Title: Kid friendly Vacations in Thimble Islands 2026 | Expedia.ca ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Thimble Islands Kid friendly Vacations ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Flight and Kid friendly hotel deals in Thimble Islands Price found within the past 48 hours. Click for updated prices. ![Hotel Alameda Highline](https://images.trvl-media.com/lodging/5000000/4340000/4339600/4339531/165c4fb8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Alameda Highline Manhattan CA $831 per person Feb 16 - Feb 19 found 18 hours ago Roundtrip flight included Toronto (YTO) to New York (JFK) 7.6/10 Good! (793 reviews) No frills but good location and meets all the needs. Reviewed on Jan 4, 2026 ![Topping Rose House](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/8b4b1f10_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Topping Rose House CA $833 per person Mar 12 - Mar 15 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9.2/10 Wonderful! (136 reviews) Great rooms, staff and food Reviewed on Sep 28, 2025 ![1 Hotel Brooklyn Bridge](https://images.trvl-media.com/lodging/16000000/15400000/15399700/15399642/7801a5d8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel Brooklyn Bridge CA $3,420 per person Mar 7 - Mar 14 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to New York (JFK) 8.8/10 Excellent! (1,000 reviews) You need more dinner options in hotel Reviewed on Jan 17, 2026 ![Loews Regency New York Hotel](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Loews Regency New York Hotel Manhattan CA $2,067 per person Mar 7 - Mar 14 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to New York (JFK) 9/10 Wonderful! (1,002 reviews) Staff were very accomodating and looked after my family well during our stay. Nothing was too difficult for them. Reviewed on Jan 17, 2026 ![The Langham, New York, Fifth Avenue](https://images.trvl-media.com/lodging/4000000/3630000/3630000/3629903/f11b4f1b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, New York, Fifth Avenue Manhattan CA $1,939 per person Mar 19 - Mar 22 found 18 hours ago Roundtrip non-stop flight included Hamilton (YHM) to New York (JFK) 9.4/10 Exceptional! (1,001 reviews) The Langham properties have become a go to for us and it’s because of the service delivery standards experienced at the London, Pasadena and NYC properties. Our 4 night stay was a busy one as our December 31st arrival meant we had to be quick at checking in time to head out for our dinner plans. Staff has always been exceptionally professional and went so far as to be recognized by two staff members from our previous stay. There are many great hotels in NYC, but the Langham’s 5th Avenue location is absolutely, positively perfect. Thank you for the warm welcome and excellent customer service. Reviewed on Jan 5, 2026 Don't see what you're looking for? See all available trips from Columbus to Thimble Islands [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-17/2026-02-24/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=HVN&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Kid friendly holidays in Thimble Islands Price found within the past 48 hours. Click for updated prices. ![The Langham, New York, Fifth Avenue](https://images.trvl-media.com/lodging/4000000/3630000/3630000/3629903/f11b4f1b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, New York, Fifth Avenue Manhattan CA $1,939 per person Mar 19 - Mar 22 found 18 hours ago Roundtrip non-stop flight included Hamilton (YHM) to New York (JFK) 9.4/10 Exceptional! (1,001 reviews) The Langham properties have become a go to for us and it’s because of the service delivery standards experienced at the London, Pasadena and NYC properties. Our 4 night stay was a busy one as our December 31st arrival meant we had to be quick at checking in time to head out for our dinner plans. Staff has always been exceptionally professional and went so far as to be recognized by two staff members from our previous stay. There are many great hotels in NYC, but the Langham’s 5th Avenue location is absolutely, positively perfect. Thank you for the warm welcome and excellent customer service. Reviewed on Jan 5, 2026 ![1 Hotel Brooklyn Bridge](https://images.trvl-media.com/lodging/16000000/15400000/15399700/15399642/7801a5d8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel Brooklyn Bridge CA $3,420 per person Mar 7 - Mar 14 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to New York (JFK) 8.8/10 Excellent! (1,000 reviews) You need more dinner options in hotel Reviewed on Jan 17, 2026 ![Loews Regency New York Hotel](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Loews Regency New York Hotel Manhattan CA $2,067 per person Mar 7 - Mar 14 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to New York (JFK) 9/10 Wonderful! (1,002 reviews) Staff were very accomodating and looked after my family well during our stay. Nothing was too difficult for them. Reviewed on Jan 17, 2026 Don't see what you're looking for? See all available trips from Columbus to Thimble Islands [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-17/2026-02-24/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=HVN&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Kid friendly holidays in Thimble Islands Price found within the past 48 hours. Click for updated prices. ![Hotel Alameda Highline](https://images.trvl-media.com/lodging/5000000/4340000/4339600/4339531/165c4fb8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Alameda Highline Manhattan CA $831 per person Feb 16 - Feb 19 found 18 hours ago Roundtrip flight included Toronto (YTO) to New York (JFK) 7.6/10 Good! (793 reviews) No frills but good location and meets all the needs. Reviewed on Jan 4, 2026 ![Topping Rose House](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/8b4b1f10_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Topping Rose House CA $833 per person Mar 12 - Mar 15 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9.2/10 Wonderful! (136 reviews) Great rooms, staff and food Reviewed on Sep 28, 2025 ![The Langham, New York, Fifth Avenue](https://images.trvl-media.com/lodging/4000000/3630000/3630000/3629903/f11b4f1b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, New York, Fifth Avenue Manhattan CA $1,939 per person Mar 19 - Mar 22 found 18 hours ago Roundtrip non-stop flight included Hamilton (YHM) to New York (JFK) 9.4/10 Exceptional! (1,001 reviews) The Langham properties have become a go to for us and it’s because of the service delivery standards experienced at the London, Pasadena and NYC properties. Our 4 night stay was a busy one as our December 31st arrival meant we had to be quick at checking in time to head out for our dinner plans. Staff has always been exceptionally professional and went so far as to be recognized by two staff members from our previous stay. There are many great hotels in NYC, but the Langham’s 5th Avenue location is absolutely, positively perfect. Thank you for the warm welcome and excellent customer service. Reviewed on Jan 5, 2026 Don't see what you're looking for? See all available trips from Columbus to Thimble Islands [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-17/2026-02-24/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=HVN&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Kid friendly holidays in Thimble Islands Price found within the past 48 hours. Click for updated prices. ![Hotel St. James](https://images.trvl-media.com/lodging/2000000/1150000/1144500/1144474/ecd19bcc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel St. James Manhattan CA $601 per person Feb 17 - Feb 21 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 8.8/10 Excellent! (6,546 reviews) Cozy and very clean love it Reviewed on Jan 17, 2026 ![Loews Regency New York Hotel](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Loews Regency New York Hotel Manhattan CA $1,733 per person Apr 8 - Apr 12 found 1 day ago Roundtrip flight included Toronto (YYZ) to New York (JFK) 9/10 Wonderful! (1,002 reviews) Staff were very accomodating and looked after my family well during our stay. Nothing was too difficult for them. Reviewed on Jan 17, 2026 ![Hotel Seville Nomad, in the Unbound Collection by Hyatt](https://images.trvl-media.com/lodging/18000000/17940000/17939200/17939186/186b385b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Seville Nomad, in the Unbound Collection by Hyatt Manhattan CA $985 per person Mar 9 - Mar 13 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to New York (JFK) 8.8/10 Excellent! (1,184 reviews) Everything at this hotel feels thoughtfully curated. The servers are warm and attentive, the menu typography is beautifully sized and easy to read, and the natural light pouring through the windows creates a stunning atmosphere. I loved the intimate private nooks, the slippers placed by the bed, and the fresh fruit bowl waiting in the room. Even the small rotary phone was a charming touch. From the live jazz in the lobby to the moments in between, the musical experience is flawless. When the band isn’t playing, even the curated streaming playlist feels perfectly chosen and elevates the atmosphere. The entire property has a gorgeous, cohesive ambiance. You can tell the team pays attention to every detail—even the tone and warmth of the staff’s voices contribute to the experience. Truly exceptional. Reviewed on Jan 15, 2026 Don't see what you're looking for? See all available trips from Columbus to Thimble Islands [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-17/2026-02-24/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=HVN&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the perfect family-friendly vacation in Thimble Islands with Expedia #### What are some benefits of booking a family-friendly vacation? Whether it's luxurious or cheap, family vacations in Thimble Islands are among the most memorable experiences you'll ever have with your family. It can be a great way to bond and explore new destinations with the people you love most. Plus, it's easy to keep an eye on your little ones without having to worry about how they are with a sitter back home. You may even meet some other families and establish long-lasting friendships. #### How can I find the best family-friendly vacations? Using search filters makes finding the perfect family-friendly vacation easy. You can implement the search filter for family-friendly accommodations specifically, but that's just the beginning. You'll also find search filters for price range along with the desired number of bedrooms, so you can ensure you have enough space for everyone you want to bring to Thimble Islands. #### Are there cheap family vacations to Thimble Islands? Price varies quite a bit, ranging from to . The price you'll be paying depends on a variety of factors, and you can filter for them all. You can implement a filter for your budget limitations and also remove any 4- and 5-star stays from your search. You can even filter by accommodation type, which can present you with cheap alternatives to what is typically considered standard. #### When should I book family-friendly vacation packages? The right time to book family-friendly vacation packages in Thimble Islands depends on what you're looking for. If you're looking to save, booking during least popular month tends to be cheaper compared to the rest of the year, though that's not always a guarantee. Keep in mind that the off-season and the busy season differ from place to place, with family-friendly vacations in Canada being very different compared to options in France and Spain, for example. #### Can I book an all-inclusive family vacation in Thimble Islands? Yes, you'll find plenty of all-inclusive family vacation packages for Thimble Islands. To see what's available, just select the all-inclusive filter on your search. #### How can I book the best family activity vacation? If you're looking to make the most out of the available activities in Thimble Islands, you'll need to consider what your family likes to do. Cater your itinerary to your family's interests, and you'll create memories that you and your kids will hold on to for the rest of your lives whether it's family ski vacations in Thimble Islands or something a bit more relaxed. #### Can I find luxury family vacations in Thimble Islands? If you're looking for a luxury family vacation to Thimble Islands, you can use search filters to find the best options available. Activate the filter for 5-star packages to only see the best of the best. Plus, you'll find a range of first-class flights available to make even the journey there top-of-the-line. #### How can I search for family vacation deals? Finding deals is easy when you take advantage of the array of available search filters. You can set budget limitations and remove 4- and 5-star options from your search. If you don't want to miss out on your favourite amenities, however, you can consider travelling during , which often have lower prices because of the off-season in Thimble Islands. #### Can I book a family vacation package that is fully refundable? If you're looking for a fully refundable reservation, you won't have to look far on Expedia. Quite a few properties in Thimble Islands are fully refundable. You can search for this feature, but always make sure to check the specific property's policies and requirements before booking. #### Why should I book my family trip with Expedia? When you book with Expedia, you can book your accommodation and your flight together, with some discounts available for doing both at once. Additionally, you may be able to enjoy special discounts with Expedia Rewards that will earn you points you can then put toward discounts for subsequent bookings. ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Top Kid friendly Vacation Destinations > - [Family vacations in the United Kingdom ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/190/United-Kingdom) > - [Family vacations in Bali ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/602651/Bali) > - [Family vacations in Ontario ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/2680/Ontario) > - [Family vacations in France ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/59/France) > - [Family vacations in Spain ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/166/Spain) > - [Family vacations in Paris ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/179898/Paris) > - [Family vacations in Switzerland ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/174/Switzerland) > - [Family vacations in Italy ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/86/Italy) > - [Family vacations in South Africa ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/165/South-Africa) > - [Family vacations in Victoria ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/1418/Victoria) > - [Family vacations in Scotland ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/11219/Scotland) > - [Family vacations in Alaska ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/203/Alaska) > - [Family vacations in Bournemouth ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/654/Bournemouth) > - [Family vacations in Philippines ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/145/Philippines) > - [Family vacations in Tenerife ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/6047194/Tenerife) > - [Family vacations in Australia ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/10/Australia) > - [Family vacations in Egypt ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/52/Egypt) > - [Family vacations in Tuscany ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/601686/Tuscany) > - [Family vacations in Panama ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/142/Panama) ## More Vacations Ideas [Flights to Thimble Islands ](https://expedia.ca/Cheap-Flights-To-Thimble-Islands.d6341069.Travel-Guide-Flights)[ Thimble Islands Hotels ](https://expedia.ca/Thimble-Islands-Hotels.d6341069.Travel-Guide-Hotels)[ Thimble Islands Vacation Rentals ](https://expedia.ca/Thimble-Islands-Vacation-Rentals.d6341069.Travel-Guide-VacationRentals)[ Thimble Islands Car Rentals ](https://expedia.ca/Car-Rentals-In-Thimble-Islands.d6341069.Car-Rental-Guide)[ Thimble Islands Vacations ](https://expedia.ca/Thimble-Islands.d6341069.Destination-Travel-Guides) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app