Middletown Vacation Rentals | Book Now, Save Up to 30%

All in pricing: Taxes and fees included

Save $610

House in Middletown, NY

Nov 16 - 19

$1,114/night

4.8

16

5 bedrooms

10 guests

$4,352$3,742total

Save $640

Entire home in Goshen, NY

Nov 16 - 21

$1,022/night

New

5 bedrooms

14 guests

$6,559$5,919total

Save $66

Preferred host

Entire home in Wurtsboro, NY

Nov 16 - 19

$226/night

5.0

4

1 bedroom

6 guests

$821$755total

Save $267

House in Cuddebackville, NY

Nov 16 - 19

$246/night

4.9

14

3 bedrooms

6 guests

$1,003$737total

Save $523

House in Chester, NY

Nov 28 - Dec 1

$685/night

4.7

122

7 bedrooms

16 guests

$2,578$2,056total

Save $249

Guests rave

House in Montgomery, NY

Nov 16 - 19

$844/night

4.9

153

6 bedrooms

16 guests

$3,109$2,860total

Save $116

Unit 1 of 2

Guests rave

Apartment in Montgomery, NY

Nov 16 - 19

$173/night

5.0

110

1 bedroom

5 guests

$701$585total

Save $120

Unit 2 of 2

Guests rave

Apartment in Montgomery, NY

Nov 16 - 19

$192/night

4.9

65

1 bedroom

4 guests

$769$649total

Save $316

Unit 2 of 3

House in Montgomery, NY

Nov 16 - 19

$566/night

5.0

1

5 bedrooms

13 guests

$2,012$1,697total

Save $153

Unit 3 of 3

Apartment in Montgomery, NY

Nov 16 - 19

$230/night

4.9

18

2 bedrooms

5 guests

$844$691total

Save $183

Unit 1 of 3

Guests rave

House in Montgomery, NY

Nov 16 - 19

$323/night

5.0

34

3 bedrooms

8 guests

$1,154$970total

Save $376

House in Huguenot, NY

Nov 16 - 19

$298/night

4.9

9

5 bedrooms

10 guests

$1,271$895total

Save $589

Guests rave

Vacation Rental in Chester, NY

Nov 18 - 21

$561/night

4.9

154

4 bedrooms

14 guests

$2,404$1,815total

Save $122

Preferred host

Entire home in Port Jervis, NY

Nov 20 - 23

$249/night

5.0

1

3 bedrooms

8 guests

$955$833total

Save $517

Villa in Monroe, NY

Sep 1 - 4

$733/night

4.7

138

3 bedrooms

12 guests

Pay only $199 today

$2,716$2,199total

Save $977

Guests rave

Entire home in Chester, NY

Nov 22 - 25

$1,436/night

5.0

24

11 bedrooms

16 guests

$5,816$4,839total

Save $83

Preferred host

Entire cottage in Monroe, NY

Mar 31 - Apr 3

$274/night

5.0

1

2 bedrooms

4 guests

Pay only $104 today

$1,034$952total

Save $672

Preferred host

Entire villa in Rock Hill, NY

Nov 19 - 22

$1,016/night

4.7

27

8 bedrooms

16 guests

$4,082$3,410total

Save $450

Guests rave

House in Monroe, NY

Nov 16 - 19

$476/night

4.9

191

3 bedrooms

8 guests

$1,878$1,427total

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Map shows last minute vacation rentals in Middletown