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Vacations by Zumper

Vacation Rentals in Middletown, NY

PRICE PER NIGHT

ACCOMMODATION TYPES

Top-Rated Vacation Rentals in Middletown, NY

Book a vacation rental in Middletown that has the highest visitor rating. Here are 6 of the best vacation rentals in Middletown.
Price drop
Beautiful Farm House, 30 acres private estate with pool
10

Excellent

·
Middletown
·
6 br
·
Sleeps 14
·
Outdoor Space · Ski In Ski Out · Swimming Pool ·
From
$643/night
Check availability
Property
House · 6 Beds · 3 baths
Amenities
Ski In Ski Out
Swimming Pool
Garage Parking
In Unit Laundry
Dishwasher
Mountains
Private Pool
Oven
Other spaces
Kitchen
Luxury Huge 6Br Suits, 8.55Bth & Indoor Pool at Goshen Vicinity NY
10

Excellent

·
Middletown
·
6 br
·
Sleeps 10
·
Pool · Garage Parking · Fireplace ·
From
$1,200/night
Check availability
Property
House · 6 Beds · 9 baths
Amenities
Pool
Garage Parking
Fireplace
Swimming Pool
In Unit Laundry
Wifi
Dishwasher
Air Conditioning
Other spaces
Kitchen
Price drop
CHARMING BOHO-STYLE COTTAGE IN MIDDLETOWN NY
10

Excellent

·
Middletown
·
3 br
·
Sleeps 9
·
Fireplace · Air Conditioning · In Unit Laundry ·
From
$233/night
Check availability
Property
Apartment · 3 Beds · 2 baths
Amenities
Fireplace
Air Conditioning
In Unit Laundry
Furnished
Swimming Pool
Other spaces
Kitchen
Price drop
Madison Lodge - Port Jervis, Hudson River
10

Excellent

·
Middletown
·
4 br
·
Sleeps 8
·
Kitchen · Wifi · In Unit Laundry ·
From
$213/night
Check availability
Property
House · 4 Beds · 2 baths
Amenities
Wifi
In Unit Laundry
Oven
Air Conditioning
Furnished
Dishwasher
Other spaces
Kitchen
Price drop
Bright - Cozy 1 BR 1 Full Bath Apt ~ 1.5 hrs from NYC - Fast WiFi & Downtown
10

Excellent

·
Middletown
·
1 br
·
Sleeps 4
·
Fitness Center · Wifi · Kitchen ·
From
$80/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Fitness Center
Wifi
In Unit Laundry
Air Conditioning
Furnished
Oven
Other spaces
Kitchen, Workspace
Price drop
Beautiful Log Cabin Style House
10

Excellent

·
Middletown
·
3 br
·
Sleeps 12
·
Furnished · In Unit Laundry · Swimming Pool ·
From
$499/night
Check availability
Property
Apartment · 3 Beds · 1 bath
Amenities
Furnished
In Unit Laundry
Swimming Pool
Dishwasher
Oven
Air Conditioning
Wifi
Pool
Other spaces
Kitchen

Our Recommended Vacation Rentals in Middletown, NY

We analyzed vacation rentals in Middletown from many property providers including but not limited to VRBO, Booking.com, Evolve, Blueground and more. We're providing our top recommended offers on the best vacation rentals in Middletown to help you find a deal for your next trip.
934 Tower Ridge Cir

No rating

·
Middletown
·
2 br
·
Fitness Center · Assigned Parking · Swimming Pool ·
From
$78/night
Min stay: 30 nights
Property
Condo · 2 Beds · 2 baths
Amenities
Fitness Center
Assigned Parking
Swimming Pool
Elevator
Price drop
La Quinta Inn & Suites by Wyndham Middletown
8.9

Very good

·
Middletown
·
1 br
·
Sleeps 4
·
Furnished · Assigned Parking · Workspace ·
From
$188/night
Check availability
Property
Hotel · 1 Bed
Amenities
Furnished
Assigned Parking
On Site Laundry
Swimming Pool
Air Conditioning
Wifi
Pool
Hot Tub
Other spaces
Workspace
Price drop
Middletown Rental with Spacious Back Deck!

No rating

·
Middletown
·
4 br
·
Sleeps 8
·
Furnished · Dishwasher · Kitchen ·
From
$395/night
Check availability
Property
Apartment · 4 Beds · 3 baths
Amenities
Furnished
Dishwasher
Wifi
Air Conditioning
Oven
Assigned Parking
Other spaces
Kitchen
Perfect Location w/ everything in a comfort single room

No rating

·
Middletown
·
1 br
·
Sleeps 1
·
Furnished · Hot Tub · Free Parking ·
From
$81/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Furnished
Hot Tub
Free Parking
Wifi
In Unit Laundry
Dishwasher
Oven
Other spaces
Kitchen
Middletown Rental w/ Spacious Back Deck!

No rating

·
Middletown
·
4 br
·
Sleeps 8
·
Kitchen · Dishwasher · Furnished ·
From
$300/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Dishwasher
Furnished
Ceiling Fan
In Unit Laundry
Wifi
Air Conditioning
Oven
Other spaces
Kitchen

Budget-Friendly Vacation Rentals in Middletown, NY

Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Middletown starting at $73. Use the price filter at the top of the page to search for more specific prices.
Price drop
$2,200 - 4 Bedroom 1 Bathroom Apartment In Middletown

No rating

·
Middletown
·
4 br
·
Assigned Parking · Hardwood Floor · Central Heat ·
From
$73/night
Min stay: 30 nights
Property
Apartment · 4 Beds · 1 bath
Amenities
Assigned Parking
Hardwood Floor
Central Heat
Microtel Inn & Suites by Wyndham Middletown
6.7

Good

·
Middletown
·
1 br
·
Sleeps 10
·
Air Conditioning · Elevator · Free Parking ·
From
$76/night
Check availability
Property
Hotel · 1 Bed
Amenities
Air Conditioning
Elevator
Free Parking
On Site Laundry
Furnished
Residents Lounge
Business Center
Wifi
Other spaces
Workspace
Kozy Kave Inn Katskills

No rating

·
Middletown
·
1 br
·
Microwave · In Unit Laundry · Furnished ·
From
$79/night
Min stay: 30 nights
Property
House · 1 Bed · 1 bath
Amenities
Microwave
In Unit Laundry
Furnished
On Site Laundry
Cable
Carpet
Air Conditioning
Expand your search criteria to see more vacation rentals near Middletown.
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Updated: September 21, 2023