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.
Ly New York Hotel

Ly New York Hotel

2.5 out of 5
Price was $380, price is now $264 per person
$264
per person
Apr 18 - Apr 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Topping Rose House

Topping Rose House

4.5 out of 5
Save 100% on your flight
Price was $1,280, price is now $744 per person
$744
per person
Apr 15 - Apr 18
found 1 day 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 $1,326, price is now $794 per person
$794
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Pestana CR7 Times Square

Pestana CR7 Times Square

4 out of 5
Price was $896, price is now $558 per person
$558
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Harpoon House

Harpoon House

3 out of 5
Save 100% on your flight
Price was $624, price is now $413 per person
$413
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Candlewood Suites New York City-Times Square by IHG

Candlewood Suites New York City-Times Square by IHG

2.5 out of 5
Price was $840, price is now $560 per person
$560
per person
Apr 24 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Court Square Hotel Long Island City New York , Belvilla District 6 Formerly Sonder

Court Square Hotel Long Island City New York , Belvilla District 6 Formerly Sonder

3.5 out of 5
Save 100% on your flight
Price was $752, price is now $503 per person
$503
per person
Apr 9 - Apr 12
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 $1,004, price is now $678 per person
$678
per person
Apr 24 - Apr 27
found 16 hours ago
Roundtrip flight included
Dallas (DAL) to Newark Liberty Intl. Airport (EWR)
The William Hotel Midtown, New York

The William Hotel Midtown, New York

2 out of 5
Save 100% on your flight
Price was $1,165, price is now $792 per person
$792
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Nova Hotel Brooklyn

Nova Hotel Brooklyn

3 out of 5
Price was $490, price is now $336 per person
$336
per person
Apr 18 - Apr 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
Price was $540, price is now $374 per person
$374
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Outsite Chelsea

Outsite Chelsea

2 out of 5
Price was $710, price is now $500 per person
$500
per person
Apr 13 - Apr 16
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)

4-night Smithtown vacations

Price found within the past 48 hours. Click for updated prices.
Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
Price was $646, price is now $422 per person
$422
per person
Apr 14 - Apr 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Topping Rose House

Topping Rose House

4.5 out of 5
Price was $1,672, price is now $916 per person
$916
per person
Apr 14 - Apr 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Save 100% on your flight
Price was $1,461, price is now $879 per person
$879
per person
Apr 27 - May 1
found 11 hours ago
Roundtrip flight included
Dallas (DAL) to Newark Liberty Intl. Airport (EWR)
Pestana CR7 Times Square

Pestana CR7 Times Square

4 out of 5
Save 100% on your flight
Price was $959, price is now $596 per person
$596
per person
Apr 24 - Apr 28
found 12 hours 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 $1,234, price is now $771 per person
$771
per person
Apr 27 - May 1
found 11 hours ago
Roundtrip flight included
Dallas (DAL) to Newark Liberty Intl. Airport (EWR)
Outsite Chelsea

Outsite Chelsea

2 out of 5
Save 100% on your flight
Price was $921, price is now $593 per person
$593
per person
Apr 27 - May 1
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Hyatt Union Square New York

Hyatt Union Square New York

4 out of 5
Price was $1,119, price is now $726 per person
$726
per person
Apr 9 - Apr 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
The Maidstone

The Maidstone

4 out of 5
Save 100% on your flight
Price was $1,435, price is now $936 per person
$936
per person
Apr 14 - Apr 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Court Square Hotel Long Island City New York , Belvilla District 6 Formerly Sonder

Court Square Hotel Long Island City New York , Belvilla District 6 Formerly Sonder

3.5 out of 5
Price was $864, price is now $572 per person
$572
per person
Apr 9 - Apr 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Interfaith 21

Interfaith 21

2 out of 5
Save 100% on your flight
Price was $838, price is now $574 per person
$574
per person
Apr 17 - Apr 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Save 100% on your flight
Price was $2,113, price is now $1,461 per person
$1,461
per person
Apr 23 - Apr 27
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.
Red Roof Inn PLUS+ Long Island - Garden City

Red Roof Inn PLUS+ Long Island - Garden City

2.5 out of 5
Price was $913, price is now $658 per person
$658
per person
Apr 15 - Apr 20
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
The William Vale

The William Vale

5 out of 5
Save 100% on your flight
Price was $1,960, price is now $1,187 per person
$1,187
per person
Apr 17 - Apr 22
found 4 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to New York (JFK)
Newark Liberty International Airport Marriott

Newark Liberty International Airport Marriott

4 out of 5
Price was $1,202, price is now $758 per person
$758
per person
Apr 23 - Apr 28
found 9 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
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 $1,707, price is now $1,081 per person
$1,081
per person
Apr 27 - May 2
found 12 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Save 100% on your flight
Price was $2,333, price is now $1,644 per person
$1,644
per person
Apr 14 - Apr 19
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
Hyatt Union Square New York

Hyatt Union Square New York

4 out of 5
Save 100% on your flight
Price was $1,928, price is now $1,365 per person
$1,365
per person
Apr 9 - Apr 14
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
Kixby

Kixby

4 out of 5
Save 100% on your flight
Price was $1,257, price is now $914 per person
$914
per person
Apr 14 - Apr 19
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
Nine Orchard

Nine Orchard

5 out of 5
Save 100% on your flight
Price was $2,054, price is now $1,502 per person
$1,502
per person
Apr 17 - Apr 22
found 4 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Newark Liberty Intl. Airport (EWR)
The Dutch Hotel Long Island City, Sonder by Marriott Bonvoy

The Dutch Hotel Long Island City, Sonder by Marriott Bonvoy

3.5 out of 5
Save 100% on your flight
Price was $1,072, price is now $785 per person
$785
per person
Apr 25 - Apr 30
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Save 100% on your flight
Price was $2,908, price is now $2,142 per person
$2,142
per person
Apr 17 - Apr 22
found 4 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Newark Liberty Intl. Airport (EWR)
WestHouse New York

WestHouse New York

5 out of 5
Save 100% on your flight
Price was $1,377, price is now $1,017 per person
$1,017
per person
Apr 27 - May 2
found 12 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Library Hotel by Library Hotel Collection

Library Hotel by Library Hotel Collection

4 out of 5
Save 100% on your flight
Price was $1,816, price is now $1,369 per person
$1,369
per person
Apr 20 - Apr 25
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Newark Liberty Intl. Airport (EWR)

6-7 night Smithtown vacations

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

Sheraton Parsippany Hotel

4 out of 5
Save 100% on your flight
Price was $899, price is now $593 per person
$593
per person
Apr 7 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Newark Liberty Intl. Airport (EWR)
Hotel St. James

Hotel St. James

2.5 out of 5
Price was $1,421, price is now $724 per person
$724
per person
Apr 22 - Apr 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Price was $1,854, price is now $1,049 per person
$1,049
per person
Apr 22 - Apr 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Price was $1,132, price is now $664 per person
$664
per person
Apr 22 - Apr 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Price was $1,997, price is now $1,217 per person
$1,217
per person
Apr 22 - Apr 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
The William Hotel Midtown, New York

The William Hotel Midtown, New York

2 out of 5
Save 100% on your flight
Price was $1,017, price is now $622 per person
$622
per person
Apr 15 - Apr 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Millennium Hotel Broadway Times Square

Millennium Hotel Broadway Times Square

4 out of 5
Price was $1,233, price is now $789 per person
$789
per person
Apr 22 - Apr 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
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 $2,040, price is now $1,312 per person
$1,312
per person
Apr 9 - Apr 15
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
Holiday Inn Express New York City Times Square by IHG

Holiday Inn Express New York City Times Square by IHG

3 out of 5
Price was $1,216, price is now $797 per person
$797
per person
Apr 22 - Apr 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Hotel Stanford

Hotel Stanford

3 out of 5
Save 100% on your flight
Price was $1,140, price is now $755 per person
$755
per person
Apr 15 - Apr 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
Price was $2,386, price is now $1,588 per person
$1,588
per person
Apr 9 - Apr 15
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Save 100% on your flight
Price was $4,166, price is now $2,792 per person
$2,792
per person
Apr 28 - May 4
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)

Flight deals to Smithtown

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

Wed, Apr 22 - Wed, Apr 22
MCO
Orlando
LGA
New York
$56 Roundtrip, found 6 days ago
$56
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Apr 22 from Orlando to New York, returning Wed, Apr 22, priced at $56 found 6 days ago
Fri, May 8 - Wed, May 13
ATL
Atlanta
LGA
New York
$56 Roundtrip, found 7 hours ago
$56
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Fri, May 8 from Atlanta to New York, returning Wed, May 13, priced at $56 found 7 hours ago
Mon, Mar 23 - Tue, Mar 24
ATL
Atlanta
JFK
New York
$56 Roundtrip, found 2 days ago
$56
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Mar 23 from Atlanta to New York, returning Tue, Mar 24, priced at $56 found 2 days ago
Tue, Apr 14 - Wed, Apr 15
ATL
Atlanta
EWR
New York
$57 Roundtrip, found 2 days ago
$57
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Apr 14 from Atlanta to New York, returning Wed, Apr 15, priced at $57 found 2 days ago
Thu, May 7 - Mon, May 11
MCO
Orlando
EWR
New York
$77 Roundtrip, found 7 hours ago
$77
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Thu, May 7 from Orlando to New York, returning Mon, May 11, priced at $77 found 7 hours ago
Thu, Apr 2 - Sun, Apr 5
PBI
West Palm Beach
ISP
Islip
$80 Roundtrip, found 1 day ago
$80
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Apr 2 from West Palm Beach to Islip, returning Sun, Apr 5, priced at $80 found 1 day ago

Top rated hotels for your Smithtown vacation

Radisson Hotel Hauppauge-Long Island

Radisson Hotel Hauppauge-Long Island

3.5 out of 5
110 Vanderbilt Motor Pkwy Hauppauge NY
Free Cancellation
4.79 mi from city center
$122 nightly
The price is $140 total per night
$140 total
Mar 15 - Mar 16
Total with taxes and fees
Located in Hauppauge, Radisson Hotel Hauppauge-Long Island is in the suburbs, a 1-minute drive from Hauppauge Industrial Park and 8 minutes from Sunken Meadow State Park.
Pool
Parking included
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
$118 nightly
The price is $135 total per night
$135 total
Mar 11 - Mar 12
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
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
$142 nightly
The price is $162 total per night
$162 total
Mar 22 - Mar 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.