Thimble Islands Vacations from $863

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The Latest Thimble Islands vacation packages

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

Hotel Riu Plaza New York Times Square

Manhattan

Save 100% on your flight

$863

per person

Nov 17 - Nov 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9/10 Wonderful! (3,389 reviews)

Nos encanto, super centrico, caminando para todos lados, el staff super

Reviewed on Oct 11, 2026

Beechmont - Perfect for Family Retreat!

North End

$1,062

per person

Dec 11 - Dec 14

found 1 day ago

Roundtrip flight included

Dallas (DFW) to New Haven (HVN)

No reviews

1 Hotel Central Park

Manhattan

$1,954

per person

Dec 23 - Dec 28

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9/10 Wonderful! (1,007 reviews)

Hotel AKA NoMad

Manhattan

$1,280

per person

Dec 22 - Dec 28

found 19 hours ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

8.8/10 Excellent! (1,040 reviews)

Great location. Nicely designed hotel. The room was very comfortable and clean.

Reviewed on Oct 10, 2026

The Plaza, A Fairmont Hotel

Manhattan

$4,231

per person

Dec 23 - Dec 28

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9/10 Wonderful! (1,002 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

$135 nightly

$155 total

Oct 27 - Oct 28

Total with taxes and fees

9.2/10 Wonderful! (2,373 reviews)

"The room was clean enough, I have been in better. The staff was fine, nothing special to note. The amenities - well I didn't see many perks to staying there, just overpriced beverages and snacks for purchase."

Reviewed on Oct 10, 2026

Motel 6 Milford, CT

111 Schoolhouse Road Milford CT

Fully refundableReserve now, pay when you stay

$70 nightly

$80 total

Oct 20 - Oct 21

Total with taxes and fees

6.6/10 (1,049 reviews)

"I wouldn’t recommend staying here from the lobby to the room and especially when you turn the heat on it reeks of smoke the lobby reeked of weed and there’s no smoking signs everywhere. I wouldn’t recommend staying here. oh and to top it off check-in’s at three. The clerk told me I had to come back ..."

Reviewed on Oct 11, 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.