Title: Middletown Vacation Rentals from CA $258: 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

![](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

In two weeks

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2026-05-29&endDate=2026-05-31&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

![Interior](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261544/w506h683x259y0-6b740411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261544/w919h683x47y0-1b7c08f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261544/w906h683x59y0-c6be118f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261544/w506h683x259y0-81ebd497.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hello Small Stone

[](https://www.expedia.ca/Middletown-Hotels-Hello-Small-Stone.h99261544.Hotel-Information)

Middletown

9.6/10

Exceptional

(5 reviews)

"The house was great. It was nice to sit and relax by the small pond in the back."

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

John H.

CA $247

CA $610 total

includes taxes & fees

Mar 4 - Mar 5

[](https://www.expedia.ca/Middletown-Hotels-Hello-Small-Stone.h99261544.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117330000/117327100/117327054/d6940742.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/118000000/117330000/117327100/117327054/9608d372.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

[](https://www.expedia.ca/Harris-Hotels-Okama-Abon-Bell-Tent.h117327054.Hotel-Information)

Harris

CA $191

CA $246 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Harris-Hotels-Okama-Abon-Bell-Tent.h117327054.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/121000000/120250000/120244100/120244044/6f19918a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/121000000/120250000/120244100/120244044/7f3a22c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120250000/120244100/120244044/1af31b03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120250000/120244100/120244044/f90023ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 1-bedroom retreat minutes from West Point!

[](https://www.expedia.ca/Highland-Falls-Hotels-Cozy-1-Bedroom-Retreat-Minutes-From-West-Point.h120244044.Hotel-Information)

Highland Falls

10/10

Exceptional

(1 review)

"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "

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

Zack C.

CA $123

CA $252 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Highland-Falls-Hotels-Cozy-1-Bedroom-Retreat-Minutes-From-West-Point.h120244044.Hotel-Information)

![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717464/dd930402.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717464/08ae7458.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717464/328adef2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717464/2c8ccdec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

[](https://www.expedia.ca/Highland-Falls-Hotels-Quiet-Apt-With-Coffee-Bar.h94717464.Hotel-Information)

Highland Falls

9.8/10

Exceptional

(16 reviews)

"Great Unit."

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

Rudy R.

CA $110

CA $365 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Highland-Falls-Hotels-Quiet-Apt-With-Coffee-Bar.h94717464.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/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)

![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)

### Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

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

Kerhonkson

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 $63

CA $210 total

includes taxes & fees

Feb 8 - Feb 9

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

![Interior](https://images.trvl-media.com/lodging/84000000/83430000/83426500/83426410/10d69ba6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/84000000/83430000/83426500/83426410/cb371140.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/84000000/83430000/83426500/83426410/0c3ccbf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/84000000/83430000/83426500/83426410/fd01a6d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dream getaway apartment in the foot of Gunks Ridge

[](https://www.expedia.ca/Wallkill-Hotels-Dream-Getaway-Apartment-In-The-Foot-Of-Gunks-Ridge.h83426410.Hotel-Information)

Wallkill

9.6/10

Exceptional

(24 reviews)

"Serg’s place was comfortable and clean! It was a perfect location for me and my friends to stay while rock climbing in the Gunks. We did not feel cramped or unsafe and the complementary tea was a hit! One thing to note is that both of the beds were low to the ground (below knee level) so if someone has knee or back problems, it might be difficult to stand up out of bed. "

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

Mary S.

CA $75

CA $222 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Wallkill-Hotels-Dream-Getaway-Apartment-In-The-Foot-Of-Gunks-Ridge.h83426410.Hotel-Information)

![Fireplace, books](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/cd189b6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/c4f41298.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/84000000/83440000/83439100/83439008/5dd44347.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/7cf93160.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

[](https://www.expedia.ca/Kerhonkson-Hotels-Dream-Cottage-In-The-Gunks.h83439008.Hotel-Information)

Kerhonkson

9.4/10

Exceptional

(12 reviews)

"Charming and relaxing cottage. Perfect location for hiking or enjoying Lake Minnewaska or Mohonk Preserve. "

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

Patrick S.

CA $117

CA $269 total

includes taxes & fees

Feb 11 - Feb 12

[](https://www.expedia.ca/Kerhonkson-Hotels-Dream-Cottage-In-The-Gunks.h83439008.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/70000000/69550000/69544900/69544886/ac221ad2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69550000/69544900/69544886/7ac74429.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/70000000/69550000/69544900/69544886/5710350e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/70000000/69550000/69544900/69544886/9236bc83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

[](https://www.expedia.ca/Beacon-Hotels-Luxe-Studio-2-On-Main-Street-Luxury-Steam-Shower.h69544886.Hotel-Information)

Beacon

10/10

Exceptional

(33 reviews)

"Great time and great place to stay "

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

S S.

CA $159

CA $344 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Beacon-Hotels-Luxe-Studio-2-On-Main-Street-Luxury-Steam-Shower.h69544886.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)

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

![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/117000000/116300000/116293600/116293556/4cc093aa.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)

###  Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

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

Warwick

9.2/10

Wonderful

(9 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 $128

CA $219 total

includes taxes & fees

Feb 17 - Feb 18

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

![Exterior](https://images.trvl-media.com/lodging/91000000/90900000/90899300/90899226/86b4cdac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/91000000/90900000/90899300/90899226/w1024h681x0y2-16a3f759.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/91000000/90900000/90899300/90899226/w1024h680x0y3-fb94b93c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90900000/90899300/90899226/w905h683x60y0-cdd484b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in the heart of the Hudson Valley, Cabin 2

[](https://www.expedia.ca/Newburgh-Hotels-Cabin-In-The-Heart-Of-The-Hudson-Valley.h90899226.Hotel-Information)

Newburgh

9.4/10

Exceptional

(31 reviews)

"A very cute, convenient, and affordable stay with timely, friendly communication from the owner. Our dog loved it and we appreciated the ability to have a private place to stay."

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

Sara B.

CA $176

CA $275 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Newburgh-Hotels-Cabin-In-The-Heart-Of-The-Hudson-Valley.h90899226.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107970000/107964300/107964203/bf85ab49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107970000/107964300/107964203/9714c3f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/108000000/107970000/107964300/107964203/96050ad7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/108000000/107970000/107964300/107964203/e7e8be7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

[](https://www.expedia.ca/Gardiner-Hotels-Modern-Zen-Chalet-At-The-Foot-Of-Gunks-W-Mt-View.h107964203.Hotel-Information)

Gardiner

10/10

Exceptional

(8 reviews)

"Great weekend getaway to reconnect with old friends!"

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

Lisa D.

CA $281

CA $462 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/Gardiner-Hotels-Modern-Zen-Chalet-At-The-Foot-Of-Gunks-W-Mt-View.h107964203.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/96000000/95250000/95247300/95247281/e1fdf271.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining tables](https://images.trvl-media.com/lodging/96000000/95250000/95247300/95247281/c0e76b96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95250000/95247300/95247281/e34ae238.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/96000000/95250000/95247300/95247281/a5eff7d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 2BR condo w/ valley views

[](https://www.expedia.ca/Vernon-Hotels-Cozy-2BR-Condo-W-Valley-Views.h95247281.Hotel-Information)

Vernon Township

9.6/10

Exceptional

(24 reviews)

"Very nice stay really clean and beautiful views thanks a lot enjoyed snowboarding at creek for the 2 days "

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

Jacqueline

CA $135

CA $347 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Vernon-Hotels-Cozy-2BR-Condo-W-Valley-Views.h95247281.Hotel-Information)

![1 bedroom, free WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/78000000/77870000/77868400/77868343/2a5a3e24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/78000000/77870000/77868400/77868343/ad8ed784.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/78000000/77870000/77868400/77868343/e3592baf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/78000000/77870000/77868400/77868343/d99fdb5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen

[](https://www.expedia.ca/Warwick-Hotels-Luxe-Penthouse-Loft-On-Main-St-Steam-Shower.h77868343.Hotel-Information)

Warwick

10/10

Exceptional

(34 reviews)

"Great location within walking distance of boutiques and restaurants. Enjoyed our stay. "

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

Cynthia W.

CA $148

CA $347 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Warwick-Hotels-Luxe-Penthouse-Loft-On-Main-St-Steam-Shower.h77868343.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/100000000/99340000/99332300/99332216/7aece28d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/100000000/99340000/99332300/99332216/839fe2a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99340000/99332300/99332216/bff58ee5_edited_ccf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/100000000/99340000/99332300/99332216/7e196e90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Heated Pool Hot Tubs Sauna Gym Mtn Views Appalachian @ Mtn Creek #225

[](https://www.expedia.ca/Vernon-Hotels-Water-Park.h99332216.Hotel-Information)

Vernon

9.8/10

Exceptional

(9 reviews)

"Nice place!!"

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

Lukasz

CA $165

CA $374 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Vernon-Hotels-Water-Park.h99332216.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/77000000/76800000/76795200/76795113/c56c6835.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76800000/76795200/76795113/9fc74ed4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/77000000/76800000/76795200/76795113/ed089268.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76800000/76795200/76795113/f1e51835.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Trails Head Cabin

[](https://www.expedia.ca/Rock-Hill-Hotels-Cozy-Cabin-Retreat.h76795113.Hotel-Information)

Rock Hill

9.8/10

Exceptional

(101 reviews)

"Really cozy stay I definitely have to come back during the summer months it was a beautiful experience !"

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

Kimaya

CA $134

CA $258 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Rock-Hill-Hotels-Cozy-Cabin-Retreat.h76795113.Hotel-Information)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90900000/90897800/90897766/w1024h681x0y2-21ff539b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90900000/90897800/90897766/c421cfb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90900000/90897800/90897766/w1024h680x0y3-8188dd85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90900000/90897800/90897766/w1024h680x0y3-d877abc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in the Heart of the Hudson Valley, Cabin 1

[](https://www.expedia.ca/Newburgh-Hotels-Cabin-In-The-Heart-Of-The-Hudson-Valley.h90897766.Hotel-Information)

Newburgh

10/10

Exceptional

(32 reviews)

"Great overnight spot, especially with a dog."

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

Ed C.

CA $231

CA $386 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Newburgh-Hotels-Cabin-In-The-Heart-Of-The-Hudson-Valley.h90897766.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/74000000/73260000/73255300/73255284/d5243acf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/74000000/73260000/73255300/73255284/e0fcea44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73260000/73255300/73255284/cd4adf28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/74000000/73260000/73255300/73255284/e13aeb0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

[](https://www.expedia.ca/Beacon-Hotels-Luxe-Studio-3-On-Main-Street-Amazing-Steam-Shower-WasherDryer.h73255284.Hotel-Information)

Beacon

9.8/10

Exceptional

(43 reviews)

"Adorable place to stay in an adorable town! "

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

Mary L.

CA $150

CA $321 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Beacon-Hotels-Luxe-Studio-3-On-Main-Street-Amazing-Steam-Shower-WasherDryer.h73255284.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/97000000/96110000/96102100/96102062/76e3be85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/97000000/96110000/96102100/96102062/a47d38a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/97000000/96110000/96102100/96102062/6692c665.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/97000000/96110000/96102100/96102062/c3bd8868.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Treeview - Cozy 2 BR Apartment - Fast WiFi \~ 1 hr from NYC - 5 mins to downtown

[](https://www.expedia.ca/Port-Jervis-Hotels-Treeview-Cozy-2-BR-Apartment-Fast-WiFi-1-Hr-From-NYC-5-Mins-To-Downtown.h96102062.Hotel-Information)

Port Jervis

10/10

Exceptional

(6 reviews)

"House was clean and parking was easy! Close to downtown Port Jervis, with some great restaurants. The owners were so kind, and were so helpful!"

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

Jen C.

CA $151

CA $457 total

includes taxes & fees

Mar 10 - Mar 11

[](https://www.expedia.ca/Port-Jervis-Hotels-Treeview-Cozy-2-BR-Apartment-Fast-WiFi-1-Hr-From-NYC-5-Mins-To-Downtown.h96102062.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/85000000/84760000/84759800/84759759/w1170h1445x0y13-8acc9af3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84760000/84759800/84759759/6c94b359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84760000/84759800/84759759/e10ff586.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/85000000/84760000/84759800/84759759/5c8baf7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2 bedroom cozy condo with parking on premises

[](https://www.expedia.ca/Vernon-Hotels-Lovely-2-Bedroom-Condo-With-Parking-On-Premises.h84759759.Hotel-Information)

Vernon Township

10/10

Exceptional

(34 reviews)

"The place was beautiful. Would highly recommended staying here. "

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

Ranada

CA $178

CA $402 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/Vernon-Hotels-Lovely-2-Bedroom-Condo-With-Parking-On-Premises.h84759759.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)

![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)

### Trails Head Tiny House

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

Rock Hill

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 $108

CA $183 total

includes taxes & fees

Mar 1 - Mar 2

[](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=2026-02-21&endDate=2026-02-22&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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=CABIN)

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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=COTTAGE)

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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=CHALET)

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## Top Middletown Hotel Reviews

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

### Tru by Hilton Middletown

10/10 Excellent

"Everything was great highly recommend "

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

"Great stay"

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

![Sleep Inn & Suites Monroe - Woodbury](https://images.trvl-media.com/lodging/21000000/20600000/20597600/20597588/0db56af9_y.jpg)

### Sleep Inn & Suites Monroe - Woodbury

10/10 Excellent

"We had a very nice stay. The room was so clean. The staff was "

[](https://expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Monroe-Woodbury.h20597588.Hotel-Information)

![Best Western Monticello](https://images.trvl-media.com/lodging/1000000/30000/26600/26518/68dcbd68_y.jpg)

### Best Western Monticello

10/10 Excellent

"Clean room. Great staff! "

[](https://expedia.ca/Monticello-Hotels-Best-Western-Monticello.h26518.Hotel-Information)

![Hampton Inn Harriman Woodbury](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/c7d384a9_y.jpg)

### Hampton Inn Harriman Woodbury

10/10 Excellent

"Room was clean- "

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

"We stayed during the recent snow service was great"

[](https://expedia.ca/Middletown-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Middletown.h4098.Hotel-Information)

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

### Resorts World Catskills Casino

10/10 Excellent

"Staff was great "

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

"Staff was friendly and efficient. Bed comfy, super quiet & safe. I stayed only to sleep for a few hours during a snowstorm to be close to the hospital down the road so I didn’t have to drive far in the snow. It was expensive but worth the safe commute to work. Their parking lot was plowed and accessible. "

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

"yup"

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

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