Title: Pine Island Vacation Rentals from CA $348: Short-Term Rentals for 2026 | Expedia.ca [Hotels in Pine Island](https://expedia.ca/Pine-Island-Hotels.d181397.Travel-Guide-Hotels)[Pine Island Car Rentals](https://expedia.ca/Car-Rentals-In-Pine-Island.d181397.Car-Rental-Guide)[Pine Island Vacation Packages](https://expedia.ca/Pine-Island.d181397.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Pine Island Vacation Rentals - ![](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 [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=181397&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=181397&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=181397&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=181397&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Pine Island vacation rentals ![Apartment](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711152/be62ef7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711152/8de040af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711152/917eed35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711152/w1346h900x0y0-2cb73b73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Monroe [](https://www.expedia.ca/Monroe-Hotels-Studio-Retreat-Near-Woodbury-Commons-Legoland.h123711152.Hotel-Information) CA $135 CA $330 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Monroe-Hotels-Studio-Retreat-Near-Woodbury-Commons-Legoland.h123711152.Hotel-Information) ![Deluxe Cabin, Garden View](https://images.trvl-media.com/lodging/124000000/123150000/123146200/123146160/e8e32e98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/124000000/123150000/123146200/123146160/2bcd47c0_edited_922e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Cabin, Garden View](https://images.trvl-media.com/lodging/124000000/123150000/123146200/123146160/9b7c9e80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/124000000/123150000/123146200/123146160/eb14770c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin in Ringwood [](https://www.expedia.ca/Ringwood-Hotels-Forava-Cabins-Tiny-Cabin-In-The-Woods.h123146160.Hotel-Information) 10/10 Exceptional (1 review) "Very cute, well decorated, quiet, and has everything we needed for a get away." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexis CA $310 CA $347 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Ringwood-Hotels-Forava-Cabins-Tiny-Cabin-In-The-Woods.h123146160.Hotel-Information) ![Apartment](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711155/e3793e31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711155/w1350h896x0y0-b3647d4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711155/2cc70a56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711155/ab3caa89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Monroe [](https://www.expedia.ca/Monroe-Hotels-Bright-Studio-Retreat-W-Deck-Nature-Views.h123711155.Hotel-Information) CA $179 CA $426 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Monroe-Hotels-Bright-Studio-Retreat-W-Deck-Nature-Views.h123711155.Hotel-Information) ![Apartment](https://images.trvl-media.com/lodging/124000000/123710000/123706400/123706319/c1793b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/124000000/123710000/123706400/123706319/de99b88d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/124000000/123710000/123706400/123706319/bcf66280.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/124000000/123710000/123706400/123706319/de519221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Monroe [](https://www.expedia.ca/Monroe-Hotels-Rustic-Lakefront-Studio-W-Deck-Workspace.h123706319.Hotel-Information) CA $135 CA $330 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Monroe-Hotels-Rustic-Lakefront-Studio-W-Deck-Workspace.h123706319.Hotel-Information) ![Apartment](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711154/901afe1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711154/d8a9dc23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711154/7aa0c18f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711154/414f3605.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Monroe [](https://www.expedia.ca/Monroe-Hotels-Cozy-Modern-Studio-Near-Lake-Porch-Fire-Pit.h123711154.Hotel-Information) CA $135 CA $330 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Monroe-Hotels-Cozy-Modern-Studio-Near-Lake-Porch-Fire-Pit.h123711154.Hotel-Information) ![Apartment](https://images.trvl-media.com/lodging/124000000/123710000/123706400/123706320/ce02298f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/124000000/123710000/123706400/123706320/2107cf79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/124000000/123710000/123706400/123706320/8067e3b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/124000000/123710000/123706400/123706320/c81a0e54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Monroe [](https://www.expedia.ca/Monroe-Hotels-Rustic-Lakefront-Studio-With-Deck-Workspace.h123706320.Hotel-Information) CA $128 CA $322 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Monroe-Hotels-Rustic-Lakefront-Studio-With-Deck-Workspace.h123706320.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=2026-01-27&endDate=2026-01-28®ionId=181397&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%2FPine-Island-Vacation-Rentals.d181397.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPine-Island-Vacation-Rentals.d181397.Travel-Guide-VacationRentals) ## Top Pine Island Hotel Reviews ![Courtyard by Marriott Middletown Goshen](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/5eeeba71_y.jpg) ### Courtyard by Marriott Middletown Goshen 10/10 Excellent "Love staying here " [](https://expedia.ca/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information) ![Hampton Inn Matamoras/Milford](https://images.trvl-media.com/lodging/3000000/2780000/2774600/2774574/e1440092_y.jpg) ### Hampton Inn Matamoras/Milford 10/10 Excellent "The hotel is well maintained Clean quiet Staff is efficient and friendly!" [](https://expedia.ca/Matamoras-Hotels-Hampton-Inn-Matamoras-Milford.h2774574.Hotel-Information) ![Best Western Hunt's Landing Hotel Matamoras/Milford](https://images.trvl-media.com/lodging/1000000/30000/27300/27210/5acfc319_y.jpg) ### Best Western Hunt's Landing Hotel Matamoras/Milford 10/10 Excellent "Room was excellent " [](https://expedia.ca/Matamoras-Hotels-Best-Western-Hunts-Landing-Hotel-MatamorasMilford.h27210.Hotel-Information) ![Hampton Inn by Hilton Middletown](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/8c9a3fbd_y.jpg) ### Hampton Inn by Hilton Middletown 10/10 Excellent "Great staffing, clean rooms!!!" [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.Hotel-Information) ![Holiday Inn Express Hotel & Suites Chester by IHG](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/02f3df9e_y.jpg) ### Holiday Inn Express Hotel & Suites Chester by IHG 10/10 Excellent "Yanki was very helpful , attentive and friendly. The breakfast was lousy ! It was the same thing every day . They had coffee and tea available. Parking was easy . Clean room . " [](https://expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) ![Americas Best Value Inn at Central Valley-Woodbury](https://images.trvl-media.com/lodging/1000000/930000/921600/921510/debdefae_y.jpg) ### Americas Best Value Inn at Central Valley-Woodbury 10/10 Excellent "Clean room, nice staff, self parking included, very closed to Woodbury Premium outlet. I'd stay at this hotel again when I go to the outlet mall in the future. " [](https://expedia.ca/Newburgh-Hotels-Americas-Best-Value-Inn-Central-Valley.h921510.Hotel-Information) ![Sleep Inn & Suites Middletown - Goshen](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/1b0779e7_y.jpg) ### Sleep Inn & Suites Middletown - Goshen 10/10 Excellent "Great" [](https://expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Middletown-Goshen](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/77a42b8a_y.jpg) ### La Quinta Inn & Suites by Wyndham Middletown-Goshen 10/10 Excellent "Very clean" [](https://expedia.ca/Middletown-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Middletown.h4098.Hotel-Information) ![Tru by Hilton Middletown](https://images.trvl-media.com/lodging/37000000/36250000/36247800/36247736/935c6486_y.jpg) ### Tru by Hilton Middletown 10/10 Excellent "Yes, room was clean.THe staff" [](https://expedia.ca/Newburgh-Hotels-Tru-By-Hilton-Middletown.h36247736.Hotel-Information) ## Find out more about Pine Island You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded. As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Pine Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do. ## Explore a world of travel with Expedia - Trending destinations on Expedia.ca - All accommodation types in Pine Island ### Trending destinations on Expedia.ca - [Canmore Vacation Rentals ](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals) - [Maui Vacation Rentals ](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Kelowna Vacation Rentals ](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals) - [Whistler Vacation Rentals ](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals) - [Florida Vacation Rentals ](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Victoria Vacation Rentals ](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals) - [Vancouver Vacation Rentals ](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals) - 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[Vacation Homes in Pine Island ](https://expedia.ca/Pine-Island-Private-Vacation-Homes.d181397-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Condo Rentals in Pine Island ](https://expedia.ca/Pine-Island-Condos.d181397-aaCondos.Travel-Guide-Accommodation) - [Apartments in Pine Island ](https://expedia.ca/Pine-Island-Apartments.d181397-aaApartments.Travel-Guide-Accommodation) - [Cottages in Pine Island ](https://expedia.ca/Pine-Island-Cottages.d181397-aaCottages.Travel-Guide-Accommodation) - [Cabin Rentals in Pine Island ](https://expedia.ca/Pine-Island-Cabins.d181397-aaCabins.Travel-Guide-Accommodation) - [Motels in Pine Island ](https://expedia.ca/Pine-Island-Motels.d181397-aaMotels.Travel-Guide-Accommodation) - [Villas in Pine Island ](https://expedia.ca/Pine-Island-Villas.d181397-aaVillas.Travel-Guide-Accommodation) - [B&B in Pine Island ](https://expedia.ca/Pine-Island-Bed-And-Breakfast.d181397-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Pine Island ](https://expedia.ca/Pine-Island-Chalets.d181397-aaChalets.Travel-Guide-Accommodation) - [RV Parks in Pine Island ](https://expedia.ca/Pine-Island-RV-Parks.d181397-aaRVParks.Travel-Guide-Accommodation) - [Guest Houses in Pine Island ](https://expedia.ca/Pine-Island-Guest-Houses.d181397-aaGuestHouses.Travel-Guide-Accommodation) - [Farmstay in Pine Island ](https://expedia.ca/Pine-Island-Agritourism.d181397-aaAgritourism.Travel-Guide-Accommodation) - [Resorts in Pine Island ](https://expedia.ca/Pine-Island-Resort-Hotels.d181397-aaResortHotels.Travel-Guide-Accommodation) - [Inns in Pine Island ](https://expedia.ca/Pine-Island-Inns.d181397-aaInns.Travel-Guide-Accommodation) - [Lodges in Pine Island ](https://expedia.ca/Pine-Island-Lodges.d181397-aaLodges.Travel-Guide-Accommodation) - [Aparthotels in Pine Island ](https://expedia.ca/Pine-Island-Apart-Hotels.d181397-aaApartHotels.Travel-Guide-Accommodation) ## Frequently asked questions ### Can I find a vacation rental in Pine Island? ### What are some of the best vacation home rentals in Pine Island? ### What can I see and do in Pine Island? ### What are vacation rentals like in Pine Island? ### Expedia's Latest Trends Hotels - 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