Cheap Vacations in Westchester County

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Westchester County vacations

Price found within the past 48 hours. Click for updated prices.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was $520, price is now $325 per person
$325
per person
Jan 16 - Jan 18
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $2,214, price is now $1,275 per person
$1,275
per person
Jan 30 - Feb 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Empire Hotel

Empire Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $767, price is now $465 per person
$465
per person
Jan 22 - Jan 27
found 17 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $1,548, price is now $975 per person
$975
per person
Jan 16 - Jan 19
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Pendry Natirar

Pendry Natirar

5 out of 5
Save 100% on your flight
Price was $1,618, price is now $1,028 per person
$1,028
per person
Jan 26 - Jan 29
found 1 day ago
Roundtrip flight included
Dallas (DAL) to New York (NYC)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,011, price is now $667 per person
$667
per person
Feb 4 - Feb 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Madison Hotel

Madison Hotel

4 out of 5
Price was $543, price is now $360 per person
$360
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

2.5 out of 5
Arlington
Save 100% on your flight
Price was $560, price is now $374 per person
$374
per person
Jan 15 - Jan 22
found 14 hours ago
Roundtrip flight included
Houston (IAH) to White Plains (HPN)
Harpoon House

Harpoon House

3 out of 5
Price was $1,035, price is now $696 per person
$696
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Paradise Stream Resort

Paradise Stream Resort

3.5 out of 5
Save 100% on your flight
Price was $801, price is now $540 per person
$540
per person
Jan 25 - Jan 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)

3-night Westchester County vacations

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Yonkers

Hampton Inn & Suites Yonkers

2.5 out of 5
Save 100% on your flight
Price was $326, price is now $218 per person
$218
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to White Plains (HPN)
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Save 100% on your flight
Price was $684, price is now $391 per person
$391
per person
Jan 10 - Jan 13
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Save 100% on your flight
Price was $1,202, price is now $709 per person
$709
per person
Jan 10 - Jan 13
found 23 hours 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 $1,548, price is now $975 per person
$975
per person
Jan 16 - Jan 19
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Pendry Natirar

Pendry Natirar

5 out of 5
Save 100% on your flight
Price was $1,618, price is now $1,028 per person
$1,028
per person
Jan 26 - Jan 29
found 1 day ago
Roundtrip flight included
Dallas (DAL) to New York (NYC)
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 $908, price is now $598 per person
$598
per person
Jan 10 - Jan 13
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Save 100% on your flight
Price was $1,011, price is now $667 per person
$667
per person
Feb 4 - Feb 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Madison Hotel

Madison Hotel

4 out of 5
Price was $543, price is now $360 per person
$360
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
Paradise Stream Resort

Paradise Stream Resort

3.5 out of 5
Save 100% on your flight
Price was $898, price is now $599 per person
$599
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Newark Liberty Intl. Airport (EWR)
Harpoon House

Harpoon House

3 out of 5
Price was $1,035, price is now $696 per person
$696
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Dome House Retreat

Dome House Retreat

4 out of 5
Save 100% on your flight
Price was $1,474, price is now $1,001 per person
$1,001
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
San Juan (SJU) to White Plains (HPN)
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Save 100% on your flight
Price was $439, price is now $299 per person
$299
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (NYC)

4-night Westchester County vacations

Price found within the past 48 hours. Click for updated prices.
voco Fiorello - LaGuardia Airport by IHG

voco Fiorello - LaGuardia Airport by IHG

4 out of 5
Save 100% on your flight
Price was $410, price is now $270 per person
$270
per person
Feb 5 - Feb 9
found 12 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 $882, price is now $541 per person
$541
per person
Jan 13 - Jan 17
found 14 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Price was $1,271, price is now $799 per person
$799
per person
Jan 20 - Jan 24
found 12 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
Fairfield Inn & Suites New York Queens/Fresh Meadows

Fairfield Inn & Suites New York Queens/Fresh Meadows

2.5 out of 5
Save 100% on your flight
Price was $424, price is now $272 per person
$272
per person
Feb 5 - Feb 9
found 12 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Price was $1,394, price is now $910 per person
$910
per person
Jan 20 - Jan 24
found 12 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
The Gallivant Times Square

The Gallivant Times Square

3.5 out of 5
Save 100% on your flight
Price was $429, price is now $284 per person
$284
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Paradise Stream Resort

Paradise Stream Resort

3.5 out of 5
Save 100% on your flight
Price was $801, price is now $540 per person
$540
per person
Jan 25 - Jan 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Hotel St. James

Hotel St. James

2.5 out of 5
Save 100% on your flight
Price was $723, price is now $494 per person
$494
per person
Jan 13 - Jan 17
found 14 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
Radio Hotel

Radio Hotel

4 out of 5
Save 100% on your flight
Price was $455, price is now $311 per person
$311
per person
Jan 21 - Jan 25
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 $906, price is now $621 per person
$621
per person
Jan 13 - Jan 17
found 14 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 $896, price is now $616 per person
$616
per person
Jan 13 - Jan 17
found 14 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
Hampton Inn & Suites Huntington Downtown

Hampton Inn & Suites Huntington Downtown

2.5 out of 5
Save 100% on your flight
Price was $600, price is now $421 per person
$421
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)

5-night Westchester County vacations

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Yonkers

Hampton Inn & Suites Yonkers

2.5 out of 5
Save 100% on your flight
Price was $468, price is now $292 per person
$292
per person
Jan 15 - Jan 20
just found
Roundtrip flight included
Houston (IAH) to White Plains (HPN)
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Price was $769, price is now $346 per person
$346
per person
Jan 20 - Jan 25
found 4 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 $704, price is now $407 per person
$407
per person
Jan 20 - Jan 25
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Save 100% on your flight
Price was $1,582, price is now $916 per person
$916
per person
Jan 20 - Jan 25
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Lexington Hotel, Autograph Collection

The Lexington Hotel, Autograph Collection

4 out of 5
Save 100% on your flight
Price was $669, price is now $390 per person
$390
per person
Jan 20 - Jan 25
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Empire Hotel

Empire Hotel

4 out of 5
Save 100% on your flight
Price was $767, price is now $465 per person
$465
per person
Jan 22 - Jan 27
found 17 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
Hyatt House Jersey City

Hyatt House Jersey City

3.5 out of 5
Save 100% on your flight
Price was $715, price is now $436 per person
$436
per person
Jan 18 - Jan 23
found 9 hours ago
Roundtrip flight included
Houston (IAH) to Newark Liberty Intl. Airport (EWR)
Nesva Hotel

Nesva Hotel

2.5 out of 5
Price was $779, price is now $491 per person
$491
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
Hotel St. James

Hotel St. James

2.5 out of 5
Save 100% on your flight
Price was $768, price is now $484 per person
$484
per person
Jan 20 - Jan 25
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Fairfield Inn & Suites New York Queens/Fresh Meadows

Fairfield Inn & Suites New York Queens/Fresh Meadows

2.5 out of 5
Save 100% on your flight
Price was $518, price is now $328 per person
$328
per person
Jan 18 - Jan 23
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Gallivant Times Square

The Gallivant Times Square

3.5 out of 5
Save 100% on your flight
Price was $478, price is now $303 per person
$303
per person
Jan 15 - Jan 20
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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 $1,033, price is now $661 per person
$661
per person
Jan 20 - Jan 25
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)

6-7 night Westchester County vacations

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

3 out of 5
Save 100% on your flight
Price was $442, price is now $287 per person
$287
per person
Jan 15 - Jan 21
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to White Plains (HPN)
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Save 100% on your flight
Price was $2,214, price is now $1,275 per person
$1,275
per person
Jan 30 - Feb 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Pendry Natirar

Pendry Natirar

5 out of 5
Save 100% on your flight
Price was $2,932, price is now $1,730 per person
$1,730
per person
Jan 15 - Jan 21
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Save 100% on your flight
Price was $1,074, price is now $654 per person
$654
per person
Jan 30 - Feb 6
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to New York (JFK)
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Save 100% on your flight
Price was $1,248, price is now $762 per person
$762
per person
Jan 30 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to New York (JFK)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Save 100% on your flight
Price was $1,902, price is now $1,216 per person
$1,216
per person
Jan 15 - Jan 21
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Gallivant Times Square

The Gallivant Times Square

3.5 out of 5
Save 100% on your flight
Price was $556, price is now $356 per person
$356
per person
Jan 22 - Jan 28
found 23 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
CODA Williamsburg

CODA Williamsburg

4 out of 5
Save 100% on your flight
Price was $1,288, price is now $825 per person
$825
per person
Jan 15 - Jan 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
The Langham, New York, Fifth Avenue

The Langham, New York, Fifth Avenue

5 out of 5
Save 100% on your flight
Price was $2,296, price is now $1,474 per person
$1,474
per person
Jan 15 - Jan 21
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Windrose On Hudson

Windrose On Hudson

3 out of 5
Save 100% on your flight
Price was $878, price is now $569 per person
$569
per person
Jan 15 - Jan 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
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 $1,414, price is now $917 per person
$917
per person
Jan 30 - Feb 6
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to New York (JFK)
Fairfield Inn & Suites New York Queens/Fresh Meadows

Fairfield Inn & Suites New York Queens/Fresh Meadows

2.5 out of 5
Save 100% on your flight
Price was $763, price is now $496 per person
$496
per person
Jan 30 - Feb 6
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to New York (JFK)

Top places to visit in Westchester County

One of my new favorite places off the Metro-North train. River views, lots of feathered visitors, and this possibly haunted house. #OnTheRoad
FlightsFlightsHotelsHotels

Yonkers

Yonkers

Flight deals to Westchester County

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

Thu, Jan 22 - Sun, Feb 1
MIA
Miami
LGA
New York
$58 Roundtrip, found 3 days ago
$58
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Jan 22 from Miami to New York, returning Sun, Feb 1, priced at $58 found 3 days ago
Fri, Jan 9 - Sun, Jan 11
MCO
Orlando
JFK
New York
$64 Roundtrip, found 5 days ago
$64
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Jan 9 from Orlando to New York, returning Sun, Jan 11, priced at $64 found 5 days ago
Wed, Feb 4 - Sun, Feb 8
MCO
Orlando
LGA
New York
$69 Roundtrip, found 3 days ago
$69
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Feb 4 from Orlando to New York, returning Sun, Feb 8, priced at $69 found 3 days ago

Top rated hotels for your Westchester County vacation

Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
540 Saw Mill River Rd Elmsford NY
Free Cancellation
Reserve now, pay when you stay
3.72 mi from city center
$127 nightly
The price is $145 total per night
$145 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
With a stay at Baymont by Wyndham White Plains - Elmsford in Elmsford, you'll be in the historical district, within a 15-minute drive of NewYork-Presbyterian - Westchester Hospital and Captain Lawrence Brewing Company.
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave White Plains NY
Free Cancellation
Reserve now, pay when you stay
6.59 mi from city center
$193 nightly
The price is $220 total per night
$220 total
Dec 18 - Dec 19
Total with taxes and fees
In the heart of White Plains, Sonesta White Plains Downtown is within a 5-minute drive of The Westchester Mall and Westchester County Center.
Royal Regency Hotel

Royal Regency Hotel

3.5 out of 5
165 Tuckahoe Rd Yonkers NY
Free Cancellation
Reserve now, pay when you stay
12.11 mi from city center
$119 nightly
The price is $140 total per night
$140 total
Dec 14 - Dec 15
Total with taxes and fees
With a stay at Royal Regency Hotel in Yonkers (Northwest Yonkers), you'll be within a 15-minute drive of Yankee Stadium and NewYork-Presbyterian - Westchester Hospital.
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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.