Title: Middletown Vacation Home Rentals from CA $137: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Middletown](https://expedia.ca/Middletown-Hotels.d8864.Travel-Guide-Hotels)[Vacation Rentals in Middletown](https://expedia.ca/Middletown-Vacation-Rentals.d8864.Travel-Guide-VacationRentals)[Flights to Middletown](https://expedia.ca/Cheap-Flights-To-Middletown.d8864.Travel-Guide-Flights)[Things to do in Middletown](https://expedia.ca/Things-To-Do-In-Middletown.d8864.Travel-Guide-Activities)[Middletown Car Rentals](https://expedia.ca/Car-Rentals-In-Middletown.d8864.Car-Rental-Guide)[Middletown Vacation Packages](https://expedia.ca/Middletown.d8864.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/b3592d5854c5ebf058517b7fb1df474d.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Vincent Ramundo # Middletown Vacation Rentals ### Change your mind Book hotels with free cancellation ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2025-10-17&endDate=2025-10-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=8864&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=8864&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=8864&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) ## Browse Select Middletown Vacation Homes ![Outdoor dining](https://images.trvl-media.com/lodging/80000000/79880000/79874000/79873967/w906h683x60y0-2991689a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/80000000/79880000/79874000/79873967/e4830f65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom](https://images.trvl-media.com/lodging/80000000/79880000/79874000/79873967/0b84e0bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/80000000/79880000/79874000/79873967/w906h683x60y0-0b53ee10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Glamping Tent & Campsite by Minnewaska State Park Kerhonkson 8.8/10 Excellent (3) "We had a great time. The tent and toilet were clean. We appreciated the water provided and the cookware. The only thing to note is that there is a bit of walking on a rocky trail before reaching the campsite (not next to the parking spot). The river was fun to explore but can be difficult for younger kids to get to. The campsite is close to Minnewaska State Park, very convenient. " CA $119 CA $212 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Kerhonkson-Hotels-Glamping-Tent-Campsite-By-Minnewaska-State-Park.h79873967.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/117000000/116300000/116295600/116295595/7917335b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/117000000/116300000/116295600/116295595/6b71b73b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116300000/116295600/116295595/e62b431c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116300000/116295600/116295595/330bb843.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town Warwick 10/10 Exceptional (3) "My girlfriend and I loved our stay here! We stayed for one night and it was perfect for what we needed. Very clean with easy self-check-in. The host was very responsive with all inquiries. Short walk to nice downtown area as well!" CA $118 CA $209 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Warwick-Hotels-Room-2-At-The-Warwick-Inn-Cozy-Elegance-In-The-Heart-Of-Town.h116295595.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119570000/119569000/119568951/189e7616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/120000000/119570000/119569000/119568951/7f6314e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119570000/119569000/119568951/92ba2e44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119570000/119569000/119568951/07f8981a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming house with brook in the picturesque Village of Wurtsboro min from shops Wurtsboro [](https://www.expedia.ca/Wurtsboro-Hotels-Charming-House-With-Brook-In-The-Picturesque-Village-Of-Wurtsboro-Min-From-Shops.h119568951.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/119000000/118170000/118164800/118164776/87b6b115.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/119000000/118170000/118164800/118164776/afe3fdf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/119000000/118170000/118164800/118164776/3add8621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/119000000/118170000/118164800/118164776/ebfc1676.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI, new paltz CA $292 CA $910 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/New-Paltz-Hotels-Welcome-To-New-Paltz-Charming-3-Bedroom-House-With-AC.h118164776.Hotel-Information) ![TV, fireplace](https://images.trvl-media.com/lodging/120000000/119380000/119376700/119376673/f1e25b91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119380000/119376700/119376673/0e496658.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119380000/119376700/119376673/ce5b3152.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119380000/119376700/119376673/417402b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Comfort Cabin by Eden Islands Montague CA $152 CA $308 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Montague-Hotels-Country-Comfort-Cabin-By-Eden-Islands.h119376673.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/e73b5292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/ee686000.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/e5f1d678.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/424d87c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### House on the Babbling Brook- Quiet 2BR + King Bed! Highland Falls 10/10 Exceptional (2) "Good stay, awesome place" CA $219 CA $588 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Highland-Falls-Hotels-House-On-The-Babbling-Brook-Quiet-2BR-King-Bed.h113522235.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/116000000/115840000/115833800/115833702/w902h683x60y0-e3856a80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/116000000/115840000/115833800/115833702/w509h683x257y0-ac46b09e.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/116000000/115840000/115833800/115833702/f90f9b8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/116000000/115840000/115833800/115833702/39648427.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Romantic spot above restaurant., ideal for the gourmet Westtown 10/10 Exceptional (3) "Hosts communicated well, the room was spacious and clean, and the restaurant downstairs is spectacular. " CA $209 CA $268 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Westtown-Hotels-Romantic-Spot-Above-Restaurant.h115833702.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117330000/117327100/117327054/9608d372.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117330000/117327100/117327054/2f10233c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117330000/117327100/117327054/d6940742.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom](https://images.trvl-media.com/lodging/118000000/117330000/117327100/117327054/060e4607.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Okama Abon Bell Tent, River View Taino Woods 15 minutes to Bethel Woods Concerts Harris CA $126 CA $172 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Harris-Hotels-Okama-Abon-Bell-Tent.h117327054.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116700000/116695900/116695811/e836b8a6_edited_d1dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116700000/116695900/116695811/w1080h803x0y799-0a6c2b25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116700000/116695900/116695811/w1080h1440x0y480-c2c7527c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116700000/116695900/116695811/c229255f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now. Forestburgh 10/10 Exceptional (9) "Lovely property in a serene and interesting setting. The hosts were so kind and communicative. We stayed for a night and enjoyed local sights and a concert in Bethel! " CA $251 CA $451 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Forestburgh-Hotels-3-Bedroom-House-In-Charming-Forestburgh-With-WiFi.h116695811.Hotel-Information) ![Shower, hair dryer](https://images.trvl-media.com/lodging/110000000/109070000/109063100/109063027/ba0ba20e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109070000/109063100/109063027/419c6253.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/110000000/109070000/109063100/109063027/a9ac9a64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/110000000/109070000/109063100/109063027/ad87218e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hudson Valley Luxury | Pool, Theater, Sleeps 28 Greenfield Park CA $1,000 CA $2,170 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Ellenville-Hotels-Hudson-Valley-Luxury-Pool.h109063027.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/101000000/100540000/100535600/100535519/5bc13913.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/101000000/100540000/100535600/100535519/d1d8291d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100540000/100535600/100535519/1eef3e41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100540000/100535600/100535519/3b0b1bad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything Kerhonkson 9.8/10 Exceptional (18) "Comfortable accommodations. Everything you need for a relaxing holiday " CA $251 CA $423 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Kerhonkson-Hotels-Cozy-Hudson-Valley-Retreat-1950s-Ranch-Close-To-Everything.h100535519.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/117000000/116370000/116362400/116362325/60f2c951.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116370000/116362400/116362325/1522d348.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116370000/116362400/116362325/77fcc776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave](https://images.trvl-media.com/lodging/117000000/116370000/116362400/116362325/a23e5d11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit Montgomery 10/10 Exceptional (1) "Guido was very responsive and thoughtful! My partner and I stayed with our small dog and it was safe, clean, well stocked and in a beautiful area. Highly recommend to those looking to stay in the area!" CA $231 CA $370 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Montgomery-Hotels-Cozy-Cabin-Gateway-I-15-Acres-W-Pool-Firepit.h116362325.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116300000/116296100/116296027/w905h683x59y0-d264c84b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/117000000/116300000/116296100/116296027/1fbe6091.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/117000000/116300000/116296100/116296027/faad0c62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/117000000/116300000/116296100/116296027/w904h683x59y0-2e98a10e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #308 Vernon Township 10/10 Exceptional (2) "We had a wonderful stay at the Appalachian Resort hosted by Milagros & Sergio. They were incredibly friendly and gave us clear and helpful explanations from the start. The room was very clean, and it was great having the water park within walking distance. They also offered flexible early check-in depending on the situation, which we really appreciated. Whenever we had questions, they responded very quickly, so we felt completely comfortable during our stay. We would love to come back again!" CA $174 CA $373 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Vernon-Hotels-Cozy-Condo-1-Bdr-1-Bath-Sleep-4-Mountain-View-308.h116296027.Hotel-Information) ![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120010000/120002100/120002003/ecbdcad5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120010000/120002100/120002003/02b924ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120010000/120002100/120002003/1a2eae94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/121000000/120010000/120002100/120002003/06636b0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tranquil 2-bedroom house with AC in Rock Hill Rock Hill CA $223 CA $414 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Rock-Hill-Hotels-Tranquil-2-Bedroom-House-With-AC-In-Rock-Hill.h120002003.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/85000000/84240000/84238600/84238522/7273e4ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/85000000/84240000/84238600/84238522/e6dde603.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/85000000/84240000/84238600/84238522/ef0ef623.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/85000000/84240000/84238600/84238522/8921c9ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi Hurleyville 10/10 Exceptional (6) "The house was adorable! It had all amenities. The hosts were super responsive. Definitely would stay there again. " CA $153 CA $331 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Hurleyville-Hotels-10-Hope-St-Romantic-Catskills-Getaway-Bungalow-FireplaceWiFi.h84238522.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/75000000/74240000/74234100/74234035/45a1c419.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/75000000/74240000/74234100/74234035/916d6786.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/75000000/74240000/74234100/74234035/5cb1f91c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74240000/74234100/74234035/ae6c0caa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ★Rare River Views & Access, Cabin by Eden Islands★ Montague 9.0/10 Wonderful (12) "Nice convenient location, near the river and town. " CA $152 CA $305 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Montague-Hotels-Rare-River-Views-Access.h74234035.Hotel-Information) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/120000000/119380000/119376700/119376679/5107f671.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/120000000/119380000/119376700/119376679/f5b9a2c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/120000000/119380000/119376700/119376679/239c70c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119380000/119376700/119376679/5421ade7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Milford-Montague Riverway Cottage Montague 8.0/10 Very good (1) "This location was great for our purpose of visiting family in Port Jervis and was easy to find - even in the dark. Due to the lack of reviews, I'm guessing that this is a new listing and that there are kinks still being worked out. Without going into too much detail, there was no way the space had recently been cleaned and the description provided on the listing seems to be lifted from one of their other properties as there was no fire pit, no fireplace, no dishwasher and the house is definitely... CA $236 CA $411 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Montague-Hotels-Charming-Milford-Montague-Riverway-Cottage.h119376679.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/85000000/84240000/84238700/84238613/115d7e2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/85000000/84240000/84238700/84238613/760c2f24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/85000000/84240000/84238700/84238613/bb1c4cb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/85000000/84240000/84238700/84238613/025052c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New! Relaxing Agrihood Bungalow Getaway-Fireplace/WiFi Hurleyville 10/10 Exceptional (2) "Clean, neat, well stocked cabin in a peaceful village. We enjoyed a walk on the nearby rail trail and is not far from other interesting sites. We would definitely recommend." CA $153 CA $324 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Hurleyville-Hotels-8-Hope-St-Relaxing-Catskills-Getaway-Bungalow-FireplaceWiFi.h84238613.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/109000000/108480000/108478400/108478343/6b2d2281.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108480000/108478400/108478343/897509a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/109000000/108480000/108478400/108478343/a1036266.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/109000000/108480000/108478400/108478343/e8896e83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### West Point Family Retreat, 5 min walk to Thayer! Highland Falls 9.6/10 Exceptional (5) "Nice houseAwesome kitchen Granddaughter loved the bunk bed and the many games" CA $627 CA $1,153 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Highland-Falls-Hotels-West-Point-Family-Retreat.h108478343.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/84000000/83520000/83518700/83518661/d477734e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83520000/83518700/83518661/8e59195b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83520000/83518700/83518661/w1024h630x0y26-bff20eb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Stovetop, coffee/tea maker, electric kettle, cookware/dishes/utensils](https://images.trvl-media.com/lodging/84000000/83520000/83518700/83518661/w588h683x218y0-4a1318f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Trails Head Tiny House Rock Hill 9.0/10 Wonderful (19) "Host was very friendly and helpful. " CA $99 CA $174 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Bouvet-Island-Hotels-Trails-Head-Tiny-House.h83518661.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=2025-10-21&endDate=2025-10-22®ionId=8864&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%2FMiddletown-Private-Vacation-Homes.d8864-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FMiddletown-Private-Vacation-Homes.d8864-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Middletown Hotel Reviews ![La Quinta Inn & Suites by Wyndham Middletown-Goshen](//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 room. Efficient staff" [](https://expedia.ca/Middletown-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Middletown.h4098.Hotel-Information) ![Best Western Hunt's Landing Hotel Matamoras/Milford](//images.trvl-media.com/lodging/1000000/30000/27300/27210/5acfc319_y.jpg) ### Best Western Hunt's Landing Hotel Matamoras/Milford 10/10 Excellent "Clean and quiet " [](https://expedia.ca/Matamoras-Hotels-Best-Western-Hunts-Landing-Hotel-MatamorasMilford.h27210.Hotel-Information) ![Sleep Inn & Suites Middletown - Goshen](//images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/1b0779e7_y.jpg) ### Sleep Inn & Suites Middletown - Goshen 10/10 Excellent "Hreat" [](https://expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.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 "This is such an awesome place to bring the family to unwind.The kids love to hangout at the pool and it’s easy to get to your room after swimming." [](https://expedia.ca/Monticello-Hotels-The-Kartrite-Resort-Indoor-Waterpark.h31681637.Hotel-Information) ![Home2 Suites by Hilton Middletown](//images.trvl-media.com/lodging/16000000/15990000/15984700/15984645/3c35a288_y.jpg) ### Home2 Suites by Hilton Middletown 10/10 Excellent "Staff was very friendly and professional. They lit the outside firepit for us to enjoy a beautiful early fall evening. Room was comfortable and stocked with what we needed." [](https://expedia.ca/Newburgh-Hotels-Home2-Suites-By-Hilton-Middletown.h15984645.Hotel-Information) ![Hampton Inn by Hilton Middletown](//images.trvl-media.com/lodging/1000000/290000/282000/281932/8c9a3fbd_y.jpg) ### Hampton Inn by Hilton Middletown 10/10 Excellent "Great for business stay " [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.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 "Good " [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.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 "Great natural setting. Comprehensive facilities." [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.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 "The rooms are spacious and comfortable! Will definitely go back. " [](https://expedia.ca/Monticello-Hotels-Resorts-World-Catskills-Casino.h23970267.Hotel-Information) ## Find out more about Middletown ## Middletown Vacation Homes information | Number of reviews | 15,512 | | --- | --- | | Accommodation | 492 Vacation Homes | | Lowest Price | CA $137 | | Highest Price | CA $341 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [Cheap Hotels in Bloomingburg](https://www.expedia.ca/Bloomingburg-Hotels-Cheap-Hotels.0-0-d3000448043-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Bloomingburg](https://www.expedia.ca/Bloomingburg-Hotels-Hotel-With-Pool.0-0-d3000448043-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Bloomingburg Hotels](https://www.expedia.ca/Bloomingburg-Hotels.d3000448043.Travel-Guide-Hotels) - [Villas in Bloomingburg](https://www.expedia.ca/Bloomingburg-Villas.d3000448043-aaVillas.Travel-Guide-Accommodation) - [Guest Houses in Bullville](https://www.expedia.ca/Bullville-Guest-Houses.d3000350713-aaGuestHouses.Travel-Guide-Accommodation) - 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