Cheap Vacations in Thimble Islands

Choose two or more items and save on your trip:

3-night Thimble Islands 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 $375, price is now $231 per person
$231
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $615, price is now $331 per person
$331
per person
Jan 15 - Jan 18
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Save 100% on your flight
Price was $489, price is now $270 per person
$270
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $424, price is now $239 per person
$239
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $397, price is now $234 per person
$234
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $652, price is now $393 per person
$393
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $1,352, price is now $835 per person
$835
per person
Feb 9 - Feb 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $784, price is now $488 per person
$488
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Hotel St. James

Hotel St. James

2.5 out of 5
Save 100% on your flight
Price was $457, price is now $289 per person
$289
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Save 100% on your flight
Price was $1,054, price is now $672 per person
$672
per person
Feb 9 - Feb 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Madison Hotel

Madison Hotel

4 out of 5
Save 100% on your flight
Price was $457, price is now $298 per person
$298
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
Pendry Natirar

Pendry Natirar

5 out of 5
Save 100% on your flight
Price was $1,656, price is now $1,080 per person
$1,080
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)

4-night Thimble Islands vacations

Price found within the past 48 hours. Click for updated prices.
Radisson Hotel Hauppauge-Long Island

Radisson Hotel Hauppauge-Long Island

3.5 out of 5
Price was $341, price is now $232 per person
$232
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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 $781, price is now $401 per person
$401
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $578, price is now $327 per person
$327
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Price was $991, price is now $590 per person
$590
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New York (JFK)
voco Fiorello - LaGuardia Airport by IHG

voco Fiorello - LaGuardia Airport by IHG

4 out of 5
Save 100% on your flight
Price was $400, price is now $248 per person
$248
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $773, price is now $492 per person
$492
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Hotel St. James

Hotel St. James

2.5 out of 5
Save 100% on your flight
Price was $597, price is now $380 per person
$380
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $846, price is now $543 per person
$543
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Windrose On Hudson

Windrose On Hudson

3 out of 5
Save 100% on your flight
Price was $593, price is now $396 per person
$396
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
Hotel Beacon

Hotel Beacon

4 out of 5
Save 100% on your flight
Price was $898, price is now $601 per person
$601
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Pendry Natirar

Pendry Natirar

5 out of 5
Save 100% on your flight
Price was $2,032, price is now $1,376 per person
$1,376
per person
Jan 28 - Feb 1
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
Fairfield Inn & Suites Newark Liberty International Airport

Fairfield Inn & Suites Newark Liberty International Airport

2.5 out of 5
Save 100% on your flight
Price was $372, price is now $253 per person
$253
per person
Jan 28 - Feb 1
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)

5-night Thimble Islands vacations

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

American Hotel

3.5 out of 5
Save 100% on your flight
Price was $664, price is now $405 per person
$405
per person
Feb 2 - Feb 7
found 6 hours ago
Roundtrip flight included
Orlando (MCO) to New York (NYC)
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $902, price is now $459 per person
$459
per person
Feb 2 - Feb 7
found 6 hours ago
Roundtrip flight included
Orlando (MCO) 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 $739, price is now $408 per person
$408
per person
Jan 14 - Jan 19
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) 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 $955, price is now $528 per person
$528
per person
Jan 14 - Jan 19
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) 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 $1,351, price is now $821 per person
$821
per person
Jan 23 - Jan 28
found 1 day ago
Roundtrip non-stop 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 $738, price is now $458 per person
$458
per person
Jan 14 - Jan 19
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) 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 $1,104, price is now $695 per person
$695
per person
Jan 14 - Jan 19
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) 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 $980, price is now $619 per person
$619
per person
Jan 14 - Jan 19
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Millennium Hotel Broadway Times Square

Millennium Hotel Broadway Times Square

4 out of 5
Save 100% on your flight
Price was $670, price is now $432 per person
$432
per person
Jan 14 - Jan 19
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) 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 $691, price is now $457 per person
$457
per person
Feb 2 - Feb 7
found 6 hours ago
Roundtrip flight included
Orlando (MCO) to New York (JFK)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
Price was $920, price is now $608 per person
$608
per person
Jan 14 - Jan 19
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Save 100% on your flight
Price was $2,145, price is now $1,451 per person
$1,451
per person
Feb 2 - Feb 7
found 6 hours ago
Roundtrip flight included
Orlando (MCO) to New York (JFK)

6-7 night Thimble Islands 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
Price was $823, price is now $364 per person
$364
per person
Feb 7 - Feb 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $950, price is now $494 per person
$494
per person
Feb 7 - Feb 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,027, price is now $571 per person
$571
per person
Feb 7 - Feb 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,362, price is now $788 per person
$788
per person
Jan 22 - Jan 28
found 1 day 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 $672, price is now $406 per person
$406
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop 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 $1,105, price is now $687 per person
$687
per person
Feb 7 - Feb 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,090, price is now $680 per person
$680
per person
Feb 7 - Feb 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Hotel St. James

Hotel St. James

2.5 out of 5
Save 100% on your flight
Price was $866, price is now $544 per person
$544
per person
Feb 7 - Feb 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
Save 100% on your flight
Price was $806, price is now $527 per person
$527
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
Price was $1,087, price is now $715 per person
$715
per person
Feb 5 - Feb 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Windrose On Hudson

Windrose On Hudson

3 out of 5
Save 100% on your flight
Price was $981, price is now $652 per person
$652
per person
Jan 27 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (NYC)
Millennium Hotel Broadway Times Square

Millennium Hotel Broadway Times Square

4 out of 5
Save 100% on your flight
Price was $676, price is now $457 per person
$457
per person
Feb 7 - Feb 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)

Flight deals to Thimble Islands

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

Mon, Dec 22 - Sun, Dec 28
GSP
Greenville
HVN
New Haven
$654 Roundtrip, found 5 days ago
$654
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Mon, Dec 22 from Greenville to New Haven, returning Sun, Dec 28, priced at $654 found 5 days ago
Thu, Dec 25 - Sun, Dec 28
GSP
Greenville
HVN
New Haven
$662 Roundtrip, found 5 days ago
$662
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Dec 25 from Greenville to New Haven, returning Sun, Dec 28, priced at $662 found 5 days ago
Mon, Dec 22 - Thu, Dec 25
GSP
Greenville
HVN
New Haven
$664 Roundtrip, found 5 days ago
$664
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Mon, Dec 22 from Greenville to New Haven, returning Thu, Dec 25, priced at $664 found 5 days ago
Sun, Dec 21 - Sun, Dec 28
GSP
Greenville
HVN
New Haven
$692 Roundtrip, found 5 days ago
$692
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sun, Dec 21 from Greenville to New Haven, returning Sun, Dec 28, priced at $692 found 5 days ago
Sun, Dec 21 - Thu, Dec 25
GSP
Greenville
HVN
New Haven
$701 Roundtrip, found 5 days ago
$701
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sun, Dec 21 from Greenville to New Haven, returning Thu, Dec 25, priced at $701 found 5 days ago
Mon, Dec 22 - Fri, Dec 26
GSP
Greenville
HVN
New Haven
$718 Roundtrip, found 5 days ago
$718
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Mon, Dec 22 from Greenville to New Haven, returning Fri, Dec 26, priced at $718 found 5 days ago

Top rated hotels for your Thimble Islands vacation

New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Free Cancellation
Reserve now, pay when you stay
9.87 mi from city center
$114 nightly
The price is $131 total per night
$131 total
Dec 25 - Dec 26
Total with taxes and fees
New Haven Hotel is centrally located in New Haven, a 4-minute walk from Shubert Theater and 5 minutes by foot from New Haven Green.
Pet friendly
Free WiFi
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street New Haven CT
Free Cancellation
10.41 mi from city center
$106 nightly
The price is $121 total per night
$121 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Located in New Haven (West River), Cambria Hotel New Haven University Area is within a 15-minute walk of Yale University and Yale-New Haven Hospital.
Pet friendly
Free WiFi
Hotel Marcel New Haven, Tapestry Collection By Hilton

Hotel Marcel New Haven, Tapestry Collection By Hilton

4 out of 5
500 Sargent Drive New Haven CT
Free Cancellation
Reserve now, pay when you stay
9.19 mi from city center
$104 nightly
The price is $120 total per night
$120 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
With a stay at Hotel Marcel New Haven, Tapestry Collection By Hilton in New Haven (Long Wharf), you'll be within a 5-minute drive of Yale University and Yale-New Haven Hospital.
Pet friendly
Parking included
Don't see what you're looking for?
See all available properties in Thimble Islands
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.