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Thimble Islands

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Thimble Islands Flights as Low as $160

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Breeze Airways
Fri, Sep 11 - Mon, Sep 14
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$160 Roundtrip, found 1 day ago
$160
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Sep 11 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Sep 14, priced at $160 found 1 day ago
Avelo Airlines
Fri, Sep 11 - Mon, Sep 14
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$165 Roundtrip, found 1 day ago
$165
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Fri, Sep 11 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Sep 14, priced at $165 found 1 day ago
Breeze Airways
Fri, Sep 11 - Mon, Sep 14
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$165 Roundtrip, found 1 day ago
$165
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Sep 11 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Sep 14, priced at $165 found 1 day ago
Breeze Airways
Thu, Dec 3 - Thu, Dec 3
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$168 Roundtrip, found 6 days ago
$168
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Dec 3 from Orlando Intl. to Tweed - New Haven Regional, returning Thu, Dec 3, priced at $168 found 6 days ago
Breeze Airways
Thu, Dec 3 - Sun, Dec 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$170 Roundtrip, found 2 days ago
$170
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Dec 3 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Dec 6, priced at $170 found 2 days ago
Breeze Airways
Fri, Sep 11 - Mon, Sep 14
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$170 Roundtrip, found 1 day ago
$170
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Sep 11 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Sep 14, priced at $170 found 1 day ago
Breeze Airways
Fri, Sep 11 - Mon, Sep 21
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$173 Roundtrip, found 2 days ago
$173
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Sep 11 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Sep 21, priced at $173 found 2 days ago
Breeze Airways
Thu, Dec 3 - Mon, Dec 7
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$174 Roundtrip, found 6 days ago
$174
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Dec 3 from Orlando Intl. to Tweed - New Haven Regional, returning Mon, Dec 7, priced at $174 found 6 days ago
Breeze Airways
Fri, Dec 4 - Sun, Dec 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$175 Roundtrip, found 14 hours ago
$175
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Fri, Dec 4 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Dec 6, priced at $175 found 14 hours ago
Breeze Airways
Fri, Sep 11 - Mon, Sep 21
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$178 Roundtrip, found 2 days ago
$178
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Sep 11 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Sep 21, priced at $178 found 2 days ago
Breeze Airways
Thu, Dec 3 - Mon, Dec 7
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$179 Roundtrip, found 6 days ago
$179
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Dec 3 from Orlando Intl. to Tweed - New Haven Regional, returning Mon, Dec 7, priced at $179 found 6 days ago
Breeze Airways
Fri, Dec 4 - Sun, Dec 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$180 Roundtrip, found 14 hours ago
$180
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Fri, Dec 4 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Dec 6, priced at $180 found 14 hours ago
Breeze Airways
Thu, Dec 3 - Thu, Dec 3
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$181 Roundtrip, found 1 day ago
$181
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Dec 3 from Orlando Intl. to Tweed - New Haven Regional, returning Thu, Dec 3, priced at $181 found 1 day ago
Breeze Airways
Fri, Sep 11 - Mon, Sep 21
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$183 Roundtrip, found 2 days ago
$183
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Sep 11 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Sep 21, priced at $183 found 2 days ago
Breeze Airways
Thu, Dec 3 - Mon, Dec 7
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$184 Roundtrip, found 6 days ago
$184
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Dec 3 from Orlando Intl. to Tweed - New Haven Regional, returning Mon, Dec 7, priced at $184 found 6 days ago
Avelo Airlines
Thu, Oct 1 - Mon, Oct 5
DJT
President Donald J. Trump Intl. Airport
HVN
Tweed - New Haven Regional
$306 Roundtrip, found 5 days ago
$306
Roundtrip
found 5 days ago
Select Avelo Airlines flight, departing Thu, Oct 1 from President Donald J. Trump Intl. Airport to Tweed - New Haven Regional, returning Mon, Oct 5, priced at $306 found 5 days ago

Cheap Flights to Thimble Islands

Fall in love at first flight with your vacation to Thimble Islands by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Thimble Islands on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Thimble Islands, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Thimble Islands

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Thimble Islands with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the HVN airport.

What is the cheapest month to fly to Thimble Islands?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Thimble Islands are in September, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Thimble Islands?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Thimble Islands.

What airport is best to fly into Thimble Islands?

When you’re planning your trip to Thimble Islands, convenience is the name of the game. Luckily, Thimble Islands Tweed - New Haven Regional Airport is nearby so you can deplane and get going on checking off everything on your Thimble Islands must-do list.

How much are flights to Thimble Islands?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Thimble Islands on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $160, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Thimble Islands?

The trick to saving a stack of cash on your flight to Thimble Islands? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $160 right now, why wait?

Thimble Islands Flight Information
Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Roundtrip price
$160

Last Minute Hotel Deals in Thimble Islands

New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Book a stay at this business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
9.2/10 Wonderful! (2,326 reviews)
"Great location, all that I needed for the trip. About an 18-minute walk from the train station."

Reviewed on Sep 8, 2026

Get rates
New Haven Hotel
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (1,000 reviews)
"Welcoming, helpful, friendly, professional front desk staff. My room was impeccably clean and tidy. The property is centrally-located with ease of accessibility to main roads and major highways, yet far enough off Boston Post Road to ensure a quiet, peaceful and restful stay. Overall, an outstanding, ..."

Reviewed on Sep 8, 2026

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Pier Blue Inn Old Saybrook - Essex
Hampton Inn & Suites New Haven - South - West Haven

Hampton Inn & Suites New Haven - South - West Haven

2.5 out of 5
510 Saw Mill Rd West Haven CT
Book a stay at this business-friendly hotel in West Haven. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (1,013 reviews)
"Tatianna the front desk receptionist was so pleasant and accommodating coming in from out of town she went above and beyond to assist us an anyway possible being in customer service is challenging and she does it with ease because of her kind spirit will definitely be back and I am also now a rewards ..."

Reviewed on Sep 7, 2026

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Hampton Inn & Suites New Haven - South - West Haven
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
490 Saw Mill Rd West Haven CT
Book a stay at this business-friendly hotel in West Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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Best Western Executive Hotel Of New Haven - West Haven
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,010 reviews)
"Excellent staff and location. The food was mediocre"

Reviewed on Sep 7, 2026

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Water's Edge Resort & Spa
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
190 Old Gate Lane Milford CT
Book a stay at this business-friendly hotel in Milford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.6/10 Excellent! (1,363 reviews)
"Nice staff"

Reviewed on Sep 8, 2026

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Hyatt Place Milford / New Haven
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St New Haven CT
Book a stay at this business-friendly hotel in New Haven. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful ...
8.6/10 Excellent! (1,097 reviews)
"Excellent staff and very clean facilities, including room, exercise room, and lobby. Backup plans for coffee/gift shop being open should be made as one day it was closed during prime morning hours. Only negative was it's right in the bar zone between Church and Chapel. If you are there Friday or ..."

Reviewed on Sep 8, 2026

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Omni New Haven Hotel at Yale
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St Branford CT
Stay at this motel in Branford. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.4/10 Good! (1,032 reviews)
"The room was clean however the bathroom needed some attention. The staff in reception were not that friendly. It was like I was putting them out of their way when it came to checking in and checking out. However, for the price, I would stay there again."

Reviewed on Sep 8, 2026

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Motel 6 New Haven - Branford, CT
See all 1,090 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.