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Hotels with a Pool in Middletown
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Hotels with a Pool in Middletown
Sleep Inn & Suites Middletown - Goshen
Sleep Inn & Suites Middletown - Goshen2.5 star property
Middletown
8.6 out of 10, Excellent, (1000)
8.6/10
Excellent
(1000)
The price is $97
$97
$115 total
includes taxes & fees
Jan 11 - Jan 12, 2026
La Quinta Inn & Suites by Wyndham Middletown-Goshen
La Quinta Inn & Suites by Wyndham Middletown-Goshen3.0 star property
Middletown
9.4 out of 10, Exceptional, (939)
9.4/10
Exceptional
(939)
The price is $105
$105
$125 total
includes taxes & fees
Dec 23 - Dec 24
8.6 out of 10, Excellent, (1000)
8.6/10
Excellent
(1000)
The price is $83
$83
$98 total
includes taxes & fees
Dec 28 - Dec 29
Courtyard by Marriott Middletown Goshen
Courtyard by Marriott Middletown Goshen3.0 star property
Middletown
8.6 out of 10, Excellent, (1002)
8.6/10
Excellent
(1002)
The price is $93
$93
$109 total
includes taxes & fees
Dec 28 - Dec 29
Holiday Inn Express & Suites Middletown - Goshen by IHG
Holiday Inn Express & Suites Middletown - Goshen by IHG2.5 star property
Middletown
8.8 out of 10, Excellent, (697)
8.8/10
Excellent
(697)
The price is $123
$123
$145 total
includes taxes & fees
Dec 21 - Dec 22
9.0 out of 10, Wonderful, (744)
9.0/10
Wonderful
(744)
The price is $147
$147
$177 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Residence Inn by Marriott Middletown Goshen
Residence Inn by Marriott Middletown Goshen3.0 star property
Middletown
9.4 out of 10, Exceptional, (317)
9.4/10
Exceptional
(317)
The price is $170
$170
$201 total
includes taxes & fees
Dec 25 - Dec 26
6.4 out of 10, (676)
6.4/10
(676)
The price is $93
$93
$109 total
includes taxes & fees
Dec 21 - Dec 22
Fairfield Inn & Suites by Marriott Goshen Middletown
Fairfield Inn & Suites by Marriott Goshen Middletown2.5 star property
Goshen
8.8 out of 10, Excellent, (1001)
8.8/10
Excellent
(1001)
The price is $101
$101
$124 total
includes taxes & fees
Dec 28 - Dec 29
8.8 out of 10, Excellent, (33)
8.8/10
Excellent
(33)
The price is $190
$190
$346 total
includes taxes & fees
Dec 22 - Dec 23
Holiday Inn Express Hotel & Suites Chester by IHG
Holiday Inn Express Hotel & Suites Chester by IHG2.5 star property
Chester
8.6 out of 10, Excellent, (1001)
8.6/10
Excellent
(1001)
The price is $82
$82
$97 total
includes taxes & fees
Dec 21 - Dec 22
9.2 out of 10, Wonderful, (233)
9.2/10
Wonderful
(233)
The price is $215
$215
$243 total
includes taxes & fees
Dec 22 - Dec 23
Best Western Hunt's Landing Hotel Matamoras/Milford
Best Western Hunt's Landing Hotel Matamoras/Milford3.0 star property
Matamoras
8.4 out of 10, Very Good, (1000)
8.4/10
Very Good
(1000)
The price is $91
$91
$99 total
includes taxes & fees
Dec 28 - Dec 29
8.8 out of 10, Excellent, (1001)
8.8/10
Excellent
(1001)
The price is $98
$98
$106 total
includes taxes & fees
Jan 16 - Jan 17, 2026
Courtyard by Marriott Newburgh Stewart Airport
Courtyard by Marriott Newburgh Stewart Airport3.0 star property
Newburgh
8.2 out of 10, Very Good, (694)
8.2/10
Very Good
(694)
The price is $97
$97
$115 total
includes taxes & fees
Jan 6 - Jan 7, 2026
9.2 out of 10, Wonderful, (1000)
9.2/10
Wonderful
(1000)
The price is $134
$134
$152 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Hampton Inn & Suites Newburgh Stewart Airport
Hampton Inn & Suites Newburgh Stewart Airport2.5 star property
Newburgh
9.2 out of 10, Wonderful, (978)
9.2/10
Wonderful
(978)
The price is $106
$106
$125 total
includes taxes & fees
Dec 28 - Dec 29
7.6 out of 10, Good, (595)
7.6/10
Good
(595)
The price is $95
$95
$107 total
includes taxes & fees
Dec 21 - Dec 22
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point2.0 star property
New Windsor
8.4 out of 10, Very Good, (1010)
8.4/10
Very Good
(1010)
The price is $101
$101
$114 total
includes taxes & fees
Jan 1 - Jan 2, 2026
8.6 out of 10, Excellent, (1108)
8.6/10
Excellent
(1108)
The price is $169
$169
$216 total
includes taxes & fees
Dec 22 - Dec 23
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.
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.
Top landmarks in Middletown
Galleria at Crystal Run
Galleria at Crystal Run
If you like shopping, take time out to go to Galleria at Crystal Run when in Middletown.
Orange County Fair Speedway
Orange County Fair Speedway
You can catch an event at Orange County Fair Speedway, located 1.4 mi (2.2 km) from central Mechanicstown.
Orange County Fairgrounds
Orange County Fairgrounds
Orange County Fairgrounds is 0.3 mi (0.6 km) from central Mechanicstown, why not stop by during your stay. If you'd also like to explore some of the parks in Mechanicstown, head to The Rock Sports Complex and Orange County Arboretum.
Paramount Theatre
Paramount Theatre
You can enjoy a show at Paramount Theatre on your trip to Middletown. While in this family-friendly area, find time to visit its shops.
Orange Regional Medical Center
Orange Regional Medical Center
Though Orange Regional Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Middletown while you are here.
Highland Lakes State Park
Highland Lakes State Park
You can take time to visit Highland Lakes State Park during your travels to Middletown. While in this family-friendly area, you can savor the top-notch restaurants.