Title: Middletown Vacation Home Rentals from CA $173: Search Top Private Vacation Homes for Rent | 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

![](https://images.trvl-media.com/place/8005/8b2c54c4-af30-4521-9b56-3bdf0a8d1a15.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

Next weekend

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=8864&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 one month

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=8864&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)

In two months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=8864&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)

## Our top choices for Middletown vacation homes

![Interior](https://images.trvl-media.com/lodging/122000000/121520000/121517700/121517645/ac8a10de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121520000/121517700/121517645/139bc94d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121520000/121517700/121517645/75a976f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Towels, soap, toilet paper](https://images.trvl-media.com/lodging/122000000/121520000/121517700/121517645/e9c28575.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Middletown

[](https://www.expedia.ca/Middletown-Hotels-Charming-Bungalow-In-Lovely-Middletown-NY.h121517645.Hotel-Information)

CA $187

CA $272 total

includes taxes & fees

Jan 16 - Jan 17

[](https://www.expedia.ca/Middletown-Hotels-Charming-Bungalow-In-Lovely-Middletown-NY.h121517645.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/124000000/123710000/123706400/123706320/24d963c0.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/124000000/123710000/123706400/123706320/2107cf79.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 19 - Jan 20

[](https://www.expedia.ca/Monroe-Hotels-Rustic-Lakefront-Studio-With-Deck-Workspace.h123706320.Hotel-Information)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/7ad8e5a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/82ecc5c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/cf889632.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/2bdd6486.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Highland Falls

[](https://www.expedia.ca/Highland-Falls-Hotels-Sleek-Escape-Modern-3-BR-4-Min-From-West-Point.h110986250.Hotel-Information)

10/10

Exceptional

(3 reviews)

"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Julio J.

CA $129

CA $559 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Highland-Falls-Hotels-Sleek-Escape-Modern-3-BR-4-Min-From-West-Point.h110986250.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/424d87c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/92f8429f.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)

![TV](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/9832ea44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Highland Falls

[](https://www.expedia.ca/Highland-Falls-Hotels-House-On-The-Babbling-Brook-Quiet-2BR-King-Bed.h113522235.Hotel-Information)

10/10

Exceptional

(6 reviews)

"Good stay, awesome place"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Scott G.

CA $126

CA $477 total

includes taxes & fees

Jan 16 - Jan 17

[](https://www.expedia.ca/Highland-Falls-Hotels-House-On-The-Babbling-Brook-Quiet-2BR-King-Bed.h113522235.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/84000000/83440000/83439600/83439540/315d7b3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83440000/83439600/83439540/2dce554c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83440000/83439600/83439540/cdecc2e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83440000/83439600/83439540/d9bc7fd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Kerhonkson

[](https://www.expedia.ca/Kerhonkson-Hotels-Dream-House-In-The-Gunks.h83439540.Hotel-Information)

10/10

Exceptional

(32 reviews)

"I love the place, very comfortable and cozy, Thank you so very much, Enjoyed a lot , Julia"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Julia K.

CA $115

CA $264 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Kerhonkson-Hotels-Dream-House-In-The-Gunks.h83439540.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)

![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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84240000/84238600/84238522/e473a315.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/85000000/84240000/84238600/84238522/d797bdd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Hurleyville

[](https://www.expedia.ca/Hurleyville-Hotels-10-Hope-St-Romantic-Catskills-Getaway-Bungalow-FireplaceWiFi.h84238522.Hotel-Information)

10/10

Exceptional

(7 reviews)

"The house was adorable! It had all amenities. The hosts were super responsive. Definitely would stay there again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Chris L.

CA $153

CA $327 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Hurleyville-Hotels-10-Hope-St-Romantic-Catskills-Getaway-Bungalow-FireplaceWiFi.h84238522.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/117000000/116300000/116293600/116293556/e4cec53f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116300000/116293600/116293556/586a41ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/117000000/116300000/116293600/116293556/80ec6f48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116300000/116293600/116293556/d8b7ae3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Warwick

[](https://www.expedia.ca/Warwick-Hotels-Room-1-At-The-Warwick-Inn-Cozy-Elegance-In-The-Heart-Of-Town.h116293556.Hotel-Information)

9.4/10

Exceptional

(8 reviews)

"I really enjoyed my stay. The room was very clean, the inn is well located in town and it is great having the restaurant below. Would stay here again! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Erin R.

CA $121

CA $213 total

includes taxes & fees

Jan 28 - Jan 29

[](https://www.expedia.ca/Warwick-Hotels-Room-1-At-The-Warwick-Inn-Cozy-Elegance-In-The-Heart-Of-Town.h116293556.Hotel-Information)

![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)

![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)

![Interior](https://images.trvl-media.com/lodging/101000000/100540000/100535600/100535519/3b0b1bad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100540000/100535600/100535519/1223c490.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Kerhonkson

[](https://www.expedia.ca/Kerhonkson-Hotels-Cozy-Hudson-Valley-Retreat-1950s-Ranch-Close-To-Everything.h100535519.Hotel-Information)

9.8/10

Exceptional

(24 reviews)

"Comfortable stay- very clean and kind host! Would highly recommend! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gretchen M.

CA $237

CA $406 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Kerhonkson-Hotels-Cozy-Hudson-Valley-Retreat-1950s-Ranch-Close-To-Everything.h100535519.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/6a09d677.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/719e347a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/3207c5e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/e5c54a16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Highland Falls

[](https://www.expedia.ca/Highland-Falls-Hotels-Lovely-3BR-Home-With-Parking-Walk-To-WP-Gate.h105177891.Hotel-Information)

10/10

Exceptional

(7 reviews)

"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Briana T.

CA $211

CA $427 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Highland-Falls-Hotels-Lovely-3BR-Home-With-Parking-Walk-To-WP-Gate.h105177891.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/117000000/116760000/116758500/116758499/1fe9eea3_edited_074f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116760000/116758500/116758499/5eb61507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116760000/116758500/116758499/7b146adf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/117000000/116760000/116758500/116758499/92496678.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in New Paltz

[](https://www.expedia.ca/New-Paltz-Hotels-Cozy-Private-Suite-In-The-Heart-Of-Beautiful-Gardiner.h116758499.Hotel-Information)

10/10

Exceptional

(7 reviews)

"Check-in was easy. Hosts very responsive to any questions and helpful to local recommendations. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Chanah B.

CA $177

CA $356 total

includes taxes & fees

Jan 16 - Jan 17

[](https://www.expedia.ca/New-Paltz-Hotels-Cozy-Private-Suite-In-The-Heart-Of-Beautiful-Gardiner.h116758499.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)

![Exterior detail](https://images.trvl-media.com/lodging/85000000/84240000/84238700/84238613/w1259h1279x0y0-e6a6d7aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/85000000/84240000/84238700/84238613/bd275d6f.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)

### Vacation Home in Hurleyville

[](https://www.expedia.ca/Hurleyville-Hotels-8-Hope-St-Relaxing-Catskills-Getaway-Bungalow-FireplaceWiFi.h84238613.Hotel-Information)

10/10

Exceptional

(2 reviews)

"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."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Holly L.

CA $153

CA $327 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Hurleyville-Hotels-8-Hope-St-Relaxing-Catskills-Getaway-Bungalow-FireplaceWiFi.h84238613.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/be15b260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/ab2c7ac1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/116022ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/8cbcd139.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Highland Falls

[](https://www.expedia.ca/Highland-Falls-Hotels-Fabulous-3bdrm-Home-Wparking.h114378708.Hotel-Information)

9.0/10

Wonderful

(4 reviews)

"Clean home, conveniently located to West Point. Very comfortable beds. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Danielle B.

CA $211

CA $416 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Highland-Falls-Hotels-Fabulous-3bdrm-Home-Wparking.h114378708.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/6b825ecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/6f93013a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/ae162913.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/8fad8a9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Highland Falls

[](https://www.expedia.ca/Highland-Falls-Hotels-3BR-West-Point-Retreat-3min-To-Back-Gate-King-Bed.h113522229.Hotel-Information)

7.6/10

Good

(5 reviews)

"Wonderful stay! The property is within walking distance of the little downtown area & had driveway parking. It was clean & plenty spacious. Property owners had great communication! This is a property with 2 units, but we were not bothered by any extra noise. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Waylon J.

CA $153

CA $608 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/Highland-Falls-Hotels-3BR-West-Point-Retreat-3min-To-Back-Gate-King-Bed.h113522229.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/36000000/35150000/35143100/35143035/21334245.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/36000000/35150000/35143100/35143035/7a8f0cf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/36000000/35150000/35143100/35143035/21349f2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/36000000/35150000/35143100/35143035/a6f4bfc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Highland Lake

[](https://www.expedia.ca/Highland-Lake-Hotels-Sweet-Old-Farmhouse-In-A-Tranquil-Setting.h35143035.Hotel-Information)

10/10

Exceptional

(2 reviews)

"The property was very easy to access and easy to navigate the area with the location. Also right across from the local yoga studio was a bonus!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anne H.

CA $276

CA $422 total

includes taxes & fees

Jan 17 - Jan 18

[](https://www.expedia.ca/Highland-Lake-Hotels-Sweet-Old-Farmhouse-In-A-Tranquil-Setting.h35143035.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122930000/122929100/122929001/120febc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122930000/122929100/122929001/7c3fd8d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122930000/122929100/122929001/bb90272b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/123000000/122930000/122929100/122929001/2f9d1a89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Cornwall

[](https://www.expedia.ca/Cornwall-Hotels-Storm-King-At-Narnia-Welcome-To-A-Slice-Of-Paradise-In-The-Hudson-Valley.h122929001.Hotel-Information)

10/10

Exceptional

(2 reviews)

"We really enjoyed our short stay at the house - it was extremely clean, the beds were comfortable, and the whole house was warm and cozy. There were thoughtful little touches all around the house - from fluffy socks for us to extra blankets, motion-sensor nightlights, and a fully equipped kitchen. Everything is newly renovated and updated. Views of the surrounding mountains are beautiful and the location is quiet and peaceful. We would visit again! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anne R.

CA $300

CA $586 total

includes taxes & fees

Jan 16 - Jan 17

[](https://www.expedia.ca/Cornwall-Hotels-Storm-King-At-Narnia-Welcome-To-A-Slice-Of-Paradise-In-The-Hudson-Valley.h122929001.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/88000000/87740000/87733200/87733136/6eb1cb3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/88000000/87740000/87733200/87733136/84a56e63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/88000000/87740000/87733200/87733136/612fa592.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, WiFi](https://images.trvl-media.com/lodging/88000000/87740000/87733200/87733136/2915b0a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Glen Spey

[](https://www.expedia.ca/Glen-Spey-Hotels-Spacious-4-Bedroom-House-With-A-Private-Pool-In-A-Quiet-Area.h87733136.Hotel-Information)

10/10

Exceptional

(7 reviews)

"Great place"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Johnny A.

CA $276

CA $615 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Glen-Spey-Hotels-Spacious-4-Bedroom-House-With-A-Private-Pool-In-A-Quiet-Area.h87733136.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/96000000/95450000/95445200/95445189/3d478b6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/96000000/95450000/95445200/95445189/1d0bf8e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/96000000/95450000/95445200/95445189/w1024h677x0y3-57491410.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95450000/95445200/95445189/w1024h679x0y2-66622731.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Rock Hill

[](https://www.expedia.ca/Rock-Hill-Hotels-Beaver-Lake-Escape.h95445189.Hotel-Information)

9.6/10

Exceptional

(29 reviews)

"Clean place, friendly and accommodating host! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Bryan A.

CA $194

CA $329 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Rock-Hill-Hotels-Beaver-Lake-Escape.h95445189.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/84000000/83520000/83518700/83518661/0839ceb1_edited_e7e1.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)

![Interior](https://images.trvl-media.com/lodging/84000000/83520000/83518700/83518661/8e59195b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83520000/83518700/83518661/d477734e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Rock Hill

[](https://www.expedia.ca/Bouvet-Island-Hotels-Trails-Head-Tiny-House.h83518661.Hotel-Information)

9.0/10

Wonderful

(19 reviews)

"Host was very friendly and helpful. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michael R.

CA $99

CA $173 total

includes taxes & fees

Jan 17 - Jan 18

[](https://www.expedia.ca/Bouvet-Island-Hotels-Trails-Head-Tiny-House.h83518661.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/106000000/105730000/105722300/105722242/014c4095.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105730000/105722300/105722242/e24d9d79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105730000/105722300/105722242/68a653de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/106000000/105730000/105722300/105722242/5ac5c592.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in New Paltz

[](https://www.expedia.ca/New-Paltz-Hotels-Riverfront-Modern-House-With-Beautiful-Views.h105722242.Hotel-Information)

9.4/10

Exceptional

(24 reviews)

"Beautiful comfortable, clean "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michal G.

CA $297

CA $547 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/New-Paltz-Hotels-Riverfront-Modern-House-With-Beautiful-Views.h105722242.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112270000/112268900/112268824/ba9be98b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/113000000/112270000/112268900/112268824/9621850a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/113000000/112270000/112268900/112268824/49d4b784.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112270000/112268900/112268824/211a8ab3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Pine Bush

[](https://www.expedia.ca/Cragsmoor-Hotels-NEW-Sunny-Family-Cabin-Near-The-Best-Hiking-Trails.h112268824.Hotel-Information)

10/10

Exceptional

(3 reviews)

"Nice property, very close to Sam’s Point trailheads. We were there to hike, so this was perfect. We would definitely book again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Amy L.

CA $159

CA $674 total

includes taxes & fees

Jan 21 - Jan 22

[](https://www.expedia.ca/Cragsmoor-Hotels-NEW-Sunny-Family-Cabin-Near-The-Best-Hiking-Trails.h112268824.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=2026-01-29&endDate=2026-01-30&regionId=8864&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

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=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=CABIN)

Aparthotels

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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=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=APARTMENT)

Private vacation homes

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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=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=CONDO)

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=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=VILLA)

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=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=COTTAGE)

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=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=CHALET)

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## Top Middletown Hotel Reviews

![Resorts World Catskills Casino](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/ecb80f49_y.jpg)

### Resorts World Catskills Casino

10/10 Excellent

"Clean room with a great view."

[](https://expedia.ca/Monticello-Hotels-Resorts-World-Catskills-Casino.h23970267.Hotel-Information)

![Super 8 by Wyndham Middletown](https://images.trvl-media.com/lodging/1000000/460000/459800/459783/63cc5778_y.jpg)

### Super 8 by Wyndham Middletown

10/10 Excellent

"Sign in and out staff were amazing. Thank you for accommodating us."

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

![Residence Inn by Marriott Middletown Goshen](https://images.trvl-media.com/lodging/49000000/48280000/48273100/48273068/9a478c40_y.jpg)

### Residence Inn by Marriott Middletown Goshen

10/10 Excellent

"Always amazing was my second time here and will stay again."

[](https://expedia.ca/Newburgh-Hotels-Residence-Inn-By-Marriott-Middletown-Goshen.h48273068.Hotel-Information)

![Mountain Creek](https://images.trvl-media.com/lodging/3000000/2900000/2899900/2899900/f09dc021_y.jpg)

### Mountain Creek

10/10 Excellent

"easy check-in/check-out"

[](https://expedia.ca/Vernon-Hotels-Mountain-Creek.h2899900.Hotel-Information)

![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)

![The Kartrite Resort & Indoor Waterpark](https://images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/90ceac4d_y.jpg)

### The Kartrite Resort & Indoor Waterpark

10/10 Excellent

"Amazing "

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

![Overlook Lodge at Bear Mountain](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6_y.jpg)

### Overlook Lodge at Bear Mountain

10/10 Excellent

"Cozy and quiet. Rooms need size. Surroundings idellic. Nature abounds."

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

![Tru by Hilton Middletown](https://images.trvl-media.com/lodging/37000000/36250000/36247800/36247736/935c6486_y.jpg)

### Tru by Hilton Middletown

10/10 Excellent

"The room was spotless & the staff was very courteous & wonderful. We would definitely stay there again."

[](https://expedia.ca/Newburgh-Hotels-Tru-By-Hilton-Middletown.h36247736.Hotel-Information)

## Find out more about Middletown

## Middletown Vacation Homes information

| Number of reviews | 176                |
| ----------------- | ------------------ |
| Accommodation     | 499 Vacation Homes |
| Lowest Price      | CA $173            |
| Highest Price     | CA $674            |

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- [Cheap Hotels in Slate Hill ](https://www.expedia.ca/Slate-Hill-Hotels-Cheap-Hotels.0-0-d6325187-tCheapHotels.Travel-Guide-Filter-Hotels)
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- [Flights to Cuddebackville ](https://www.expedia.ca/Cheap-Flights-To-Cuddebackville.d3000448273.Travel-Guide-Flights)
- [Flights to New Hampton ](https://www.expedia.ca/Cheap-Flights-To-New-Hampton.d177852.Travel-Guide-Flights)
- [Flights to New York ](https://www.expedia.ca/Cheap-Flights-To-New-York.d178293.Travel-Guide-Flights)
- [Flights from Bloomingburg ](https://www.expedia.ca/lp/flights/3000448043/flights-from-bloomingburg)
- [Flights from Florida ](https://www.expedia.ca/lp/flights/553248634999145056/flights-from-florida)
- [Flights from Slate Hill ](https://www.expedia.ca/lp/flights/6325187/flights-from-slate-hill)
- [Flights from Toronto (YYZ) to New York (NYC) ](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york)

- [Visit Bloomingburg ](https://www.expedia.ca/Bloomingburg.dx3000448043)
- [Legoland® New York ](https://www.expedia.ca/LEGOLAND-New-York-Goshen.d553248635997928006.Vacation-Attraction)
- [Orange County Fair Speedway ](https://www.expedia.ca/Orange-County-Fair-Speedway-Middletown.d6182288.Vacation-Attraction)
- [Visit Slate Hill ](https://www.expedia.ca/Slate-Hill.dx6325187)

- [Car rental Goshen ](https://www.expedia.ca/Car-Rentals-In-Goshen.d8005.Car-Rental-Guide)
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- [Car rentals near Orange County ](https://www.expedia.ca/Destinations-In-Orange-County.d553248635083901431.Car-Rental-Destinations)
- [Hertz Rental Cars in Campbell Hall ](https://www.expedia.ca/Hertz-Car-Rentals-In-Campbell-Hall.d6338665-c40.Car-Rental-Guide-Suppliers)

- [Things to do in Goshen ](https://www.expedia.ca/Things-To-Do-In-Goshen.d8005.Travel-Guide-Activities)

- [Book Vacation Homes in Middletown on Expedia.com ](https://www.expedia.com/Middletown-Private-Vacation-Homes.d8864-aaPrivateVacationHomes.Travel-Guide-Accommodation)