Title: Highland, NY Cottage Rentals from $180 | Expedia.com [Highland Travel Guide](https://expedia.com/Highland.dx115050)[Hotels in Highland](https://expedia.com/Highland-Hotels.d115050.Travel-Guide-Hotels)[Vacation Rentals in Highland](https://expedia.com/Highland-Vacation-Rentals.d115050.Travel-Guide-VacationRentals)[Flights to Highland](https://expedia.com/Cheap-Flights-To-Highland.d115050.Travel-Guide-Flights)[Things to do in Highland](https://expedia.com/Things-To-Do-In-Highland.d115050.Travel-Guide-Activities)[Car Rentals in Highland](https://expedia.com/Car-Rentals-In-Highland.d115050.Car-Rental-Guide)[Highland Vacation Packages](https://expedia.com/Highland.d115050.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/115050/513f001c-86fc-4f9b-8930-057b5d34aed2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Allison Alano Flores ![](https://images.trvl-media.com/place/115050/513f001c-86fc-4f9b-8930-057b5d34aed2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=115050&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 two months [May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=115050&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=115050&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 24 - Jul 26](https://www.expedia.com/Hotel-Search?regionId=115050&startDate=2026-07-24&endDate=2026-07-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Highland cottages ![Exterior](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/dabdeda4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/7cf93160.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace, books](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/4fbee988.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace, books](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/cd189b6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks [](https://www.expedia.com/Kerhonkson-Hotels-Dream-Cottage-In-The-Gunks.h83439008.Hotel-Information) Kerhonkson 9.4/10 Exceptional (13 reviews) "Charming and relaxing cottage. Perfect location for hiking or enjoying Lake Minnewaska or Mohonk Preserve. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patrick S. $178 nightly $180 total Apr 9 - Apr 10 Total with taxes and fees [](https://www.expedia.com/Kerhonkson-Hotels-Dream-Cottage-In-The-Gunks.h83439008.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34350000/34340500/34340496/35f82f66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34350000/34340500/34340496/87bd4bba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34350000/34340500/34340496/2a189477.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, stereo](https://images.trvl-media.com/lodging/35000000/34350000/34340500/34340496/73cda0ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Streamside Cottage Half Mile to Town of Woodstock [](https://www.expedia.com/Woodstock-Hotels-Streamside-Cottage-Half-Mile-To-Town-Of-Woodstock.h34340496.Hotel-Information) Woodstock 10/10 Exceptional (275 reviews) "Jane was very nice and accommodating, the cottage was very clean and comfortable, a very relaxing and calming place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Scott $266 nightly $298 total Apr 16 - Apr 17 Total with taxes and fees [](https://www.expedia.com/Woodstock-Hotels-Streamside-Cottage-Half-Mile-To-Town-Of-Woodstock.h34340496.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/110000000/109790000/109781600/109781517/w1287h838x1y0-d9ab4558.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/110000000/109790000/109781600/109781517/147d3620.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/110000000/109790000/109781600/109781517/c3a6ab07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109790000/109781600/109781517/446f5ba8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kapitan’s cottage a Rustic Private Catskill Getaway Near Kingston [](https://www.expedia.com/Kingston-Hotels-Private-In-Nature-Upstate-Rustic-Kapitans-Cottage-Pet-Friendly.h109781517.Hotel-Information) Kingston 9.6/10 Exceptional (10 reviews) "We had a great time. Place is convenient located in proximity of Rosendale and Kingston " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carol N. $347 nightly $389 total Apr 15 - Apr 16 Total with taxes and fees [](https://www.expedia.com/Kingston-Hotels-Private-In-Nature-Upstate-Rustic-Kapitans-Cottage-Pet-Friendly.h109781517.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33910000/33906300/33906244/45714c00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/34000000/33910000/33906300/33906244/5d0b5fdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33910000/33906300/33906244/cd08754d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33910000/33906300/33906244/98243311.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream [](https://www.expedia.com/Kingston-Hotels-Charming-Woodstock-Teahouse-Cottage-By-The-Sawkill-Creek-Trout-Stream.h33906244.Hotel-Information) woodstock 9.0/10 Wonderful (47 reviews) "A gem just minutes from the heart of Woodstock!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susannah H. $278 nightly $311 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Kingston-Hotels-Charming-Woodstock-Teahouse-Cottage-By-The-Sawkill-Creek-Trout-Stream.h33906244.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113160000/113159700/113159615/5de49e46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113160000/113159700/113159615/ffdabe30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113160000/113159700/113159615/6a029a41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113160000/113159700/113159615/d4499593.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro [](https://www.expedia.com/Bloomingburg-Hotels-Charming-Cottage-In-The-Lower-Catskills-Near-Ellenville-And-Wurtsboro.h113159615.Hotel-Information) Bloomingburg 10/10 Exceptional (1 review) "The place was as described, quaint, clean, no issues with communication or check in" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen H. $190 nightly $214 total Apr 17 - Apr 18 Total with taxes and fees [](https://www.expedia.com/Bloomingburg-Hotels-Charming-Cottage-In-The-Lower-Catskills-Near-Ellenville-And-Wurtsboro.h113159615.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.com/Hotel-Search?startDate=2026-04-15&endDate=2026-04-16®ionId=115050&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.com/Hotel-Search?destination=Highland%2C+New+York%2C+United+States+of+America®ionId=115050&latLong=41.720928%2C-73.960136&adults=2&startDate=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=CABIN) Cottages [](https://www.expedia.com/Hotel-Search?destination=Highland%2C+New+York%2C+United+States+of+America®ionId=115050&latLong=41.720928%2C-73.960136&adults=2&startDate=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=COTTAGE) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Highland%2C+New+York%2C+United+States+of+America®ionId=115050&latLong=41.720928%2C-73.960136&adults=2&startDate=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=VACATION_HOME) Apartments [](https://www.expedia.com/Hotel-Search?destination=Highland%2C+New+York%2C+United+States+of+America®ionId=115050&latLong=41.720928%2C-73.960136&adults=2&startDate=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=APARTMENT) Villas [](https://www.expedia.com/Hotel-Search?destination=Highland%2C+New+York%2C+United+States+of+America®ionId=115050&latLong=41.720928%2C-73.960136&adults=2&startDate=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=VILLA) Chalets [](https://www.expedia.com/Hotel-Search?destination=Highland%2C+New+York%2C+United+States+of+America®ionId=115050&latLong=41.720928%2C-73.960136&adults=2&startDate=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=CHALET) ![](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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FHighland-Cottages.d115050-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FHighland-Cottages.d115050-aaCottages.Travel-Guide-Accommodation) ## Top Highland Hotel Reviews ![SureStay Plus Hotel by Best Western Highland Poughkeepsie](https://images.trvl-media.com/lodging/1000000/920000/918800/918797/11ffbd82_y.jpg) ### SureStay Plus Hotel by Best Western Highland Poughkeepsie 10/10 Excellent "Breakfast was great, and also I would like to give an 100% to Ryan the night auditor, great service beyond. He represent what is a service about. Awesome n Outstanding " [](https://expedia.com/Poughkeepsie-Hotels-SureStay-Plus-Hotel-By-Best-Western-Highland-Poughkeepsie.h918797.Hotel-Information) ![Hyatt Place Poughkeepsie / Hudson Valley](https://images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/9bb388bd_y.jpg) ### Hyatt Place Poughkeepsie / Hudson Valley 10/10 Excellent "Super friendly staff. Beautiful, clean rooms. Great indoor pool and gym." [](https://expedia.com/Poughkeepsie-Hotels-Hyatt-Place-Poughkeepsie.h37960419.Hotel-Information) ![Woodstock Way Hotel](https://images.trvl-media.com/lodging/92000000/91580000/91577900/91577819/f0a67aac_y.jpg) ### Woodstock Way Hotel 10/10 Excellent "Stunning flat! Super clean." [](https://expedia.com/Woodstock-Hotels-Woodstock-Way-Hotel.h91577819.Hotel-Information) ![Inn at Bellefield / Hyde Park, Residence Inn by Marriott](https://images.trvl-media.com/lodging/100000000/99860000/99850800/99850733/1ee75d40_y.jpg) ### Inn at Bellefield / Hyde Park, Residence Inn by Marriott 10/10 Excellent "Hotel gym was fantastic, storyteller restaurant food & drinks amazing. One of the best complimentary breakfasts we’ve ever had. Plan on returning. 5 stars all the way!" [](https://expedia.com/Hyde-Park-Hotels-Inn-At-Bellefield-Hyde-Park.h99850733.Hotel-Information) ![Spark by Hilton Fishkill](https://images.trvl-media.com/lodging/1000000/10000/2700/2642/b112328f_y.jpg) ### Spark by Hilton Fishkill 10/10 Excellent "The breakfast menu can improve when people stay more than one night. Room space is good." [](https://expedia.com/Fishkill-Hotels-Spark-By-Hilton-Fishkill.h2642.Hotel-Information) ![Hampton Inn by Hilton New Paltz](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/dab27d3b_y.jpg) ### Hampton Inn by Hilton New Paltz 10/10 Excellent "The hotel was nice and clean. No musty stale smell in the room. Breakfast had a good variety with plenty of seating." [](https://expedia.com/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information) ![DoubleTree by Hilton Poughkeepsie Convention Center](https://images.trvl-media.com/lodging/1000000/20000/14600/14563/875b6b8c_y.jpg) ### DoubleTree by Hilton Poughkeepsie Convention Center 10/10 Excellent "The staff was helpful and friendly " [](https://expedia.com/Poughkeepsie-Hotels-Poughkeepsie-Grand-Hotel.h14563.Hotel-Information) ![Best Western Plus Kingston Hotel And Conference Center](https://images.trvl-media.com/lodging/1000000/10000/6100/6056/d26fbbb0_y.jpg) ### Best Western Plus Kingston Hotel And Conference Center 8/10 Good "Hotel is very dated 70s, dark, poor lighting everything is dark beige and dark brown, walls doors, carpet. " [](https://expedia.com/Kingston-Hotels-Best-Western-Plus-Kingston-Hotel-And-Conference-Center.h6056.Hotel-Information) ![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/38c7288e_y.jpg) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point 8/10 Good "Good" [](https://expedia.com/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ## Find out more about Highland ## Highland Cottages information | Number of reviews | 346 | | ----------------- | ------------ | | Accommodation | 114 Cottages | | Lowest Price | $180 | | Highest Price | $389 | ## Frequently asked questions ### Why book your cottage in Highland with Expedia? ### How can I find cheap cottages in Highland? ### What is there to do in Highland near my cottage? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Hotels near Walkway Over the Hudson State Historic Park ](https://www.expedia.com/Walkway-Over-The-Hudson-State-Historic-Park-Hotels.0-l6222117-0.Travel-Guide-Filter-Hotels) - 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