Title: Town of Highlands Vacation Home Rentals from CA $360: Search Top Private Vacation Homes for Rent | Expedia.ca [Town of Highlands Hotels](https://expedia.ca/Destinations-In-Town-Of-Highlands.d553248635976002149.Hotel-Destinations)[Vacation Rentals in Town of Highlands](https://expedia.ca/Destinations-In-Town-Of-Highlands.d553248635976002149.Vacation-Rental-Destinations)[Town of Highlands Car Rentals](https://expedia.ca/Destinations-In-Town-Of-Highlands.d553248635976002149.Car-Rental-Destinations)[Town of Highlands Vacations](https://expedia.ca/Town-Of-Highlands.d553248635976002149.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/61740e0ab5bcc439bc35d6aac5a94e5b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Town of Highlands Vacation Rentals ## Compare and save ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976002149&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976002149&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976002149&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976002149&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cities in Town of Highlands ![](https://mediaim.expedia.com/destination/1/d0cc470cce0c12eec31b3f6f28539bc4.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### West Point [](https://expedia.ca/West-Point-Private-Vacation-Homes.d9700-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/0dd0b78def315096bc47a57bca0e3daf.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Highland Falls [](https://expedia.ca/Highland-Falls-Private-Vacation-Homes.d9540-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Featured Vacation Homes in Town of Highlands ![Terrace/patio](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863201/07973626.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863201/c485256a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863201/dc1cc284.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863201/fa190f5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9 Newburgh 9.8/10 Exceptional (15) "The house was beautiful inside and out. Owners were so nice and made sure we had everything we needed for our weekend getaway." [](https://www.expedia.ca/Newburgh-Hotels-Ultimate-Lakeside-Getaway-On-5-Acres-Private-Dock.h114863201.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/101000000/100670000/100661800/100661800/eb403423.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100670000/100661800/100661800/719061a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/101000000/100670000/100661800/100661800/774e864f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/101000000/100670000/100661800/100661800/b92fd186.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Home with Hot Tub, Kayaks, and Fast Wifi Greenwood Lake 10/10 Exceptional (23) "Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. " CA $300 CA $724 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Greenwood-Lake-Hotels-Waterfront-Modern-Home-WFast-Wifi-400m-From-DT.h100661800.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71960000/71952400/71952323/f6623e06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71960000/71952400/71952323/550eef50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/72000000/71960000/71952400/71952323/5aa43ade.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/72000000/71960000/71952400/71952323/0229fe97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Privacy in the hills one hour from NYC and minutes to Breakneck Mtn. Carmel Hamlet 10/10 Exceptional (90) "My family and I loved this property! We enjoyed walking around the woods and exploring. The house was well equipped and was really charming. We also loved sightseeing around the near by towns. Definitely a place to come back to stay again. " [](https://www.expedia.ca/Carmel-Hotels-Lost-In-The-Woods.h71952323.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/2af1ac8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, coffee/tea maker, electric kettle](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/7aae90a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/fbb02298.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, coffee/tea maker, electric kettle](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/1bd3c0a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo Fishkill 9.6/10 Exceptional (36) "Great place for a quiet stay" CA $383 CA $489 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Fishkill-Hotels-Large-Relaxing-Family-Retreat-In-The-Hudson-Valley-With-Theatre-And-Gazebo.h111183358.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/25000000/24920000/24911200/24911110/3deb5ed4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, stereo](https://images.trvl-media.com/lodging/25000000/24920000/24911200/24911110/934cc725.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/25000000/24920000/24911200/24911110/ae7ed8ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/25000000/24920000/24911200/24911110/5f06c884.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views Newburgh 10/10 Exceptional (308) "We had the most relaxing 3 night stay at Don's vacation home. It is spacious and comfortable. Orange Lake right out the back door was a beautiful backdrop all throughout the day. Don gave us great recommendations for local restaurants too.It was the perfect weekend." [](https://www.expedia.ca/Newburgh-Hotels-Private-Lakefront-Home-With-Kayaks-Stunning-Sunsets-Panoramic-View.h24911110.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/64000000/63530000/63528000/63527962/9f0ce022.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/64000000/63530000/63528000/63527962/70096d79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/64000000/63530000/63528000/63527962/852b7fdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/64000000/63530000/63528000/63527962/c553f5f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Large,Cozy,Bright Apartment, Business Themed. Newburgh 8.8/10 Excellent (15) "Very cozy stay with responsive host" CA $564 CA $914 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Newburgh-Hotels-Large.h63527962.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/113000000/112790000/112784900/112784826/7cc4752c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112790000/112784900/112784826/e0425cf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games](https://images.trvl-media.com/lodging/113000000/112790000/112784900/112784826/dec10f13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games](https://images.trvl-media.com/lodging/113000000/112790000/112784900/112784826/b8165061.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick Warwick 9.8/10 Exceptional (12) "We were very comfortable and enjoyed our stay. We enjoyed the deer and bunnies!" [](https://www.expedia.ca/Warwick-Hotels-Stunning-10-Acre-Luxury-Retreat-Breathtaking-Views-4BR.h112784826.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96410000/96402700/96402683/w1267h816x1y0-efb023de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96410000/96402700/96402683/dc2d11be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball, table tennis](https://images.trvl-media.com/lodging/97000000/96410000/96402700/96402683/w1250h789x1y5-d69ff69b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96410000/96402700/96402683/w1280h786x2y0-10a0429d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Our home is perfect for relaxing and having lots of fun, with near by activity’s Highland 9.8/10 Exceptional (6) "My family and I had a great time at this property. Located on a beautiful property. Very relaxing and coordinating with the property owner was very easy. " [](https://www.expedia.ca/Highland-Hotels-Our-Home-Is-Perfect-For-Relaxing-And-Having-Lots-Of-Fun.h96402683.Hotel-Information) ![Children's area](https://images.trvl-media.com/lodging/113000000/112590000/112586800/112586795/19ba220c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/113000000/112590000/112586800/112586795/30bbd2c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/113000000/112590000/112586800/112586795/240ecec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112590000/112586800/112586795/13a74fde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hickory on Willow Lake Fishkill 9.6/10 Exceptional (4) "Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus" CA $592 CA $851 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Fishkill-Hotels-Hickory-On-Willow-Lake.h112586795.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/40000000/39570000/39568700/39568647/656ba2ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39570000/39568700/39568647/1b9910e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/40000000/39570000/39568700/39568647/57345d23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/40000000/39570000/39568700/39568647/1e567779.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY Beacon 10/10 Exceptional (22) "Despite the weather we had a great time. The house is very comfortable, well a pointed, nicely updated and was spotless when we arrived. Location is good too!" [](https://www.expedia.ca/Beacon-Hotels-Stunning-5-Acre-Family-Friendly-Home.h39568647.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/97000000/96850000/96842000/96841918/10c9994b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/97000000/96850000/96842000/96841918/8165e236.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96850000/96842000/96841918/c9e7f08f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/97000000/96850000/96842000/96841918/45c2db90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St. Nyack 9.0/10 Wonderful (6) "Large comfortable home in great location with multiple views of the Hudson. Our family had a pleasant stay and would definitely return to Castle in the Sky." [](https://www.expedia.ca/Nyack-Hotels-Castle-In-The-Sky-Beautifully-Renovated-Victorian-One-Block-From-Main-St.h96841918.Hotel-Information) ![Outdoor banquet area](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/76b5d504.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/fe2ef847.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor banquet area](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/df2c75ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/e858b8f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castle Retreat w/ Pool, BBQ, Game Room & Pets OK! Ossining 8.6/10 Excellent (4) "We booked the property because our family is growing too large for all of the children and grandchildren to spend the holidays together. The “holiday house” as our 4 year old coined it was the perfect place to spend Christmas and Hanukkah. Large yet cozy and very well appointed. All of our communication with proprietors was prompt and helpful, and they had the driveway salted and plowed within hours of the (very picturesque) snowfall the day before Christmas. I would happily book here again. " CA $644 CA $1,312 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Ossining-Hotels-Castle-Cozy-Winter-Wonderland-Events.h101852343.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102350000/102342400/102342378/w1179h783x0y2-92eb770e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/103000000/102350000/102342400/102342378/w1179h783x0y0-6faa5ff0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/103000000/102350000/102342400/102342378/5bb48ca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102350000/102342400/102342378/w1179h786x0y7-46a94465.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon. Carmel Hamlet 10/10 Exceptional (17) "We had a great stay and had everything we needed!" CA $626 CA $1,207 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Carmel-Hotels-Beautiful-Escape-Hudson-Valley-LakeHouse-90min-From-NYC-30min-From-Beacon.h102342378.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96800000/96792000/96791987/80501412.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/97000000/96800000/96792000/96791987/e653cd5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96800000/96792000/96791987/8a0b8636.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96800000/96792000/96791987/f100f04d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cabin with Sauna & Firepit! Monroe 9.2/10 Wonderful (35) "We had a peaceful stay here while we were in town for a few days.The cabin was very cute, clean, and the neighborhood/ neighbors were very quiet. The steps into the bathroom and bedroom were illuminated and the upstairs loft was a cool getaway for our teenager.Recommend taking a bigger vehicle that can take a rough gravel road." [](https://www.expedia.ca/Monroe-Hotels-Cozy-Cabin-With-Sauna-Firepit.h96791987.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/118000000/117680000/117670700/117670643/cf723149.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/118000000/117680000/117670700/117670643/w1020h679x4y4-1952ce42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/118000000/117680000/117670700/117670643/22afb54c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117680000/117670700/117670643/10e384fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Secluded Luxury Home – Peaceful, Comfortable, and Fully Private. Mount Kisco 2.0/10 (1) "The property is lovely and the home spacious. Unfortunately we found the home not to be maintained well or properly cleaned. There was significant mold in the master bath shower, dirty and torn upholstery, stained sheets and rugs, dirty pots and pans, dirty shelves, holes in walls, hanging fixtures, dirty bug filled window sills, loose faucets, non working tub sprayer, dirty outdoor furniture and many more issues. When we voiced concerns to the host we were told to vacate immediately and had no... [](https://www.expedia.ca/Mount-Kisco-Hotels-Secluded-Luxury-Home-Peaceful.h117670643.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96950000/96948900/96948871/d6974351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96950000/96948900/96948871/cf847f79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/97000000/96950000/96948900/96948871/bf114ae9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96950000/96948900/96948871/b5ebd0d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Woodbury Cottage Woodbury 8.8/10 Excellent (25) "A cozy place to stay. " [](https://www.expedia.ca/Central-Valley-Hotels-The-Woodbury-Cottage.h96948871.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/119000000/118710000/118701200/118701194/88d67ada.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/119000000/118710000/118701200/118701194/05f24842.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118710000/118701200/118701194/f64ff049.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/119000000/118710000/118701200/118701194/18dc1ff0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harriman Outdoor Center - White Oak Cabin Haverstraw CA $311 CA $360 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Pomona-Hotels-Harriman-Outdoor-Center-White-Oak-Cabin.h118701194.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/45000000/44130000/44126500/44126447/59415cb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/45000000/44130000/44126500/44126447/w1421h960x0y0-1bf6f7e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/45000000/44130000/44126500/44126447/1b246a76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Golf](https://images.trvl-media.com/lodging/45000000/44130000/44126500/44126447/426fcbad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Queen City Cottage Poughkeepsie 7.4/10 Good (16) "We had a great stay! Good location and the house was very clean. Would definitely stay here again!" [](https://www.expedia.ca/Poughkeepsie-Hotels-The-Queen-City-Cottage.h44126447.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/27000000/26690000/26681500/26681452/e2144f45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/27000000/26690000/26681500/26681452/bfac06f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/27000000/26690000/26681500/26681452/379cf32c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/27000000/26690000/26681500/26681452/517b5054.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St. Highland Falls 10/10 Exceptional (39) "Everything was good. Heather was very attentive." [](https://www.expedia.ca/Newburgh-Hotels-Our-Rockbound-Highland-Home-2-Blocks-From-Thayer-Gate-12-Block-To-Main-St.h26681452.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/58000000/57720000/57717500/57717475/f694e29a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/58000000/57720000/57717500/57717475/72784002.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/58000000/57720000/57717500/57717475/edaafa13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/58000000/57720000/57717500/57717475/ebbce3fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Greenwood Lake Lakefront Luxury Hewitt 10/10 Exceptional (142) "We had the best time. The home was so clean and comfortable, and the views were beautiful. Cheryl is an amazing host and has stocked the home with everything needed to enjoy your stay. We hope to visit again!" [](https://www.expedia.ca/West-Milford-Hotels-Greenwood-Lake-Lakefront-Luxury.h57717475.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.ca/Hotel-Search?startDate=2025-10-13&endDate=2025-10-14®ionId=553248635976002149&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&openPlayBack=true) ![](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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FTown-Of-Highlands-Private-Vacation-Homes.d553248635976002149-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FTown-Of-Highlands-Private-Vacation-Homes.d553248635976002149-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Town of Highlands Hotel Reviews ![TAPA HOTEL ](//images.trvl-media.com/lodging/102000000/101760000/101751700/101751621/7a31b033_y.jpg) ### TAPA HOTEL 10/10 Excellent "This place was absolutely perfect—clean, efficient, courteous, comfortable, dog-friendly, convenient, and worth every (very reasonable!) penny. " [](https://expedia.ca/Mahwah-Hotels-TAPA-HOTEL.h101751621.Hotel-Information) ![Hampton Inn Nanuet](//images.trvl-media.com/lodging/2000000/1560000/1551400/1551336/af6569cb_y.jpg) ### Hampton Inn Nanuet 10/10 Excellent "Good Breakfast " [](https://expedia.ca/Nyack-Hotels-Hampton-Inn-Nanuet.h1551336.Hotel-Information) ![Holiday Inn Express West Point by IHG](//images.trvl-media.com/lodging/1000000/870000/860300/860232/59004f41_y.jpg) ### Holiday Inn Express West Point by IHG 10/10 Excellent "Easy check in. Helpful staff." [](https://expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-West-Point.h860232.Hotel-Information) ![Overlook Lodge at Bear Mountain](//images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6_y.jpg) ### Overlook Lodge at Bear Mountain 10/10 Excellent "Wonderful staff!" [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Armoni Inn & Suites](//images.trvl-media.com/lodging/1000000/20000/12100/12036/5f0c23aa_y.jpg) ### Armoni Inn & Suites 10/10 Excellent "Nice price, nice staff." [](https://expedia.ca/Orangeburg-Hotels-Armoni-Inn-Suites.h12036.Hotel-Information) ![Hampton Inn Harriman Woodbury](//images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/c7d384a9_y.jpg) ### Hampton Inn Harriman Woodbury 10/10 Excellent "Great place to stay, very clean and conveniently located" [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![Hotel Nyack, a JdV by Hyatt Hotel](//images.trvl-media.com/lodging/12000000/11950000/11943100/11943081/a38df02c_y.jpg) ### Hotel Nyack, a JdV by Hyatt Hotel 10/10 Excellent "Staff at the front desk and restaurant were thoughtful and responsive. The hotel and room were beautifully designed. The decor made it feel very much like a boutique hotel. Thanks!" [](https://expedia.ca/Nyack-Hotels-Hotel-Nyack.h11943081.Hotel-Information) ![West Gate Inn Nyack](//images.trvl-media.com/lodging/6000000/5850000/5843400/5843352/393dcf26_y.jpg) ### West Gate Inn Nyack 10/10 Excellent "This place basic but super clean and comfortable. The welcome was warm and I’m actually excited to try the hot breakfast buffet in the morning! I have a feeling it’s going to be pretty great. Easy highway access, plenty of stuff around including a c-store across the street. Taco Boys is a fantastic neighborhood spot up the street definitely worth a try. Loved it!!" [](https://expedia.ca/Nyack-Hotels-West-Gate-Inn-Nyack.h5843352.Hotel-Information) ![Holiday Inn Express Ramsey-Mahwah by IHG](//images.trvl-media.com/lodging/1000000/10000/4700/4613/97efb314_y.jpg) ### Holiday Inn Express Ramsey-Mahwah by IHG 10/10 Excellent "The breakfast was great" [](https://expedia.ca/Ramsey-Hotels-Holiday-Inn-Express-Ramsey-Mahwah.h4613.Hotel-Information) ## Find out more about Town of Highlands ## Town of Highlands Vacation Homes information | Number of reviews | 787 | | --- | --- | | Accommodation | 304 Vacation Homes | | Lowest Price | CA $360 | | Highest Price | CA $1,312 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [5 Star Hotels in West Point](https://www.expedia.ca/5Star-West-Point-Hotels.s50-0-d9700.Travel-Guide-Filter-Hotels) - [Farmstay in Bear Mountain](https://www.expedia.ca/Bear-Mountain-Agritourism.d183639-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Bear Mountain](https://www.expedia.ca/Bear-Mountain-Apart-Hotels.d183639-aaApartHotels.Travel-Guide-Accommodation) - 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