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.
East Norwich Inn

East Norwich Inn

2.5 out of 5
Save 100% on your flight
Price was $747, price is now $465 per person
$465
per person
Oct 17 - Oct 20
found 1 day 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 $2,747, price is now $1,462 per person
$1,462
per person
Oct 8 - Oct 11
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 $3,144, price is now $1,937 per person
$1,937
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Prince Kitano New York

The Prince Kitano New York

4.5 out of 5
Save 100% on your flight
Price was $1,112, price is now $734 per person
$734
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New York (JFK)
Hotel 48LEX New York

Hotel 48LEX New York

4.5 out of 5
Save 100% on your flight
Price was $850, price is now $564 per person
$564
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Chatwal, In The Unbound Collection By Hyatt

The Chatwal, In The Unbound Collection By Hyatt

5 out of 5
Save 100% on your flight
Price was $2,065, price is now $1,380 per person
$1,380
per person
Sep 23 - Sep 26
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Save 100% on your flight
Price was $1,197, price is now $805 per person
$805
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Omni Berkshire Place

Omni Berkshire Place

4 out of 5
Save 100% on your flight
Price was $1,614, price is now $1,086 per person
$1,086
per person
Oct 9 - Oct 12
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 $1,142, price is now $770 per person
$770
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Hotel AKA NoMad

Hotel AKA NoMad

4 out of 5
Save 100% on your flight
Price was $1,369, price is now $929 per person
$929
per person
Oct 9 - Oct 12
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Park Lane New York

Park Lane New York

5 out of 5
Save 100% on your flight
Price was $1,540, price is now $1,045 per person
$1,045
per person
Oct 9 - Oct 12
found 1 day 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 $1,605, price is now $1,094 per person
$1,094
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)

4-night Thimble Islands vacations

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

42 Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,253, price is now $826 per person
$826
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip non-stop 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 $1,838, price is now $1,020 per person
$1,020
per person
Oct 10 - Oct 14
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 $1,801, price is now $1,002 per person
$1,002
per person
Oct 10 - Oct 14
found 1 day 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 $2,968, price is now $1,682 per person
$1,682
per person
Oct 17 - Oct 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Freehand New York

Freehand New York

4 out of 5
Save 100% on your flight
Price was $1,399, price is now $879 per person
$879
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The William Hotel Midtown, New York

The William Hotel Midtown, New York

3.5 out of 5
Save 100% on your flight
Price was $1,532, price is now $966 per person
$966
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Park Lane New York

Park Lane New York

5 out of 5
Save 100% on your flight
Price was $1,537, price is now $995 per person
$995
per person
Oct 1 - Oct 5
found 8 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to New York (JFK)
W New York - Times Square

W New York - Times Square

4.5 out of 5
Save 100% on your flight
Price was $1,275, price is now $834 per person
$834
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The High Line Hotel

The High Line Hotel

4 out of 5
Save 100% on your flight
Price was $2,129, price is now $1,400 per person
$1,400
per person
Oct 1 - Oct 5
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Royalton New York

Royalton New York

4 out of 5
Save 100% on your flight
Price was $1,409, price is now $930 per person
$930
per person
Sep 30 - Oct 4
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
CIVILIAN Hotel

CIVILIAN Hotel

4 out of 5
Save 100% on your flight
Price was $1,307, price is now $872 per person
$872
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Lombardy Hotel

The Lombardy Hotel

4 out of 5
Save 100% on your flight
Price was $1,476, price is now $989 per person
$989
per person
Oct 19 - Oct 23
found 9 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.
Radio Hotel

Radio Hotel

4 out of 5
Save 100% on your flight
Price was $999, price is now $642 per person
$642
per person
Oct 2 - Oct 7
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to New York (JFK)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $5,280, price is now $2,415 per person
$2,415
per person
Oct 14 - Oct 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Seven Beach Lane

Seven Beach Lane

2 out of 5
Save 100% on your flight
Price was $2,284, price is now $1,225 per person
$1,225
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
Ink 48 Hotel

Ink 48 Hotel

4.5 out of 5
Save 100% on your flight
Price was $2,190, price is now $1,300 per person
$1,300
per person
Oct 6 - Oct 11
found 1 day 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 $3,565, price is now $2,128 per person
$2,128
per person
Oct 17 - Oct 22
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 $2,028, price is now $1,266 per person
$1,266
per person
Oct 14 - Oct 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Freehand New York

Freehand New York

4 out of 5
Save 100% on your flight
Price was $1,591, price is now $1,011 per person
$1,011
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Park Lane New York

Park Lane New York

5 out of 5
Save 100% on your flight
Price was $2,321, price is now $1,494 per person
$1,494
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New York (JFK)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Save 100% on your flight
Price was $2,596, price is now $1,675 per person
$1,675
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New York (JFK)
Hotel Park Ave NYC

Hotel Park Ave NYC

4.5 out of 5
Save 100% on your flight
Price was $1,877, price is now $1,215 per person
$1,215
per person
Oct 6 - Oct 11
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 $2,417, price is now $1,580 per person
$1,580
per person
Oct 12 - Oct 17
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 $2,326, price is now $1,525 per person
$1,525
per person
Oct 12 - Oct 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.
Radio Hotel

Radio Hotel

4 out of 5
Save 100% on your flight
Price was $1,463, price is now $881 per person
$881
per person
Oct 14 - Oct 20
found 11 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Price was $2,801, price is now $1,494 per person
$1,494
per person
Oct 14 - Oct 20
found 11 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 $2,643, price is now $1,416 per person
$1,416
per person
Oct 14 - Oct 20
found 11 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
Price was $2,288, price is now $1,289 per person
$1,289
per person
Oct 14 - Oct 20
found 11 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
OYO Times Square

OYO Times Square

4 out of 5
Save 100% on your flight
Price was $1,631, price is now $931 per person
$931
per person
Oct 14 - Oct 20
found 11 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Save 100% on your flight
Price was $1,569, price is now $928 per person
$928
per person
Oct 14 - Oct 20
found 11 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
The William Hotel Midtown, New York

The William Hotel Midtown, New York

3.5 out of 5
Save 100% on your flight
Price was $2,409, price is now $1,491 per person
$1,491
per person
Oct 14 - Oct 20
found 11 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
The Hotel @ Fifth Avenue

The Hotel @ Fifth Avenue

3.5 out of 5
Save 100% on your flight
Price was $1,920, price is now $1,219 per person
$1,219
per person
Oct 14 - Oct 20
found 11 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
CIVILIAN Hotel

CIVILIAN Hotel

4 out of 5
Save 100% on your flight
Price was $1,936, price is now $1,258 per person
$1,258
per person
Oct 14 - Oct 20
found 11 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
Hotel St. James

Hotel St. James

3 out of 5
Save 100% on your flight
Price was $1,723, price is now $1,120 per person
$1,120
per person
Sep 26 - Oct 2
found 8 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 $2,167, price is now $1,413 per person
$1,413
per person
Oct 14 - Oct 20
found 11 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Save 100% on your flight
Price was $1,844, price is now $1,204 per person
$1,204
per person
Sep 26 - Oct 2
found 8 hours ago
Roundtrip flight included
Dallas (DFW) 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, Nov 15 - Fri, Nov 20
DTW
Detroit
HVN
New Haven
$100 Roundtrip, found 4 days ago
$100
Roundtrip
found 4 days ago
Select Avelo Airlines flight, departing Sun, Nov 15 from Detroit to New Haven, returning Fri, Nov 20, priced at $100 found 4 days ago
Sun, Nov 15 - Fri, Nov 20
DTW
Detroit
HVN
New Haven
$130 Roundtrip, found 2 days ago
$130
Roundtrip
found 2 days ago
Select Avelo Airlines flight, departing Sun, Nov 15 from Detroit to New Haven, returning Fri, Nov 20, priced at $130 found 2 days ago
Fri, Nov 6 - Fri, Nov 13
ORD
Chicago
HVN
New Haven
$130 Roundtrip, found 2 days ago
$130
Roundtrip
found 2 days ago
Select Avelo Airlines flight, departing Fri, Nov 6 from Chicago to New Haven, returning Fri, Nov 13, priced at $130 found 2 days ago

Top rated hotels for your Thimble Islands vacation

Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St Branford CT
Free Cancellation
3.5 mi from city center
$72 nightly
The price is $83 total per night
$83 total
Sep 1 - Sep 2
Total with taxes and fees
Located in Branford, Motel 6 New Haven - Branford, CT is within a 15-minute drive of Yale University and Yale-New Haven Hospital.
Pet friendly
Parking included
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Free Cancellation
18.2 mi from city center
$87 nightly
The price is $100 total per night
$100 total
Aug 25 - Aug 26
Total with taxes and fees
With a stay at Pier Blue Inn Old Saybrook - Essex in Old Saybrook (Saybrook Manor), you'll be within a 15-minute drive of Hammonasset Beach State Park and Chalker Beach.
Pet friendly
Parking included
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Free Cancellation
Reserve now, pay when you stay
16.63 mi from city center
$266 nightly
The price is $306 total per night
$306 total
Aug 31 - Sep 1
Total with taxes and fees
With a stay at Water's Edge Resort & Spa in Westbrook (Westbrook Center), you'll be a 4-minute drive from Tanger Outlets and 8 minutes from Clinton Crossing Premium Outlets.
On private beach
Pool
Don't see what you're looking for?
See all available properties in Thimble Islands
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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.