Little Bear Island Vacation Packages

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

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

Ready to book your vacation to Little Bear Island?

 

Choose your dates

Little Bear Island Hotel Deals

Mill Falls Resort Collection at the Lake

Mill Falls Resort Collection at the Lake

3 out of 5
281 Daniel Webster Hwy Meredith NH
The price is CA $181 per night from Mar 2 to Mar 3
CA $181
CA $255 total
Mar 2 - Mar 3
includes taxes & fees
8.4/10 Very Good! (945 reviews)
Beautiful view, great room! Loved the hot tub and indoor/outdoor pool.

Reviewed on Feb 21, 2026

Mill Falls Resort Collection at the Lake
Steele Hill Resorts

Steele Hill Resorts

3 out of 5
516 Steele Hill Road Sanbornton NH
The price is CA $259 per night from Mar 1 to Mar 2
CA $259
CA $281 total
Mar 1 - Mar 2
includes taxes & fees
8.4/10 Very Good! (769 reviews)
A lot of stuff missing in the kitchen. I ask for a cutting board which it never made it. Room was a bit dirty. Tv not working.

Reviewed on Feb 20, 2026

Steele Hill Resorts
Winnisquam Lake Inn

Winnisquam Lake Inn

3 out of 5
788 Laconia Rd Tilton NH
Fully refundableReserve now, pay when you stay
The price is CA $110 per night from Feb 24 to Feb 25
CA $110
CA $119 total
Feb 24 - Feb 25
includes taxes & fees
6.8/10 (829 reviews)
Our room was clean and spacious. The staff were so friendly and the view of the lake was beautiful from our room.

Reviewed on Feb 22, 2026

Winnisquam Lake Inn
See all 1,779 properties in Little Bear Island
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

Can I cancel my flight booking to Little Bear Island due to COVID-19?
Many airlines now offer greater flexibility due to COVID-19. Our Customer Service Portal will help solve most queries about flight changes or cancellations. It's also worth scanning over the terms and conditions of your chosen carrier — preferably before you make a booking!
What's the best way to find cheap flights to Little Bear Island that have flexible change policies?
It's as easy as can be with Expedia. Step 1: Type in your travel details and click on "Search." Second step: Check the "No change fee" box just below the "Flexible change policies" filter on the top left of your screen. Step 3. Grab a cheap and flexible flight to Little Bear Island.
What are some of the general tips for travelers to Little Bear Island during the COVID-19 outbreak?
The COVID-19 outbreak has led to dramatic changes to how we travel. If you're flying to Little Bear Island, the following tips will help you navigate these new challenges and rules:
  • Before you lock in a flight, find out if any travel bans or restrictions apply — in both your destination and origin. Stay informed with the latest updates by reviewing government and airport websites.
  • When you go through airport checkpoints, keep your face mask on. You will be asked to briefly lower it for identification purposes. Those who refuse to wear a face mask may face civil penalties and may also be denied boarding.
  • Instead of handing a TSA officer your boarding pass, position it straight on the scanner yourself. Then, hold it up for inspection.
  • One liquid hand sanitizer container is now allowed in your carry-on baggage. It must be no larger than 12 oz (350 ml), and you'll have to remove it from your bag at the X-ray machine for scanning.
  • Put any personal items (like your phone, wallet and keys) in your carry-on instead of a bin to minimize handling during the screening process.
  • Separate any food you're carrying for X-ray scanning. Food items often trigger the alarm. Putting them in a clear plastic bag and into a bin reduces the need for a TSA agent to touch and inspect your belongings.

Which airlines fly to Little Bear Island?
Book your seat with Cape Air and then start organizing your Little Bear Island travel agenda. This popular carrier has 1785 flights a month to Logan Intl. Airport (BOS), a central gateway.
How can I find cheap tickets to Little Bear Island?
To get your hands on a great deal to Little Bear Island, book well in advance. Also think about using Expedia's "flexible dates" feature above your search results. This will show you the cheapest prices for nearby days. In the last seven days, was the best price for a flight to Little Bear Island.
How much is a flight to Little Bear Island?
You could have locked in a round-trip ticket to Little Bear Island from anywhere between and in the last seven days. For one-way journeys from (), the lowest amount paid during this period was .
What are the most popular airports to fly into in Little Bear Island?
A major entryway to Little Bear Island, around 12051 flights taxi into Logan Intl. Airport (BOS) every month. Find an unbeatable deal, lock in your seat and get ready to explore this fantastic region.
When is the cheapest time to fly to Little Bear Island?
Jetting off on a Tuesday, followed by a Monday, is usually the best way to secure the cheapest flight. Avoid the weekends if you can, because Saturday is typically the most expensive day of the week. Spend the dollars you saved having a good time in Little Bear Island instead!
How much is a plane ticket to Little Bear Island?
In the last seven days, plane fares varied between and . Swipe through our fabulous deals to Little Bear Island, pick your favorite and then start packing your bags.
Which airlines with flights to Little Bear Island employ COVID-19 cleanliness policies?
Physical distancing is just the start of new aviation measures to help combat COVID-19. From the moment you collect your tickets, these airlines will whisk you away to Little Bear Island with comfort and confidence:
  • JetBlue - this airline is known for keeping the middle seat empty and capped capacity flights.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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.