Cheap Vacations in Orange County

Choose two or more items and save on your trip:

Orange County vacations

Price found within the past 48 hours. Click for updated prices.
Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Save 100% on your flight
Price was $926, price is now $527 per person
$527
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $5,280, price is now $2,415 per person
$2,415
per person
Oct 14 - Oct 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was $2,801, price is now $1,494 per person
$1,494
per person
Oct 14 - Oct 20
found 19 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $2,643, price is now $1,416 per person
$1,416
per person
Oct 14 - Oct 20
found 19 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
Seven Beach Lane

Seven Beach Lane

2 out of 5
Save 100% on your flight
Price was $2,284, price is now $1,225 per person
$1,225
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $2,288, price is now $1,289 per person
$1,289
per person
Oct 14 - Oct 20
found 19 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
Price was $2,968, price is now $1,682 per person
$1,682
per person
Oct 17 - Oct 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
OYO Times Square

OYO Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,631, price is now $931 per person
$931
per person
Oct 14 - Oct 20
found 19 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Save 100% on your flight
Price was $1,569, price is now $928 per person
$928
per person
Oct 14 - Oct 20
found 19 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,463, price is now $881 per person
$881
per person
Oct 14 - Oct 20
found 19 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)

3-night Orange County vacations

Price found within the past 48 hours. Click for updated prices.
Log Comfort 3

Log Comfort 3

3 out of 5
Save 100% on your flight
Price was $446, price is now $306 per person
$306
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $2,596, price is now $1,437 per person
$1,437
per person
Oct 9 - Oct 12
found 17 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Hotel St. James

Hotel St. James

3 out of 5
Save 100% on your flight
Price was $926, price is now $527 per person
$527
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
East Norwich Inn

East Norwich Inn

2.5 out of 5
Save 100% on your flight
Price was $747, price is now $465 per person
$465
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Park Lane New York

Park Lane New York

5 out of 5
Save 100% on your flight
Price was $1,281, price is now $809 per person
$809
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
OYO Times Square

OYO Times Square

4 out of 5
Save 100% on your flight
Price was $906, price is now $572 per person
$572
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Freehand New York

Freehand New York

4 out of 5
Save 100% on your flight
Price was $947, price is now $616 per person
$616
per person
Sep 29 - Oct 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Hotel 48LEX New York

Hotel 48LEX New York

4.5 out of 5
Save 100% on your flight
Price was $850, price is now $564 per person
$564
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Chatwal, In The Unbound Collection By Hyatt

The Chatwal, In The Unbound Collection By Hyatt

5 out of 5
Save 100% on your flight
Price was $2,065, price is now $1,380 per person
$1,380
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Hotel AKA NoMad

Hotel AKA NoMad

4 out of 5
Save 100% on your flight
Price was $1,369, price is now $929 per person
$929
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Save 100% on your flight
Price was $2,495, price is now $1,711 per person
$1,711
per person
Oct 16 - Oct 19
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Frederick Hotel Tribeca, a Small Luxury Hotel

The Frederick Hotel Tribeca, a Small Luxury Hotel

4.5 out of 5
Save 100% on your flight
Price was $1,158, price is now $797 per person
$797
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)

4-night Orange County vacations

Price found within the past 48 hours. Click for updated prices.
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Save 100% on your flight
Price was $1,105, price is now $714 per person
$714
per person
Oct 12 - Oct 16
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Save 100% on your flight
Price was $2,968, price is now $1,682 per person
$1,682
per person
Oct 17 - Oct 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Save 100% on your flight
Price was $2,101, price is now $1,258 per person
$1,258
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Save 100% on your flight
Price was $2,147, price is now $1,288 per person
$1,288
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Park Lane New York

Park Lane New York

5 out of 5
Save 100% on your flight
Price was $1,537, price is now $995 per person
$995
per person
Oct 1 - Oct 5
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to New York (JFK)
The High Line Hotel

The High Line Hotel

4 out of 5
Save 100% on your flight
Price was $2,129, price is now $1,400 per person
$1,400
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
42 Hotel

42 Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,253, price is now $826 per person
$826
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to New York (JFK)
Royalton New York

Royalton New York

4 out of 5
Save 100% on your flight
Price was $1,409, price is now $930 per person
$930
per person
Sep 30 - Oct 4
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
W New York - Times Square

W New York - Times Square

4.5 out of 5
Save 100% on your flight
Price was $1,240, price is now $830 per person
$830
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to New York (JFK)
The Lombardy Hotel

The Lombardy Hotel

4 out of 5
Save 100% on your flight
Price was $1,476, price is now $989 per person
$989
per person
Oct 19 - Oct 23
found 17 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Hotel @ Fifth Avenue

The Hotel @ Fifth Avenue

3.5 out of 5
Save 100% on your flight
Price was $1,419, price is now $953 per person
$953
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Sela V Hotel

Sela V Hotel

4 out of 5
Save 100% on your flight
Price was $1,112, price is now $761 per person
$761
per person
Sep 29 - Oct 3
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)

5-night Orange County vacations

Price found within the past 48 hours. Click for updated prices.
Radio Hotel

Radio Hotel

4 out of 5
Save 100% on your flight
Price was $999, price is now $642 per person
$642
per person
Oct 2 - Oct 7
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to New York (JFK)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $5,280, price is now $2,415 per person
$2,415
per person
Oct 14 - Oct 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Seven Beach Lane

Seven Beach Lane

2 out of 5
Save 100% on your flight
Price was $2,284, price is now $1,225 per person
$1,225
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Save 100% on your flight
Price was $2,466, price is now $1,450 per person
$1,450
per person
Oct 14 - Oct 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Ink 48 Hotel

Ink 48 Hotel

4.5 out of 5
Save 100% on your flight
Price was $2,190, price is now $1,300 per person
$1,300
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Save 100% on your flight
Price was $3,565, price is now $2,128 per person
$2,128
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Save 100% on your flight
Price was $2,718, price is now $1,631 per person
$1,631
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
Price was $2,028, price is now $1,266 per person
$1,266
per person
Oct 14 - Oct 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Freehand New York

Freehand New York

4 out of 5
Save 100% on your flight
Price was $1,591, price is now $1,011 per person
$1,011
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Hotel @ Fifth Avenue

The Hotel @ Fifth Avenue

3.5 out of 5
Save 100% on your flight
Price was $1,498, price is now $956 per person
$956
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Hotel Park Ave NYC

Hotel Park Ave NYC

4.5 out of 5
Save 100% on your flight
Price was $1,877, price is now $1,215 per person
$1,215
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Save 100% on your flight
Price was $3,291, price is now $2,158 per person
$2,158
per person
Sep 30 - Oct 5
found 1 hour ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)

6-7 night Orange County vacations

Price found within the past 48 hours. Click for updated prices.
Radio Hotel

Radio Hotel

4 out of 5
Save 100% on your flight
Price was $1,463, price is now $881 per person
$881
per person
Oct 14 - Oct 20
found 19 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Price was $2,801, price is now $1,494 per person
$1,494
per person
Oct 14 - Oct 20
found 19 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Save 100% on your flight
Price was $2,643, price is now $1,416 per person
$1,416
per person
Oct 14 - Oct 20
found 19 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
Price was $2,288, price is now $1,289 per person
$1,289
per person
Oct 14 - Oct 20
found 19 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
OYO Times Square

OYO Times Square

4 out of 5
Save 100% on your flight
Price was $1,631, price is now $931 per person
$931
per person
Oct 14 - Oct 20
found 19 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Save 100% on your flight
Price was $1,569, price is now $928 per person
$928
per person
Oct 14 - Oct 20
found 19 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
The William Hotel Midtown, New York

The William Hotel Midtown, New York

3.5 out of 5
Save 100% on your flight
Price was $2,409, price is now $1,491 per person
$1,491
per person
Oct 14 - Oct 20
found 19 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
The Hotel @ Fifth Avenue

The Hotel @ Fifth Avenue

3.5 out of 5
Save 100% on your flight
Price was $1,920, price is now $1,219 per person
$1,219
per person
Oct 14 - Oct 20
found 19 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
Hotel 32 32

Hotel 32 32

4 out of 5
Save 100% on your flight
Price was $1,759, price is now $1,136 per person
$1,136
per person
Sep 28 - Oct 5
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
CIVILIAN Hotel

CIVILIAN Hotel

4 out of 5
Save 100% on your flight
Price was $1,936, price is now $1,258 per person
$1,258
per person
Oct 14 - Oct 20
found 19 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
Hotel St. James

Hotel St. James

3 out of 5
Save 100% on your flight
Price was $1,723, price is now $1,120 per person
$1,120
per person
Sep 26 - Oct 2
found 16 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Save 100% on your flight
Price was $2,167, price is now $1,413 per person
$1,413
per person
Oct 14 - Oct 20
found 19 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)

Top places to visit in Orange County

Beautiful Autumn View in Bear Mountain State Park
FlightsFlightsHotelsHotels

Middletown

Middletown

Flight deals to Orange County

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Thu, Dec 10 - Sun, Dec 13
FLL
Fort Lauderdale
SWF
Newburgh
$86 Roundtrip, found 4 days ago
$86
Roundtrip
found 4 days ago
Select Allegiant Air flight, departing Thu, Dec 10 from Fort Lauderdale to Newburgh, returning Sun, Dec 13, priced at $86 found 4 days ago
Thu, Dec 3 - Sun, Dec 6
PIE
St. Petersburg
SWF
Newburgh
$125 Roundtrip, found 10 hours ago
$125
Roundtrip
found 10 hours ago
Select Allegiant Air flight, departing Thu, Dec 3 from St. Petersburg to Newburgh, returning Sun, Dec 6, priced at $125 found 10 hours ago
Thu, Sep 24 - Sat, Sep 26
MCO
Orlando
SWF
Newburgh
$154 Roundtrip, found 6 days ago
$154
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Sep 24 from Orlando to Newburgh, returning Sat, Sep 26, priced at $154 found 6 days ago

Top rated hotels for your Orange County vacation

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
Free Cancellation
5.57 mi from city center
$110 nightly
The price is $130 total per night
$130 total
Sep 13 - Sep 14
Total with taxes and fees
With a stay at Sleep Inn & Suites Middletown - Goshen, you'll be centrally located in Middletown, within a 15-minute drive of LEGOLAND® New York and Orange County Community College.
Pool
Breakfast included
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
551 Route 211 E Middletown NY
Free Cancellation
Reserve now, pay when you stay
5.02 mi from city center
$123 nightly
The price is $146 total per night
$146 total
Aug 30 - Aug 31
Total with taxes and fees
With a stay at La Quinta Inn & Suites by Wyndham Middletown-Goshen in Middletown, you'll be in a shopping district, within a 10-minute drive of LEGOLAND® New York and Orange County Fairgrounds.
Pool
Breakfast included
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
Free Cancellation
Reserve now, pay when you stay
18.15 mi from city center
$169 nightly
The price is $208 total per night
$208 total
Aug 25 - Aug 26
Total with taxes and fees
When you stay at Overlook Lodge at Bear Mountain in Bear Mountain, you'll be in a state park, a 1-minute drive from Bear Mountain State Park and 7 minutes from United States Military Academy.
Pool
Spa
Don't see what you're looking for?
See all available properties in Orange County
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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.