Title: Middletown Vacation Rentals from CA $258: Short-Term Rentals for 2026 | Expedia.ca

[Hotels in Middletown](https://expedia.ca/Middletown-Hotels.d8864.Travel-Guide-Hotels)[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)

![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)

- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg)  
###  
Change your mind  
Book hotels with free cancellation
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg)  
###  
Treat yourself  
Sign in to save 10% or more on thousands of hotels  
[Sign in](https://www.expedia.ca/login)
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg)  
###  
Be picky  
Search almost a million properties worldwide

## Check prices for these dates

In two weeks

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 12 - Jun 14](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2026-06-12&endDate=2026-06-14&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)

![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)

![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)

### 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 $245

CA $606 total

includes taxes & fees

Mar 4 - Mar 5

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

![Property grounds](https://images.trvl-media.com/lodging/77000000/76800000/76795200/76795113/ed089268.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)

![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 18 - Feb 19

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

![Exterior](https://images.trvl-media.com/lodging/91000000/90900000/90899300/90899226/w482h683x271y0-974b294e.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)

"Great host! Cute tiny house with everything we needed. Location great as well. "

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

Lisa R.

CA $176

CA $272 total

includes taxes & fees

Feb 23 - Feb 24

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

![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/95000000/94720000/94717500/94717464/1cd6d553.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)

### 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 $135

CA $394 total

includes taxes & fees

Feb 24 - Feb 25

[](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)

![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)

![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83440000/83439600/83439540/842e96ae.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 $81

CA $227 total

includes taxes & fees

Feb 23 - Feb 24

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

![Interior](https://images.trvl-media.com/lodging/78000000/77880000/77873000/77873000/c906d781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/78000000/77880000/77873000/77873000/a5c7e11e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/78000000/77880000/77873000/77873000/5ff61fe6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/78000000/77880000/77873000/77873000/14f7c5c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxe Loft on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!

[](https://www.expedia.ca/Warwick-Hotels-Luxe-Loft-On-Main-StZeroG-King-Bed.h77873000.Hotel-Information)

Warwick

10/10

Exceptional

(42 reviews)

"The host is the best. I have stayed multiple times and have never been disappointed. The location is convenient to shops and restaurants. Will be happy to come back anytime. "

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

Cynthia W.

CA $147

CA $338 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Warwick-Hotels-Luxe-Loft-On-Main-StZeroG-King-Bed.h77873000.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)

![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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83430000/83426500/83426410/877cc95b.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 $74

CA $221 total

includes taxes & fees

Mar 3 - Mar 4

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

![Property grounds](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/3a9ea66f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/dfec5e09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/c55e3667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/5ed95c10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

[](https://www.expedia.ca/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information)

Fort Montgomery

9.8/10

Exceptional

(131 reviews)

"Amazing place Thanks for the stay "

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

Julien C.

CA $256

CA $414 total

includes taxes & fees

Mar 8 - Mar 9

[](https://www.expedia.ca/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/04adf8dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/e2587dd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/19de180c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/a8c5ab99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

[](https://www.expedia.ca/Beacon-Hotels-Luxe-Studio-4-On-Main-Street-Luxury-Steam-Shower.h69240003.Hotel-Information)

Beacon

10/10

Exceptional

(53 reviews)

"We havld a good time. The room was comfortable and perfectly located!"

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

Brandy C.

CA $157

CA $335 total

includes taxes & fees

Mar 19 - Mar 20

[](https://www.expedia.ca/Beacon-Hotels-Luxe-Studio-4-On-Main-Street-Luxury-Steam-Shower.h69240003.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)

![Interior](https://images.trvl-media.com/lodging/117000000/116300000/116293600/116293556/d8b7ae3f.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)

###  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 $120

CA $210 total

includes taxes & fees

Feb 23 - Feb 24

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

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

![Fireplace, books](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/4fbee988.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)

### 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 $102

CA $250 total

includes taxes & fees

Feb 24 - Feb 25

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

![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90900000/90897800/90897766/w1024h681x0y0-cfce0679.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 $230

CA $381 total

includes taxes & fees

Feb 23 - Feb 24

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

![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)

![Living area](https://images.trvl-media.com/lodging/96000000/95250000/95247300/95247281/0207be64.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)

### 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 $141

CA $357 total

includes taxes & fees

Feb 23 - Feb 24

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

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/74000000/73260000/73255300/73255284/0caac60d.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)

![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)

### 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

(44 reviews)

"Adorable place to stay in an adorable town! "

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

Mary L.

CA $153

CA $323 total

includes taxes & fees

Feb 23 - Feb 24

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

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/46000000/45750000/45742900/45742802/a27e5755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/46000000/45750000/45742900/45742802/03710a7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/46000000/45750000/45742900/45742802/c225355f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/46000000/45750000/45742900/45742802/5e31b747.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy country efficiency in the Hudson Valley

[](https://www.expedia.ca/Newburgh-Hotels-Cozy-Country-Efficiency-In-The-Hudson-Valley.h45742802.Hotel-Information)

Newburgh

9.8/10

Exceptional

(66 reviews)

"Clean, simple, and comfortable with clear host directions on arrival, checkin & checkout."

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

Lou F.

CA $225

CA $431 total

includes taxes & fees

Feb 21 - Feb 22

[](https://www.expedia.ca/Newburgh-Hotels-Cozy-Country-Efficiency-In-The-Hudson-Valley.h45742802.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/105000000/104970000/104965400/104965399/feb0c593.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Coffee and/or coffee maker](https://images.trvl-media.com/lodging/105000000/104970000/104965400/104965399/c01759b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/105000000/104970000/104965400/104965399/3424405a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/105000000/104970000/104965400/104965399/d8180870.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Hudson Valley Apt 202 - King/Queen/Twin

[](https://www.expedia.ca/Montgomery-Hotels-Modern-Hudson-Valley-Apt-202-KingQueenTwin.h104965399.Hotel-Information)

Montgomery

9.8/10

Exceptional

(16 reviews)

"We had a great stay!! I booked for a “get ready” spot for my wedding and it was everything I could have dreamed of. Everything was perfect and very clean! Can’t wait to book again Very centrally located near some amazing small boutiques, a couple restaurants. The town seemed like a popular spot on the weekend! "

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

Tiffani H.

CA $205

CA $371 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Montgomery-Hotels-Modern-Hudson-Valley-Apt-202-KingQueenTwin.h104965399.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/78000000/77290000/77280600/77280503/541d91ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/78000000/77290000/77280600/77280503/537494b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/78000000/77290000/77280600/77280503/5a612bda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/78000000/77290000/77280600/77280503/d2d9d4e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Country House w/Hot Tub, Deck, Grill & Fire Pit

[](https://www.expedia.ca/Goshen-Hotels-Renovated-House-WHot-Tub.h77280503.Hotel-Information)

Goshen

10/10

Exceptional

(60 reviews)

"This cottage was perfect for our stay. We have family nearby and this was the perfect retreat after busy days. We will be booking again. The space is clean and welcoming the land is beautiful! "

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

Heather A.

CA $352

CA $697 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Goshen-Hotels-Renovated-House-WHot-Tub.h77280503.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)

![Interior](https://images.trvl-media.com/lodging/75000000/74240000/74234100/74234035/5464adbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/75000000/74240000/74234100/74234035/a952c9f5.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)

### ★Rare River Views & Access, Cabin by Eden Islands★

[](https://www.expedia.ca/Montague-Hotels-Rare-River-Views-Access.h74234035.Hotel-Information)

Montague

9.0/10

Wonderful

(13 reviews)

"Nice convenient location, near the river and town. "

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

Steve W.

CA $116

CA $182 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Montague-Hotels-Rare-River-Views-Access.h74234035.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/71000000/70580000/70576700/70576621/29709777.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/71000000/70580000/70576700/70576621/c78c43b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/71000000/70580000/70576700/70576621/2954f439.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/71000000/70580000/70576700/70576621/9cc8bfa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa Verde B&B, Greenwood Lake NY, 1

[](https://www.expedia.ca/Monroe-Hotels-House.h70576621.Hotel-Information)

Monroe

10/10

Exceptional

(31 reviews)

"Great host. Home is very clean and well appointed. Would definitely stay here again."

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

Thomas

CA $214

CA $364 total

includes taxes & fees

Feb 21 - Feb 22

[](https://www.expedia.ca/Monroe-Hotels-House.h70576621.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)

![Exterior](https://images.trvl-media.com/lodging/84000000/83520000/83518700/83518661/d477734e.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)

![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)

### 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 $182 total

includes taxes & fees

Mar 8 - Mar 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=2026-03-03&endDate=2026-03-04&regionId=8864&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=VR_SPRING_PROMO_8864)

## 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=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&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=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=VACATION_HOME)

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=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=COTTAGE)

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=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=APARTMENT)

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=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=CONDO)

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=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=APART_HOTEL)

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=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=VILLA)

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=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=CHALET)

![](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-Vacation-Rentals.d8864.Travel-Guide-VacationRentals)[

Sign up, it's free

](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FMiddletown-Vacation-Rentals.d8864.Travel-Guide-VacationRentals)

## Top Middletown Hotel Reviews

![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

"Rooms were clean and staff at the front where nice. However, the food at their restaurant took way to long to come out and the price was not worth it. Overall, we had an amazing time. I totally recommend it."

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

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

### Best Western Monticello

10/10 Excellent

"Yes"

[](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

"The hotel was very clean and the staff especially the check in were very friendly and accommodating. Would stay there again. "

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

"Great cozy and peaceful stay!"

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

![Sleep Inn & Suites Middletown - Goshen](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/1b0779e7_y.jpg)

### Sleep Inn & Suites Middletown - Goshen

10/10 Excellent

"Best hotel so far... Friendly staff very clean everything and quiet for the most part... "

[](https://expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.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

"Still the same. Best value in the area. Period"

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

"Room was huge, clean and nice views"

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

"Loved our stay. Great room and great lobby. "

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

"Room was clean & comfortable. Staff was accommodating and friendly."

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

## Explore a world of travel with Expedia

- Trending destinations on Expedia.ca
- All accommodation types in Middletown

### Trending destinations on Expedia.ca

- [Canmore Vacation Rentals ](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals)
- [Maui Vacation Rentals ](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals)
- [Kelowna Vacation Rentals ](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals)
- [Whistler Vacation Rentals ](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Victoria Vacation Rentals ](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals)
- [Vancouver Vacation Rentals ](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals)
- [Palm Springs Vacation Rentals ](https://www.expedia.ca/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals)
- [Tofino Vacation Rentals ](https://www.expedia.ca/Tofino-Vacation-Rentals.d6094955.Travel-Guide-VacationRentals)
- [Calgary Vacation Rentals ](https://www.expedia.ca/Calgary-Vacation-Rentals.d178245.Travel-Guide-VacationRentals)
- [Costa Rica Vacation Rentals ](https://www.expedia.ca/Destinations-In-Costa-Rica.d42.Vacation-Rental-Destinations)
- [Vancouver Island Vacation Rentals ](https://www.expedia.ca/Vancouver-Island-Vacation-Rentals.d6058387.Travel-Guide-VacationRentals)
- [Puerto Vallarta Vacation Rentals ](https://www.expedia.ca/Puerto-Vallarta-Vacation-Rentals.d180016.Travel-Guide-VacationRentals)
- [Hawaii Vacation Rentals ](https://www.expedia.ca/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Toronto Vacation Rentals ](https://www.expedia.ca/Toronto-Vacation-Rentals.d178314.Travel-Guide-VacationRentals)
- [Banff Vacation Rentals ](https://www.expedia.ca/Banff-Vacation-Rentals.d10550.Travel-Guide-VacationRentals)
- [Penticton Vacation Rentals ](https://www.expedia.ca/Penticton-Vacation-Rentals.d4135.Travel-Guide-VacationRentals)
- [Osoyoos Vacation Rentals ](https://www.expedia.ca/Osoyoos-Vacation-Rentals.d181782.Travel-Guide-VacationRentals)
- [Mont Tremblant Vacation Rentals ](https://www.expedia.ca/Mont-Tremblant-Vacation-Rentals.d55374.Travel-Guide-VacationRentals)
- [Big White Ski Resort Vacation Rentals ](https://www.expedia.ca/Big-White-Ski-Resort-Vacation-Rentals.d6058319.Travel-Guide-VacationRentals)
- [Ontario Vacation Rentals ](https://www.expedia.ca/Destinations-In-Ontario.d11178.Vacation-Rental-Destinations)
- [British Columbia Vacation Rentals ](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations)
- [Prince Edward Island Vacation Rentals ](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations)
- [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

- [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

### Can I find a vacation rental in Middletown?

### What are some of the best vacation home rentals that Middletown has to offer?

### How many vacation rentals are there in Middletown?

### What’s there to see and do in Middletown?

### What’s a vacation rental in Middletown like?

![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg)

## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app