Thimble Islands Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Thimble Islands Vacation Deals
Price found within the past 48 hours. Click for updated prices.
LGA AIRPORT
Queens
CA $3,276
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
10/10 Exceptional! (2 reviews)
The best airbnb Ive stayed at in New York with the best price for our family of 6. The place was so clean, amenities looked brand new. It had a homey feel to it, my kids didnt want to leave. We will definently be booking again in the future.
Reviewed on Dec 24, 2025
Ready to book your vacation to Thimble Islands?
Thimble Islands Hotel Deals
New Haven Hotel
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
CA $179
CA $206 total
Oct 11 - Oct 12
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
CA $115
CA $132 total
Oct 12 - Oct 13
includes taxes & fees
Motel 6 Milford, CT
111 Schoolhouse Road Milford CT
Fully refundableReserve now, pay when you stay
CA $106
CA $122 total
Sep 30 - Oct 1
includes taxes & fees
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
How much does a Thimble Islands vacation package cost?
Tailor make your Thimble Islands package from as low as CA $1,120. Pick from any combination of flights, hotels and rental cars to craft the escape you've been dreaming about for ages. Be sure to add on a few activities!
How do I get a cheap travel package to Thimble Islands?
Bundle your bookings with Expedia to save big bucks on your next big adventure. With over 550 partner airlines and 1,000,000 hotels worldwide, your Thimble Islands vacation package can be tailored exactly to suit your travel style. With all that extra cash, why not throw in a few interesting activities and tours? It's an easy way to unlock even more bargains. That vacation you've always dreamed of in Thimble Islands is much closer than you thought!
Where should I stay in Thimble Islands?
A getaway to Thimble Islands isn't complete without seeing Stony Creek Museum. Why not book a hotel near this popular tourist attraction?
What are the top hotels in Thimble Islands?
Get your vacation off to a great start by staying at Private Island Victorian Estate. It's one of most sought-after hotels in Thimble Islands. Another leading option is Money Island Home With Deck, Kayak And Paddleboards.
How far in advance should I book my Thimble Islands vacation?
It can be tricky to know when is the ideal time to book your trip to Thimble Islands. But typically the earlier you book, the more affordable the prices. Sometimes, you can lock in your flights and hotels up to 12 months prior to your departure date. If you're eager to escape on a last-minute getaway, no need to stress! There are unbeatable bargains popping up on Expedia every day.
What does an Expedia Thimble Islands travel package include?
It comes down to what you're after. If you're traveling solo, you might decide to bundle flights and hotels. Taking the whole family to Thimble Islands? A travel package including flights, hotels and rental cars might suit you better. Expedia gives you the freedom to tailor your travel package.
What should I know before booking a Thimble Islands travel package?
Bundling your bookings into a Thimble Islands vacation package is the easiest way to organize your trip. Not only that, you'll save when you combine your flights, hotels and car rentals. Once you've booked, why not add on a tour or an activity?
Can I choose my airline with a Thimble Islands Expedia vacation package?
Yes — that's one of the best things about an Expedia vacation package. You get to decide. We have more than 550 partner airlines all over the world, so you have loads of choice when creating your Thimble Islands getaway.
If I'm not able to travel, can I cancel my Thimble Islands vacation package?
Plans can change unexpectedly, so yes. You may be able to change or cancel your Thimble Islands vacation package at no cost if you've booked in the last 24 hours. For bookings older than that, you can still make the necessary changes, but your car rental company, hotel or airline may charge additional fees. Looking for more information? Look up our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.
Explore a world of travel with Expedia
- New Haven Village Suites
- B&B in Guilford
- American Inn
- Branford Hotels
- Motels in North Branford
- New Haven Hotels
- Pet-Friendly Hotels in Branford
- Apartments in Branford
- Cheap Hotels in New Haven
- Hotels near Tweed - New Haven Regional
- Holiday Inn Express Branford
- Vacation Homes in Stony Creek
- Rodeway Inn & Suites Branford
- Pet-Friendly Hotels in Guilford
- Hotels near Yale University
- Thimble Islands Bed & Breakfast
- Red Roof Inn PLUS+ & Suites Guilford
- B&B in Stony Creek
- Flights from Hartford (BDL) to New Haven (HVN)
- Flights to Guilford
- Flights from Flagstaff (FLG) to New Haven (HVN)
- Flights from Newark Liberty Intl. Airport (EWR) to New Haven (HVN)
- Flights from Detroit (DTW) to New Haven (HVN)
- Flights from Regina (YQR) to New Haven (HVN)
- Flights from Dallas (DFW) to New Haven (HVN)
- Flights to Branford
- Flights from Buffalo (BUF) to New Haven (HVN)
- Flights from Montreal (YUL) to New Haven (HVN)
- Flights from Toronto (YTO) to New Haven (HVN)
- Flights from Winnipeg (YWG) to New Haven (HVN)
- Flights from St. John's (YYT) to New Haven (HVN)
- Flights from Clarksburg (CKB) to New Haven (HVN)
- Flights from Philadelphia (PHL) to New Haven (HVN)
- Flights from London (LHR) to New Haven (HVN)
- Flights from Thimble Islands
- Flights from Calgary (YYC) to New Haven (HVN)
- Flights from New York (JFK) to New Haven (HVN)
- Flights from Vancouver (YVR) to New Haven (HVN)
- Flights from Tweed - New Haven Regional
- Flights from Kingston (YGK) to New Haven (HVN)
- Flights from Amarillo (AMA) to New Haven (HVN)
- Flights from Valdosta (VLD) to New Haven (HVN)
- Flights from Fredericton (YFC) to New Haven (HVN)
- Flights to New Haven
- Flights from Branford
- Flights from Kitchener (YKF) to New Haven (HVN)
- Flights to Connecticut
- Flights from Seattle (SEA) to New Haven (HVN)
- Flights from Nairobi (NBO) to New Haven (HVN)
- Flights from Edmonton (YEG) to New Haven (HVN)
- Flights from San Francisco (SFO) to New Haven (HVN)
- Flights from Toronto (YYZ) to New Haven (HVN)
- Flights from Oshawa (YOO) to New Haven (HVN)
- Flights from Charlottetown Alexander B. Campbell Airport (YYG) to New Haven (HVN)
- Flights from Ottawa (YOW) to New Haven (HVN)
- Flights from Halifax (YHZ) to New Haven (HVN)
- Flights from Toronto (YYZ) to Hartford (BDL)
- Flights from Saskatoon (YXE) to New Haven (HVN)
- Flights from Paducah (PAH) to New Haven (HVN)
- Flights from Boston (BOS) to New Haven (HVN)
- Flights from Bellingham (BLI) to New Haven (HVN)
- Flights from Kelowna (YLW) to New Haven (HVN)
- Flights from Burlington (BTV) to New Haven (HVN)
- Flights from Chicago (MDW) to New Haven (HVN)
- Mark Twain House & Museum
- Mohegan Sun Casino
- Connecticut State Capital
- Lebanon Vacations
- Mystic Vacations
- New Britain Vacations
- Connecticut Science Center
- J. M. Sarnik & Sons' The Old General Store
- Visit Branford
- Sterling Memorial Library at Yale University
- Glastonbury Vacations
- Monroe Plaza Shopping Center
- Hartford Vacations
- Avon Vacations
- New Haven Vacations
- Preston Vacations
- Branford Vacations
- Connecticut Vacations
- Stamford Vacations
- Olde Mistick Village
- Ocean Beach Park
- Foxwoods Resort Casino
- Lighthouse Point Park
- Yale University
- Essex Steam Train
- Pilgrim Mall Shopping Center
- Elizabeth Park
- Riverside Park
- Bushnell Park
- Visit New Haven
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
