Title: Ossining Holiday Homes from £102: Search Holiday Homes in Ossining | Expedia.co.uk [Hotels in Ossining](https://expedia.co.uk/Ossining-Hotels.d6190653.Travel-Guide-Hotels)[Holiday Rentals in Ossining](https://expedia.co.uk/Ossining-Holiday-Rentals.d6190653.Travel-Guide-HolidayRentals)[Ossining Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Ossining.d6190653.Car-Hire-Guide)[Ossining Holidays](https://expedia.co.uk/Ossining.d6190653.Holidays-City-Breaks) ![Main building at Maryknoll](https://images.trvl-media.com/place/3000449058/eaa5b59e-44e4-4686-a478-33459da1d8df.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by louann ohora ![](https://images.trvl-media.com/place/3000449058/eaa5b59e-44e4-4686-a478-33459da1d8df.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 [6 Mar - 8 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=6190653&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [17 Apr - 19 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=6190653&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [15 May - 17 May](https://www.expedia.co.uk/Hotel-Search?regionId=6190653&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [12 Jun - 14 Jun](https://www.expedia.co.uk/Hotel-Search?regionId=6190653&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Ossining holiday homes ![Outdoor banquet area](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/05588dfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/51ae2321.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/f958fa55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/6407ae3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castle Retreat w/ Pool, BBQ, Game Room & Pets OK! [](https://www.expedia.co.uk/Ossining-Hotels-Castle-Retreat-W-Pool.h101852343.Hotel-Information) Ossining 9.2/10 Wonderful (7 reviews) "Communication was excellent. The house itself is older and fine for its age, but " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jonathan O. £712 includes taxes & fees 17 Mar - 18 Mar [](https://www.expedia.co.uk/Ossining-Hotels-Castle-Retreat-W-Pool.h101852343.Hotel-Information) ![Villa | 5 bedrooms](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/6e503ed4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa | 5 bedrooms](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/b0adc70f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa | 5 bedrooms](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/ae91b214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa | 5 bedrooms](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/w3000h1944x0y0-bf620bb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW 45 Wolden Rd Ossining NY 10562 [](https://www.expedia.co.uk/Ossining-Hotels-Foliage-At-Westchester-Manor-Near-Sleepy-Hollow.h121520491.Hotel-Information) Ossining £664 includes taxes & fees 16 Mar - 17 Mar [](https://www.expedia.co.uk/Ossining-Hotels-Foliage-At-Westchester-Manor-Near-Sleepy-Hollow.h121520491.Hotel-Information) ![TV, fireplace](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/38809636.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/8bc06f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/07a03d02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/416c2b95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike. [](https://www.expedia.co.uk/Carmel-Hotels-Lux-Bungalow-On-Gorgeous-Lake-Relax-Explore-Nearby-Towns-Ski-Kayak-Hike.h101941777.Hotel-Information) Carmel Hamlet 9.8/10 Exceptional (13 reviews) "We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hannah P. £259 includes taxes & fees 24 Feb - 25 Feb [](https://www.expedia.co.uk/Carmel-Hotels-Lux-Bungalow-On-Gorgeous-Lake-Relax-Explore-Nearby-Towns-Ski-Kayak-Hike.h101941777.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/113000000/112370000/112364900/112364813/3138ca99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/113000000/112370000/112364900/112364813/ebebe95b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/113000000/112370000/112364900/112364813/bdaff4ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/113000000/112370000/112364900/112364813/2730f6d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi [](https://www.expedia.co.uk/Stamford-Hotels-Charming-2-Bedroom-House-In-Fabulous-Stamford-With-AC.h112364813.Hotel-Information) Waterside 10/10 Exceptional (11 reviews) "Fantastic place. We had a great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sara C. £259 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Stamford-Hotels-Charming-2-Bedroom-House-In-Fabulous-Stamford-With-AC.h112364813.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/32d0bc6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/d9fd7f11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/449fc3a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/e5a3641b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Contemporary Cozy Cottage [](https://www.expedia.co.uk/Lake-Peekskill-Hotels-Contemporary-Cozy-Cottage.h102145832.Hotel-Information) Lake Peekskill 10/10 Exceptional (31 reviews) "Very clean comfortable quiet place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mauro C. £313 includes taxes & fees 20 Feb - 21 Feb [](https://www.expedia.co.uk/Lake-Peekskill-Hotels-Contemporary-Cozy-Cottage.h102145832.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/424d87c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/e5f1d678.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/92f8429f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/e73b5292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### House on the Babbling Brook- Quiet 2BR + King Bed! [](https://www.expedia.co.uk/Highland-Falls-Hotels-House-On-The-Babbling-Brook-Quiet-2BR-King-Bed.h113522235.Hotel-Information) Highland Falls 10/10 Exceptional (6 reviews) "Good stay, awesome place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Scott G. £263 includes taxes & fees 20 Feb - 21 Feb [](https://www.expedia.co.uk/Highland-Falls-Hotels-House-On-The-Babbling-Brook-Quiet-2BR-King-Bed.h113522235.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/58000000/57350000/57343700/57343699/f2e7ce71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Casino](https://images.trvl-media.com/lodging/58000000/57350000/57343700/57343699/6073858e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, Netflix](https://images.trvl-media.com/lodging/58000000/57350000/57343700/57343699/w1170h771x0y0-9623bf5d.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/58000000/57350000/57343700/57343699/9101db47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nice Cozy Room By Empire City Casino And Cross County Shopping Center [](https://www.expedia.co.uk/Yonkers-Hotels-Nice-Cozy-Room-By-Empire-City-Casino-And-Cross-County-Shopping-Center.h57343699.Hotel-Information) Southeast Yonkers 8.2/10 Very good (18 reviews) "Great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jordan S. £102 includes taxes & fees 20 Feb - 21 Feb [](https://www.expedia.co.uk/Yonkers-Hotels-Nice-Cozy-Room-By-Empire-City-Casino-And-Cross-County-Shopping-Center.h57343699.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/84000000/83720000/83719600/83719534/951a6af7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/84000000/83720000/83719600/83719534/f53f774c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/84000000/83720000/83719600/83719534/c34214f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, WiFi](https://images.trvl-media.com/lodging/84000000/83720000/83719600/83719534/w1230h827x3y0-aaaf2e31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheerful Home in Yonkers NY [](https://www.expedia.co.uk/Yonkers-Hotels-Cheerful-Home-In-Yonkers-NY.h83719534.Hotel-Information) Lincoln Park 7.6/10 Good (4 reviews) "Nice neighborhood,open concept.Hreat space for my entire family.Kitchen big and spacious. Beds are huge. Definitely will stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tanya J. £430 includes taxes & fees 20 Feb - 21 Feb [](https://www.expedia.co.uk/Yonkers-Hotels-Cheerful-Home-In-Yonkers-NY.h83719534.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/123000000/122930000/122929100/122929001/120febc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/123000000/122930000/122929100/122929001/bb90272b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122930000/122929100/122929001/7c3fd8d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122930000/122929100/122929001/2f9d1a89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King [](https://www.expedia.co.uk/Cornwall-Hotels-Storm-King-At-Narnia-Welcome-To-A-Slice-Of-Paradise-In-The-Hudson-Valley.h122929001.Hotel-Information) Cornwall 10/10 Exceptional (5 reviews) £281 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Cornwall-Hotels-Storm-King-At-Narnia-Welcome-To-A-Slice-Of-Paradise-In-The-Hudson-Valley.h122929001.Hotel-Information) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/7ad8e5a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/82ecc5c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/2bdd6486.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/cf889632.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleek Escape: Modern 3 BR- 4 Min from West Point ! [](https://www.expedia.co.uk/Highland-Falls-Hotels-Sleek-Escape-Modern-3-BR-4-Min-From-West-Point.h110986250.Hotel-Information) Highland Falls 10/10 Exceptional (4 reviews) "Very nice apartment in Highland Falls. Each bedroom has nice closet space and the master is very large. Remodeled very well and comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) chris f. £323 includes taxes & fees 4 Mar - 5 Mar [](https://www.expedia.co.uk/Highland-Falls-Hotels-Sleek-Escape-Modern-3-BR-4-Min-From-West-Point.h110986250.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/7ce63cd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/5b614a2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/e1560e45.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/115000000/114610000/114606200/114606188/ffa97c31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich. [](https://www.expedia.co.uk/Greenwich-Hotels-2-Bedroom-And-1-Full-Bath-In-Lakeside-Home-With-Private-Dock.h114606188.Hotel-Information) Greenwich 9.8/10 Exceptional (27 reviews) "Beautiful space, excellent communication from the hosts. Would stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Crystal £186 includes taxes & fees 8 Mar - 9 Mar [](https://www.expedia.co.uk/Greenwich-Hotels-2-Bedroom-And-1-Full-Bath-In-Lakeside-Home-With-Private-Dock.h114606188.Hotel-Information) ![TV, fireplace, books, offices](https://images.trvl-media.com/lodging/84000000/83980000/83980000/83979908/59c98581.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83980000/83980000/83979908/d45254db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83980000/83980000/83979908/a18fd2fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83980000/83980000/83979908/01af0402.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Beach Home near Stamford Downtown/Shippan [](https://www.expedia.co.uk/Stamford-Hotels-New-Beach-Home-Near-Stamford-DowntownShippan.h83979908.Hotel-Information) Cove - East Side - Shippan 10/10 Exceptional (24 reviews) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kyra S. £646 includes taxes & fees 20 Feb - 21 Feb [](https://www.expedia.co.uk/Stamford-Hotels-New-Beach-Home-Near-Stamford-DowntownShippan.h83979908.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/79000000/78410000/78400400/78400391/86ae4160.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78410000/78400400/78400391/185a287e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/79000000/78410000/78400400/78400391/a65c4dd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/79000000/78410000/78400400/78400391/1e85a3aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near... [](https://www.expedia.co.uk/Stamford-Hotels-Modern-3-Bdrm-Home-W-Parking.h78400391.Hotel-Information) West Side 9.4/10 Exceptional (6 reviews) "Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dave J. [](https://www.expedia.co.uk/Stamford-Hotels-Modern-3-Bdrm-Home-W-Parking.h78400391.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/106000000/105360000/105358700/105358651/df26ff7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/106000000/105360000/105358700/105358651/634ccf4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](https://images.trvl-media.com/lodging/106000000/105360000/105358700/105358651/24e015e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105360000/105358700/105358651/bdb4c2f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury 3 BR Near NYC with Easy Parking [](https://www.expedia.co.uk/Yonkers-Hotels-Luxury-3-BR-Near-NYC-With-Easy-Parking.h105358651.Hotel-Information) Bryn Mawr £427 includes taxes & fees 20 Feb - 21 Feb [](https://www.expedia.co.uk/Yonkers-Hotels-Luxury-3-BR-Near-NYC-With-Easy-Parking.h105358651.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/96000000/95770000/95764600/95764526/575b2a63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/96000000/95770000/95764600/95764526/6ea08c86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95770000/95764600/95764526/760d8df7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/96000000/95770000/95764600/95764526/d8954b82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfortable 1 family home in Tuckahoe that's near train [](https://www.expedia.co.uk/Tuckahoe-Hotels-Comfortable-1-Family-Home-In-Tuckahoe-Thats-Near-Train.h95764526.Hotel-Information) Tuckahoe £517 includes taxes & fees 20 Feb - 21 Feb [](https://www.expedia.co.uk/Tuckahoe-Hotels-Comfortable-1-Family-Home-In-Tuckahoe-Thats-Near-Train.h95764526.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/6b825ecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/8fad8a9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/6f93013a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/973f29b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3BR West Point Retreat-3min to Back Gate+ King Bed [](https://www.expedia.co.uk/Highland-Falls-Hotels-3BR-West-Point-Retreat-3min-To-Back-Gate-King-Bed.h113522229.Hotel-Information) Highland Falls 8.0/10 Very good (6 reviews) "Excellent host, house is very clean. The queen and king beds are comfortable. The sound of the brook is relaxing. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Penny D. £332 includes taxes & fees 4 Mar - 5 Mar [](https://www.expedia.co.uk/Highland-Falls-Hotels-3BR-West-Point-Retreat-3min-To-Back-Gate-King-Bed.h113522229.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/6a09d677.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/f77cbaf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/719e347a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/3207c5e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lovely 3BR Home with parking-Walk to WP Gate! [](https://www.expedia.co.uk/Highland-Falls-Hotels-Lovely-3BR-Home-With-Parking-Walk-To-WP-Gate.h105177891.Hotel-Information) Highland Falls 10/10 Exceptional (7 reviews) "Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Briana T. £273 includes taxes & fees 17 Mar - 18 Mar [](https://www.expedia.co.uk/Highland-Falls-Hotels-Lovely-3BR-Home-With-Parking-Walk-To-WP-Gate.h105177891.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/be15b260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/116022ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/ab2c7ac1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/8cbcd139.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fabulous 3bdrm Home w/parking! [](https://www.expedia.co.uk/Highland-Falls-Hotels-Fabulous-3bdrm-Home-Wparking.h114378708.Hotel-Information) Highland Falls 9.2/10 Wonderful (5 reviews) "Clean home, conveniently located to West Point. Very comfortable beds. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Danielle B. £256 includes taxes & fees 9 Mar - 10 Mar [](https://www.expedia.co.uk/Highland-Falls-Hotels-Fabulous-3bdrm-Home-Wparking.h114378708.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/115000000/114640000/114637300/114637256/4675a87a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/115000000/114640000/114637300/114637256/92f79611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Blackout curtains, free WiFi](https://images.trvl-media.com/lodging/115000000/114640000/114637300/114637256/8a87cb23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/115000000/114640000/114637300/114637256/62b642d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3BR Prime Luxury near NYC w Arcade Room [](https://www.expedia.co.uk/Yonkers-Hotels-3BR-Prime-Luxury-Near-NYC-W-Arcade-Room.h114637256.Hotel-Information) Southeast Yonkers 8.0/10 Very good (1 review) "We thought we rented the entire property, but was half of it. expect a lot of stairs. No bath tubs but two showers. some door knobs and locks need maintenance, but overall nice clean rooms." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller £300 includes taxes & fees 23 Feb - 24 Feb [](https://www.expedia.co.uk/Yonkers-Hotels-3BR-Prime-Luxury-Near-NYC-W-Arcade-Room.h114637256.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/92000000/92000000/91998600/91998590/a15ca564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/92000000/92000000/91998600/91998590/bb3d83e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/92000000/91998600/91998590/cc196904.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/92000000/92000000/91998600/91998590/5b69a2fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 3 Bd Home Pet Friendly, Parking and Laundry [](https://www.expedia.co.uk/Stamford-Hotels-Spacious-3-Bd-Home-Pet-Friendly.h91998590.Hotel-Information) Cove - East Side - Shippan 9.4/10 Exceptional (3 reviews) "the home was nice clean if in the area I would stay here again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) james w. £330 includes taxes & fees 20 Feb - 21 Feb [](https://www.expedia.co.uk/Stamford-Hotels-Spacious-3-Bd-Home-Pet-Friendly.h91998590.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=2026-03-05&endDate=2026-03-06®ionId=6190653&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Holiday Sale Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save. [Book now](https://expedia.co.uk/cheap-deals?rfrr=AA_SPRING_PROMO_6190653) ## Find holiday rentals that suit your style Aparthotels [](https://www.expedia.co.uk/Hotel-Search?destination=Ossining%2C+New+York%2C+United+States+of+America®ionId=6190653&latLong=41.162872%2C-73.861526&adults=2&startDate=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=APART_HOTEL) Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Ossining%2C+New+York%2C+United+States+of+America®ionId=6190653&latLong=41.162872%2C-73.861526&adults=2&startDate=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=APARTMENT) Cabins [](https://www.expedia.co.uk/Hotel-Search?destination=Ossining%2C+New+York%2C+United+States+of+America®ionId=6190653&latLong=41.162872%2C-73.861526&adults=2&startDate=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=CABIN) Villas [](https://www.expedia.co.uk/Hotel-Search?destination=Ossining%2C+New+York%2C+United+States+of+America®ionId=6190653&latLong=41.162872%2C-73.861526&adults=2&startDate=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=VILLA) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Ossining%2C+New+York%2C+United+States+of+America®ionId=6190653&latLong=41.162872%2C-73.861526&adults=2&startDate=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=VACATION_HOME) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Ossining%2C+New+York%2C+United+States+of+America®ionId=6190653&latLong=41.162872%2C-73.861526&adults=2&startDate=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=COTTAGE) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=Ossining%2C+New+York%2C+United+States+of+America®ionId=6190653&latLong=41.162872%2C-73.861526&adults=2&startDate=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=CONDO) Residences [](https://www.expedia.co.uk/Hotel-Search?destination=Ossining%2C+New+York%2C+United+States+of+America®ionId=6190653&latLong=41.162872%2C-73.861526&adults=2&startDate=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=RESIDENCE) ![](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%2FOssining-Private-Holiday-Homes.d6190653-aaPrivateHolidayHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FOssining-Private-Holiday-Homes.d6190653-aaPrivateHolidayHomes.Travel-Guide-Accommodation) ## Top Ossining Hotel Reviews ![Westchester Marriott](https://images.trvl-media.com/lodging/1000000/20000/10900/10829/w3995h2667x0y0-3f6e8d0f_y.jpg) ### Westchester Marriott 10/10 Excellent "Rooms were spotless.. staff was very accommodating... hospitalilty at its best!" [](https://expedia.co.uk/Tarrytown-Hotels-Westchester-Marriott.h10829.Hotel-Information) ![Hampton Inn & Suites Yonkers - Westchester](https://images.trvl-media.com/lodging/16000000/15740000/15731000/15730982/2770772f_y.jpg) ### Hampton Inn & Suites Yonkers - Westchester 10/10 Excellent "Very clean " [](https://expedia.co.uk/White-Plains-Hotels-Hampton-Inn-Suites-Yonkers-Westchester.h15730982.Hotel-Information) ![Baymont by Wyndham White Plains - Elmsford](https://images.trvl-media.com/lodging/1000000/10000/500/438/w8985h6000x10y0-9d556f34_y.jpg) ### Baymont by Wyndham White Plains - Elmsford 10/10 Excellent "Room was clean" [](https://expedia.co.uk/White-Plains-Hotels-La-Quinta-Inn-Suites-By-Wyndham-White-Plains-Elmsford.h438.Hotel-Information) ![Royal Regency Hotel](https://images.trvl-media.com/lodging/1000000/50000/40900/40814/c5903df6_y.jpg) ### Royal Regency Hotel 10/10 Excellent "The customer service and cleanliness of the room made our stay amazing. I would recommend this hotel to anyone who wants to to get away for a while , the area is nice and quiet " [](https://expedia.co.uk/White-Plains-Hotels-Royal-Regency-Hotel.h40814.Hotel-Information) ![Ramada by Wyndham Bronx](https://images.trvl-media.com/lodging/1000000/470000/462500/462463/c9951f9d_y.jpg) ### Ramada by Wyndham Bronx 10/10 Excellent "Great place! " [](https://expedia.co.uk/New-York-Hotels-Ramada-By-Wyndham-Bronx.h462463.Hotel-Information) ![Hampton Inn White Plains/Tarrytown](https://images.trvl-media.com/lodging/1000000/30000/23300/23291/d5b0e16e_y.jpg) ### Hampton Inn White Plains/Tarrytown 10/10 Excellent "Very clean room, great staff and the breakfast selection was the best!" [](https://expedia.co.uk/White-Plains-Hotels-Hampton-Inn-White-Plains.h23291.Hotel-Information) ![Royal Hotel Bronx](https://images.trvl-media.com/lodging/93000000/92010000/92007800/92007795/18a85357_y.jpg) ### Royal Hotel Bronx 10/10 Excellent "Great hotel great price " [](https://expedia.co.uk/New-York-Hotels-Royal-Hotel-Bronx.h92007795.Hotel-Information) ![LIV Hotel Bronx](https://images.trvl-media.com/lodging/118000000/117970000/117967600/117967593/1c497b69_y.jpg) ### LIV Hotel Bronx 10/10 Excellent "The room was spotless.yet only one washcloth.plus 2 towels" [](https://expedia.co.uk/New-York-Hotels-LIV-Hotel-Bronx.h117967593.Hotel-Information) ![DoubleTree by Hilton Stamford](https://images.trvl-media.com/lodging/1000000/10000/5300/5292/f2f8be91_y.jpg) ### DoubleTree by Hilton Stamford 10/10 Excellent "great staff!" [](https://expedia.co.uk/Stamford-Hotels-Hilton-Stamford-Hotel-Executive-Meeting-Center.h5292.Hotel-Information) ## Find out more about Ossining ## Ossining Holiday Homes information | Number of reviews | 163 | | ----------------- | ----------------- | | Accommodation | 325 Holiday Homes | | Lowest Price | £102 | | Highest Price | £712 | ## Explore a world of travel with Expedia - More ways to book - [Book Holiday Homes in Ossining on Expedia.com ](https://www.expedia.com/Ossining-Private-Vacation-Homes.d6190653-aaPrivateVacationHomes.Travel-Guide-Accommodation)