Thimble Islands Vacations from $875

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The Latest Thimble Islands vacation packages

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

The Inn At Fox Hollow Hotel

Save 100% on your flight

$875

per person

Dec 24 - Dec 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9.2/10 Wonderful! (1,006 reviews)

Excellent through and through!

Reviewed on Oct 13, 2026

Night Hotel Broadway

Manhattan

$941

per person

Dec 7 - Dec 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

7.6/10 Good! (3,714 reviews)

Beechmont - Perfect for Family Retreat!

North End

Save 100% on your flight

$894

per person

Nov 13 - Nov 15

found 8 hours ago

Roundtrip flight included

Atlanta (ATL) to New Haven (HVN)

No reviews

1 Hotel Brooklyn Bridge

Save 100% on your flight

$1,455

per person

Jan 4 - Jan 9

found 18 hours ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9/10 Wonderful! (1,007 reviews)

Hotel Riu Plaza Manhattan Times Square

Manhattan

Save 100% on your flight

$1,125

per person

Dec 24 - Dec 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9.2/10 Wonderful! (4,026 reviews)

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Thimble Islands Hotel Deals

New Haven Hotel

229 George Street New Haven CT

Fully refundableReserve now, pay when you stay

$133 nightly

$153 total

Oct 27 - Oct 28

Total with taxes and fees

9.2/10 Wonderful! (2,391 reviews)

"Spacious room, great location! Didn’t like the noisy bathroom fan and air conditioner."

Reviewed on Oct 14, 2026

Motel 6 Milford, CT

111 Schoolhouse Road Milford CT

Fully refundableReserve now, pay when you stay

$70 nightly

$80 total

Oct 25 - Oct 26

Total with taxes and fees

6.6/10 (1,055 reviews)

"The hotel is an apartment building basically drug deals in the parking lot police literally patrol the area constantly. The font desk is a joke. People are hanging around the lobby and outside. My impression is that this hotel is a half way house. I was talking to a person and he said he h1s been ..."

Reviewed on Oct 14, 2026

Motel 6 New Haven - Branford, CT

320 E Main St Branford CT

Fully refundable

$64 nightly

$73 total

Nov 8 - Nov 9

Total with taxes and fees

See all 1,091 properties in Thimble Islands

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.