Title: Highland Vacation Rentals from $223: Search Short-Term Rentals | Expedia.com [Highland Travel Guide](https://expedia.com/Highland.dx115050)[Hotels in Highland](https://expedia.com/Highland-Hotels.d115050.Travel-Guide-Hotels)[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) ![Walking across the walkway over the Hudson, get there early to avoid parking issues. Great place to walk your dog!](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 [Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=115050&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=115050&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three 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 four 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) ## Our top choices for Highland vacation rentals ![House | 7 bedrooms](https://images.trvl-media.com/lodging/122000000/121910000/121901300/121901234/af5902b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House | 7 bedrooms](https://images.trvl-media.com/lodging/122000000/121910000/121901300/121901234/643a1d73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House | 7 bedrooms](https://images.trvl-media.com/lodging/122000000/121910000/121901300/121901234/e36fc455.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House | 7 bedrooms](https://images.trvl-media.com/lodging/122000000/121910000/121901300/121901234/a935500d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Cornwall [](https://www.expedia.com/Cornwall-Hotels-West-Point-Villa-Jacuzzi-Pool-BBQ-Games-Pets.h121901234.Hotel-Information) [](https://www.expedia.com/Cornwall-Hotels-West-Point-Villa-Jacuzzi-Pool-BBQ-Games-Pets.h121901234.Hotel-Information) ![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711152/be62ef7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711152/28da73c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711152/w1346h900x0y0-2cb73b73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711152/8de040af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Monroe [](https://www.expedia.com/Monroe-Hotels-Studio-Retreat-Near-Woodbury-Commons-Legoland.h123711152.Hotel-Information) [](https://www.expedia.com/Monroe-Hotels-Studio-Retreat-Near-Woodbury-Commons-Legoland.h123711152.Hotel-Information) ![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711155/e3793e31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711155/w1350h896x0y0-b3647d4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711155/ab3caa89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711155/2cc70a56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Monroe [](https://www.expedia.com/Monroe-Hotels-Bright-Studio-Retreat-W-Deck-Nature-Views.h123711155.Hotel-Information) [](https://www.expedia.com/Monroe-Hotels-Bright-Studio-Retreat-W-Deck-Nature-Views.h123711155.Hotel-Information) ![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711154/901afe1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711154/414f3605.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711154/91a23b03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711154/7aa0c18f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Monroe [](https://www.expedia.com/Monroe-Hotels-Cozy-Modern-Studio-Near-Lake-Porch-Fire-Pit.h123711154.Hotel-Information) [](https://www.expedia.com/Monroe-Hotels-Cozy-Modern-Studio-Near-Lake-Porch-Fire-Pit.h123711154.Hotel-Information) ![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/124000000/123710000/123706400/123706320/ce02298f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/124000000/123710000/123706400/123706320/da2a0ae3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/124000000/123710000/123706400/123706320/c81a0e54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/124000000/123710000/123706400/123706320/f3cbf51d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Monroe [](https://www.expedia.com/Monroe-Hotels-Rustic-Lakefront-Studio-With-Deck-Workspace.h123706320.Hotel-Information) [](https://www.expedia.com/Monroe-Hotels-Rustic-Lakefront-Studio-With-Deck-Workspace.h123706320.Hotel-Information) ![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/124000000/123710000/123706400/123706319/c1793b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/124000000/123710000/123706400/123706319/de519221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/124000000/123710000/123706400/123706319/f2c259f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/124000000/123710000/123706400/123706319/bcf66280.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Monroe [](https://www.expedia.com/Monroe-Hotels-Rustic-Lakefront-Studio-W-Deck-Workspace.h123706319.Hotel-Information) [](https://www.expedia.com/Monroe-Hotels-Rustic-Lakefront-Studio-W-Deck-Workspace.h123706319.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=2026-03-12&endDate=2026-03-13®ionId=115050&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-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=VR_SPRING_PROMO_115050) ## 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=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&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=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&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=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&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=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&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=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=VILLA) Condos [](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=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=CONDO) 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=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&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-Vacation-Rentals.d115050.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FHighland-Vacation-Rentals.d115050.Travel-Guide-VacationRentals) ## Top Highland Hotel Reviews ![Inn at Bellefield / Hyde Park, Residence Inn by Marriott](https://images.trvl-media.com/lodging/100000000/99860000/99850800/99850733/w4000h2662x0y0-e2ffacae_y.jpg) ### Inn at Bellefield / Hyde Park, Residence Inn by Marriott 10/10 Excellent "Clean room, staff, and amenities were phenomenal " [](https://expedia.com/Hyde-Park-Hotels-Inn-At-Bellefield-Hyde-Park.h99850733.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 "Clean Room, courteous front desk attendants" [](https://expedia.com/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information) ![Courtyard by Marriott Poughkeepsie](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2_y.jpg) ### Courtyard by Marriott Poughkeepsie 10/10 Excellent "Easy check-in/out. Staff very personable. Clean. " [](https://expedia.com/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information) ![Hampton Inn Kingston](https://images.trvl-media.com/lodging/2000000/1670000/1662000/1661941/21cb7965_y.jpg) ### Hampton Inn Kingston 10/10 Excellent "Clean and friendly staff " [](https://expedia.com/Kingston-Hotels-Hampton-Inn-Kingston.h1661941.Hotel-Information) ![Hampton Inn by Hilton New Paltz](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/bd59d6cb_y.jpg) ### Hampton Inn by Hilton New Paltz 10/10 Excellent "Great nice friendly staff good breakfast clean room well maintained but the pool did not feel heated which is fine" [](https://expedia.com/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.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 "I recently stayed at the Hyatt Place Poughkeepsie and had a mixed experience. First, the positives: the staff were absolutely awesome—super friendly and helpful from check-in to check-out. The room was spotless, and the pool was clean and well-maintained, which we really enjoyed. However, I was disappointed by the breakfast situation. I was under the impression that breakfast was free, as it is at most Hyatt Place locations, but I ended up having to pay for it. It seems this location might be one of the few testing a "paid breakfast" model or requiring a specific room rate to get it for free. Pro-tip: Check your booking details or ask at the front desk before you head down to eat so you aren't surprised by the bill!" [](https://expedia.com/Poughkeepsie-Hotels-Hyatt-Place-Poughkeepsie.h37960419.Hotel-Information) ![Holiday Inn Express & Suites Kingston-Ulster by IHG](https://images.trvl-media.com/lodging/17000000/16110000/16102700/16102650/815da7c6_y.jpg) ### Holiday Inn Express & Suites Kingston-Ulster by IHG 10/10 Excellent "Staff was amazing and super sweet " [](https://expedia.com/Kingston-Hotels-Holiday-Inn-Express-Suites-Kingston-Ulster.h16102650.Hotel-Information) ![Beekman Arms Hotel](https://images.trvl-media.com/lodging/13000000/12620000/12611900/12611810/ab673905_y.jpg) ### Beekman Arms Hotel 10/10 Excellent "Yes, except the bathtub faucet was consistently leaking" [](https://expedia.com/Poughkeepsie-Hotels-Beekman-Arms-Hotel.h12611810.Hotel-Information) ![Best Western Plus Kingston Hotel And Conference Center](https://images.trvl-media.com/lodging/1000000/10000/6100/6056/d4db98bc_y.jpg) ### Best Western Plus Kingston Hotel And Conference Center 10/10 Excellent "Keep it up" [](https://expedia.com/Kingston-Hotels-Best-Western-Plus-Kingston-Hotel-And-Conference-Center.h6056.Hotel-Information) ## Find out more about Highland **Everything you need to know about Highland vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Highland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on. There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Highland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. **Highland vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Highland. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Highland in high season. Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $223 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals! **How to find incredible deals on Highland rentals** At Expedia, we put the best Highland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. To find some top Highland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Highland vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Highland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. ## Explore a world of travel with Expedia - Trending destinations on Expedia.com - All accommodation types in Highland ### Trending destinations on Expedia.com - [Destin Vacation Rentals ](https://www.expedia.com/Destin-Vacation-Rentals.d6906.Travel-Guide-VacationRentals) - [Panama City Vacation Rentals ](https://www.expedia.com/Panama-City-Beach-Vacation-Rentals.d8021.Travel-Guide-VacationRentals) - [Hilton Head Vacation Rentals ](https://www.expedia.com/Hilton-Head-Island-Vacation-Rentals.d601684.Travel-Guide-VacationRentals) - [Gulf Shores Vacation Rentals ](https://www.expedia.com/Gulf-Shores-Vacation-Rentals.d603078.Travel-Guide-VacationRentals) - [Key West Vacation Rentals ](https://www.expedia.com/Key-West-Vacation-Rentals.d1187.Travel-Guide-VacationRentals) - [Gatlinburg Vacation Rentals ](https://www.expedia.com/Gatlinburg-Vacation-Rentals.d7474.Travel-Guide-VacationRentals) - 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[Vacation Homes in Highland ](https://expedia.com/Highland-Private-Vacation-Homes.d115050-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Apartments in Highland ](https://expedia.com/Highland-Apartments.d115050-aaApartments.Travel-Guide-Accommodation) - [Cottages in Highland ](https://expedia.com/Highland-Cottages.d115050-aaCottages.Travel-Guide-Accommodation) - [Cabin Rentals in Highland ](https://expedia.com/Highland-Cabins.d115050-aaCabins.Travel-Guide-Accommodation) - [B&B in Highland ](https://expedia.com/Highland-Bed-And-Breakfast.d115050-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Farmstay in Highland ](https://expedia.com/Highland-Agritourism.d115050-aaAgritourism.Travel-Guide-Accommodation) - [Motels in Highland ](https://expedia.com/Highland-Motels.d115050-aaMotels.Travel-Guide-Accommodation) - [Villas in Highland ](https://expedia.com/Highland-Villas.d115050-aaVillas.Travel-Guide-Accommodation) - [Guest Houses in Highland ](https://expedia.com/Highland-Guest-Houses.d115050-aaGuestHouses.Travel-Guide-Accommodation) - 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