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) ![Interior](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/c4f41298.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 8 - Apr 9 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) ![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) ### 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 $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) ![Smart TV](https://images.trvl-media.com/lodging/110000000/109790000/109781600/109781517/966dbd3a.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) ![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. $341 nightly $381 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) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33910000/33906300/33906244/45714c00.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) ![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) ![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. $280 nightly $314 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/114000000/113160000/113159700/113159615/6a029a41.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) ### 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=2026-04-13&endDate=2026-04-14®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=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&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=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&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=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&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=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&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=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&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=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&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 ![Courtyard by Marriott Poughkeepsie](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2_y.jpg) ### Courtyard by Marriott Poughkeepsie 10/10 Excellent "Hotel was very clean and check in and out was quick and effecient. Compimentary breakfast or at least coffee would have been nice, as most similar hotels offer. Also the bar did not open til 6pm....we would have liked to have had a cocktail when we checked in at 4 or 5 prior to leaving for the function we had to go to. Overall very nice hotel." [](https://expedia.com/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.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 6/10 Okay "First there were no cookies offered at check-in. We had to go down later to ask. This is their schtick, you’d think they be on top of it. Not a huge deal but again- it’s their thing… the cookies… Second-Located next to a convention center so we’re told if you leave the garage there might not be parking later! This is why we stayed here so there was parking available. Figure something out! Have specific parking for your guests! Should be priority. Third- the room had visible crumbs on the floor, the toilet handle had to be held in order to flush entirely and this was not a quick process. The shower did not get hot until the shower ended- 10 minutes. The room temperature was 75 upon arrival, The air was adjusted- maintenance was called later in the evening, the solution- opened a window. The temperature was 76 when we left the next day with the window open! Checkout is at 11\. At 930 housekeeping is knocking on the door to see if we’ve checked out! This is not a hotel I would stay at again. " [](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 10/10 Excellent "Had a pleasant and comfortable stay." [](https://expedia.com/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.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 "The only drawback of this hotel is the Storyteller restaurant and lounge. It's such a beautiful room but the options there are so limited if you want to just relax and have a drink or small bite in the afternoon. I was there with my family from 3pm - 5pm and we managed to get coffee and one iced tea but it was not as easy as you'd think for such a lovely room and bar." [](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 6/10 Okay "Only hot option was hard boiled eggs. Toaster only toasted light, even on dark option. Place was clean and organized. No vending machines anywhere in the building. Our room on the third floor smelled like dirty socks unless the AC was on. The thermostat only worked when it wanted to. Saw the front desk lady throw her cigarette down in front of the main door on her way in. " [](https://expedia.com/Fishkill-Hotels-Spark-By-Hilton-Fishkill.h2642.Hotel-Information) ![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) ![HYATT house Fishkill/Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1340000/1336000/1335929/w3836h2558x4y3-858cbdd6_y.jpg) ### HYATT house Fishkill/Poughkeepsie 10/10 Excellent "Very friendly staff, bed was a little soft for my liking." [](https://expedia.com/Poughkeepsie-Hotels-HYATT-House-FishkillPoughkeepsie.h1335929.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) ## Find out more about Highland ## Highland Cottages information | Number of reviews | 345 | | ----------------- | ------------ | | Accommodation | 114 Cottages | | Lowest Price | $180 | | Highest Price | $381 | ## 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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