Vacation Rentals in Middletown, NY

43 rentals

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.
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
$660/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
Outdoor Space, Kitchen
Hudson Lodge - Port Jervis, Hudson River
10

Excellent

·
Middletown
·
2 br
·
Sleeps 4
·
Fireplace · Dishwasher · Residents Lounge ·
From
$129/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
Fireplace
Dishwasher
Residents Lounge
Carpet
In Unit Laundry
Oven
Air Conditioning
Wifi
Other spaces
Deck, Balcony, Kitchen
Madison Lodge - Port Jervis, Hudson River
10

Excellent

·
Middletown
·
4 br
·
Sleeps 8
·
Kitchen · Wifi · In Unit Laundry ·
From
$152/night
Check availability
Property
House · 4 Beds · 2 baths
Amenities
Wifi
In Unit Laundry
Oven
Air Conditioning
Furnished
Dishwasher
Other spaces
Kitchen, Outdoor Space
Cozy Haven: A Romantic Retreat in our Tiny House!
10

Excellent

·
Middletown
·
1 br
·
Sleeps 2
·
Fireplace · Hot Tub · Kitchen ·
From
$246/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Fireplace
Hot Tub
Furnished
Wifi
Air Conditioning
Other spaces
Kitchen
Luminous Studio: Vibrant Living Experience
10

Excellent

·
Middletown
·
Studio
·
Sleeps 2
·
Kitchen · Wifi · Storage ·
From
$96/night
Check availability
Property
Condo · Studio · 1 bath
Amenities
Wifi
Storage
Air Conditioning
In Unit Laundry
On Site Laundry
Business Center
Furnished
Other spaces
Kitchen, Workspace
Chic Haven: Modern and Stylish and Cozy Ambiance
10

Excellent

·
Middletown
·
Studio
·
Sleeps 2
·
Storage · Kitchen · Hardwood Floor ·
From
$90/night
Check availability
Property
Condo · Studio · 1 bath
Amenities
Storage
Hardwood Floor
On Site Laundry
In Unit Laundry
Air Conditioning
Furnished
Wifi
Free Parking
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.
Compact Studio Suite Couples or Solo Travelers

No rating

·
Middletown
·
1 br
·
Sleeps 2
·
Package Service · Air Conditioning · Wifi ·
From
$113/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Package Service
Air Conditioning
Wifi
Furnished
In Unit Laundry
Other spaces
Kitchen
Central Studio Haven for Explorers

No rating

·
Middletown
·
1 br
·
Sleeps 2
·
Kitchen · Air Conditioning · Furnished ·
From
$130/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Air Conditioning
Furnished
Wifi
In Unit Laundry
Other spaces
Kitchen
Superb and Cozy Studio

No rating

·
Middletown
·
1 br
·
Sleeps 2
·
Wifi · Air Conditioning · In Unit Laundry ·
From
$113/night
Check availability
Property
Condo · 1 Bed · 1 bath
Amenities
Wifi
Air Conditioning
In Unit Laundry
Furnished
Other spaces
Kitchen
Cozy and Convenient Studio in Vibrant Neighborhood

No rating

·
Middletown
·
1 br
·
Sleeps 2
·
Kitchen · Wifi · Air Conditioning ·
From
$117/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Wifi
Air Conditioning
Furnished
Assigned Parking
In Unit Laundry
Other spaces
Kitchen
Contemporary Studio for Work and Play

No rating

·
Middletown
·
1 br
·
Sleeps 2
·
Air Conditioning · Furnished · In Unit Laundry ·
From
$116/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Air Conditioning
Furnished
In Unit Laundry
Wifi
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 $74. Use the price filter at the top of the page to search for more specific prices.
Standard Single Room2 with Shared Bathroom l Dining Patio

No rating

·
Middletown
·
1 br
·
Sleeps 2
·
Hot Tub · Kitchen · In Unit Laundry ·
From
$74/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Hot Tub
In Unit Laundry
Assigned Parking
Oven
Dishwasher
Furnished
Wifi
Free Parking
Other spaces
Kitchen
Microtel Inn & Suites by Wyndham Middletown
6.6

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
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
Other spaces
Outdoor Space
Tru By Hilton Middletown
8

Very good

·
Middletown
·
1 br
·
Sleeps 4
·
Furnished · On Site Laundry · Residents Lounge ·
From
$81/night
Check availability
Property
Hotel · 1 Bed
Amenities
Furnished
On Site Laundry
Residents Lounge
Business Center
Assigned Parking
Free Parking
Wheelchair Accessible
Air Conditioning
Other spaces
Workspace, Outdoor Space
Holiday Inn Express & Suites - Middletown - Goshen, an IHG Hotel
8.6

Very good

·
Middletown
·
Studio
·
Sleeps 6
·
Assigned Parking · Outdoor Space · Pool ·
From
$83/night
Check availability
Property
Hotel · Studio
Amenities
Assigned Parking
Pool
Residents Lounge
On Site Laundry
Smoking Allowed
Carpet
Business Center
Swimming Pool
Other spaces
Outdoor Space, Workspace
Perfect Location w/ everything in a comfort single room
10

Excellent

·
Middletown
·
1 br
·
Sleeps 1
·
Furnished · Hot Tub · Free Parking ·
From
$89/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Furnished
Hot Tub
Free Parking
Wifi
In Unit Laundry
Dishwasher
Oven
Other spaces
Kitchen
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Updated: February 29, 2024