Cheap Vacations in Thimble Islands

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3-night Thimble Islands 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 $651, price is now $463 per person
$463
per person
May 30 - Jun 2
found 22 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to New York (JFK)
Park Lane New York

Park Lane New York

5 out of 5
Price was $1,197, price is now $799 per person
$799
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
42 Hotel

42 Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,020, price is now $686 per person
$686
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Save 100% on your flight
Price was $2,448, price is now $1,676 per person
$1,676
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
Omni Berkshire Place

Omni Berkshire Place

4 out of 5
Price was $1,133, price is now $781 per person
$781
per person
Jun 5 - Jun 8
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 $1,278, price is now $881 per person
$881
per person
Jun 5 - Jun 8
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 $1,018, price is now $712 per person
$712
per person
May 30 - Jun 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
Price was $1,399, price is now $980 per person
$980
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to New York (JFK)
The Plaza, A Fairmont Hotel

The Plaza, A Fairmont Hotel

5 out of 5
Save 100% on your flight
Price was $3,580, price is now $2,522 per person
$2,522
per person
Jun 19 - Jun 22
found 20 hours ago
Roundtrip flight included
Dallas (DAL) to Newark Liberty Intl. Airport (EWR)
Sound View Greenport

Sound View Greenport

4 out of 5
Price was $1,728, price is now $1,218 per person
$1,218
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to New York (JFK)
Pointe Plaza Hotel

Pointe Plaza Hotel

3 out of 5
Save 100% on your flight
Price was $814, price is now $577 per person
$577
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
The Pridwin Hotel

The Pridwin Hotel

4 out of 5
Price was $2,253, price is now $1,597 per person
$1,597
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to New York (JFK)

4-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 $1,058, price is now $707 per person
$707
per person
Jun 15 - Jun 19
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 $1,636, price is now $1,032 per person
$1,032
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Asbury Ocean Club Hotel

Asbury Ocean Club Hotel

4 out of 5
Save 100% on your flight
Price was $7,550, price is now $4,902 per person
$4,902
per person
Jun 18 - Jun 22
found 17 hours 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 $1,819, price is now $1,187 per person
$1,187
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Save 100% on your flight
Price was $1,190, price is now $800 per person
$800
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Casa Francesca 6BR Villa & Heated Pool

Casa Francesca 6BR Villa & Heated Pool

3.5 out of 5
Save 100% on your flight
Price was $6,050, price is now $4,076 per person
$4,076
per person
Jun 18 - Jun 22
found 17 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Save 100% on your flight
Price was $3,144, price is now $2,164 per person
$2,164
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
The George

The George

4 out of 5
Save 100% on your flight
Price was $3,040, price is now $2,103 per person
$2,103
per person
Jun 17 - Jun 21
found 20 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
The Asbury Hotel

The Asbury Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,838, price is now $1,273 per person
$1,273
per person
Jun 18 - Jun 22
found 17 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
OYO Times Square

OYO Times Square

4 out of 5
Price was $1,461, price is now $1,024 per person
$1,024
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Peachtree Suites

Peachtree Suites

2.5 out of 5
Save 100% on your flight
Price was $1,158, price is now $820 per person
$820
per person
Jun 20 - Jun 24
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
Price was $1,668, price is now $1,185 per person
$1,185
per person
May 31 - Jun 4
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)

5-night Thimble Islands vacations

Price found within the past 48 hours. Click for updated prices.
Windrose On Hudson

Windrose On Hudson

3 out of 5
Save 100% on your flight
Price was $1,025, price is now $694 per person
$694
per person
Jun 1 - Jun 6
found 7 hours ago
Roundtrip flight included
Tampa (TPA) to New York (JFK)
Seven Beach Lane

Seven Beach Lane

2 out of 5
Price was $2,782, price is now $1,374 per person
$1,374
per person
Jun 7 - Jun 12
found 24 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 $4,021, price is now $2,504 per person
$2,504
per person
Jun 12 - Jun 17
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
Save 100% on your flight
Price was $1,327, price is now $831 per person
$831
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Save 100% on your flight
Price was $1,451, price is now $945 per person
$945
per person
Jun 12 - Jun 17
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
Save 100% on your flight
Price was $2,121, price is now $1,397 per person
$1,397
per person
Jun 15 - Jun 20
found 18 hours ago
Roundtrip flight included
Dallas (DAL) to Newark Liberty Intl. Airport (EWR)
The Plaza, A Fairmont Hotel

The Plaza, A Fairmont Hotel

5 out of 5
Save 100% on your flight
Price was $5,074, price is now $3,344 per person
$3,344
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip 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 $2,177, price is now $1,435 per person
$1,435
per person
Jun 15 - Jun 20
found 18 hours ago
Roundtrip flight included
Dallas (DAL) to Newark Liberty Intl. Airport (EWR)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
Price was $2,043, price is now $1,358 per person
$1,358
per person
Jun 7 - Jun 12
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Ace Hotel New York

Ace Hotel New York

4 out of 5
Save 100% on your flight
Price was $1,317, price is now $882 per person
$882
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
CODA Williamsburg

CODA Williamsburg

4 out of 5
Save 100% on your flight
Price was $1,635, price is now $1,098 per person
$1,098
per person
Jun 7 - Jun 12
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Hampton Inn Garden City Long Island

Hampton Inn Garden City Long Island

2.5 out of 5
Save 100% on your flight
Price was $1,249, price is now $843 per person
$843
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)

6-7 night Thimble Islands vacations

Price found within the past 48 hours. Click for updated prices.
Hotel 32 32

Hotel 32 32

4 out of 5
Save 100% on your flight
Price was $1,240, price is now $869 per person
$869
per person
May 28 - Jun 3
found 1 hour 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
Price was $2,605, price is now $1,529 per person
$1,529
per person
Jun 17 - Jun 24
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
Save 100% on your flight
Price was $1,875, price is now $1,111 per person
$1,111
per person
May 28 - Jun 3
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Save 100% on your flight
Price was $1,433, price is now $898 per person
$898
per person
Jun 7 - Jun 13
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
Price was $1,921, price is now $1,215 per person
$1,215
per person
May 28 - Jun 3
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Price was $2,046, price is now $1,333 per person
$1,333
per person
Jun 17 - Jun 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
The Plaza, A Fairmont Hotel

The Plaza, A Fairmont Hotel

5 out of 5
Price was $7,632, price is now $5,037 per person
$5,037
per person
Jun 17 - Jun 24
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 $1,962, price is now $1,342 per person
$1,342
per person
Jun 17 - Jun 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
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 $1,875, price is now $1,303 per person
$1,303
per person
Jun 17 - Jun 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Price was $2,507, price is now $1,768 per person
$1,768
per person
Jun 17 - Jun 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Citadines Connect Fifth Avenue New York

Citadines Connect Fifth Avenue New York

3.5 out of 5
Save 100% on your flight
Price was $1,257, price is now $888 per person
$888
per person
May 28 - Jun 3
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The George

The George

4 out of 5
Save 100% on your flight
Price was $5,039, price is now $3,586 per person
$3,586
per person
May 31 - Jun 7
found 17 hours ago
Roundtrip non-stop flight included
San Juan (SJU) 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.

Sun, May 24 - Thu, May 28
DTW
Detroit
HVN
New Haven
$85 Roundtrip, found 5 days ago
$85
Roundtrip
found 5 days ago
Select Avelo Airlines flight, departing Sun, May 24 from Detroit to New Haven, returning Thu, May 28, priced at $85 found 5 days ago
Sun, May 24 - Thu, May 28
DTW
Detroit
HVN
New Haven
$99 Roundtrip, found 2 days ago
$99
Roundtrip
found 2 days ago
Select Avelo Airlines flight, departing Sun, May 24 from Detroit to New Haven, returning Thu, May 28, priced at $99 found 2 days ago
Thu, Jun 4 - Sat, Jun 6
MYR
Myrtle Beach
HVN
New Haven
$112 Roundtrip, found 5 days ago
$112
Roundtrip
found 5 days ago
Select Avelo Airlines flight, departing Thu, Jun 4 from Myrtle Beach to New Haven, returning Sat, Jun 6, priced at $112 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
9.87 mi from city center
$135 nightly
The price is $155 total per night
$155 total
May 3 - May 4
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
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St New Haven CT
Free Cancellation
Reserve now, pay when you stay
9.82 mi from city center
$119 nightly
The price is $137 total per night
$137 total
May 25 - May 26
Total with taxes and fees
With a stay at Omni New Haven Hotel at Yale, you'll be centrally located in New Haven, steps from New Haven Green and within a 10-minute walk of Yale University.
Pet friendly
Free WiFi
Motel 6 Milford, CT

Motel 6 Milford, CT

2 out of 5
111 Schoolhouse Road Milford CT
Free Cancellation
Reserve now, pay when you stay
17.42 mi from city center
$80 nightly
The price is $92 total per night
$92 total
May 7 - May 8
Total with taxes and fees
When you stay at Motel 6 Milford, CT in Milford, you'll be in the business district, within a 15-minute drive of Yale University and Hartford HealthCare Amphitheater.
Pet friendly
Parking included
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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.

Top Picks

^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.