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.
Allegria Hotel

Allegria Hotel

4 out of 5
Price was $1,023, price is now $721 per person
$721
per person
Oct 14 - Oct 17
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 $2,644, price is now $1,366 per person
$1,366
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 $1,733, price is now $1,051 per person
$1,051
per person
Oct 14 - Oct 17
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 $1,685, price is now $1,027 per person
$1,027
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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 $1,184, price is now $801 per person
$801
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Royalton New York

Royalton New York

4 out of 5
Save 100% on your flight
Price was $1,362, price is now $928 per person
$928
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
42 Hotel

42 Hotel

3.5 out of 5
Price was $1,078, price is now $745 per person
$745
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
One Grove

One Grove

2 out of 5
Save 100% on your flight
Price was $1,160, price is now $813 per person
$813
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New York (JFK)
Citadines Connect Fifth Avenue - Times Square New York

Citadines Connect Fifth Avenue - Times Square New York

3.5 out of 5
Save 100% on your flight
Price was $1,157, price is now $814 per person
$814
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
2 bedroom luxury Empire State VIEW

2 bedroom luxury Empire State VIEW

2 out of 5
Save 100% on your flight
Price was $2,190, price is now $1,544 per person
$1,544
per person
Oct 21 - Oct 24
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 $1,349, price is now $954 per person
$954
per person
Oct 14 - Oct 17
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
Save 100% on your flight
Price was $1,677, price is now $1,188 per person
$1,188
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)

4-night Thimble Islands vacations

Price found within the past 48 hours. Click for updated prices.
Eurostars Wall Street

Eurostars Wall Street

4 out of 5
Save 100% on your flight
Price was $1,199, price is now $763 per person
$763
per person
Oct 8 - Oct 12
found 8 hours ago
Roundtrip flight included
Orlando (MCO) 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 $2,052, price is now $1,202 per person
$1,202
per person
Sep 30 - Oct 4
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 $1,988, price is now $1,264 per person
$1,264
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
The High Line Hotel

The High Line Hotel

4 out of 5
Save 100% on your flight
Price was $1,903, price is now $1,235 per person
$1,235
per person
Oct 1 - Oct 5
found 2 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to New York (JFK)
Park Terrace Hotel

Park Terrace Hotel

4 out of 5
Save 100% on your flight
Price was $1,537, price is now $1,049 per person
$1,049
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
CODA Williamsburg

CODA Williamsburg

4 out of 5
Save 100% on your flight
Price was $1,801, price is now $1,235 per person
$1,235
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
The Lombardy Hotel

The Lombardy Hotel

4 out of 5
Save 100% on your flight
Price was $1,384, price is now $962 per person
$962
per person
Oct 1 - Oct 5
found 1 day 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 $1,138, price is now $816 per person
$816
per person
Sep 30 - Oct 4
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Hampton Inn Madison Square Garden Area Hotel

Hampton Inn Madison Square Garden Area Hotel

3 out of 5
Save 100% on your flight
Price was $1,642, price is now $1,186 per person
$1,186
per person
Sep 30 - Oct 4
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
42 Hotel

42 Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,649, price is now $1,191 per person
$1,191
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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 $1,427, price is now $1,038 per person
$1,038
per person
Sep 30 - Oct 4
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
PUBLIC, an Ian Schrager hotel

PUBLIC, an Ian Schrager hotel

4 out of 5
Save 100% on your flight
Price was $1,728, price is now $1,258 per person
$1,258
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)

5-night Thimble Islands vacations

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

Aura Hotel Brooklyn

4 out of 5
Save 100% on your flight
Price was $1,325, price is now $848 per person
$848
per person
Oct 15 - Oct 20
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 $4,514, price is now $2,379 per person
$2,379
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Save 100% on your flight
Price was $4,056, price is now $2,400 per person
$2,400
per person
Sep 30 - Oct 5
found 6 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Save 100% on your flight
Price was $3,291, price is now $2,158 per person
$2,158
per person
Sep 30 - Oct 5
found 6 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Price was $1,857, price is now $1,232 per person
$1,232
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Freehand New York

Freehand New York

4 out of 5
Save 100% on your flight
Price was $1,928, price is now $1,283 per person
$1,283
per person
Oct 14 - Oct 19
found 20 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
WestHouse Hotel New York, an SLH Hotel

WestHouse Hotel New York, an SLH Hotel

5 out of 5
Save 100% on your flight
Price was $1,966, price is now $1,316 per person
$1,316
per person
Sep 30 - Oct 5
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Park Lane New York

Park Lane New York

5 out of 5
Save 100% on your flight
Price was $2,169, price is now $1,454 per person
$1,454
per person
Sep 30 - Oct 5
found 20 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Omni Berkshire Place

Omni Berkshire Place

4 out of 5
Save 100% on your flight
Price was $1,847, price is now $1,242 per person
$1,242
per person
Sep 30 - Oct 5
found 18 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
101 HOTEL Manhattan New York City

101 HOTEL Manhattan New York City

2 out of 5
Save 100% on your flight
Price was $1,784, price is now $1,208 per person
$1,208
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New York (JFK)
Sela V Hotel

Sela V Hotel

4 out of 5
Save 100% on your flight
Price was $1,763, price is now $1,217 per person
$1,217
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)

6-7 night Thimble Islands 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 $1,722, price is now $1,143 per person
$1,143
per person
Oct 16 - Oct 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 $2,807, price is now $1,676 per person
$1,676
per person
Oct 16 - Oct 22
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 $2,433, price is now $1,524 per person
$1,524
per person
Oct 13 - Oct 19
found 5 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Ink 48 Hotel

Ink 48 Hotel

4.5 out of 5
Save 100% on your flight
Price was $2,286, price is now $1,501 per person
$1,501
per person
Oct 7 - Oct 13
found 7 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Hotel 32 32

Hotel 32 32

4 out of 5
Save 100% on your flight
Price was $2,413, price is now $1,600 per person
$1,600
per person
Oct 11 - Oct 18
found 9 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
Park Lane New York

Park Lane New York

5 out of 5
Save 100% on your flight
Price was $2,807, price is now $1,890 per person
$1,890
per person
Oct 11 - Oct 18
found 9 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
The Gotham Hotel

The Gotham Hotel

4.5 out of 5
Save 100% on your flight
Price was $2,131, price is now $1,455 per person
$1,455
per person
Sep 30 - Oct 6
found 20 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
The Ridge Hotel

The Ridge Hotel

3 out of 5
Save 100% on your flight
Price was $1,749, price is now $1,195 per person
$1,195
per person
Oct 16 - Oct 22
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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 $7,693, price is now $5,336 per person
$5,336
per person
Oct 11 - Oct 18
found 9 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
Artezen Hotel

Artezen Hotel

4 out of 5
Price was $2,041, price is now $1,449 per person
$1,449
per person
Oct 13 - Oct 20
found 3 hours ago
Roundtrip flight included
Chicago (ORD) 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 $1,784, price is now $1,271 per person
$1,271
per person
Oct 16 - Oct 22
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 $2,617, price is now $1,488 per person
$1,488
per person
Oct 4 - Oct 9
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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 5 days ago
$100
Roundtrip
found 5 days ago
Select Avelo Airlines flight, departing Sun, Nov 15 from Detroit to New Haven, returning Fri, Nov 20, priced at $100 found 5 days ago
Sun, Nov 15 - Fri, Nov 20
DTW
Detroit
HVN
New Haven
$130 Roundtrip, found 3 days ago
$130
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Sun, Nov 15 from Detroit to New Haven, returning Fri, Nov 20, priced at $130 found 3 days ago
Fri, Nov 6 - Fri, Nov 13
ORD
Chicago
HVN
New Haven
$130 Roundtrip, found 3 days ago
$130
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Fri, Nov 6 from Chicago to New Haven, returning Fri, Nov 13, priced at $130 found 3 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
Reserve now, pay when you stay
18.2 mi from city center
$87 nightly
The price is $100 total per night
$100 total
Aug 26 - Aug 27
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
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
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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.