Title: Book the Best HISTORIC Hotels in Red Oaks Mill in 2026 | Expedia.ca [Red Oaks Mill Travel Guide](https://expedia.ca/Poughkeepsie-Red-Oaks-Mill.dx553248634998900489)[Vacation Rentals in Poughkeepsie](https://expedia.ca/Poughkeepsie-Vacation-Rentals.d6056317.Travel-Guide-VacationRentals)[Flights to Poughkeepsie](https://expedia.ca/Cheap-Flights-To-Poughkeepsie.d6056317.Travel-Guide-Flights)[Things to do in Poughkeepsie](https://expedia.ca/Things-To-Do-In-Poughkeepsie.d6056317.Travel-Guide-Activities)[Red Oaks Mill Car Rentals](https://expedia.ca/Car-Rentals-In-Red-Oaks-Mill.d553248634998900489.Car-Rental-Guide)[Red Oaks Mill Vacations](https://expedia.ca/Red-Oaks-Mill.d553248634998900489.Destination-Travel-Guides) ![panoramic view of mid hudson bridge over hudson river valley (poughkeepsie, upstate new york) sunny day train station wide angle sun glare crossing suspension small town travel metro north](https://images.trvl-media.com/place/553248634998900489/43dfaefc-f04f-45b7-bc35-40574f714c7b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Red Oaks Mill, NY from CA $131 - ![](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 Red Oaks Mill Historic Hotels Tonight [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=553248634998900489&startDate=2025-12-12&endDate=2025-12-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248634998900489&startDate=2025-12-13&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248634998900489&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248634998900489&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Red Oaks Mill historic hotels ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/833333a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/9a6a049d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/1765b81e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Poughkeepsie [](https://www.expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information) Poughkeepsie 8.8/10 Excellent (1001) "Clean room and friendly staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelly CA $115 CA $131 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/f57ee72e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/c73b0205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/f3387c76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/2f96f964.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Fishkill [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Fishkill.h119273.Hotel-Information) Fishkill 8.6/10 Excellent (1000) "Clean, friendly, nice pool!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kate CA $129 CA $146 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Fishkill.h119273.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/31000000/30530000/30528700/30528653/1d436988.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/31000000/30530000/30528700/30528653/8e6a9ec3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Suite, Non Smoking | Balcony](https://images.trvl-media.com/lodging/31000000/30530000/30528700/30528653/4eb28f6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/31000000/30530000/30528700/30528653/41817d7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn the Woods Bed and Breakfast [](https://www.expedia.ca/Poughkeepsie-Hotels-Inn-The-Woods-Bed-And-Breakfast.h30528653.Hotel-Information) Hyde Park 9.8/10 Exceptional (136) "Harry was great, room clean and fresh, breakfast amazing " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frank CA $252 CA $285 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/Poughkeepsie-Hotels-Inn-The-Woods-Bed-And-Breakfast.h30528653.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/72000000/71560000/71554400/71554330/caba39f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71560000/71554400/71554330/e260a20c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71560000/71554400/71554330/d66159f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/72000000/71560000/71554400/71554330/f2a122ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hot Tub - Fire Pit - BBQ - Hammock - Colonial [](https://www.expedia.ca/Kingston-Hotels-Charming-Hudson-Valley-Luxury-Getaway.h71554330.Hotel-Information) Kingston 9.4/10 Exceptional (22) "This was a great stay away, just for a couple of quiet days. Inside the house was excellent. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dennis M. CA $124 CA $319 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Kingston-Hotels-Charming-Hudson-Valley-Luxury-Getaway.h71554330.Hotel-Information) ![Hiking](https://images.trvl-media.com/lodging/18000000/17910000/17902100/17902038/c194d854.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snowshoeing](https://images.trvl-media.com/lodging/18000000/17910000/17902100/17902038/f7f60f7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/18000000/17910000/17902100/17902038/6ae0b5c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, blackout drapes](https://images.trvl-media.com/lodging/18000000/17910000/17902100/17902038/dd233577.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Journey Inn Bed & Breakfast [](https://www.expedia.ca/Poughkeepsie-Hotels-Journey-Inn-Bed-Breakfast.h17902038.Hotel-Information) Hyde Park 9.6/10 Exceptional (338) "Great staff, the breakfast was amazing, location to surrounding attractions was great! I would stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shawn CA $309 CA $349 total includes taxes & fees Dec 13 - Dec 14 [](https://www.expedia.ca/Poughkeepsie-Hotels-Journey-Inn-Bed-Breakfast.h17902038.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/68000000/67270000/67268600/67268558/9224e1b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/68000000/67270000/67268600/67268558/b528caee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/68000000/67270000/67268600/67268558/aeb97fc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/68000000/67270000/67268600/67268558/b338553a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Omega special, Sunday night thru Thursday night 5 NIGHT MINIMUM, 3 miles away, [](https://www.expedia.ca/Poughkeepsie-Hotels-Private-Bed-Bath-On-Secluded-30-Acre-Farm.h67268558.Hotel-Information) Clinton Corners 8.2/10 Very good (11) "The propert my, grounds and location is just charming. Hosts were stellar and welcoming. Accomodations warm and inviting." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dawn B. CA $193 CA $265 total includes taxes & fees Dec 13 - Dec 14 [](https://www.expedia.ca/Poughkeepsie-Hotels-Private-Bed-Bath-On-Secluded-30-Acre-Farm.h67268558.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/69000000/68780000/68773100/68773092/447949bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/69000000/68780000/68773100/68773092/1941c471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/69000000/68780000/68773100/68773092/6d7fbb92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/69000000/68780000/68773100/68773092/8e24845d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private room on secluded 7 acres , access to entire house including patio, porch [](https://www.expedia.ca/Clinton-Corners-Hotels-Private-Room-On-Secluded-7-Acres.h68773092.Hotel-Information) Clinton Corners 8.6/10 Excellent (30) "It was just as advertised! Host was nice included fruit and coffee " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) matt w. CA $207 CA $281 total includes taxes & fees Dec 13 - Dec 14 [](https://www.expedia.ca/Clinton-Corners-Hotels-Private-Room-On-Secluded-7-Acres.h68773092.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/04adf8dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/e2587dd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/a8c5ab99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/19de180c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer [](https://www.expedia.ca/Beacon-Hotels-Luxe-Studio-4-On-Main-Street-Luxury-Steam-Shower.h69240003.Hotel-Information) Beacon 10/10 Exceptional (49) "Great room and location. A nice home base for exploring the area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bob G. CA $152 CA $335 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Beacon-Hotels-Luxe-Studio-4-On-Main-Street-Luxury-Steam-Shower.h69240003.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/40000000/40000000/39997000/39996972/10e984da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/40000000/40000000/39997000/39996972/3e77c02f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/40000000/40000000/39997000/39996972/a32e6868.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/40000000/40000000/39997000/39996972/05ca61ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Church Des Artistes a Hudson Valley retreat [](https://www.expedia.ca/Kingston-Hotels-Church-Des-Artistes-A-Hudson-Valley-Retreat.h39996972.Hotel-Information) Rondout 9.8/10 Exceptional (10) "Beautiful, unique stay! Julie was really kind walking us through the ins and outs of the property during check-in. So much care and attention put into every room. And the book collection is amazing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Molly M. CA $2,066 CA $3,519 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Kingston-Hotels-Church-Des-Artistes-A-Hudson-Valley-Retreat.h39996972.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=2025-12-26&endDate=2025-12-27®ionId=553248634998900489&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Red Oaks Mill Hotel Reviews ![Courtyard by Marriott Poughkeepsie](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2_y.jpg) ### Courtyard by Marriott Poughkeepsie 10/10 Excellent "Buisness friendly, breakfast, gym room, quiet, good customer service " [](https://expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information) ![Hampton Inn & Suites Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/47fa2e85_y.jpg) ### Hampton Inn & Suites Poughkeepsie 10/10 Excellent "😍" [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information) ![SureStay Plus Hotel by Best Western Highland Poughkeepsie](https://images.trvl-media.com/lodging/1000000/920000/918800/918797/960f4844_y.jpg) ### SureStay Plus Hotel by Best Western Highland Poughkeepsie 10/10 Excellent "Nice staff, large rooms " [](https://expedia.ca/Poughkeepsie-Hotels-SureStay-Plus-Hotel-By-Best-Western-Highland-Poughkeepsie.h918797.Hotel-Information) ![The Thayer Hotel at West Point](https://images.trvl-media.com/lodging/6000000/5800000/5792300/5792279/c0c1b35f_y.jpg) ### The Thayer Hotel at West Point 10/10 Excellent "Well renovated, well-maintained historical and charming hotel right on campus of West Point. Staff were helpful, & each room featured a different veteran’s biography. Overlooks the Hudson River. On site restaurant. We greatly enjoyed our stay." [](https://expedia.ca/Newburgh-Hotels-Thayer-Hotel.h5792279.Hotel-Information) ![Holiday Inn Express Poughkeepsie by IHG](https://images.trvl-media.com/lodging/1000000/20000/12200/12157/9d729415_y.jpg) ### Holiday Inn Express Poughkeepsie by IHG 10/10 Excellent "The was extremely clean" [](https://expedia.ca/Poughkeepsie-Hotels-Holiday-Inn-Express-Poughkeepsie.h12157.Hotel-Information) ![Beekman Arms Hotel](https://images.trvl-media.com/lodging/13000000/12620000/12611900/12611810/ab673905_y.jpg) ### Beekman Arms Hotel 10/10 Excellent "Everything was great" [](https://expedia.ca/Poughkeepsie-Hotels-Beekman-Arms-Hotel.h12611810.Hotel-Information) ![Minnewaska Lodge](https://images.trvl-media.com/lodging/2000000/1210000/1201800/1201707/3be04d40_y.jpg) ### Minnewaska Lodge 10/10 Excellent "It’s a great place in the spectacular location. Very comfortable and inviting and spacious." [](https://expedia.ca/Poughkeepsie-Hotels-Minnewaska-Lodge.h1201707.Hotel-Information) ![Howard Johnson by Wyndham Newburgh/West Point](https://images.trvl-media.com/lodging/1000000/10000/7700/7652/8a35f36a_y.jpg) ### Howard Johnson by Wyndham Newburgh/West Point 10/10 Excellent "Excellent " [](https://expedia.ca/Newburgh-Hotels-Howard-Johnson-By-Wyndham-NewburghWest-Point.h7652.Hotel-Information) ![DoubleTree by Hilton Poughkeepsie Convention Center](https://images.trvl-media.com/lodging/1000000/20000/14600/14563/acc87956_y.jpg) ### DoubleTree by Hilton Poughkeepsie Convention Center 10/10 Excellent "It was very comfortable and the staff was polite and helpful." [](https://expedia.ca/Poughkeepsie-Hotels-Poughkeepsie-Grand-Hotel.h14563.Hotel-Information) ## Frequently asked questions ### What can a history buff expect from a stay in Red Oaks Mill? ### How many historically relevant hotels will I find in Red Oaks Mill? ### What are the must-see historical sites and other places in Red Oaks Mill? ### What is a historic hotel like in Red Oaks Mill? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in Red Oaks Mill have modern facilities? ## Explore a world of travel with Expedia - Lodging - Flights - More ways to book - [Hotels with Free Parking in Arlington ](https://www.expedia.ca/Arlington-Poughkeepsie-Hotels-Hotels-With-Free-Parking.0-n553248634999048383-0-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Arlington ](https://www.expedia.ca/Arlington-Poughkeepsie-Hotels-Luxury-Hotel.0-n553248634999048383-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in Arlington ](https://www.expedia.ca/Arlington-Poughkeepsie-Hotels-Wedding-Hotels.0-n553248634999048383-0-tWeddingHotels.Travel-Guide-Filter-Hotels) - 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