Title: Book the Best Hotels with CHILDCARE in Skidmore Academy Historic District in 2026 | Expedia.ca [Skidmore Academy Historic District Travel Guide](https://expedia.ca/Ashland-Skidmore-Academy-Historic-District.dx553248635976482103)[Vacation Rentals in Ashland](https://expedia.ca/Ashland-Vacation-Rentals.d6290.Travel-Guide-VacationRentals)[Flights to Ashland](https://expedia.ca/Cheap-Flights-To-Ashland.d6290.Travel-Guide-Flights)[Things to do in Ashland](https://expedia.ca/Things-To-Do-In-Ashland.d6290.Travel-Guide-Activities)[Skidmore Academy Historic District Car Rentals](https://expedia.ca/Car-Rentals-In-Skidmore-Academy-Historic-District.d553248635976482103.Car-Rental-Guide)[Skidmore Academy Historic District Vacations](https://expedia.ca/Skidmore-Academy-Historic-District.d553248635976482103.Destination-Travel-Guides) ![Aerial view of Ashland, Oregon](https://images.trvl-media.com/place/553248635976482103/8e257b0c-49b6-4a00-9cd9-fbf87a8384c5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with Childcare in Skidmore Academy Historic District, OR from CA $95 - ![](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 Skidmore Academy Historic District Hotels with Childcare Tonight [Dec 19 - Dec 20](https://www.expedia.ca/Hotel-Search?regionId=553248635976482103&startDate=2025-12-19&endDate=2025-12-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 20 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976482103&startDate=2025-12-20&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976482103&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976482103&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) No exact matches found, but these alternatives could be just right ## Recommended hotels in Skidmore Academy Historic District ![Abigail Rockefeller](https://images.trvl-media.com/lodging/5000000/4970000/4966500/4966403/996815d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/5000000/4970000/4966500/4966403/5d4e8a03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/5000000/4970000/4966500/4966403/8cce1780.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/5000000/4970000/4966500/4966403/0a4690bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Abigail’s Bed & Breakfast Inn [](https://www.expedia.ca/Medford-Hotels-Abigails-Bed-Breakfast-Inn.h4966403.Hotel-Information) Skidmore Academy Historic District 9.4/10 Exceptional (62) "Best B and B in Ashland we have ever stayed at in thirty years . Amazing food and very comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew CA $248 CA $277 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Medford-Hotels-Abigails-Bed-Breakfast-Inn.h4966403.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/113000000/112020000/112015600/112015563/00b0cdb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/113000000/112020000/112015600/112015563/51a41959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/113000000/112020000/112015600/112015563/48af1fe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112020000/112015600/112015563/ddefdff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming carriage house in Ashland near downtown [](https://www.expedia.ca/Ashland-Hotels-Charming-Carriage-House-In-Ashland-Near-Downtown.h112015563.Hotel-Information) Skidmore Academy Historic District 10/10 Exceptional (6) "Enjoyed our stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie M. CA $143 CA $285 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Ashland-Hotels-Charming-Carriage-House-In-Ashland-Near-Downtown.h112015563.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1580000/1573400/1573382/7ace6696.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1580000/1573400/1573382/b4c1b610.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/2000000/1580000/1573400/1573382/5284c096.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1580000/1573400/1573382/7cb6fc44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Medford-Central Point by IHG [](https://www.expedia.ca/Medford-Hotels-Holiday-Inn-Express-Hotel-Suites-Medford-Central-Point.h1573382.Hotel-Information) Central Point 9.0/10 Wonderful (1001) "Very nice room and the staff accommodated our request for a quiet room. Breakfast was very good, with a nice selection. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caren CA $123 CA $138 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Medford-Hotels-Holiday-Inn-Express-Hotel-Suites-Medford-Central-Point.h1573382.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/3500/3448/9eb7c716.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/3500/3448/1be41ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/1000000/10000/3500/3448/ac72a052.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/3500/3448/2ee8917d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Ashland [](https://www.expedia.ca/Medford-Hotels-Comfort-Inn-Suites.h3448.Hotel-Information) Ashland 8.8/10 Excellent (1007) "Staff was excellent and very nice and room was clean and location is good Town is very cool 👍" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas CA $114 CA $115 total includes taxes & fees Jan 18 - Jan 19, 2026 [](https://www.expedia.ca/Medford-Hotels-Comfort-Inn-Suites.h3448.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/b7c87028.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/5f7e6be2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/2acbb0d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Two Queen Room, Mountainside | Mountain view](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/4093c3d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stratford Inn [](https://www.expedia.ca/Medford-Hotels-Stratford-Inn.h2758881.Hotel-Information) Siskiyou-Hargadine Historic District 9.4/10 Exceptional (1605) "Very clean room, affordable and extremely friendly staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shalene CA $112 CA $124 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Medford-Hotels-Stratford-Inn.h2758881.Hotel-Information) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/50000/42900/42817/59b368f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/50000/42900/42817/3002105e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Land view from property](https://images.trvl-media.com/lodging/1000000/50000/42900/42817/236ca3c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/50000/42900/42817/3d32a00a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Flagship Inn of Ashland [](https://www.expedia.ca/Medford-Hotels-Flagship-Inn-Of-Ashland.h42817.Hotel-Information) Ashland 8.8/10 Excellent (1197) "Huge room Great check in Very comfortable My 5th stay here " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael L CA $91 CA $102 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Medford-Hotels-Flagship-Inn-Of-Ashland.h42817.Hotel-Information) ![Panoramic Room, 1 King Bed, Jetted Tub, Mountain View | Terrace/patio](https://images.trvl-media.com/lodging/13000000/12380000/12372400/12372363/2d34db80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family House | Private kitchen](https://images.trvl-media.com/lodging/13000000/12380000/12372400/12372363/52c43a54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/13000000/12380000/12372400/12372363/609741f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, pillowtop beds](https://images.trvl-media.com/lodging/13000000/12380000/12372400/12372363/01670d2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Callahan's Mountain Lodge [](https://www.expedia.ca/Medford-Hotels-Callahans-Mountain-Lodge.h12372363.Hotel-Information) Ashland 8.8/10 Excellent (1166) "Beautiful place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel CA $134 CA $157 total includes taxes & fees Jan 19 - Jan 20, 2026 [](https://www.expedia.ca/Medford-Hotels-Callahans-Mountain-Lodge.h12372363.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/1000000/670000/661000/660933/86190d91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/670000/661000/660933/c5aa855a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/670000/661000/660933/59ddab0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/670000/661000/660933/cd01e6a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ashland Springs Hotel [](https://www.expedia.ca/Medford-Hotels-Ashland-Springs-Hotel.h660933.Hotel-Information) Historic Downtown District 9.2/10 Wonderful (1006) "Small room but wonderful view and comfortable bed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica CA $120 CA $154 total includes taxes & fees Jan 16 - Jan 17, 2026 [](https://www.expedia.ca/Medford-Hotels-Ashland-Springs-Hotel.h660933.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/920000/916000/915968/7580c086.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/916000/915968/3c8278b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/916000/915968/cf48b0cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Room, 3 Queen Beds (No Pets Allowed)](https://images.trvl-media.com/lodging/1000000/920000/916000/915968/e32a2cac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Timbers INN and Suites [](https://www.expedia.ca/Medford-Hotels-Timbers-Motel.h915968.Hotel-Information) Ashland 8.6/10 Excellent (1002) "Room very good and vintage 70s style. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James P CA $86 CA $95 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Medford-Hotels-Timbers-Motel.h915968.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/85000000/84250000/84243300/84243241/b35208e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/85000000/84250000/84243300/84243241/b00c5aed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/85000000/84250000/84243300/84243241/87545a04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/85000000/84250000/84243300/84243241/ca32d6e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Springhill Suites By Marriott Medford Airport [](https://www.expedia.ca/Medford-Hotels-Springhill-Suites-By-Marriott-Medford-Airport.h84243241.Hotel-Information) Medford 9.6/10 Exceptional (1004) "Nice inexpensive hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gary CA $151 CA $170 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Medford-Hotels-Springhill-Suites-By-Marriott-Medford-Airport.h84243241.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=2026-01-02&endDate=2026-01-03®ionId=553248635976482103&adults=2&property_amenities_group_explore=babysitting_or_childcare&sort=RECOMMENDED&openPlayBack=true) ## Top Skidmore Academy Historic District Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [3 Star Hotels in Ashland ](https://www.expedia.ca/3Star-Ashland-Hotels.s30-0-d6290.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Ashland ](https://www.expedia.ca/4Star-Ashland-Hotels.s40-0-d6290.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Ashland ](https://www.expedia.ca/5Star-Ashland-Hotels.s50-0-d6290.Travel-Guide-Filter-Hotels) - [Hotels near Allen Elizabethan Theatre ](https://www.expedia.ca/Allen-Elizabethan-Theatre-Hotels.0-l6078449-0.Travel-Guide-Filter-Hotels) - [Aparthotels in Ashland ](https://www.expedia.ca/Ashland-Apart-Hotels.d6290-aaApartHotels.Travel-Guide-Accommodation) - 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