Cheap Vacations in Smithtown

Choose two or more items and save on your trip:

3-night Smithtown 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 $454, price is now $312 per person
$312
per person
Mar 8 - Mar 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New York (JFK)
Hotel Alameda Highline

Hotel Alameda Highline

4.5 out of 5
Price was $1,979, price is now $417 per person
$417
per person
Mar 13 - Mar 16
found 9 hours ago
Roundtrip flight included
Orlando (ORL) 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 $680, price is now $377 per person
$377
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was $803, price is now $494 per person
$494
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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 $860, price is now $549 per person
$549
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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 $850, price is now $550 per person
$550
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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 $814, price is now $528 per person
$528
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
New York Marriott Downtown

New York Marriott Downtown

4 out of 5
Save 100% on your flight
Price was $902, price is now $585 per person
$585
per person
Mar 14 - Mar 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New York (JFK)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $1,743, price is now $1,137 per person
$1,137
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Walker Hotel Greenwich Village

Walker Hotel Greenwich Village

4.5 out of 5
Save 100% on your flight
Price was $739, price is now $510 per person
$510
per person
Mar 6 - Mar 9
found 2 hours ago
Roundtrip flight included
Orlando (MCO) to New York (JFK)
Pendry Natirar

Pendry Natirar

5 out of 5
Save 100% on your flight
Price was $1,682, price is now $1,170 per person
$1,170
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Save 100% on your flight
Price was $1,068, price is now $743 per person
$743
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)

4-night Smithtown vacations

Price found within the past 48 hours. Click for updated prices.
The Hewitt Wellington Hotel

The Hewitt Wellington Hotel

3 out of 5
Price was $464, price is now $339 per person
$339
per person
Feb 20 - Feb 24
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Newark Liberty Intl. Airport (EWR)
Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Save 100% on your flight
Price was $1,663, price is now $981 per person
$981
per person
Mar 7 - Mar 11
found 5 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Price was $652, price is now $409 per person
$409
per person
Feb 19 - Feb 23
found 3 hours ago
Roundtrip flight included
Orlando (MCO) to New York (JFK)
American Hotel

American Hotel

3.5 out of 5
Save 100% on your flight
Price was $600, price is now $379 per person
$379
per person
Feb 20 - Feb 24
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Newark Liberty Intl. Airport (EWR)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Price was $1,424, price is now $970 per person
$970
per person
Mar 14 - Mar 18
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Somerset Hills Hotel, Tapestry Collection by Hilton

Somerset Hills Hotel, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $566, price is now $389 per person
$389
per person
Feb 20 - Feb 24
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Newark Liberty Intl. Airport (EWR)
Windrose On Hudson

Windrose On Hudson

3 out of 5
Save 100% on your flight
Price was $752, price is now $519 per person
$519
per person
Mar 12 - Mar 16
found 8 hours ago
Roundtrip flight included
San Juan (SJU) to New York (LGA)
The Iroquois New York

The Iroquois New York

4.5 out of 5
Save 100% on your flight
Price was $1,343, price is now $934 per person
$934
per person
Mar 7 - Mar 11
found 5 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
The George

The George

4 out of 5
Save 100% on your flight
Price was $1,009, price is now $706 per person
$706
per person
Feb 20 - Feb 24
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Newark Liberty Intl. Airport (EWR)
Park Lane New York

Park Lane New York

5 out of 5
Save 100% on your flight
Price was $1,201, price is now $862 per person
$862
per person
Feb 26 - Mar 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Asbury Ocean Club Hotel

Asbury Ocean Club Hotel

4 out of 5
Save 100% on your flight
Price was $959, price is now $695 per person
$695
per person
Feb 20 - Feb 24
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Newark Liberty Intl. Airport (EWR)
Pendry Natirar

Pendry Natirar

5 out of 5
Save 100% on your flight
Price was $2,512, price is now $1,831 per person
$1,831
per person
Feb 27 - Mar 3
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)

5-night Smithtown vacations

Price found within the past 48 hours. Click for updated prices.
Best Western Plus Meadowlands

Best Western Plus Meadowlands

3.5 out of 5
Save 100% on your flight
Price was $552, price is now $372 per person
$372
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Save 100% on your flight
Price was $895, price is now $452 per person
$452
per person
Feb 25 - Mar 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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 $1,164, price is now $647 per person
$647
per person
Feb 25 - Mar 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Hotel St. James

Hotel St. James

2.5 out of 5
Save 100% on your flight
Price was $828, price is now $477 per person
$477
per person
Feb 25 - Mar 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
Price was $856, price is now $511 per person
$511
per person
Feb 25 - Mar 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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 $821, price is now $500 per person
$500
per person
Feb 25 - Mar 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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 $1,123, price is now $702 per person
$702
per person
Feb 25 - Mar 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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 $1,009, price is now $631 per person
$631
per person
Feb 25 - Mar 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
The Westin New York Grand Central

The Westin New York Grand Central

4.5 out of 5
Save 100% on your flight
Price was $1,034, price is now $651 per person
$651
per person
Feb 25 - Mar 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Price was $1,613, price is now $1,032 per person
$1,032
per person
Mar 13 - Mar 18
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New York (JFK)
Arthouse Hotel New York City

Arthouse Hotel New York City

4 out of 5
Save 100% on your flight
Price was $741, price is now $490 per person
$490
per person
Feb 25 - Mar 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Hilton Garden Inn Westchester Dobbs Ferry, NY

Hilton Garden Inn Westchester Dobbs Ferry, NY

3 out of 5
Save 100% on your flight
Price was $594, price is now $402 per person
$402
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)

6-7 night Smithtown vacations

Price found within the past 48 hours. Click for updated prices.
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Save 100% on your flight
Price was $1,202, price is now $666 per person
$666
per person
Mar 1 - Mar 7
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Hotel St. James

Hotel St. James

2.5 out of 5
Save 100% on your flight
Price was $1,269, price is now $711 per person
$711
per person
Mar 1 - Mar 7
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $4,181, price is now $2,388 per person
$2,388
per person
Mar 11 - Mar 18
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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 $1,269, price is now $726 per person
$726
per person
Mar 1 - Mar 7
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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 $1,678, price is now $962 per person
$962
per person
Mar 1 - Mar 7
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
Price was $1,291, price is now $752 per person
$752
per person
Mar 1 - Mar 7
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
The Westin New York Grand Central

The Westin New York Grand Central

4.5 out of 5
Save 100% on your flight
Price was $1,416, price is now $846 per person
$846
per person
Mar 1 - Mar 7
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
CODA Williamsburg

CODA Williamsburg

4 out of 5
Price was $1,187, price is now $735 per person
$735
per person
Feb 19 - Feb 25
found 19 hours ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Price was $3,357, price is now $2,084 per person
$2,084
per person
Mar 11 - Mar 18
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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 $1,388, price is now $862 per person
$862
per person
Mar 1 - Mar 7
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Hotel Hendricks

Hotel Hendricks

4 out of 5
Save 100% on your flight
Price was $1,087, price is now $693 per person
$693
per person
Mar 11 - Mar 17
found 1 hour ago
Roundtrip flight included
Orlando (ORL) to New York (JFK)
The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Price was $3,998, price is now $2,667 per person
$2,667
per person
Mar 11 - Mar 18
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)

Flight deals to Smithtown

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

Wed, Feb 4 - Sat, Feb 7
MCO
Orlando
LGA
New York
$50 Roundtrip, found 3 days ago
$50
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Wed, Feb 4 from Orlando to New York, returning Sat, Feb 7, priced at $50 found 3 days ago
Sat, Feb 14 - Wed, Feb 18
MCO
Orlando
EWR
New York
$54 Roundtrip, found 2 days ago
$54
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sat, Feb 14 from Orlando to New York, returning Wed, Feb 18, priced at $54 found 2 days ago
Tue, Feb 10 - Wed, Feb 25
MIA
Miami
EWR
New York
$55 Roundtrip, found 1 day ago
$55
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Feb 10 from Miami to New York, returning Wed, Feb 25, priced at $55 found 1 day ago

Top rated hotels for your Smithtown vacation

Hyatt Regency Long Island

Hyatt Regency Long Island

4 out of 5
1717 Motor Parkway Hauppauge NY
Free Cancellation
Reserve now, pay when you stay
3.3 mi from city center
$143 nightly
The price is $164 total per night
$164 total
Jan 19 - Jan 20
Total with taxes and fees
Located in Hauppauge, Hyatt Regency Long Island is by the ocean, within a 5-minute drive of Hauppauge Industrial Park and Lakeland County Park.
Pool
Parking included
Hilton Garden Inn Westbury

Hilton Garden Inn Westbury

3 out of 5
1575 Privado Rd Westbury NY
Free Cancellation
Reserve now, pay when you stay
21.69 mi from city center
$113 nightly
The price is $126 total per night
$126 total
Jan 25 - Jan 26
Total with taxes and fees
With a stay at Hilton Garden Inn Westbury in Westbury, you'll be in a shopping district, within a 15-minute drive of UBS Arena and Eisenhower Park.
Pool
Pet friendly
Holiday Inn Express Hauppauge-Long Island

Holiday Inn Express Hauppauge-Long Island

2.5 out of 5
2050 Express Dr S Hauppauge NY
Free Cancellation
3.51 mi from city center
$115 nightly
The price is $131 total per night
$131 total
Jan 22 - Jan 23
Total with taxes and fees
Located in Hauppauge, Holiday Inn Express Hauppauge-Long Island is a 2-minute drive from Hauppauge Industrial Park and 8 minutes from SUSA Orlin & Cohen Sports Complex.
Pool
Breakfast included
Don't see what you're looking for?
See all available properties in Smithtown
View all properties
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.