Title: Top Chalets in Town of Olive in 2026 | Expedia.ca [Town of Olive Hotels](https://expedia.ca/Destinations-In-Town-Of-Olive.d553248635976002351.Hotel-Destinations)[Vacation Rentals in Town of Olive](https://expedia.ca/Destinations-In-Town-Of-Olive.d553248635976002351.Vacation-Rental-Destinations)[Town of Olive Car Rentals](https://expedia.ca/Destinations-In-Town-Of-Olive.d553248635976002351.Car-Rental-Destinations)[Town of Olive Vacations](https://expedia.ca/Town-Of-Olive.d553248635976002351.Destination-Travel-Guides) ![Peak Color Panorama from Slide Mountain](https://images.trvl-media.com/place/129957/2da1e74f-da99-4202-aa17-66e477ec0194.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Chalets in Town of Olive ## 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 Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976002351&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976002351&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) In one month [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976002351&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976002351&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Town of Olive chalets ![Exterior](https://images.trvl-media.com/lodging/45000000/44430000/44424600/44424552/d073e7ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/45000000/44430000/44424600/44424552/3e075dc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/45000000/44430000/44424600/44424552/0af6bedf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/45000000/44430000/44424600/44424552/a025bc09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Fleischmanns [](https://www.expedia.ca/Kingston-Hotels-Vrbo-Property.h44424552.Hotel-Information) 9.6/10 Exceptional (64) "Nice place. Enjoyed the hot tub. Good restaurant down the road. Just what we needed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) john C. [](https://www.expedia.ca/Kingston-Hotels-Vrbo-Property.h44424552.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/39000000/38320000/38310300/38310263/w1175h759x1y1-18403454.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/39000000/38320000/38310300/38310263/30a8bf90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table tennis, video library](https://images.trvl-media.com/lodging/39000000/38320000/38310300/38310263/3b5d7681.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/39000000/38320000/38310300/38310263/w1176h757x0y3-071e6138.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Fleischmanns [](https://www.expedia.ca/Fleischmanns-Hotels-Stunning-Catskills-Cabin-Getaway.h38310263.Hotel-Information) 10/10 Exceptional (131) "Absolutely fabulous place we stayed for my daughter’s wedding. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert Joseph J. [](https://www.expedia.ca/Fleischmanns-Hotels-Stunning-Catskills-Cabin-Getaway.h38310263.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/111000000/110760000/110752300/110752244/f24e9197.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110760000/110752300/110752244/92b2eff7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, foosball, table tennis, books](https://images.trvl-media.com/lodging/111000000/110760000/110752300/110752244/4c7980a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110760000/110752300/110752244/5c66ce3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in New Paltz [](https://www.expedia.ca/New-Paltz-Hotels-Spacious-A-Frame-W-Game-Room.h110752244.Hotel-Information) 10/10 Exceptional (13) "Absolutely stunning A-frame! Super spacious, very clean/tidy, lots of room to hang inside, downstairs or have a fire outdoors. Beautiful area not far from New Paltz. We had such a fantastic time and would recommend this place to any group staying in the area! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Danielle O. CA $737 CA $1,383 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/New-Paltz-Hotels-Spacious-A-Frame-W-Game-Room.h110752244.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494630/50582458.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494630/f968c690.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494630/3c139273.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494630/eaaa858b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Tannersville [](https://www.expedia.ca/Tannersville-Hotels-Jessies-Harvest-House-Suite.h117494630.Hotel-Information) 10/10 Exceptional (3) "Perfect, clean space for a quick overnight. Very close proximity to all that the area has to offer." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew M. CA $129 CA $238 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Tannersville-Hotels-Jessies-Harvest-House-Suite.h117494630.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/47000000/46150000/46147200/46147200/02fa6579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/47000000/46150000/46147200/46147200/a4931ebe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/47000000/46150000/46147200/46147200/82969d67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, music library, computer monitors](https://images.trvl-media.com/lodging/47000000/46150000/46147200/46147200/2b8956bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Lanesville [](https://www.expedia.ca/Hunter-Hotels-Private-Chalet-Close-To-Ski-Resort.h46147200.Hotel-Information) 9.8/10 Exceptional (8) "Cozy stay for our family of four!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kasey S. [](https://www.expedia.ca/Hunter-Hotels-Private-Chalet-Close-To-Ski-Resort.h46147200.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/77000000/76320000/76318200/76318123/eb198c48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/77000000/76320000/76318200/76318123/047be124.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/77000000/76320000/76318200/76318123/71412ffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/77000000/76320000/76318200/76318123/44260a94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Big Indian [](https://www.expedia.ca/Big-Indian-Hotels-Cozy-Catskill-Chalet.h76318123.Hotel-Information) 10/10 Exceptional (18) "Stayed for a wedding nearby and it was the perfect place to spend family time together and have enough beds for everyone to sleep in. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leah I. CA $556 CA $1,151 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Big-Indian-Hotels-Cozy-Catskill-Chalet.h76318123.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/113000000/112150000/112143300/112143298/ea514bb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112150000/112143300/112143298/0434bd21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112150000/112143300/112143298/e3ea4ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112150000/112143300/112143298/0a1aa53d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Hunter [](https://www.expedia.ca/Hunter-Hotels-1-Mile-From-Ski-Slope-And-Festivals-125-Nightly-Fee.h112143298.Hotel-Information) 9.6/10 Exceptional (14) "Beautiful location in a well kept property! Highly recommend it." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $234 CA $375 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Hunter-Hotels-1-Mile-From-Ski-Slope-And-Festivals-125-Nightly-Fee.h112143298.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494618/57ea4514.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494618/71b41d08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494618/ea584011.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494618/3bed5fbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Tannersville [](https://www.expedia.ca/Tannersville-Hotels-Jessies-Harvest-House.h117494618.Hotel-Information) 10/10 Exceptional (1) "cute little spot! very nice place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David R. CA $163 CA $280 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Tannersville-Hotels-Jessies-Harvest-House.h117494618.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/92000000/91780000/91774400/91774336/a59c2e31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91780000/91774400/91774336/f37b8f89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/92000000/91780000/91774400/91774336/6fa2c82d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/92000000/91780000/91774400/91774336/dbb717ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Jewett [](https://www.expedia.ca/Jewett-Hotels-Beautiful-Chalet.h91774336.Hotel-Information) 9.8/10 Exceptional (21) "Incredible stay! The house was beautiful and well equipped. We loved being in pretty close proximity to some great towns too. Already talking about going back next summer" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Casey H. [](https://www.expedia.ca/Jewett-Hotels-Beautiful-Chalet.h91774336.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/117000000/116780000/116776300/116776217/3d7019b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116780000/116776300/116776217/785e8bb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116780000/116776300/116776217/5053b8fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116780000/116776300/116776217/93418b20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Tannersville [](https://www.expedia.ca/Tannersville-Hotels-Jessies-Harvest-House-Room-1-Cozy-Chalet-In-Lovely-Tannersville-With-WiFi.h116776217.Hotel-Information) CA $163 CA $280 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Tannersville-Hotels-Jessies-Harvest-House-Room-1-Cozy-Chalet-In-Lovely-Tannersville-With-WiFi.h116776217.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494620/a78d7cf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494620/901cc9d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494620/82ba52fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494620/w2045h1365x3y0-b9635d9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Tannersville [](https://www.expedia.ca/Tannersville-Hotels-Jessies-Harvest-House.h117494620.Hotel-Information) CA $163 CA $280 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Tannersville-Hotels-Jessies-Harvest-House.h117494620.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/113000000/112090000/112088200/112088150/ea69ae10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112090000/112088200/112088150/894c2cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![9 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/113000000/112090000/112088200/112088150/00fe272f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/113000000/112090000/112088200/112088150/w1826h1133x0y1-0cf54c15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Hunter [](https://www.expedia.ca/Hunter-Hotels-The-Hunter-Chalet.h112088150.Hotel-Information) 10/10 Exceptional (5) "Big house with an awesome view! We really enjoyed our stay and appreciated the close proximity to town. The host was responsive and accommodating, thank you!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristen K. [](https://www.expedia.ca/Hunter-Hotels-The-Hunter-Chalet.h112088150.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107970000/107964300/107964203/75814d07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/108000000/107970000/107964300/107964203/f4e99560.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/108000000/107970000/107964300/107964203/bf49ff1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/108000000/107970000/107964300/107964203/6eacbc86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Gardiner [](https://www.expedia.ca/Gardiner-Hotels-Modern-Zen-Chalet-At-The-Foot-Of-Gunks-W-Mt-View.h107964203.Hotel-Information) 10/10 Exceptional (7) "Great weekend getaway to reconnect with old friends!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa D. CA $235 CA $403 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Gardiner-Hotels-Modern-Zen-Chalet-At-The-Foot-Of-Gunks-W-Mt-View.h107964203.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/94000000/93780000/93777200/93777185/281116d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/94000000/93780000/93777200/93777185/2045ca89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93780000/93777200/93777185/b83930b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93780000/93777200/93777185/w467h683x271y0-91ffbc58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Willow [](https://www.expedia.ca/Willow-Hotels-Cozy-Silo-With-Sunset-Views.h93777185.Hotel-Information) 9.8/10 Exceptional (16) "The house was even better than advertised. We loved staying here." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth C. [](https://www.expedia.ca/Willow-Hotels-Cozy-Silo-With-Sunset-Views.h93777185.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/93000000/92370000/92364900/92364886/52e78c32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/93000000/92370000/92364900/92364886/w903h683x60y0-abde3db5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/93000000/92370000/92364900/92364886/89ac8fde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92370000/92364900/92364886/w1920h1280x0y0-36f9ad99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Hunter Highlands [](https://www.expedia.ca/Hunter-Hotels-3bdrm-Cabin-Chalet-Upstate.h92364886.Hotel-Information) [](https://www.expedia.ca/Hunter-Hotels-3bdrm-Cabin-Chalet-Upstate.h92364886.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/88000000/87130000/87129900/87129887/dd23bc2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/88000000/87130000/87129900/87129887/w518h683x248y0-d3b67c2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87130000/87129900/87129887/91db5e9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/88000000/87130000/87129900/87129887/w466h683x287y0-3e9029bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Hunter [](https://www.expedia.ca/Hunter-Hotels-Never-Lonesome-Hunter-Smart-4bd-Getaway-Near-Mtn.h87129887.Hotel-Information) 10/10 Exceptional (4) "We loved our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Georgie P. [](https://www.expedia.ca/Hunter-Hotels-Never-Lonesome-Hunter-Smart-4bd-Getaway-Near-Mtn.h87129887.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/112000000/111990000/111983100/111983040/823b74db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111990000/111983100/111983040/9178944b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111990000/111983100/111983040/04258bcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111990000/111983100/111983040/84d93ab4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Jewett [](https://www.expedia.ca/Jewett-Hotels-Luxe-Party-Retreat-TheaterKaraokeGamesHot-Tubswimming-Pool.h111983040.Hotel-Information) 10/10 Exceptional (2) "Super fun home with a lot of bells and whistles!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bennett Z. [](https://www.expedia.ca/Jewett-Hotels-Luxe-Party-Retreat-TheaterKaraokeGamesHot-Tubswimming-Pool.h111983040.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101340000/101336100/101336016/ad7ca122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101340000/101336100/101336016/81c01c34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101340000/101336100/101336016/4c531e7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101340000/101336100/101336016/2573baf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Tannersville [](https://www.expedia.ca/Tannersville-Hotels-5-Star-Gorgeous-Cliffside-Chalet-W-Panoramic-Views.h101336016.Hotel-Information) 10/10 Exceptional (1) "This home is a beautiful refuge. Lots of windows offer breathtaking views and colorful sunsets. The house is well-furnished and equipped. The owner was accessible and invested in our comfort in his home. Renters should understand, however, that the primary bedroom is in a loft, with no shades or drapes to cover the windows. If all that light/exposure would be a sleep issue for other renters, they should bring a good sleep mask. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jamie [](https://www.expedia.ca/Tannersville-Hotels-5-Star-Gorgeous-Cliffside-Chalet-W-Panoramic-Views.h101336016.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119380000/119372800/119372796/37b0ad42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/120000000/119380000/119372800/119372796/2d696156.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119380000/119372800/119372796/5bcc4613.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119380000/119372800/119372796/5d9431b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Fleischmanns [](https://www.expedia.ca/Fleischmanns-Hotels-Crows-Nest-Mtn-Chalet-Hot-Tub.h119372796.Hotel-Information) [](https://www.expedia.ca/Fleischmanns-Hotels-Crows-Nest-Mtn-Chalet-Hot-Tub.h119372796.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/88000000/87140000/87130300/87130240/590e59c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87140000/87130300/87130240/w1016h683x4y0-3608d393.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, travel crib, free WiFi](https://images.trvl-media.com/lodging/88000000/87140000/87130300/87130240/w986h683x19y0-943e8d42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/88000000/87140000/87130300/87130240/w509h683x257y0-f87a7d16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Phoenicia [](https://www.expedia.ca/Phoenicia-Hotels-Never-Lonesome-Woodland-Valley-Cozy-2bd-Cottage.h87130240.Hotel-Information) 9.4/10 Exceptional (12) "Super cute place. Stayed for a wedding with my 10-year-old daughter. She wanted to move there. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) james m. [](https://www.expedia.ca/Phoenicia-Hotels-Never-Lonesome-Woodland-Valley-Cozy-2bd-Cottage.h87130240.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=2026-01-01&endDate=2026-01-02®ionId=553248635976002351&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-Olive-Chalets.d553248635976002351-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FTown-Of-Olive-Chalets.d553248635976002351-aaChalets.Travel-Guide-Accommodation) ## Top Town of Olive Hotel Reviews ![Americas Best Value Inn New Paltz](https://images.trvl-media.com/lodging/1000000/900000/897900/897882/1c07aec9_y.jpg) ### Americas Best Value Inn New Paltz 10/10 Excellent "Very nice hotel clean room and quite large! Bathroom was nice bed was comfortable. Staff was also very nice. Only thing I will mention as it's important to some people - breakfast had no hot options like eggs etc. They had whole wheat bread regular bread and waffles that you can put into the toaster. Apart from that there were yogurts and a few other things but nothing hot. Coffee machine was really nice with lots of different options for many different kinds of coffee as well as hot chocolate. All in all nice stay with a nice room. One more important thing - there is no elevator. There are only two floors but if you're on the second floor take into account you'll have to take your luggage up the steps. " [](https://expedia.ca/Poughkeepsie-Hotels-Americas-Best-Value-Inn-New-Paltz.h897882.Hotel-Information) ![Hampton Inn Kingston](https://images.trvl-media.com/lodging/2000000/1670000/1662000/1661941/21cb7965_y.jpg) ### Hampton Inn Kingston 10/10 Excellent "The hotel is great and great location. " [](https://expedia.ca/Kingston-Hotels-Hampton-Inn-Kingston.h1661941.Hotel-Information) ![Beekman Arms Hotel](https://images.trvl-media.com/lodging/13000000/12620000/12611900/12611810/ab673905_y.jpg) ### Beekman Arms Hotel 10/10 Excellent "A beautiful hotel and we look forward to seeing it again when renovations are completed " [](https://expedia.ca/Poughkeepsie-Hotels-Beekman-Arms-Hotel.h12611810.Hotel-Information) ![Hunter Lodge, a Bluebird by Lark](https://images.trvl-media.com/lodging/65000000/64240000/64238700/64238678/c80f19a7_y.jpg) ### Hunter Lodge, a Bluebird by Lark 10/10 Excellent "I loved this hotel! It definitely gives mountain vibes, the decor is perfect. The shower and beds were excellent, the service and the staff are amazing. I was pleasantly surprised - I can be very particular with my hotel stays, I want it to be at least as comfortable as home if not better. Between the fireplaces going, that ski lodge decor, and the hotel smells beautiful. The only reason I gave the breakfast four stars- it is so cool that it is free, but I would love a hot protein option even if I had to pay for it. but honestly everything was above and beyond!" [](https://expedia.ca/Kingston-Hotels-The-Hunter-Inn.h64238678.Hotel-Information) ![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 "Breakfast is the best! " [](https://expedia.ca/Hyde-Park-Hotels-Inn-At-Bellefield-Hyde-Park.h99850733.Hotel-Information) ![Urban Cowboy Lodge](https://images.trvl-media.com/lodging/43000000/42570000/42566500/42566439/a8a403ae_y.jpg) ### Urban Cowboy Lodge 10/10 Excellent "In room 205 at Forest Haus, there is no curtain over the balcony door window. Because of this it got very bright in the room as soon as the sun came up. There were also lady bugs all over the room. They didn’t really bother us but also didn’t expect that. " [](https://expedia.ca/Big-Indian-Hotels-Urban-Cowboy-Lodge.h42566439.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 "Great" [](https://expedia.ca/Kingston-Hotels-Holiday-Inn-Express-Suites-Kingston-Ulster.h16102650.Hotel-Information) ![Courtyard by Marriott Kingston](https://images.trvl-media.com/lodging/2000000/1370000/1364000/1363973/a5bfb382_y.jpg) ### Courtyard by Marriott Kingston 10/10 Excellent " Lean room, quiet location and comfortable bed." [](https://expedia.ca/Kingston-Hotels-Courtyard-By-Marriott-Kingston.h1363973.Hotel-Information) ![Minnewaska Lodge](https://images.trvl-media.com/lodging/2000000/1210000/1201800/1201707/3be04d40_y.jpg) ### Minnewaska Lodge 10/10 Excellent "This place is really a hidden gem. We could not have been happier with our stay." [](https://expedia.ca/Poughkeepsie-Hotels-Minnewaska-Lodge.h1201707.Hotel-Information) ## Find out more about Town of Olive ## Town of Olive Chalets information | Number of reviews | 312 | | ----------------- | ---------- | | Accommodation | 33 Chalets | | Lowest Price | CA $238 | | Highest Price | CA $1,383 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [4 Star Hotels in West Shokan ](https://www.expedia.ca/4Star-West-Shokan-Hotels.s40-0-d3000450105.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Woodstock ](https://www.expedia.ca/5Star-Woodstock-Hotels.s50-0-d176573.Travel-Guide-Filter-Hotels) - [Hotels near Ashokan Rail Trail- Woodstock Dike Trailhead ](https://www.expedia.ca/Ashokan-Rail-Trail-Woodstock-Dike-Trailhead-Hotels.0-l553248635997964716-0.Travel-Guide-Filter-Hotels) - [B&B in Bearsville ](https://www.expedia.ca/Bearsville-Bed-And-Breakfast.d3000448019-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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