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Orange County Accommodation: Most Popular Cities to Stay

Sunrise image of the Arrigoni Bridge in Middletown, CT
Holiday RentalsHoliday Rentals

Middletown

Middletown

Our top choices for Orange County holiday rentals

Design Apartment, Patio, Garden View | Private kitchen | Coffee/tea maker

Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
4.0 star property
Goshen
The price is 8.177.328 ₫
10.068.516 ₫ total
includes taxes & fees
18 Jun - 19 Jun
Historic Horse Barn Apartment in Goshen
House (3 Bedrooms) | Interior

Updated Home w/ Patio Half Mile to West Point

Updated Home w/ Patio Half Mile to West Point
3.0 star property
Highland Falls
The price is 6.454.525 ₫
16.379.477 ₫ total
includes taxes & fees
2 Jun - 3 Jun
Updated Home w/ Patio Half Mile to West Point
House, Smoking | 7 bedrooms

West Point Summer Pool Jacuzzi Events Pets OK

West Point Summer Pool Jacuzzi Events Pets OK
2.0 star property
Cornwall
The price is 23.926.354 ₫
41.951.141 ₫ total
includes taxes & fees
1 Jun - 2 Jun
West Point Summer Pool Jacuzzi Events Pets OK
House (4 Bedrooms) | Interior

Family Home Close to Warwick, 5 Mi to Lake!

Family Home Close to Warwick, 5 Mi to Lake!
3.0 star property
Monroe
The price is 7.242.400 ₫
19.035.397 ₫ total
includes taxes & fees
26 Jun - 27 Jun
Family Home Close to Warwick, 5 Mi to Lake!
Apartment (0 Bedroom) | Interior

Close to Trails: Studio w/ Water Views

Close to Trails: Studio w/ Water Views
3.0 star property
Westbrookville
The price is 4.819.488 ₫
9.005.332 ₫ total
includes taxes & fees
11 Jun - 12 Jun
Close to Trails: Studio w/ Water Views
House (1 Bedroom) | Interior

Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
The price is 6.452.320 ₫
11.763.764 ₫ total
includes taxes & fees
11 Jun - 12 Jun
Hike & Fish: Outdoor Retreat Near Trails
House, Smoking | 5 bedrooms

Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is 29.341.437 ₫
44.939.683 ₫ total
includes taxes & fees
23 Jun - 24 Jun
Summer Pool Oasis Custom Bar Arcade Pool Table
House (5 Bedrooms) | Interior

Ossining Vacation Rental Near River, Trails & Mta!

Ossining Vacation Rental Near River, Trails & Mta!
3.0 star property
Ossining
The price is 8.058.816 ₫
23.238.360 ₫ total
includes taxes & fees
31 May - 1 Jun
Ossining Vacation Rental Near River, Trails & Mta!
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.
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Top Orange County Hotel Reviews

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

10/10 Excellent
"Very close to Shopping sighting and family"
Aron 2-night trip
Posted 9 hours ago
Sleep Inn & Suites Monroe - Woodbury