Thimble Islands Holidays from £1,486

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Top Thimble Islands Flight + Hotel Deals

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

Ink 48 Hotel

4.5 out of 5
Manhattan
Price was £2,247, price is now £1,486 per person
£1,486
per person
29 Dec - 3 Jan
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8.4/10 Very good! (1,813 reviews)
Great stay, great hotel. Will definitely return.

Reviewed on 28 Oct 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was £3,179, price is now £1,837 per person
£1,837
per person
1 Dec - 5 Dec
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (3,435 reviews)

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was £3,822, price is now £2,240 per person
£2,240
per person
10 Dec - 15 Dec
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
9/10 Wonderful! (1,004 reviews)

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was £3,175, price is now £1,864 per person
£1,864
per person
1 Dec - 5 Dec
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)

The William Hotel Midtown, New York

The William Hotel Midtown, New York

3.5 out of 5
Manhattan
Price was £2,251, price is now £1,505 per person
£1,505
per person
29 Dec - 3 Jan
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.4/10 Exceptional! (275 reviews)
Our room was clean and comfortable, (beds, linens and towels) but the rug on the floor had a couple of stains. The window curtains need to be replaced. The inside (the side that faces the window) was old so when you brushed up against the curtain you ended up with white powder dust all over your clothes. Of course, you only touched the inside of the curtain when you came in from the outside patio. The colors in the room were nice and bright but didn't go with the rest of the vibe of the hotel. The staff was amazing, always a smile and hello, and very helpful when we checked out with our luggage. We had to check out at 11am but didn't leave for the airport until 1pm so, they held our bags for us while we walked around a bit. One main thing to consider when booking this hotel, which I didn't think of, when entering the hotel, you have some very steep steps to walk up, and if you have luggage, it can be a challenge to carry up the stairs. There are no bellmen at this hotel. We didn't know until we were leaving that there was a back entrance through a restaurant beneath the hotel that you can roll your luggage through to take an elevator to the hotel reception desk. We like the "Speak Easy" vibe of the hotel, but the lighting was just a little too dark for our liking. The location of the hotel was nice (Midtown). It was easy to go in any direction to get where we wanted to go. There are lots of restaurants around this area which was nice.

Reviewed on 27 Oct 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

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
The price is £111 per night from 22 Nov to 23 Nov
£111
22 Nov - 23 Nov
includes taxes & fees
New Haven Hotel
Motel 6 Milford, CT

Motel 6 Milford, CT

2 out of 5
111 Schoolhouse Road Milford CT
Fully refundableReserve now, pay when you stay
The price is £60 per night from 10 Nov to 11 Nov
£60
10 Nov - 11 Nov
includes taxes & fees
6.6/10 (1,065 reviews)
"I strongly advise others to think twice before staying at this location. Do not reserve a room here—not now, not in the future. Based on my experience I had with a particular staff member named Avy, I would never recommend this hotel to anyone. Management needs to take accountability and address ..."

Reviewed on 28 Oct 2026

Motel 6 Milford, CT
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
The price is £70 per night from 15 Nov to 16 Nov
£70
15 Nov - 16 Nov
includes taxes & fees
8/10 Very good! (1,000 reviews)
"The room had a musty smell when we entered and didn't resemble in the least how it was presented on the website. The room looked dirty, pillows looked old and stained yellow. The television didn't work. The shower barely had any pressure. The employees were very nice."

Reviewed on 27 Oct 2026

Pier Blue Inn Old Saybrook - Essex
See all 1,106 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.
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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

* 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.