74ad07e_y.jpg) ### Moxy Madison Downtown 10/10 Excellent "We loved the vibe in the hotel and it’s proximity to the concert venue." [](https://expedia.co.uk/Madison-Hotels-Moxy-Madison-Downtown.h103383944.Hotel-Information) ![Hampton Inn & Suites Madison / Downtown](https://images.trvl-media.com/lodging/7000000/6850000/6842700/6842611/13390bcb_y.jpg) ### Hampton Inn & Suites Madison / Downtown 10/10 Excellent "Great amenities, location, and staff. " [](https://expedia.co.uk/Madison-Hotels-Hampton-Inn-Suites-Madison-Downtown.h6842611.Hotel-Information) ![Holiday Inn Hotel & Suites Madison West - Middleton by IHG](https://images.trvl-media.com/lodging/1000000/550000/548500/548482/dee9f1bc_y.jpg) ### Holiday Inn Hotel & Suites Madison West - Middleton by IHG 10/10 Excellent "Room was fairly clean, pool was easily accessible (ask for wrist band at check in), and the breakfast was great. Perfect mini trip for our family (2yo + 7yo) in cold January." [](https://expedia.co.uk/Madison-Hotels-Holiday-Inn-Hotel-Suites-Madison-West.h548482.Hotel-Information) ![DoubleTree by Hilton Madison East](https://images.trvl-media.com/lodging/1000000/10000/3200/3157/a90c37bb_y.jpg) ### DoubleTree by Hilton Madison East 10/10 Excellent "Great staff, nice room , great bartender , great shuttle driver " [](https://expedia.co.uk/Madison-Hotels-DoubleTree-By-Hilton-Madison-East.h3157.Hotel-Information) ![Tru by Hilton Madison West, WI](https://images.trvl-media.com/lodging/23000000/22170000/22166300/22166216/dd80421a_y.jpg) ### Tru by Hilton Madison West, WI 10/10 Excellent "Great stay. Very comfortable." [](https://expedia.co.uk/Madison-Hotels-Tru-By-Hilton-Madison-West.h22166216.Hotel-Information) ![DoubleTree by Hilton Madison Downtown](https://images.trvl-media.com/lodging/1000000/20000/12000/11944/7654de65_y.jpg) ### DoubleTree by Hilton Madison Downtown 10/10 Excellent "Everything" [](https://expedia.co.uk/Madison-Hotels-DoubleTree-By-Hilton-Madison-Downtown.h11944.Hotel-Information) ![Baymont Inn & Suites by Wyndham Madison](https://images.trvl-media.com/lodging/60000000/59960000/59957100/59957100/08c3cafb_y.jpg) ### Baymont Inn & Suites by Wyndham Madison 10/10 Excellent "Great room. Good price, nice staff at front desk. Comfortable bed. Seemed all clean. Great shower. Very happy with my stay." [](https://expedia.co.uk/Madison-Hotels-Baymont-By-Wyndham-Madison-South.h59957100.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Madison American Center](https://images.trvl-media.com/lodging/1000000/70000/66500/66424/d7e153c1_y.jpg) ### La Quinta Inn & Suites by Wyndham Madison American Center 10/10 Excellent "clean room wonderful staff great continental breakfast" [](https://expedia.co.uk/Madison-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Madison-American-Center.h66424.Hotel-Information) ![The Madison Concourse Hotel and Governor's Club](https://images.trvl-media.com/lodging/1000000/30000/28500/28447/fb616a0c_y.jpg) ### The Madison Concourse Hotel and Governor's Club 10/10 Excellent "Yes every thing was nice" [](https://expedia.co.uk/Madison-Hotels-The-Madison-Concourse-Hotel-And-Governors-Club.h28447.Hotel-Information) ## Find out more about Windsor **Everything you need to know about** **Windsor** **holiday rentals** Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/Villas)... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. **Windsor holiday rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in . Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Windsor holiday rentals we have selected for you start as low as £101 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Windsor rentals** At Expedia, we put the best Windsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor holiday. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. ## Explore a world of travel with Expedia - Trending destinations on Expedia.co.uk ### Trending destinations on Expedia.co.uk - [Holiday Rentals in the Cotswold ](https://www.expedia.co.uk/lp/b/vr/cotswold) - [Holiday Rentals in Lake District ](https://www.expedia.co.uk/lp/b/vr/lake-district) - [Devon Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Devon.d6046196.Holiday-Rental-Destinations) - [Norfolk Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Norfolk.d6046223.Holiday-Rental-Destinations) - [Bedfordshire Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Bedfordshire.d6046189.Holiday-Rental-Destinations) - [Dorset Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Dorset.d6046198.Holiday-Rental-Destinations) - [Northumberland Holiday Rentals ](https://www.expedia.com/Destinations-In-Northumberland.d6046225.Vacation-Rental-Destinations) - [Herefordshire Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Herefordshire.d6046203.Holiday-Rental-Destinations) - [Essex Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Essex.d6046201.Holiday-Rental-Destinations) - [Cumbria Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Cumbria.d6046194.Holiday-Rental-Destinations) - [Yorkshire Holiday Rentals ](https://www.expedia.co.uk/Yorkshire-Holiday-Rentals.d6342462.Travel-Guide-HolidayRentals) - [South Wales Holiday Rentals ](https://www.expedia.co.uk/South-Wales-Holiday-Rentals.d6054274.Travel-Guide-HolidayRentals) - [North Wales Holiday Rentals ](https://www.expedia.co.uk/North-Wales-Holiday-Rentals.d6054276.Travel-Guide-HolidayRentals) - [London Holiday Rentals ](https://www.expedia.co.uk/London-Holiday-Rentals.d178279.Travel-Guide-HolidayRentals) - [York Holiday Rentals ](https://www.expedia.co.uk/York-Holiday-Rentals.d5489.Travel-Guide-HolidayRentals) - [Blackpool Holiday Rentals ](https://www.expedia.co.uk/Blackpool-Holiday-Rentals.d619.Travel-Guide-HolidayRentals) - [Isle of Wight Holiday Rentals ](https://www.expedia.com/Destinations-In-Isle-Of-Wight.d6046218.Vacation-Rental-Destinations) - [Scarborough Holiday Rentals ](https://www.expedia.co.uk/Scarborough-Holiday-Rentals.d5680.Travel-Guide-HolidayRentals) - [Edinburgh Holiday Rentals ](https://www.expedia.co.uk/Edinburgh-Holiday-Rentals.d6069845.Travel-Guide-HolidayRentals) - [Bath Holiday Rentals ](https://www.expedia.co.uk/Bath-Holiday-Rentals.d6084496.Travel-Guide-HolidayRentals) - [Bournemouth Holiday Rentals ](https://www.expedia.co.uk/Bournemouth-Holiday-Rentals.d654.Travel-Guide-HolidayRentals) - [England Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-England.d11218.Holiday-Rental-Destinations) - [Scotland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Scotland.d11219.Holiday-Rental-Destinations) - [Cornwall Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Cornwall.d6046193.Holiday-Rental-Destinations) - [Wales Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Wales.d11220.Holiday-Rental-Destinations) - [Northern Ireland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Northern-Ireland.d11221.Holiday-Rental-Destinations) ## Frequently asked questions ### Can I find a holiday rental in Windsor? ### What are some of the best holiday rentals that Windsor has to offer? ### What can I see and do in Windsor? ### What are holiday rentals like in Windsor? ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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