Title: Town of Highland Vacation Rentals from $160: Search Short-Term Rentals | Expedia.com [Town of Highland Hotels](https://expedia.com/Destinations-In-Town-Of-Highland.d553248635976002184.Hotel-Destinations)[Car Rentals in Town of Highland](https://expedia.com/Destinations-In-Town-Of-Highland.d553248635976002184.Car-Rental-Destinations)[Town of Highland Vacations](https://expedia.com/Town-Of-Highland.d553248635976002184.Destination-Travel-Guides) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.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 ## Top Cities in Town of Highland ![Barryville, New York](https://images.trvl-media.com/place/6069726/5af18903-fe76-4a6e-b144-ff203490f6ee.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Barryville [](https://expedia.com/Barryville-Vacation-Rentals.d6069726.Travel-Guide-VacationRentals) ## Our top choices for Town of Highland vacation rentals ![Premium Cabin | View from room](https://images.trvl-media.com/lodging/73000000/72380000/72374200/72374196/b3326a39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room | Private kitchenette | Microwave, coffee/tea maker, electric kettle, cookware/dishes/utensils](https://images.trvl-media.com/lodging/73000000/72380000/72374200/72374196/f9e87bdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Cabin | In-room dining](https://images.trvl-media.com/lodging/73000000/72380000/72374200/72374196/53f4d8cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72380000/72374200/72374196/1a541606.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Rex Hotel [](https://www.expedia.com/Greentown-Hotels-The-Rex.h72374196.Hotel-Information) Greentown 9.6/10 Exceptional (29 reviews) "Place was very cozy, clean and relaxing" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Racquel $169 nightly $185 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/Greentown-Hotels-The-Rex.h72374196.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/101000000/100310000/100305100/100305048/6cd2eb0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, towels, soap, shampoo](https://images.trvl-media.com/lodging/101000000/100310000/100305100/100305048/e8bb4156.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Tent, 2 Double Beds, Hot Tub | Free WiFi, bed sheets](https://images.trvl-media.com/lodging/101000000/100310000/100305100/100305048/84cfcd31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100310000/100305100/100305048/eedcab48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ferncrest Campground [](https://www.expedia.com/Greentown-Hotels-Ferncrest.h100305048.Hotel-Information) Greentown 9.4/10 Exceptional (16 reviews) "Attentive staff, very detailed information about the campground. Gorgeous, rustic yet fantastic facilities. Second year visiting and we’ll be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Penrhyn $209 nightly $228 total Feb 9 - Feb 10 Total with taxes and fees [](https://www.expedia.com/Greentown-Hotels-Ferncrest.h100305048.Hotel-Information) ![Apartment (0 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369761/fa957375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (0 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369761/21da3033.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (0 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369761/d01ab563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (0 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369761/f734cc29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Close to Trails: Studio w/ Water Views [](https://www.expedia.com/Basher-Kill-Studio-W-Water-Views-Close-To-Trails.h114369761.Hotel-Information) Westbrookville $211 nightly $238 total Feb 28 - Mar 1 Total with taxes and fees [](https://www.expedia.com/Basher-Kill-Studio-W-Water-Views-Close-To-Trails.h114369761.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=2026-02-20&endDate=2026-02-21®ionId=553248635976002184&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=Town+of+Highland%2C+New+York%2C+United+States+of+America®ionId=553248635976002184&latLong=41.529846%2C-74.897491&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=CABIN) Apartments [](https://www.expedia.com/Hotel-Search?destination=Town+of+Highland%2C+New+York%2C+United+States+of+America®ionId=553248635976002184&latLong=41.529846%2C-74.897491&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=APARTMENT) Villas [](https://www.expedia.com/Hotel-Search?destination=Town+of+Highland%2C+New+York%2C+United+States+of+America®ionId=553248635976002184&latLong=41.529846%2C-74.897491&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=VILLA) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Town+of+Highland%2C+New+York%2C+United+States+of+America®ionId=553248635976002184&latLong=41.529846%2C-74.897491&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=APART_HOTEL) Cottages [](https://www.expedia.com/Hotel-Search?destination=Town+of+Highland%2C+New+York%2C+United+States+of+America®ionId=553248635976002184&latLong=41.529846%2C-74.897491&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=COTTAGE) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Town+of+Highland%2C+New+York%2C+United+States+of+America®ionId=553248635976002184&latLong=41.529846%2C-74.897491&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=VACATION_HOME) Condos [](https://www.expedia.com/Hotel-Search?destination=Town+of+Highland%2C+New+York%2C+United+States+of+America®ionId=553248635976002184&latLong=41.529846%2C-74.897491&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=CONDO) Chalets [](https://www.expedia.com/Hotel-Search?destination=Town+of+Highland%2C+New+York%2C+United+States+of+America®ionId=553248635976002184&latLong=41.529846%2C-74.897491&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&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%2FDestinations-In-Town-Of-Highland.d553248635976002184.Vacation-Rental-Destinations)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Town-Of-Highland.d553248635976002184.Vacation-Rental-Destinations) ## Top Town of Highland Hotel Reviews ![The Kartrite Resort & Indoor Waterpark](https://images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/90ceac4d_y.jpg) ### The Kartrite Resort & Indoor Waterpark 10/10 Excellent "Great stay" [](https://expedia.com/Monticello-Hotels-The-Kartrite-Resort-Indoor-Waterpark.h31681637.Hotel-Information) ![Best Western Monticello](https://images.trvl-media.com/lodging/1000000/30000/26600/26518/68dcbd68_y.jpg) ### Best Western Monticello 10/10 Excellent "Clean room. Great staff! " [](https://expedia.com/Monticello-Hotels-Best-Western-Monticello.h26518.Hotel-Information) ![The Alder at Resorts World Catskills](https://images.trvl-media.com/lodging/101000000/101000000/100997000/100996967/9db559da_y.jpg) ### The Alder at Resorts World Catskills 10/10 Excellent "GREAT SPOT" [](https://expedia.com/Monticello-Hotels-The-Alder-At-Resorts-World-Catskills.h100996967.Hotel-Information) ![Cove Haven Resort](https://images.trvl-media.com/lodging/1000000/40000/34700/34685/efde6748_y.jpg) ### Cove Haven Resort 10/10 Excellent "It was the setting. While I’m not into Hallmark movies, my wife very much is and we both referenced that throughout our stay. The staff was amazing, the fact that the deer in the area are so calm and feed is readily available at the gift shop helped my wife feel like a Disney princess. The events and amenities work well to have a full day without leaving the campus. A favorite of mine was talking to an old gentleman in the Blizzard lounge while playing checkers with my wife and just sharing life stories. It was cozy and we are definitely coming back in the future. It was worth the cost (we had a pool in our room!). We are already talking with my brother and his wife about dueling couples next time. Amazing stay. Definitely recommend!" [](https://expedia.com/Lakeville-Hotels-Cove-Haven-Resort.h34685.Hotel-Information) ![Resorts World Catskills Casino](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/ecb80f49_y.jpg) ### Resorts World Catskills Casino 10/10 Excellent "Staff was great " [](https://expedia.com/Monticello-Hotels-Resorts-World-Catskills-Casino.h23970267.Hotel-Information) ![Ledges Hotel](https://images.trvl-media.com/lodging/6000000/5330000/5320100/5320032/7e678dea_y.jpg) ### Ledges Hotel 10/10 Excellent "Beautiful setting. The Lounge area and fireplace were perfect for a winter stay. The history of the building gave it an extra layer of interest. The rooms were unique, a nice mix of modern industrial and comfort. The bar and restaurant were fantastic, loved the view of the snowy waterfall. We’d love to return in the warmer weather to enjoy the outdoor decks. " [](https://expedia.com/Hawley-Hotels-Ledges-Hotel.h5320032.Hotel-Information) ![Villa Roma Resort and Conference Center](https://images.trvl-media.com/lodging/1000000/910000/902000/901998/2e43c618_y.jpg) ### Villa Roma Resort and Conference Center 10/10 Excellent "School trip. Got my own room " [](https://expedia.com/Monticello-Hotels-Villa-Roma-Resort-And-Conference-Center.h901998.Hotel-Information) ![Hampton Inn Monticello](https://images.trvl-media.com/lodging/76000000/75040000/75030700/75030626/41b49dd0_y.jpg) ### Hampton Inn Monticello 10/10 Excellent "Our stay was great. Clean room and comfortable. Breakfast was a cherry on top. Will stay again. " [](https://expedia.com/Monticello-Hotels-Hampton-Inn-Monticello.h75030626.Hotel-Information) ![Four Seasons For Fun](https://images.trvl-media.com/lodging/101000000/100660000/100655800/100655797/84504c56_y.jpg) ### Four Seasons For Fun 10/10 Excellent "Great spot" [](https://expedia.com/Lakeville-Hotels-Four-Seasons-For-Fun.h100655797.Hotel-Information) ## Find out more about Town of Highland ## Discover your perfect Town of Highland vacation rental with Expedia #### How many vacation rentals are available in Town of Highland? Expedia has plenty of vacation rentals to choose from in and around Town of Highland, so you’re guaranteed to find the right one for you. #### How much is a vacation rental in Town of Highland? The selection of Town of Highland vacation rentals we have selected for you start as low as $160 per night. Entering your travel dates in the search wizard you might find even better deals! #### What type of vacation rental can I get in Town of Highland? Vacation rentals in Town of Highland come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Town of Highland vacation rentals to suit everyone. #### Why should I choose a vacation rental in Town of Highland? Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Town of Highland vacation rental often works out to be a fantastic, cost-effective option for [groups](https://www.expedia.com/lp/b/vr/large) and [families](https://www.expedia.com/lp/b/vr/family) visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. #### How do I find the best deal on a vacation rental in Town of Highland? Find vacation rentals in Town of Highland by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Town of Highland. #### What amenities are available in a vacation rental in Town of Highland? The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a [swimming pool](https://www.expedia.com/lp/b/vr/private-pool) is more your thing. Of course, there’s always the treat of having [your own hot tub](https://www.expedia.com/lp/b/vr/hot-tub). Expedia has a vast range of amenities in Town of Highland vacation rentals designed to suit every budget and trip type. #### When is the best time to stay in a vacation rental in Town of Highland? Everytime is a great time to head to Town of Highland! Staying in a Town of Highland vacation rentals you will always find lots going on to keep you entertained. #### Why book a vacation rental with Expedia? Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Town of Highland. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Town of Highland vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Town of Highland, you can save even more. #### Can I cancel my vacation rental through Expedia? Yes, you can cancel or change your Town of Highland vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted. ## Explore a world of travel with Expedia - Popular Town of Highland Cities - All accommodation types in Town of Highland - [Barryville Vacation Rentals ](https://expedia.com/Barryville-Vacation-Rentals.d6069726.Travel-Guide-VacationRentals) - [Vacation Homes in Town of Highland ](https://expedia.com/Town-Of-Highland-Private-Vacation-Homes.d553248635976002184-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Cottages in Town of Highland ](https://expedia.com/Town-Of-Highland-Cottages.d553248635976002184-aaCottages.Travel-Guide-Accommodation) - [Cabin Rentals in Town of Highland ](https://expedia.com/Town-Of-Highland-Cabins.d553248635976002184-aaCabins.Travel-Guide-Accommodation) - [Chalets in Town of Highland ](https://expedia.com/Town-Of-Highland-Chalets.d553248635976002184-aaChalets.Travel-Guide-Accommodation) - [Apartments in Town of Highland ](https://expedia.com/Town-Of-Highland-Apartments.d553248635976002184-aaApartments.Travel-Guide-Accommodation) - [Farmstay in Town of Highland ](https://expedia.com/Town-Of-Highland-Agritourism.d553248635976002184-aaAgritourism.Travel-Guide-Accommodation) - [RV Parks in Town of Highland ](https://expedia.com/Town-Of-Highland-RV-Parks.d553248635976002184-aaRVParks.Travel-Guide-Accommodation) - [Resorts in Town of Highland ](https://expedia.com/Town-Of-Highland-Resorts.d553248635976002184-aaResorts.Travel-Guide-Accommodation) - [Villas in Town of Highland ](https://expedia.com/Town-Of-Highland-Villas.d553248635976002184-aaVillas.Travel-Guide-Accommodation) - [Motels in Town of Highland ](https://expedia.com/Town-Of-Highland-Motels.d553248635976002184-aaMotels.Travel-Guide-Accommodation) - [Inns in Town of Highland ](https://expedia.com/Town-Of-Highland-Inns.d553248635976002184-aaInns.Travel-Guide-Accommodation) - [B&B in Town of Highland ](https://expedia.com/Town-Of-Highland-Bed-And-Breakfast.d553248635976002184-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Town of Highland ](https://expedia.com/Town-Of-Highland-Guest-Houses.d553248635976002184-aaGuestHouses.Travel-Guide-Accommodation) - [Condo Rentals in Town of Highland ](https://expedia.com/Town-Of-Highland-Condos.d553248635976002184-aaCondos.Travel-Guide-Accommodation) - [Aparthotels in Town of Highland ](https://expedia.com/Town-Of-Highland-Apart-Hotels.d553248635976002184-aaApartHotels.Travel-Guide-Accommodation) - [Lodges in Town of Highland ](https://expedia.com/Town-Of-Highland-Lodges.d553248635976002184-aaLodges.Travel-Guide-Accommodation) - [Country Houses in Town of Highland ](https://expedia.com/Town-Of-Highland-Country-House.d553248635976002184-aaCountryHouse.Travel-Guide-Accommodation)