Title: Highland, NY Cottage Rentals from $181 | 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 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=115050&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=115050&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=115050&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 17 - Jul 19](https://www.expedia.com/Hotel-Search?regionId=115050&startDate=2026-07-17&endDate=2026-07-19&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) ![Fireplace, books](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/cd189b6a.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) ### 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. $179 nightly $181 total Apr 9 - Apr 10 Total with taxes and fees [](https://www.expedia.com/Kerhonkson-Hotels-Dream-Cottage-In-The-Gunks.h83439008.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) ![Interior](https://images.trvl-media.com/lodging/110000000/109790000/109781600/109781517/446f5ba8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/110000000/109790000/109781600/109781517/966dbd3a.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) ### 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. $340 nightly $380 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/Kingston-Hotels-Private-In-Nature-Upstate-Rustic-Kapitans-Cottage-Pet-Friendly.h109781517.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/35000000/34350000/34340500/34340496/9b6fcb92.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) ### 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 (274 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 $264 nightly $296 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) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33910000/33906300/33906244/45714c00.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33910000/33906300/33906244/82fe8688.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) ### 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. $277 nightly $310 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) ![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) ![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) ### 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 1 - Apr 2 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=2026-04-12&endDate=2026-04-13®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=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&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=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&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=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&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=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&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=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&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=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&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 ![Beekman Arms and Delamater Inn](https://images.trvl-media.com/lodging/13000000/12620000/12611900/12611810/b86d31e8_y.jpg) ### Beekman Arms and Delamater Inn 8/10 Good "Room was clean, simple, and quiet. Efficient check--in and check-out. Continental breakfast was a cut above the usual, with good-quality pastries and plenty of options. I would have liked an easy chair and reading lamp in my room, but otherwise it was a nice place to stay - a beautiful historic property. Will try the tavern next time." [](https://expedia.com/Poughkeepsie-Hotels-Beekman-Arms-Hotel.h12611810.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 staff was very courteous & friendly. The room was clean & the breakfast menu was great serving different options every morning. We will stay here again the next time we are in New Paltz." [](https://expedia.com/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information) ![Spark by Hilton Fishkill](https://images.trvl-media.com/lodging/1000000/10000/2700/2642/b112328f_y.jpg) ### Spark by Hilton Fishkill 6/10 Okay "Breakfast was minimal. Room was very clean. Staff not very friendly." [](https://expedia.com/Fishkill-Hotels-Spark-By-Hilton-Fishkill.h2642.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 8/10 Good "Great location for touring the area. RIght across from CIA entrance. Very convenient. Fantastic breakfast. Comfortable room. Only complaint was that the pillows were uncomfortable." [](https://expedia.com/Hyde-Park-Hotels-Inn-At-Bellefield-Hyde-Park.h99850733.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 "The room was very clean and quiet" [](https://expedia.com/Poughkeepsie-Hotels-Hyatt-Place-Poughkeepsie.h37960419.Hotel-Information) ![Residence Inn by Marriott Kingston](https://images.trvl-media.com/lodging/16000000/15720000/15715300/15715238/8885aa53_y.jpg) ### Residence Inn by Marriott Kingston 6/10 Okay "Nice enough place prices adequate" [](https://expedia.com/Kingston-Hotels-Residence-Inn-By-Marriott-Kingston.h15715238.Hotel-Information) ![Hampton Inn & Suites Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/ee108dad_y.jpg) ### Hampton Inn & Suites Poughkeepsie 4/10 Poor "The breakfast menu was fresh and the coffee at all times was a nice perk. The staff at checkout was rude and even though we had asked for adjoining rooms, we were not provided that at check in. We were instead given rooms on opposite floors. There was something spilled on the side table and something on the bottom of the bathroom door. " [](https://expedia.com/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.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 "Clean room, nice staff: front desk Brittany is very nice. Breakfast staff super nice! The hotel looks like new." [](https://expedia.com/Poughkeepsie-Hotels-Poughkeepsie-Grand-Hotel.h14563.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 "Convenient, clean and friendly.. " [](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 | 345 | | ----------------- | ------------ | | Accommodation | 114 Cottages | | Lowest Price | $181 | | Highest Price | $380 | ## 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) - [Poughkeepsie Hotels ](https://www.expedia.com/Poughkeepsie-Hotels.d6056317.Travel-Guide-Hotels) - [Hotels near Marist College ](https://www.expedia.com/Marist-College-Hotels.0-l6158002-0.Travel-Guide-Filter-Hotels) - 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