Title: Top Chalets in Town of Highland in 2025 | Expedia.ca [Town of Highland Hotels](https://expedia.ca/Destinations-In-Town-Of-Highland.d553248635976002184.Hotel-Destinations)[Vacation Rentals in Town of Highland](https://expedia.ca/Destinations-In-Town-Of-Highland.d553248635976002184.Vacation-Rental-Destinations)[Town of Highland Car Rentals](https://expedia.ca/Destinations-In-Town-Of-Highland.d553248635976002184.Car-Rental-Destinations)[Town of Highland Vacations](https://expedia.ca/Town-Of-Highland.d553248635976002184.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/3146ab2e29e7af7aee4a5793bcc1fd64.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Ginie Ying # Chalets in Town of Highland ## Compare and save ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](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) ![](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 In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976002184&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976002184&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976002184&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976002184&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Featured Chalets in Town of Highland ![Outdoor spa tub](https://images.trvl-media.com/lodging/34000000/33570000/33563100/33563013/af264c81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, table tennis](https://images.trvl-media.com/lodging/34000000/33570000/33563100/33563013/3c88ead5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33570000/33563100/33563013/270-19951729.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, table tennis](https://images.trvl-media.com/lodging/34000000/33570000/33563100/33563013/6ae44ec1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakefront on Wallenpaupack with Hot Tub - Pet Friendly Lakeville 9.4/10 Exceptional (75) "Grand children enjoyed swimming fishing and being outside. Loved the house and location. My whole family had a relaxing enjoyable time. " [](https://www.expedia.ca/Lakeville-Hotels-Lakefront-On-Wallenpaupack-With-Hot-Tub-Pet-Friendly.h33563013.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/110000000/109320000/109316700/109316672/ec320b4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109320000/109316700/109316672/b3ff6296.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/110000000/109320000/109316700/109316672/6b510919.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, offices](https://images.trvl-media.com/lodging/110000000/109320000/109316700/109316672/3f2447a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Masthope Chalet | 4 Bdrm | Firepit & Kayaks | A/C Lackawaxen 8.6/10 Excellent (8) "First off, CJ is one of the best. He is great about communicating everything you need to know and then some. And he is super responsive. The house was excellent and exactly as advertised. We loved it and will be back! Thank you CJ!" [](https://www.expedia.ca/Lackawaxen-Hotels-Ski-Big-Bear-Lackawaxen-Home.h109316672.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/96000000/95310000/95305800/95305776/w1044h701x8y0-99d1395b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95310000/95305800/95305776/w1242h826x0y320-077a08f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95310000/95305800/95305776/w1051h701x1y0-28a4e6ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/96000000/95310000/95305800/95305776/6e5f1545.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Chalet with Arcades, Pool Table, Fire pit, Lake, Pools & Ski Lifts Lackawaxen 9.6/10 Exceptional (12) "Great community and the property had a good amount of privacy from neighbors. " [](https://www.expedia.ca/Lackawaxen-Hotels-The-Perfect-Four-Season-Getaway-Masthope-Chalet.h95305776.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/28000000/27120000/27118700/27118668/25d313b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/28000000/27120000/27118700/27118668/eeea923a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27120000/27118700/27118668/350651b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/28000000/27120000/27118700/27118668/d6694cba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ★★ - Highly Rated Waterfront: Hot Tub, Fireplace, Pet Friendly! -★★ Wallenpaupauk Lake Estates 9.8/10 Exceptional (301) "It was very quiet, nice view from the porch. The house was very clean. We also enjoyed the hot tub. " CA $419 CA $820 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Lake-Ariel-Hotels-Luxury-Waterfront-Hot-Tub.h27118668.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/118000000/117640000/117633400/117633383/cef0ac31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/118000000/117640000/117633400/117633383/f102c8fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117640000/117633400/117633383/af43f859_edited_1c57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117640000/117633400/117633383/w907h683x58y0-b29c1715.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Catskill Getaway • Near Bethel Woods & Hiking & HOT TUB Parksville 10/10 Exceptional (1) "Beautiful and modern house in the middle of the forest. " CA $421 CA $991 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Parksville-Hotels-The-Catskill-Getaway-Near-Bethel-Woods-Hiking.h117633383.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/92000000/91560000/91559700/91559660/w1204h748x0y0-9fd116e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91560000/91559700/91559660/58f4bab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/92000000/91560000/91559700/91559660/8c12d923.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/92000000/91560000/91559700/91559660/3299daf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bali's Cottage-Cozy Chalet in WLE-Wallenpaupack Lake Estates-Walk to Pool Wallenpaupauk Lake Estates 10/10 Exceptional (21) "The cottage was lovely and very clean. The owners were super responsive and attentive to our needs. I would definitely stay there again!" [](https://www.expedia.ca/Lakeville-Hotels-Cozy-Chalet-In-WLE-2-BedroomsLoft2-Full-Baths-BBQFirepit.h91559660.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/64000000/63870000/63865100/63865060/cc745ec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, video games, books](https://images.trvl-media.com/lodging/64000000/63870000/63865100/63865060/fe996c73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/64000000/63870000/63865100/63865060/9f9c66b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/64000000/63870000/63865100/63865060/b171eddf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa MiaNova: A Modern Hideout in the Woods. Lake Ariel 9.4/10 Exceptional (13) "We had a great time! House fit all 11 of us very comfortably. Kids enjoyed the basement with the arcades." [](https://www.expedia.ca/Lake-Ariel-Hotels-Villa-MiaNova-A-Modern-Hideout-In-The-Woods.h63865060.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/83000000/82870000/82866700/82866672/713f261f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82870000/82866700/82866672/59506068.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/83000000/82870000/82866700/82866672/1a2a9d12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, offices](https://images.trvl-media.com/lodging/83000000/82870000/82866700/82866672/w1194h793x3y2-cde226a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Lookout \* Lake \* Masthope \* Firepit \* Arcade Lackawaxen 10/10 Exceptional (13) "We’ve been coming to Lackawaxen for decades because of family and this booking was a treat for us so we could have our own space - with AC!, our own kitchen, nice wooded area, plenty of beds, etc." [](https://www.expedia.ca/Lackawaxen-Hotels-The-Lookout-3-Bed-Chalet-Masthope-Firepit.h82866672.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/66000000/65310000/65301700/65301642/6b143b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/66000000/65310000/65301700/65301642/3f50b8d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/66000000/65310000/65301700/65301642/99e39028.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/66000000/65310000/65301700/65301642/cfa86255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Catskills Lakefront Escape with Hot Tub Thompson 9.8/10 Exceptional (19) "Everyone had a place to sleep! Very clean! Great hot tub! " [](https://www.expedia.ca/Monticello-Hotels-Catskills-Lakefront-Escape-With-Hot-Tub.h65301642.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116660000/116654900/116654890/d6b947b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/117000000/116660000/116654900/116654890/9563a6f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/117000000/116660000/116654900/116654890/ad2d9639.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/117000000/116660000/116654900/116654890/2425daa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Welcome to On the Rocks a charming retreat located near Lake Wallenpaupack Wallenpaupauk Lake Estates 10/10 Exceptional (2) "My experience at this house was fantastic. The cleanliness and layout were impressive, making it a comfortable stay. The location offered both convenience and privacy, which I truly appreciated. Additionally, it was well-stocked with toiletries. I would absolutely choose to stay here again." [](https://www.expedia.ca/Lake-Ariel-Hotels-Welcome-To-On-The-Rocks-A-Charming-Retreat-Located-Near-Lake-Wallenpaupack.h116654890.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/33000000/32590000/32583400/32583344/b4140ea4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/33000000/32590000/32583400/32583344/274fabf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/33000000/32590000/32583400/32583344/f67df807.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/33000000/32590000/32583400/32583344/a5a32532.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Masthope modern log-cabin sided retreat! Lackawaxen 9.8/10 Exceptional (115) "Second time staying at this property. Great location and close proximity to all amenities. Very relaxing getaway. Will be back next year. " [](https://www.expedia.ca/Hawley-Hotels-Masthope-Modern-Log-Cabin-Sided-Retreat.h32583344.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33570000/33568200/33568105/6ac91c9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33570000/33568200/33568105/2b33dfc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33570000/33568200/33568105/1024ab3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, DVD player](https://images.trvl-media.com/lodging/34000000/33570000/33568200/33568105/4030ff9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Briar Hill North Lakefront Contemporary with Private Dock Lakeville 9.4/10 Exceptional (53) "Beautiful house, plenty of room, comfortable and perfect spot on the lake ." [](https://www.expedia.ca/Lakeville-Hotels-Briar-Hill-North-Lakefront-Contemporary-With-Private-Dock.h33568105.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91440000/91431900/91431835/87cd5f5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/92000000/91440000/91431900/91431835/d1310563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/92000000/91440000/91431900/91431835/094e87dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91440000/91431900/91431835/f73b9588.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakes with Resort Amenities in Lake Ariel Wallenpaupauk Lake Estates 10/10 Exceptional (2) "The house was perfect. It was very clean & fully stocked. Tamara was so easy to get a hold of if I had any questions. She returned messages immediately. I would definitely rent this house again." [](https://www.expedia.ca/Pocono-Lake-Hotels-Skiing-Tubing-In-Lake-Ariel.h91431835.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/79000000/78390000/78386200/78386128/025a1043.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/79000000/78390000/78386200/78386128/35f190d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78390000/78386200/78386128/9f9cb305.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78390000/78386200/78386128/68c81e79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relax at Sunset View in the Hideout Resort Lake Ariel 9.6/10 Exceptional (9) "The location the house was amazing. Little stuffy and warm in the downstairs. Family had a great time there. Having some games there was really nice on the one day it rained there. Thanks again. Would highly recommend" [](https://www.expedia.ca/Lake-Ariel-Hotels-Relax-At-Sunset-View-Entire-Chalet-The-Hideout-Resort.h78386128.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90990000/90985200/90985150/2c811e66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/91000000/90990000/90985200/90985150/51e47465.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/91000000/90990000/90985200/90985150/a1881881.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90990000/90985200/90985150/5aa81f9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ★Chic Chalet River Views & Access★ Montague 7.4/10 Good (3) "Dirty. Ants. Not well stocked." CA $237 CA $419 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Montague-Hotels-Chic-Chalet-River-Views-Access.h90985150.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104510000/104503800/104503719/8f902f1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104510000/104503800/104503719/96dc2194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104510000/104503800/104503719/20177081.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/105000000/104510000/104503800/104503719/35d861af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Chalet - Rustic Retreat Narrowsburg 8.8/10 Excellent (10) "Just enough accommodations for a comfortable stay." CA $196 CA $471 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Narrowsburg-Hotels-The-Chalet-Rustic-Retreat.h104503719.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/117000000/116950000/116948400/116948304/a6240015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116950000/116948400/116948304/fd8de77e.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/117000000/116950000/116948400/116948304/e0eda1b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116950000/116948400/116948304/8cc6c92c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fall & Winter Forest Retreat: Ski, Spa & Sauna- Poconos & Narrowsburg, NY Lackawaxen 10/10 Exceptional (1) "It was such a beautiful home! It was so perfect. Easy access and so welcoming! Thank you again!" [](https://www.expedia.ca/Lackawaxen-Hotels-Cozy-Ski-Or-Summer-Retreat-Sauna-Spa-Amenities-Included-Pet-Friendly.h116948304.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/64000000/63080000/63077000/63076997/5f04cae3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/64000000/63080000/63077000/63076997/fab8112d_edited_40df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/64000000/63080000/63077000/63076997/df3a4468.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/64000000/63080000/63077000/63076997/e0fef67a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Masthope Luxury retreat 4bd King size bed , Jacuzzi 5 min to pools & lake… Lackawaxen 10/10 Exceptional (12) "The kids loved the community pool and a place that had bumper boats." [](https://www.expedia.ca/Lackawaxen-Hotels-Masthope-Retreat-Huge-Family-Friendly-Spl-Rates-Bookings-May-June.h63076997.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/35000000/34340000/34337800/34337718/w799h599x1y1-8218f235.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34340000/34337800/34337718/03f09435.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34340000/34337800/34337718/c4626578.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/35000000/34340000/34337800/34337718/c9d77d64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury 4BR Chalet-5 Mins. to Pool/Lake/Ski-Game Room in Basement Lackawaxen 10/10 Exceptional (76) "Community was beautiful Plenty to do Felt very safe Home. Was clean and comfortable for tHe 5 days we stayed " [](https://www.expedia.ca/Lackawaxen-Hotels-Luxury-4BR-Chalet-5-Mins-To-PoolLakeSki-Game-Room-In-Basement.h34337718.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/104000000/103820000/103818200/103818106/49874359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103820000/103818200/103818106/fa61ed22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, stereo](https://images.trvl-media.com/lodging/104000000/103820000/103818200/103818106/a07d48b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, stereo](https://images.trvl-media.com/lodging/104000000/103820000/103818200/103818106/d3990a99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ABomb! Adorable 2-bdrm Chalet with Lots of Room! Wurtsboro 9.6/10 Exceptional (5) "Was the perfect spot to come back too after a long day in the sun. The campfire was welcoming and the house its self was just beautiful. Wish we didnt have to leave! Was the perfect girls trip spot and wohld recommend this to anyone ♥️♥️" [](https://www.expedia.ca/Wurtsboro-Hotels-ABomb-Adorable-2-Bdrm-Chalet-With-Lots-Of-Room.h103818106.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=2025-10-25&endDate=2025-10-26®ionId=553248635976002184&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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-Highland-Chalets.d553248635976002184-aaChalets.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FTown-Of-Highland-Chalets.d553248635976002184-aaChalets.Travel-Guide-Accommodation) ## Top Town of Highland Hotel Reviews ![High Point Motel](//images.trvl-media.com/lodging/108000000/107260000/107254000/107253932/dad3e76a_y.jpg) ### High Point Motel 10/10 Excellent "Perfect getaway! The layout of the rooms is cute. Each one has its own personality. This is my home away from home. Melanie is amazing! It's peaceful and quiet. The sunrise is spectacular. Great place to stay. I'll be back again. " [](https://expedia.ca/Sussex-Hotels-High-Point-Motel.h107253932.Hotel-Information) ![Best Western Monticello](//images.trvl-media.com/lodging/1000000/30000/26600/26518/68dcbd68_y.jpg) ### Best Western Monticello 10/10 Excellent "Parking was free, convenient easy " [](https://expedia.ca/Monticello-Hotels-Best-Western-Monticello.h26518.Hotel-Information) ![Ledges Hotel](//images.trvl-media.com/lodging/6000000/5330000/5320100/5320032/7e678dea_y.jpg) ### Ledges Hotel 10/10 Excellent "Ambience of the stream and waterfall was relaxing. Steps to restaurant were steep and not well lit." [](https://expedia.ca/Hawley-Hotels-Ledges-Hotel.h5320032.Hotel-Information) ![Days Inn by Wyndham Wurtsboro](//images.trvl-media.com/lodging/1000000/40000/34300/34237/3073e3e0_y.jpg) ### Days Inn by Wyndham Wurtsboro 10/10 Excellent "Clean room" [](https://expedia.ca/Monticello-Hotels-Days-Inn-By-Wyndham-Wurtsboro.h34237.Hotel-Information) ![Resorts World Catskills Casino](//images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/ecb80f49_y.jpg) ### Resorts World Catskills Casino 10/10 Excellent "AMAZING " [](https://expedia.ca/Monticello-Hotels-Resorts-World-Catskills-Casino.h23970267.Hotel-Information) ![The Kartrite Resort & Indoor Waterpark](//images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/90ceac4d_y.jpg) ### The Kartrite Resort & Indoor Waterpark 10/10 Excellent "I took my daughter to The Kartrite Resort for her birthday, and we had an amazing time! The staff was friendly, the place was spotless, and the vibe was perfect for families. Such a great experience we’ll definitely be back! " [](https://expedia.ca/Monticello-Hotels-The-Kartrite-Resort-Indoor-Waterpark.h31681637.Hotel-Information) ![The Alder at Resorts World Catskills](//images.trvl-media.com/lodging/101000000/101000000/100997000/100996967/9db559da_y.jpg) ### The Alder at Resorts World Catskills 10/10 Excellent "Great place to stay " [](https://expedia.ca/Monticello-Hotels-The-Alder-At-Resorts-World-Catskills.h100996967.Hotel-Information) ![Cove Haven Resort](//images.trvl-media.com/lodging/1000000/40000/34700/34685/efde6748_y.jpg) ### Cove Haven Resort 10/10 Excellent "The staff and amenities are top notch. The food and drinks are excellent, and the activities have something for everyone " [](https://expedia.ca/Lakeville-Hotels-Cove-Haven-Resort.h34685.Hotel-Information) ![Hampton Inn Matamoras/Milford](//images.trvl-media.com/lodging/3000000/2780000/2774600/2774574/e1440092_y.jpg) ### Hampton Inn Matamoras/Milford 10/10 Excellent "Stay here every year and the rooms are clean and the staff is very griendly and professional" [](https://expedia.ca/Matamoras-Hotels-Hampton-Inn-Matamoras-Milford.h2774574.Hotel-Information) ## Find out more about Town of Highland ## Town of Highland Chalets information | Number of reviews | 646 | | --- | --- | | Accommodation | 59 Chalets | | Lowest Price | CA $419 | | Highest Price | CA $991 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Aparthotels in Barryville](https://www.expedia.ca/Barryville-Apart-Hotels.d6069726-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Barryville](https://www.expedia.ca/Barryville-Bed-And-Breakfast.d6069726-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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