Title: Webster County Cottages | Expedia.ca [Webster County Hotels](https://expedia.ca/Destinations-In-Webster-County.d553248635976431895.Hotel-Destinations)[Vacation Rentals in Webster County](https://expedia.ca/Destinations-In-Webster-County.d553248635976431895.Vacation-Rental-Destinations)[Webster County Car Rentals](https://expedia.ca/Destinations-In-Webster-County.d553248635976431895.Car-Rental-Destinations)[Webster County Vacations](https://expedia.ca/Webster-County.d553248635976431895.Destination-Travel-Guides) ![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__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 In two weeks [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976431895&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=553248635976431895&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976431895&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=553248635976431895&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Webster County cottages ![Exterior](https://images.trvl-media.com/lodging/92000000/91980000/91974400/91974327/5f4e60e9.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/92000000/91980000/91974400/91974327/7cd9f548.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/92000000/91980000/91974400/91974327/2e416966.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/92000000/91980000/91974400/91974327/6e3447cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grandpa's Comfy Cottage [](https://www.expedia.ca/Madisonville-Hotels-Grandpas-Comfy-Cottage.h91974327.Hotel-Information) Madisonville 10/10 Exceptional (4 reviews) "Everything we needed and close to everything else 👍" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Scott W. [](https://www.expedia.ca/Madisonville-Hotels-Grandpas-Comfy-Cottage.h91974327.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/91000000/90360000/90353900/90353872/3043b99e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/91000000/90360000/90353900/90353872/58cbb3da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90360000/90353900/90353872/ca7dfd0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90360000/90353900/90353872/bdb9a7cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grandma's Cozy Cottage [](https://www.expedia.ca/Madisonville-Hotels-Grandmas-Cottage.h90353872.Hotel-Information) Madisonville 9.0/10 Wonderful (9 reviews) "Nice stay while waiting for apartment to be ready. Cute and quiet neighborhood " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara D. [](https://www.expedia.ca/Madisonville-Hotels-Grandmas-Cottage.h90353872.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/74000000/73100000/73092800/73092737/57a98b30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73100000/73092800/73092737/d986423d.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/74000000/73100000/73092800/73092737/4a086263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/74000000/73100000/73092800/73092737/c1687713.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private, cozy,classic, simple. Centrally located to hospital, uptown. [](https://www.expedia.ca/Madisonville-Hotels-Private.h73092737.Hotel-Information) Madisonville 10/10 Exceptional (3 reviews) "Cozy little place no far from all the things in Madisonville. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle S. [](https://www.expedia.ca/Madisonville-Hotels-Private.h73092737.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/72000000/71100000/71090700/71090647/155c4ba0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/72000000/71100000/71090700/71090647/cbff6bdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71100000/71090700/71090647/d3d56b1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/72000000/71100000/71090700/71090647/01dec153.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Midtown Cottage- Self Check-In & Centrally Located in Owensboro [](https://www.expedia.ca/Owensboro-Hotels-Midtown-Cottage-Self-Check-In-Centrally-Located-In-Owensboro.h71090647.Hotel-Information) Owensboro 10/10 Exceptional (12 reviews) "We were there for a tennis tournament and it was the perfect location. It worked out so well for all of us." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Noel K. [](https://www.expedia.ca/Owensboro-Hotels-Midtown-Cottage-Self-Check-In-Centrally-Located-In-Owensboro.h71090647.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/114000000/113050000/113049900/113049878/0a36a2f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/114000000/113050000/113049900/113049878/8d514aab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/114000000/113050000/113049900/113049878/443a4008.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/114000000/113050000/113049900/113049878/6900824f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Log Cabin Retreat in Kentucky: Fire Pit & Grill! [](https://www.expedia.ca/Owensboro-Hotels-Lakefront-Log-Cabin-In-Kentucky-Fire-Pit-Grill.h113049878.Hotel-Information) Owensboro [](https://www.expedia.ca/Owensboro-Hotels-Lakefront-Log-Cabin-In-Kentucky-Fire-Pit-Grill.h113049878.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/104000000/103410000/103402000/103401968/7188d079.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103410000/103402000/103401968/b27670fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, bed sheets](https://images.trvl-media.com/lodging/104000000/103410000/103402000/103401968/823946b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103410000/103402000/103401968/6506ca3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Riverview Cottage with AC in Evansville [](https://www.expedia.ca/Evansville-Hotels-Charming-Riverview-Cottage-With-AC-In-Evansville.h103401968.Hotel-Information) Evansville [](https://www.expedia.ca/Evansville-Hotels-Charming-Riverview-Cottage-With-AC-In-Evansville.h103401968.Hotel-Information) ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/120000000/119440000/119436500/119436437/2429abca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/120000000/119440000/119436500/119436437/eb7073eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/120000000/119440000/119436500/119436437/04f25db6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/120000000/119440000/119436500/119436437/2e892699.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Lake & Dock: Log Cabin, 2 Mi to Clay! [](https://www.expedia.ca/Clay-Hotels-Private-Lake-Dock-Log-Cabin.h119436437.Hotel-Information) Clay [](https://www.expedia.ca/Clay-Hotels-Private-Lake-Dock-Log-Cabin.h119436437.Hotel-Information) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94540000/94539200/94539193/73caf27c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94540000/94539200/94539193/3cc0d475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94540000/94539200/94539193/0f8294a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94540000/94539200/94539193/03c25b81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Ohio River Home With Water Views & Porch! [](https://www.expedia.ca/Cave-In-Rock-Hotels-Charming-Ohio-River-Home-With-Water-Views-Porch.h94539193.Hotel-Information) Cave-in-Rock [](https://www.expedia.ca/Cave-In-Rock-Hotels-Charming-Ohio-River-Home-With-Water-Views-Porch.h94539193.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=2026-02-10&endDate=2026-02-11®ionId=553248635976431895&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Webster+County%2C+Kentucky%2C+United+States+of+America®ionId=553248635976431895&latLong=37.518443%2C-87.683159&adults=2&startDate=2026-04-26&d1=2026-04-26&endDate=2026-04-29&d2=2026-04-29&lodging=CABIN) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Webster+County%2C+Kentucky%2C+United+States+of+America®ionId=553248635976431895&latLong=37.518443%2C-87.683159&adults=2&startDate=2026-04-26&d1=2026-04-26&endDate=2026-04-29&d2=2026-04-29&lodging=APARTMENT) Villas [](https://www.expedia.ca/Hotel-Search?destination=Webster+County%2C+Kentucky%2C+United+States+of+America®ionId=553248635976431895&latLong=37.518443%2C-87.683159&adults=2&startDate=2026-04-26&d1=2026-04-26&endDate=2026-04-29&d2=2026-04-29&lodging=VILLA) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Webster+County%2C+Kentucky%2C+United+States+of+America®ionId=553248635976431895&latLong=37.518443%2C-87.683159&adults=2&startDate=2026-04-26&d1=2026-04-26&endDate=2026-04-29&d2=2026-04-29&lodging=COTTAGE) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Webster+County%2C+Kentucky%2C+United+States+of+America®ionId=553248635976431895&latLong=37.518443%2C-87.683159&adults=2&startDate=2026-04-26&d1=2026-04-26&endDate=2026-04-29&d2=2026-04-29&lodging=VACATION_HOME) ![](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%2FWebster-County-Cottages.d553248635976431895-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWebster-County-Cottages.d553248635976431895-aaCottages.Travel-Guide-Accommodation) ## Top Webster County Hotel Reviews ![Greenfield Inn & Suites Owensboro, KY Airport](https://images.trvl-media.com/lodging/1000000/70000/63100/63087/93e5516e_y.jpg) ### Greenfield Inn & Suites Owensboro, KY Airport 10/10 Excellent "This is not a fancy hotel, but it is very clean, well staffed, family friendly and conveniently located. I appreciate that there are still affordable locations that strive to be great. I appreciate them so Much and will certainly stay here again if passing through!" [](https://expedia.ca/Owensboro-Hotels-Wingfield-Inn-Suites.h63087.Hotel-Information) ![Fairfield Inn by Marriott Owensboro](https://images.trvl-media.com/lodging/1000000/70000/64200/64180/87f21c63_y.jpg) ### Fairfield Inn by Marriott Owensboro 10/10 Excellent "All was great. Will be back!" [](https://expedia.ca/Owensboro-Hotels-Fairfield-Inn-By-Marriott-Owensboro.h64180.Hotel-Information) ![Sleep Inn Henderson-Evansville South](https://images.trvl-media.com/lodging/1000000/110000/105600/105545/3a841059_y.jpg) ### Sleep Inn Henderson-Evansville South 10/10 Excellent "Great time" [](https://expedia.ca/Owensboro-Hotels-Sleep-Inn-Henderson-Evansville-South.h105545.Hotel-Information) ![Comfort Inn & Suites Madisonville](https://images.trvl-media.com/lodging/3000000/2920000/2911300/2911258/33a8d8ee_y.jpg) ### Comfort Inn & Suites Madisonville 10/10 Excellent "Overall nice." [](https://expedia.ca/Madisonville-Hotels-Comfort-Inn-And-Suites.h2911258.Hotel-Information) ![Wingate by Wyndham Owensboro](https://images.trvl-media.com/lodging/1000000/300000/296100/296068/79304407_y.jpg) ### Wingate by Wyndham Owensboro 10/10 Excellent "Very friendly and helpful staff. Good breakfast. Rooms were very clean and modern " [](https://expedia.ca/Owensboro-Hotels-Sleep-Inn.h296068.Hotel-Information) ![Super 8 by Wyndham Owensboro](https://images.trvl-media.com/lodging/1000000/50000/49900/49863/bda5e2e0_y.jpg) ### Super 8 by Wyndham Owensboro 10/10 Excellent "Yes!!!! Staff are so wonderful too!" [](https://expedia.ca/Owensboro-Hotels-Super-8-By-Wyndham-Owensboro.h49863.Hotel-Information) ![Comfort Suites](https://images.trvl-media.com/lodging/1000000/910000/909800/909708/c8fec3e4_y.jpg) ### Comfort Suites 10/10 Excellent "Everyone was absolutely wonderful there during our stay. The only problem was at the current time their hot tub was broke but they couldn't help that They didn't order the part. Other than that absolutely a wonderful experience. They definitely came in clutch. We needed a new place to stay because Roadway inn had cockroaches and stains." [](https://expedia.ca/Owensboro-Hotels-Comfort-Suites.h909708.Hotel-Information) ![Baymont by Wyndham Madisonville](https://images.trvl-media.com/lodging/1000000/60000/56000/55985/7146a17e_y.jpg) ### Baymont by Wyndham Madisonville 10/10 Excellent "Great customer service. Clean and efficient. " [](https://expedia.ca/Madisonville-Hotels-Baymont-By-Wyndham-Madisonville.h55985.Hotel-Information) ![Days Inn by Wyndham Madisonville](https://images.trvl-media.com/lodging/1000000/10000/4400/4376/92a931d8_y.jpg) ### Days Inn by Wyndham Madisonville 10/10 Excellent "The room was immaculate. " [](https://expedia.ca/Madisonville-Hotels-Days-Inn-By-Wyndham-Madisonville.h4376.Hotel-Information) ## Find out more about Webster County ## Webster County Cottages information | Number of reviews | 27 | | ----------------- | ---------- | | Accommodation | 8 Cottages | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Calhoun Hotels ](https://www.expedia.ca/Calhoun-Hotels.d553248634999117027.Travel-Guide-Hotels) - [Cheap Hotels in Charleston ](https://www.expedia.ca/Charleston-Hotels-Cheap-Hotels.0-0-d553248635975848719-tCheapHotels.Travel-Guide-Filter-Hotels) - [Farmstay in Clay ](https://www.expedia.ca/Clay-Agritourism.d6338711-aaAgritourism.Travel-Guide-Accommodation) - [Luxury Hotels in Clay ](https://www.expedia.ca/Clay-Hotels-Luxury-Hotel.0-0-d6338711-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Clay ](https://www.expedia.ca/Clay-Hotels-Spa-Hotel.0-0-d6338711-tSpaHotel.Travel-Guide-Filter-Hotels) - 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