Title: Middletown Vacation Rentals from CA $388: Short-Term Rentals for 2026 | Expedia.ca

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![Route 17 in ny is a great road to view the fall foliage](https://images.trvl-media.com/place/8005/8b2c54c4-af30-4521-9b56-3bdf0a8d1a15.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Vincent Ramundo

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## Check prices for these dates

In two weeks

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=8864&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 two months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 17 - Jul 19](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2026-07-17&endDate=2026-07-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Middletown vacation rentals

![House (1 Bedroom) | Living area](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369793/780cac79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369793/d5ed89f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369793/18ffe7af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369793/1d322732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hike & Fish: Outdoor Retreat Near Trails

[](https://www.expedia.ca/Hike-Fish-Outdoor-Retreat-On-The-Basher-Kill.h114369793.Hotel-Information)

Westbrookville

CA $226

CA $422 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/Hike-Fish-Outdoor-Retreat-On-The-Basher-Kill.h114369793.Hotel-Information)

![House](https://images.trvl-media.com/lodging/122000000/121910000/121901300/121901234/af5902b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/122000000/121910000/121901300/121901234/643a1d73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/122000000/121910000/121901300/121901234/d25435a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/122000000/121910000/121901300/121901234/e36fc455.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### NEW 5 Trinity Pl Cornwall NY 12518

[](https://www.expedia.ca/Cornwall-Hotels-West-Point-Villa-Jacuzzi-Pool-BBQ-Games-Pets.h121901234.Hotel-Information)

Cornwall

CA $763

CA $1,611 total

includes taxes & fees

Mar 25 - Mar 26

[](https://www.expedia.ca/Cornwall-Hotels-West-Point-Villa-Jacuzzi-Pool-BBQ-Games-Pets.h121901234.Hotel-Information)

![Apartment (0 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369761/fa957375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (0 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369761/725d33a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (0 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369761/f734cc29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (0 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369761/d01ab563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Close to Trails: Studio w/ Water Views

[](https://www.expedia.ca/Basher-Kill-Studio-W-Water-Views-Close-To-Trails.h114369761.Hotel-Information)

Westbrookville

CA $167

CA $327 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/Basher-Kill-Studio-W-Water-Views-Close-To-Trails.h114369761.Hotel-Information)

![Apartment](https://images.trvl-media.com/lodging/121000000/120130000/120124500/120124415/24011166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | Exterior](https://images.trvl-media.com/lodging/121000000/120130000/120124500/120124415/2b8a99fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/121000000/120130000/120124500/120124415/b40325c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | Exterior](https://images.trvl-media.com/lodging/121000000/120130000/120124500/120124415/ed9e6966.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2 Lake Cabins Pool+hottub Game Room 23acs

[](https://www.expedia.ca/Highland-Lake-Hotels-2-Lake-Cabins-Poolhottub-Game-Room-23acs.h120124415.Hotel-Information)

Highland Lake

CA $232

CA $1,295 total

includes taxes & fees

Mar 31 - Apr 1

[](https://www.expedia.ca/Highland-Lake-Hotels-2-Lake-Cabins-Poolhottub-Game-Room-23acs.h120124415.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=2026-04-07&endDate=2026-04-08&regionId=8864&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America&regionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=COTTAGE)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America&regionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=CABIN)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America&regionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America&regionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=APARTMENT)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America&regionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=VILLA)

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America&regionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=APART_HOTEL)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America&regionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=CONDO)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America&regionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=CHALET)

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## Top Middletown Hotel Reviews

![Hampton Inn by Hilton Middletown](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/88d2ecc5_y.jpg)

### Hampton Inn by Hilton Middletown

2/10 Terrible

"so smelly"

[](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.Hotel-Information)

![The Kartrite Resort & Indoor Waterpark](https://images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/7b139e0a_y.jpg)

### The Kartrite Resort & Indoor Waterpark

10/10 Excellent

"Nice"

[](https://expedia.ca/Monticello-Hotels-The-Kartrite-Resort-Indoor-Waterpark.h31681637.Hotel-Information)

![Super 8 by Wyndham Middletown](https://images.trvl-media.com/lodging/1000000/460000/459800/459783/d86611d0_y.jpg)

### Super 8 by Wyndham Middletown

2/10 Terrible

"V"

[](https://expedia.ca/Newburgh-Hotels-Super-8-By-Wyndham-Middletown.h459783.Hotel-Information)

![Home2 Suites by Hilton Middletown](https://images.trvl-media.com/lodging/16000000/15990000/15984700/15984645/3c35a288_y.jpg)

### Home2 Suites by Hilton Middletown

10/10 Excellent

"I booked two rooms for two nights I booked a month ahead of my stay. I called twice to verify my stay. I get there to find out they booked my two rooms on two different floors. When I complained about it the manger told me that it's not a guarantee to get rooms next to each other. After literally 15 minutes they were able to get me rooms next to each other and when I mention I had more kids coming because I booked for six children and only show up with two I was yelled at that there are no parties I said I am aware of that this is I booked for six children so that it would not be a party the manger just walked away after that "

[](https://expedia.ca/Newburgh-Hotels-Home2-Suites-By-Hilton-Middletown.h15984645.Hotel-Information)

![Best Western Hunt's Landing Hotel Matamoras/Milford](https://images.trvl-media.com/lodging/1000000/30000/27300/27210/54a4e005_y.jpg)

### Best Western Hunt's Landing Hotel Matamoras/Milford

10/10 Excellent

"The Staff was Awesome! From Hotel to Resturant and Bar ."

[](https://expedia.ca/Matamoras-Hotels-Best-Western-Hunts-Landing-Hotel-MatamorasMilford.h27210.Hotel-Information)

![Holiday Inn Express Hotel & Suites Chester by IHG](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/8648b91b_y.jpg)

### Holiday Inn Express Hotel & Suites Chester by IHG

8/10 Good

"Parking was easy- lady at the front desk was great. Room was good "

[](https://expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information)

![Courtyard by Marriott Middletown Goshen](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/5a64b5a6_y.jpg)

### Courtyard by Marriott Middletown Goshen

10/10 Excellent

"Was very clean and nice "

[](https://expedia.ca/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information)

![Overlook Lodge at Bear Mountain](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/679bdd4c_y.jpg)

### Overlook Lodge at Bear Mountain

10/10 Excellent

"Beautiful location. "

[](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information)

![Hampton Inn Harriman Woodbury](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/e0fcb0f3_y.jpg)

### Hampton Inn Harriman Woodbury

10/10 Excellent

"The room is small but fairly clean. I didn’t see any stains anywhere. Bathroom has a nice size, no closet. Small cabinet with a mini fridge and tv, so the side. The staff were super nice and gave cookies when checking in. The shuttle bus was supposed to run from 9 to 9 but stopped at 5pm (the driver had left). I didn’t get to try the breakfast but they have tea and coffee in the lobby. Sugar, milk is on the table. If you don’t like the coffee, there’s dunkin and Starbucks nearby. The view is lackluster, I was looking at the highway for the most part and parking lot. Must go’s are the outlet malls which is a 10 minute drive with the stoplights. Parking is almost impossible."

[](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information)

## Find out more about Middletown

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 Middletown. 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.   

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- [Vacation Homes in Middletown ](https://expedia.ca/Middletown-Private-Vacation-Homes.d8864-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Middletown ](https://expedia.ca/Middletown-Apartments.d8864-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Middletown ](https://expedia.ca/Middletown-Cottages.d8864-aaCottages.Travel-Guide-Accommodation)
- [Cabin Rentals in Middletown ](https://expedia.ca/Middletown-Cabins.d8864-aaCabins.Travel-Guide-Accommodation)
- [Condo Rentals in Middletown ](https://expedia.ca/Middletown-Condos.d8864-aaCondos.Travel-Guide-Accommodation)
- [Villas in Middletown ](https://expedia.ca/Middletown-Villas.d8864-aaVillas.Travel-Guide-Accommodation)
- [Motels in Middletown ](https://expedia.ca/Middletown-Motels.d8864-aaMotels.Travel-Guide-Accommodation)
- [Farmstay in Middletown ](https://expedia.ca/Middletown-Agritourism.d8864-aaAgritourism.Travel-Guide-Accommodation)
- [Chalets in Middletown ](https://expedia.ca/Middletown-Chalets.d8864-aaChalets.Travel-Guide-Accommodation)
- [RV Parks in Middletown ](https://expedia.ca/Middletown-RV-Parks.d8864-aaRVParks.Travel-Guide-Accommodation)
- [B&B in Middletown ](https://expedia.ca/Middletown-Bed-And-Breakfast.d8864-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Guest Houses in Middletown ](https://expedia.ca/Middletown-Guest-Houses.d8864-aaGuestHouses.Travel-Guide-Accommodation)
- [Inns in Middletown ](https://expedia.ca/Middletown-Inns.d8864-aaInns.Travel-Guide-Accommodation)
- [Lodges in Middletown ](https://expedia.ca/Middletown-Lodges.d8864-aaLodges.Travel-Guide-Accommodation)
- [Resorts in Middletown ](https://expedia.ca/Middletown-Resort-Hotels.d8864-aaResortHotels.Travel-Guide-Accommodation)
- [Aparthotels in Middletown ](https://expedia.ca/Middletown-Apart-Hotels.d8864-aaApartHotels.Travel-Guide-Accommodation)
- [Holiday Park Resorts in Middletown ](https://expedia.ca/Middletown-Holiday-Parks.d8864-aaHolidayParks.Travel-Guide-Accommodation)

## Frequently asked questions

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