Apartments under $2,000 for Rent in Middletown, NY
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1 BED$1,850
Stevens Manor Apartments
644 Silver Lake Scotchtown Rd, Middletown, NY 10941 -
1 BED$1,800+2 BEDS$1,950+
Slatewood Apartments
579 E Main St, Middletown, NY 10940 -
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1 BED$1,720+2 BEDS$1,995+
Sutton Hill Apartments
2 Underhill Rd, Middletown, NY 10940 -
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1 BED$817+2 BEDS$1,229+3 BEDS$1,411+Deerfield Commons
2 Edward Diana Way, Middletown, NY 10941 -
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STUDIO$1,450+1 BED$1,699+Crestwood Apartments
92 Fitzgerald Dr, Middletown, NY 10940 -
2 BEDS$2,000Stoneridge Manor Apartments
22-26 Stoneridge Rd, Middletown, NY 10941 -
1 BED$1,695+2 BEDS$1,895+
Kensington Manor
1 Kensington Mnr, Middletown, NY 10941 -
STUDIO, 1 BATH$1,970133-3 Wickham Ave Unit ID1056802P
133-3 Wickham Ave, Middletown, NY 10940 -
STUDIO, 1 BATH$1,97094 Cottage St Unit ID1056809P
94 Cottage St, Middletown, NY 10940 -
STUDIO, 1 BATH$1,970
11 Prince St Unit ID1056810P
11 Prince St, Middletown, NY 10940 -
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STUDIO, 1 BATH$1,97098 Cottage St Unit ID1056800P
98 Cottage St, Middletown, NY 10940 -
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STUDIO, 1 BATH$1,970
73 Cottage St Unit ID1056796P
73 Cottage St, Middletown, NY 10940 -
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STUDIO, 1 BATH$1,970
73 Cottage St Unit ID1056801P
73 Cottage St, Middletown, NY 10940 -
STUDIO, 1 BATH$1,970
149 Wickham Ave Unit ID1056804P
149 Wickham Ave, Middletown, NY 10940 -
3 BEDS, 2 BATHS$2,000
390 Crystal Run Rd Unit 107 A
390 Crystal Run Rd, Middletown, NY 10941 -
2 BEDS, 1 BATH$2,00049 Lake Ave Unit 2
49 Lake Ave, Middletown, NY 10940 -
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1 BED, 1 BATH$1,95019 Bloomingburg Rd
19 Bloomingburg Rd, Middletown, NY 10940 -
1 BED, 1 BATH$1,80037 North St Unit 201 second floor
37 North St, Middletown, NY 10940 -
2 BEDS, 1 BATH$1,700
203 W Main St Unit #1
203 W Main St, Middletown, NY 10940 -
1 BED, 1 BATH$1,950
19 Bloomingburg Rd
19 Bloomingburg Rd, Middletown, NY 10940 -
2 BEDS, 1 BATH$1,500
25 Beacon St Unit 1
25 Beacon St, Middletown, NY 10940 -
2 BEDS, 2 BATHS$1,995
296 Ruth Ct
296 Ruth Ct, Middletown, NY 10940 -
1 BED, 1 BATH$1,500
44 John St Unit 3
44 John St, Middletown, NY 10940 -
2 BEDS, 1 BATH$2,000
49 Lake Ave Unit 2
49 Lake Ave, Middletown, NY 10940 -
2 BEDS, 1 BATH$1,900
464 NY-17M Unit 2
464 NY-17M, Middletown, NY 10940 -
1 BED, 1 BATH$1,500
30 E Main St Unit 6
30 E Main St, Middletown, NY 10940 -
1 BED, 1 BATH$1,700
2213 Mt Hope Rd Unit B
2213 Mt Hope Rd, Middletown, NY 10940 -
1 BED, 1 BATH$1,700
2 E Main St Unit 4
2 E Main St, Middletown, NY 10940 -
1 BED, 1 BATH$1,700
2213 Mt Hope Rd Unit C
2213 Mt Hope Rd, Middletown, NY 10940 -
3 BEDS, 2 BATHS$1,850
108 North St Unit 301
108 North St, Middletown, NY 10940 -
2 BEDS, 1 BATH$1,600
New - 35 Crescent Place Unit 1F
35 Crescent Pl, Middletown, NY 10940 -
2 BEDS, 1 BATH$2,000
30 Crans Rd
30 Crans Rd, Middletown, NY 10941 -
STUDIO$1,850
Cottage Suites Unit 307
52-89 Cottage St, Middletown, NY 10940
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Clear All FiltersMiddletown at a Glance
Middletown, NY Apartments for Rent
Middletown is the largest city in Orange County, located in New York's Hudson Valley region near the Wallkill River and the foothills of the Shawangunk Mountains. Incorporated as a city in 1888, it developed as an important railroad hub in the 19th and early 20th centuries, attracting manufacturing businesses that helped shape its growth. Those searching for apartments for rent in Middletown will discover a mix of restored Victorian properties and newer residential developments, with one-bedroom options averaging around $1,936 per month.
Renting in Middletown offers convenient access to both nature and city conveniences. The downtown area features diverse dining options and the restored Paramount Theatre, which hosts films and live performances throughout the year. Highland Lakes State Park provides outdoor recreation nearby, while the Galleria at Crystal Run offers shopping just outside city limits. The presence of SUNY Orange's main campus adds educational opportunities to the area, and Middletown's location between Port Jervis and Newburgh provides straightforward access to major transportation routes for commuters heading to other parts of the Hudson Valley or the greater New York metropolitan area.
Renting in Middletown
Average Rental Rates and Apartment Sizes
- Apartment Type Average Sq Ft Average Rent
- Studio 407 Sq Ft $1,630 / mo
- 1 Bedroom 804 Sq Ft $1,941 / mo
- 2 Bedrooms 1,012 Sq Ft $2,310 / mo
- 3 Bedrooms 1,291 Sq Ft $2,519 / mo
- 4 Bedrooms 1,800 Sq Ft $3,532 / mo
Top Budget-Friendly Neighborhoods in Middletown
(For 1 bedroom apartments)- Neighborhoods Average Sq Ft Average Rent
- Middletown/Goshen 759 Sq Ft $2,032/mo
- Winding Brooke Estates 804 Sq Ft $2,237/mo
Getting Around Middletown
Education
Data provided by GreatSchools.org 2025 © 2025. All rights reserved.
Apartments for Rent Near Middletown
Middletown Apartments for Rent in Your Budget
- Apartments with Move-In Specials in Middletown, NY
- Middletown Apartments Under $900
- Middletown Apartments Under $1,000
- Middletown Apartments Under $1,100
- Middletown Apartments Under $1,200
- Middletown Apartments Under $1,300
- Middletown Apartments Under $1,400
- Middletown Apartments Under $1,500
- Middletown Apartments Under $1,600
- Middletown Apartments Under $1,700
- Middletown Apartments Under $1,800
- Middletown Apartments Under $1,900
- Middletown Apartments Under $2,000
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About Our Deals
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Best Value
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Rent Specials
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Note: Based on community-supplied data and independent market research. Subject to change without notice.