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.
Hilton Garden Inn New York/Manhattan-Midtown East
Manhattan
Price was CA $1,642, price is now CA $1,036 per person
CA $1,036
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
7.8/10 Good! (1,761 reviews)
Elevators could use some work.
Reviewed on Jun 23, 2026
The Towers at Lotte New York Palace
Manhattan
Price was CA $3,709, price is now CA $2,292 per person
CA $2,292
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (680 reviews)
A clean professional hotel. The down side is that it is very expensive and whilst the staff are very professional, they could not be described as warm and friendly. But maybe that could be said for New York service generally.
Thank you ~ Jon
Reviewed on Jun 20, 2026
1 Hotel Brooklyn Bridge
Price was CA $5,064, price is now CA $3,161 per person
CA $3,161
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,000 reviews)
Excellent and well kept hotel. Friendly and helpful staff. Awesome location.
Reviewed on Jun 6, 2026
Hotel Riu Plaza Manhattan Times Square
Manhattan
Price was CA $3,485, price is now CA $2,239 per person
CA $2,239
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,636 reviews)
Clean, very close to Times Square, and helpful staff. We arrived earlier than the check-in time, and we were provided with courtesy showers and the gym. We loved the room view, and showers were really modern and clean.
Reviewed on Jun 26, 2026
Thimble Islands Hotel Deals
New Haven Hotel
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
The price is CA $158 per night from Jul 5 to Jul 6
CA $158
CA $182 total
Jul 5 - Jul 6
includes taxes & fees
9.2/10 Wonderful! (2,190 reviews)
"If you want to hear the neighboring rooms toilet flush and conversations, this is the hotel for you! You can hear everything the other room is doing, even if they aren’t being loud. The most annoying was hearing everyone’s toilet flushing. The shower dripped and night and you have to pay for parking ..."
Reviewed on Jun 25, 2026
Motel 6 New Haven - Branford, CT
320 E Main St Branford CT
Fully refundable
The price is CA $101 per night from Jul 1 to Jul 2
CA $101
CA $118 total
Jul 1 - Jul 2
includes taxes & fees
7.2/10 Good! (1,005 reviews)
"Budget and pet friendly. Clean but not spotless, staff accommodating yet not quite friendly. A basic room with clean bed. This would fall into the get-what-you-pay-for category."
Reviewed on Jun 26, 2026
Hilton Garden Inn Milford
291 Old Gate Lane Milford CT
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from Jun 28 to Jun 29
CA $163
CA $188 total
Jun 28 - Jun 29
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"We enjoyed our stay. The young lady at the front desk was extremely friendly and helpful. Would’ve been nice if the pool was warm."
Reviewed on Jun 24, 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
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.
