Thimble Islands Vacations from $800

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The Latest Thimble Islands vacation packages

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

Beechmont - Perfect for Family Retreat!

North End

Save 100% on your flight

$800

per person

Nov 6 - Nov 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New Haven (HVN)

No reviews

1 Hotel Brooklyn Bridge

$1,274

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9/10 Wonderful! (1,005 reviews)

1 Hotel Central Park

Manhattan

Save 100% on your flight

$2,682

per person

Nov 3 - Nov 10

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9/10 Wonderful! (1,006 reviews)

Excellent experience in a great location!

Reviewed on Aug 24, 2026

5th & 55th Residence Club

Manhattan

Save 100% on your flight

$4,801

per person

Oct 29 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

8.4/10 Very Good! (5 reviews)

Night Hotel Broadway

Manhattan

Save 100% on your flight

$888

per person

Oct 29 - Nov 2

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

7.6/10 Good! (3,515 reviews)

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Thimble Islands Hotel Deals

Motel 6 New Haven - Branford, CT

320 E Main St Branford CT

Fully refundable

$72 nightly

$83 total

Sep 1 - Sep 2

Total with taxes and fees

7.4/10 Good! (1,025 reviews)

"The staff was fabulous, friendly, accommodating and helpful. 5 stars to the staff. The room, most specifically the floor along the edges, jams and corners could have been cleaner. The bathroom was average at best."

Reviewed on Aug 26, 2026

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

Fully refundableReserve now, pay when you stay

$83 nightly

$95 total

Aug 27 - Aug 28

Total with taxes and fees

8/10 Very Good! (1,001 reviews)

"Spider in my bed . Key didn’t work couldn’t get my things and refrigerator was full of my food"

Reviewed on Aug 25, 2026

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT

$259 nightly

$298 total

Sep 17 - Sep 18

Total with taxes and fees

8.8/10 Excellent! (1,014 reviews)

"Just an outstanding hotel in a breathtakingly beautiful setting!! I couldn’t be more impressed & look forward to returning! 10 stars!!"

Reviewed on Aug 26, 2026

See all 1,095 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.