Thimble Islands Holidays from £873
Book a Hotel + Flight or Car together to unlock savings
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- Better togetherSave up to £750 when you book a flight and hotel together*
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Top Thimble Islands Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Collective Retreats Governors Island
Manhattan
£873
per person
12 Oct - 15 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to New York (JFK)
8.6/10 Excellent! (109 reviews)
Incredible place for a late summer stay and spa get-away minutes from Manhattan. Will definitely be back!
Reviewed on 6 Sept 2026
Hotel St. James
Manhattan
£925
per person
9 Nov - 13 Nov
found 1 day ago
Return flight included
Edinburgh (EDI) to New York (JFK)
8.8/10 Excellent! (7,930 reviews)
Very good hotel for the price. I had quite a large room with a nice comfortable bed, the bathroom was clean with a good shower. The staff were very pleasant. The location was excellent. I would stay there again.
Reviewed on 8 Sept 2026
1 Hotel Brooklyn Bridge
£1,859
per person
15 Oct - 19 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to New York (JFK)
9/10 Wonderful! (1,013 reviews)
I enjoyed my stay.
The staff here is remarkable and they go above and beyond to please their customers.
I’m looking forward to staying here again in 2 weeks! =)
Reviewed on 8 Sept 2026
Thimble Islands Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Tweed - New Haven Regional Airport (HVN) |
Top hotels in Thimble Islands
New Haven Hotel
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
£114
30 Sept - 1 Oct
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
£72
10 Sept - 11 Sept
includes taxes & fees
8/10 Very good! (1,015 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 8 Sept 2026
Hampton Inn & Suites New Haven - South - West Haven
510 Saw Mill Rd West Haven CT
Fully refundableReserve now, pay when you stay
£115
14 Sept - 15 Sept
includes taxes & fees
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 7 Sept 2026
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.
Frequently asked questions
Why should I book my Thimble Islands holiday with Expedia?
With excellent-value airfares, car hire and accommodation options all in one place, Expedia makes arranging your Thimble Islands break hassle-free. What's more, we can help you bundle your bookings into a package holiday so you can enjoy even more savings. Pick from fabulous retreats, add your flights and/or a hire car (and maybe also some fun tours and activities!) and score incredible prices. Need to cancel? Expedia has a flexible cancellation policy for many reservations. To learn more, make your way to our Customer Service Portal link.
When is the best time of year to holiday in Thimble Islands?
If you want to experience the buzz of Thimble Islands in the peak season, lock in your escape for June, July and August. December, January and February are usually the quietest months of the year. Arrange your escape to Thimble Islands according to what type of holiday you're looking for. January is the coolest month, when daytime temperatures average 0ºC. In July, the warmest period, you will experience temperatures of around 25ºC during the day.
What is the top hotel for my holiday in Thimble Islands?
The Inn at Mystic is an ideal base for a fabulous getaway in Thimble Islands, offering all the conveniences you need and more.
How do I get a cheap holiday to Thimble Islands?
Lock in flights that suit your busy schedule, add a hotel room to your booking and watch the savings pile up with a Thimble Islands holiday. It's that easy! From flights and hotels to tours and hire cars, Expedia is your gateway to cheap travel. And with over 400 airlines and 321,000 properties across the globe to choose from, you'll never be short of choice. Learn more about how you can save money on your holiday when you combine your flight and hotel bookings with Expedia.
What should I do on my Thimble Islands holiday?
Make sure your holiday in Thimble Islands is an unforgettable one by stopping by its well-known attractions. Connecticut Sportsplex, East Haven Town Beach, Bill Miller's Castle and Stony Creek Brewery are just some of the things we recommend seeing while you're in the city.
Do I need a visa for my Thimble Islands holiday?
Visa requirements for Thimble Islands vary depending on your nationality and the reason for your visit. Be sure to check official government websites to determine if you need a visa for your trip. Here you'll also find the most up-to-date information, including details about application procedures or supporting documentation that may be necessary. Enquire about your visa requirements in advance to ensure a hassle-free travel experience. Finally, check to see that your passport is valid for at least six months from the date of your return.
What should I wear on my Thimble Islands holiday?
First, consider the types of things you'll be doing during your Thimble Islands trip and choose versatile pieces that you can easily mix and match. For fashion inspiration or information on any dress codes, look up style blogs or social media accounts. Be sure to check the weather forecast so you can pack accordingly. The warmest month in Thimble Islands is July, with average daily temperatures of 25ºC. If you're on holiday during the coolest month of January, the mercury hovers around 0ºC during the day.
What does an Expedia Thimble Islands holiday include?
Expedia has everything you need to organise your Thimble Islands getaway, but what goes into your package is entirely up to you. Pick from a combination of hotels, hire cars and flights. In search of some tours or experiences to keep you busy? Once you've made your booking, you can add them too. No matter your budget or style, there's a deal to match your needs. Expedia features all kinds of properties, with the most popular in Thimble Islands including private holiday homes and cottages. With Expedia, you'll always have the freedom and flexibility to tailor your holiday however you want.
Does Expedia offer Book Now, Pay Later Thimble Islands holidays?
Your bank balance shouldn't get in the way of going on holiday, so Expedia has come up with a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book your dream getaway without draining your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your escape. Check out these flexible payment options:
- Pay monthly holidays: Make your holiday dreams come true sooner with Klarna's manageable payment plans. If paying across multiple transactions works for you, choose this option during the checkout process.
- No-deposit holidays: When you see an amazing deal but your budget doesn't quite cover it yet, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to lock in your escape.
Can I choose my airline with a Thimble Islands Expedia holiday?
Yes — and it's easy too. Expedia has access to more than 400 partner airlines all over the world. Our holiday packages give you the flexibility to pick from available flight, hotel or activity options that fit your needs.
Explore a world of travel with Expedia
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
