Photo by Vincent Ramundo

Search Middletown Villa Rentals from CA $1,120

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16

Browse Select Middletown Villas

7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space
Fridge, microwave, oven, stovetop

7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

8.0 out of 10, Very good, (1)
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space
Simply Unforgettable HotTub, Pool, Pets, <1 Hr NYC
TV, fireplace, video games, table tennis

Simply Unforgettable HotTub, Pool, Pets, <1 Hr NYC

10.0 out of 10, Exceptional, (77)
"Lovely stay at large and clean home with great kitchen and pool area. Lots of room for everyone and attentive hosts"
Simply Unforgettable HotTub, Pool, Pets, <1 Hr NYC
Family Fun Getaway near Cascade Lake in Warwick NY
Fridge, microwave, oven, stovetop

Family Fun Getaway near Cascade Lake in Warwick NY

7.6 out of 10, Good, (10)
"Our family really enjoyed our stay in this house! The game room especially was a big hit! We would definitely love to come back here again soon!"
Family Fun Getaway near Cascade Lake in Warwick NY
MODERN FARMHOUSE HOME ON 5-ACRE DREAM PROPERTY
Fridge, microwave, oven, stovetop

MODERN FARMHOUSE HOME ON 5-ACRE DREAM PROPERTY

9.4 out of 10, Exceptional, (18)
"We enjoyed our stay. The kitchen is extremely well done and filled with everything you need. Excellent coffee pods, comfortable beds, spacious backyard. "
MODERN FARMHOUSE HOME ON 5-ACRE DREAM PROPERTY
The Station House: A Dream Catskills Getaway
Dining

The Station House: A Dream Catskills Getaway

9.8 out of 10, Exceptional, (7)
"We really enjoy are stay , this place had everything from the hot tub to the pool table to tennis table the house was gigantic plenty of space for the entire family ."
The Station House: A Dream Catskills Getaway
Malkita Aria: Mountainview Escape with Postcard-Perfect Scenery
Fridge, microwave, oven, stovetop

Malkita Aria: Mountainview Escape with Postcard-Perfect Scenery

10.0 out of 10, Exceptional, (27)
"The house was a lovely and just right for our group! Host was always very prompt to answer any questions."
Malkita Aria: Mountainview Escape with Postcard-Perfect Scenery
Hemlock Estate: Indoor Hot Tub, Heated Pool, Game Room; Spacious, Ski & More!
Indoor pool, outdoor pool

Hemlock Estate: Indoor Hot Tub, Heated Pool, Game Room; Spacious, Ski & More!

9.4 out of 10, Exceptional, (33)
"Great Property. Clean and Spacious. "
Hemlock Estate: Indoor Hot Tub, Heated Pool, Game Room; Spacious, Ski & More!
Private Estate 9BR w/Pool, Hot Tub & Scenic Views!
Interior

Private Estate 9BR w/Pool, Hot Tub & Scenic Views!

5.0 out of 10, (4)
"We had an amazing time at this beautiful home, Sophia was very helpful with any questions we had she even helped us with attractions in the area"
Private Estate 9BR w/Pool, Hot Tub & Scenic Views!
Luxury School House Retreat With Sauna & Pool- 1HR from NYC
Outdoor pool, a heated pool

Luxury School House Retreat With Sauna & Pool- 1HR from NYC

10.0 out of 10, Exceptional, (17)
"We stayed for the night at the property for my sister’s bachelorette party. We had a wonderful time and enjoyed our stay. Lots of space and comfortable accommodations."
The price is CA $1,120
CA $1,906 total
includes taxes & fees
Sep 3 - Sep 4
Luxury School House Retreat With Sauna & Pool- 1HR from NYC
Charming 3-bedroom villa with WiFi, AC in fabulous Monroe
Interior

Charming 3-bedroom villa with WiFi, AC in fabulous Monroe

10.0 out of 10, Exceptional, (1)
"Nice property"
Charming 3-bedroom villa with WiFi, AC in fabulous Monroe
Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY.
Interior

Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY.

2.0 star property
8.6 out of 10, Excellent, (8)
"Big, spacious and clean. The area is calm and shops are within 5 min driving distance"
Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY.
Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard
Exterior detail

Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard

9.4 out of 10, Exceptional, (9)
"A spacious house with a to-die-for pool, game room in basement, plenty of storage and refrigerators for all your wonderful culinary desires, comfortable beds, and well divided together and private spaces."
Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard
Luxe Mountain Getaway Fire Pit Arcade Hot Tub Pool
Pool

Luxe Mountain Getaway Fire Pit Arcade Hot Tub Pool

10.0 out of 10, Exceptional, (3)
"This property was adorable. We loved the area."
Luxe Mountain Getaway Fire Pit Arcade Hot Tub Pool
Luxurious & Tranquil ~ Pool ~ Fire Pit ~ Backyard!
Terrace/patio

Luxurious & Tranquil ~ Pool ~ Fire Pit ~ Backyard!

6.0 out of 10, (1)
"The pictures are accurate but when you get there you see the furniture is flimsy, the cabinets and drawers fall off when you touch them and the yard is a disaster. There is so much stagnant water the mosquitos look like drones!"
Luxurious & Tranquil ~ Pool ~ Fire Pit ~ Backyard!
Spacious Lakefront Hideaway with Hot Tub & Kayaks
Living area

Spacious Lakefront Hideaway with Hot Tub & Kayaks

5.0 out of 10, (2)
Spacious Lakefront Hideaway with Hot Tub & Kayaks
Beautiful modern villa with pool suana hot tub...
Property grounds

Beautiful modern villa with pool suana hot tub...

10.0 out of 10, Exceptional, (2)
"It's exactly how it looks in the picture.. beautiful grounds, nice neighborhood, spottless house, the heated pool was amazing and of course the jacuzzi and spa were great! I'm really impressed with this beautiful vacation!"
Beautiful modern villa with pool suana hot tub...
Perfect home for a dream retreat + POOL
Interior

Perfect home for a dream retreat + POOL

6.0 out of 10, (2)
"We definitely intend on coming back to enjoy the pool!!"
Perfect home for a dream retreat + POOL
Country Manor at Millers Rock with Pool-1 Hour from NYC
Property grounds

Country Manor at Millers Rock with Pool-1 Hour from NYC

Country Manor at Millers Rock with Pool-1 Hour from NYC
Picturesque, Cozy & Fun ~ GameRoom ~ Spacious Yard
Terrace/patio

Picturesque, Cozy & Fun ~ GameRoom ~ Spacious Yard

10.0 out of 10, Exceptional, (1)
"Loved the home didn't realize when booking it was in such a secluded spot so come prepared. House was clean minus some hair in the tubs (around drain) the closet doors attacked my sister (needs to be reinstalled and tightened) upon opening and a few draw coverings fell off. we couldn't find a broom until 10 mins before checkout (we looked all weekend )other wise the place was amazing my sister is already talking about booking in the warmer months because the yard is amazing"
Picturesque, Cozy & Fun ~ GameRoom ~ Spacious Yard
Modern Villa with private pond near Legoland and Delaware River.
Property grounds

Modern Villa with private pond near Legoland and Delaware River.

8.0 out of 10, Very good, (4)
"Beautiful property and big enough for 2 families to spend a weekend. Hope to return again soon"
Modern Villa with private pond near Legoland and Delaware River.
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Hotel Reviews

Resorts World Catskills Casino

Resorts World Catskills Casino

10/10 Excellent
"Nice resort. Few other things to do besides the casino."
Deirdra 3-night trip
Posted 2 days ago
Resorts World Catskills Casino