Title: Book the Best PET FRIENDLY Hotels in Winterset, IA from CA $82 - Winterset Dog-Friendly Hotels | Expedia.ca [Hotels in Winterset](https://expedia.ca/Winterset-Hotels.d181516.Travel-Guide-Hotels)[Vacation Rentals in Winterset](https://expedia.ca/Winterset-Vacation-Rentals.d181516.Travel-Guide-VacationRentals)[Flights to Winterset](https://expedia.ca/Cheap-Flights-To-Winterset.d181516.Travel-Guide-Flights)[Winterset Car Rentals](https://expedia.ca/Car-Rentals-In-Winterset.d181516.Car-Rental-Guide)[Winterset Vacation Packages](https://expedia.ca/Winterset.d181516.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/830fc6762ccc71fc6b71a5e80242e57e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Tonette Pineda✈⛵🚌🚉🚃🚅🚀 # Find Pet-friendly Hotels in Winterset, IA from CA $82 ![](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 availability on Winterset Pet-friendly Hotels Tonight [Oct 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=181516&startDate=2025-10-26&endDate=2025-10-27&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 27 - Oct 28](https://www.expedia.ca/Hotel-Search?regionId=181516&startDate=2025-10-27&endDate=2025-10-28&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=181516&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=181516&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winterset Pet-friendly Hotels ![Lobby](https://images.trvl-media.com/lodging/11000000/10450000/10446900/10446857/f46e6906.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10450000/10446900/10446857/2d580455.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/11000000/10450000/10446900/10446857/0d76b175.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/11000000/10450000/10446900/10446857/690e7790.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cobblestone Inn & Suites - Winterset, IA Winterset 9.2/10 Wonderful (699) "Great place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steve CA $133 CA $150 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Winterset-Hotels-Cobblestone-Inn-Suites-Winterset.h10446857.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/1000000/440000/440000/439956/92067e48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/440000/440000/439956/b2873398.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/440000/440000/439956/93de0c43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/440000/440000/439956/85a99793.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Covered Bridge Inn Winterset 9.0/10 Wonderful (754) "Breakfast was top notch for the price." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Raymond CA $83 CA $91 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Winterset-Hotels-Covered-Bridge-Inn.h439956.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/110000000/109920000/109912000/109911921/d76101e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109920000/109912000/109911921/1ff9cb47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109920000/109912000/109911921/970f38af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109920000/109912000/109911921/42938e53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 1855 Stone Farmhouse Retreat – Cozy Stays & Picturesque Views Await Winterset 10/10 Exceptional (1) "Highly recommend a stay at the old stone farm! The owner was super responsive and helpful leading up to and during our trip. The place is absolutely beautiful and we enjoyed lazy mornings on the farm and ending out day around the fire pit at night. It was clean and cozy and the perfect background for curling up with a book and taking fun pictures outside. Our daughter loved getting to know all the animals and spent hours at the fence watching them do their thing and feeding them. The house is... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) kim m. CA $346 CA $691 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Winterset-Hotels-Charming-1855-Stone-Farmhouse-Retreat-Cozy-Stays-Picturesque-Views-Await.h109911921.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/6000000/5630000/5628800/5628747/23d54adb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/6000000/5630000/5628800/5628747/8b01e34c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/6000000/5630000/5628800/5628747/212a33f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/6000000/5630000/5628800/5628747/4886c0e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakeside Hotel Casino Osceola 8.0/10 Very good (1022) "Easy parking, nice views, easy to get around" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dan CA $96 CA $128 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Osceola-Hotels-Lakeside-Hotel-Casino.h5628747.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/12000000/11120000/11110300/11110264/44fe7428.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Double Bed](https://images.trvl-media.com/lodging/12000000/11120000/11110300/11110264/de2a2feb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Double Beds](https://images.trvl-media.com/lodging/12000000/11120000/11110300/11110264/b36bba35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/12000000/11120000/11110300/11110264/11a27a95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Evergreen Inn Osceola 9.0/10 Wonderful (677) "Wonderful staff, easy check in & out. Comfortable and Clean place to stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $73 CA $82 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Osceola-Hotels-Evergreen-Inn.h11110264.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/15000000/15000000/14993300/14993246/423f0302.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/15000000/15000000/14993300/14993246/a50d62e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Queen Bed](https://images.trvl-media.com/lodging/15000000/15000000/14993300/14993246/d0c9c088.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/15000000/15000000/14993300/14993246/36f1a5a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stuart Motor Lodge Stuart 8.8/10 Excellent (491) "Clean room, friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason CA $84 CA $94 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Atlantic-Hotels-Stuart-Motor-Lodge.h14993246.Hotel-Information) ![Desk, laptop workspace, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/1000000/70000/64300/64224/f2b63f8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/70000/64300/64224/11bfc987.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/70000/64300/64224/39dd45ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/70000/64300/64224/755041e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Osceola Osceola 8.6/10 Excellent (58) "Worth the stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Scott CA $126 CA $141 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Osceola-Hotels-Quality-Inn-Osceola.h64224.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/80000/77600/77590/01d93670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/80000/77600/77590/6b178c72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/80000/77600/77590/4a8285f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed with Sofa bed](https://images.trvl-media.com/lodging/1000000/80000/77600/77590/cf87adb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn and Suites by Marriott Des Moines West West Des Moines 9.0/10 Wonderful (1043) "Great stay, staff very friendly " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Matthew CA $129 CA $144 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Des-Moines-Hotels-Fairfield-Inn-And-Suites-By-Marriott-Des-Moines-West.h77590.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/990000/980800/980750/9a4e02d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/990000/980800/980750/45613da8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/990000/980800/980750/66848e5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, blackout drapes, soundproofing](https://images.trvl-media.com/lodging/1000000/990000/980800/980750/8fba2edb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Osceola IA Osceola 8.6/10 Excellent (221) "Very convenient location and wonderful staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sandra CA $101 CA $113 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Osceola-Hotels-Super-8-By-Wyndham-Osceola-IA.h980750.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/7000000/6820000/6810100/6810039/b5113be3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/7000000/6820000/6810100/6810039/d35bd821.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/7000000/6820000/6810100/6810039/bc52cdf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/7000000/6820000/6810100/6810039/a75af44a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### AmericInn by Wyndham Osceola Osceola 8.8/10 Excellent (582) "Nice location, good breakfast and helpful staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher CA $165 CA $185 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Osceola-Hotels-AmericInn-By-Wyndham-Osceola.h6810039.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=2025-11-09&endDate=2025-11-10®ionId=181516&adults=2&amenities=PETS&sort=RECOMMENDED&openPlayBack=true) ## Top Winterset Hotel Reviews ![Stoney Creek Hotel Des Moines - Johnston](//images.trvl-media.com/lodging/2000000/1160000/1152300/1152222/8b967b66_y.jpg) ### Stoney Creek Hotel Des Moines - Johnston 10/10 Excellent "Large cottage. Friendly staff. Very clean" [](https://expedia.ca/Des-Moines-Hotels-Stoney-Creek-Hotel-Des-Moines-Johnston.h1152222.Hotel-Information) ![Motel 6 West Des Moines, IA](//images.trvl-media.com/lodging/1000000/990000/986100/986072/e3428772_y.jpg) ### Motel 6 West Des Moines, IA 10/10 Excellent "Nice staff" [](https://expedia.ca/Des-Moines-Hotels-Motel-6-West-Des-Moines.h986072.Hotel-Information) ![Cobblestone Inn & Suites - Winterset, IA](//images.trvl-media.com/lodging/11000000/10450000/10446900/10446857/f46e6906_y.jpg) ### Cobblestone Inn & Suites - Winterset, IA 10/10 Excellent "Great place to stay. " [](https://expedia.ca/Winterset-Hotels-Cobblestone-Inn-Suites-Winterset.h10446857.Hotel-Information) ![Wildwood Lodge](//images.trvl-media.com/lodging/8000000/7600000/7599000/7598985/c7d37989_y.jpg) ### Wildwood Lodge 10/10 Excellent "Very nice property. Friendly staff. Beautiful lobby." [](https://expedia.ca/Des-Moines-Hotels-Wildwood-Lodge.h7598985.Hotel-Information) ![Revel Hotel Des Moines Urbandale, Tapestry Collection by Hilton](//images.trvl-media.com/lodging/1000000/120000/119100/119096/b673e89d_y.jpg) ### Revel Hotel Des Moines Urbandale, Tapestry Collection by Hilton 10/10 Excellent "N/A - Did not visit bar." [](https://expedia.ca/Des-Moines-Hotels-Revel-Hotel-Des-Moines-Urbandale.h119096.Hotel-Information) ![Drury Inn & Suites West Des Moines](//images.trvl-media.com/lodging/2000000/1840000/1836200/1836184/2af2a76d_y.jpg) ### Drury Inn & Suites West Des Moines 10/10 Excellent "Always one of the best Drury Inns out there. " [](https://expedia.ca/Des-Moines-Hotels-Drury-Inn-Suites-West-Des-Moines.h1836184.Hotel-Information) ![Holiday Inn Express & Suites Des Moines Downtown by IHG](//images.trvl-media.com/lodging/13000000/12760000/12756300/12756236/7f9d044a_y.jpg) ### Holiday Inn Express & Suites Des Moines Downtown by IHG 10/10 Excellent "Helpful staff, offered recommendations, accommodatng to runners in town for the race" [](https://expedia.ca/Des-Moines-Hotels-Holiday-Inn-Express-Suites-Des-Moines-Downtown.h12756236.Hotel-Information) ![Country Inn & Suites by Radisson, Des Moines West, IA](//images.trvl-media.com/lodging/1000000/100000/99800/99780/1bd10ea8_y.jpg) ### Country Inn & Suites by Radisson, Des Moines West, IA 10/10 Excellent "Room was clean, breakfast was good and the price was right. " [](https://expedia.ca/Des-Moines-Hotels-Country-Inn-Suites-By-Radisson.h99780.Hotel-Information) ![Hyatt Place West Des Moines Jordan Creek](//images.trvl-media.com/lodging/17000000/16120000/16112600/16112546/f70b7069_y.jpg) ### Hyatt Place West Des Moines Jordan Creek 10/10 Excellent "Good" [](https://expedia.ca/Des-Moines-Hotels-Hyatt-Place-West-Des-Moines-Jordan-Creek.h16112546.Hotel-Information) ## Frequently asked questions ### What's the best pet-friendly hotel in Winterset? > [Cobblestone Inn & Suites - Winterset, IA](https://www.expedia.ca/Winterset-Hotels-Cobblestone-Inn-Suites-Winterset.h10446857.Hotel-Information) is a top dog-friendly hotel, and offers a restaurant along with free WiFi for its human guests. [Covered Bridge Inn](https://www.expedia.ca/Winterset-Hotels-Covered-Bridge-Inn.h439956.Hotel-Information) is another good option for a stay with your pet. ### What's the best time of year to travel to Winterset with my pet? > When you travel with your pet, keeping track of the weather can make the trip safe and fun for everyone. The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Winterset are January, February, November, and March, with each month seeing an average of 9 inches of snowfall. ### What is there to see and do with your pet in Winterset? > See the local sights and visit John Wayne Birthplace Museum and The Winterset Stage. 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