Squirrel Island Trips (flight + hotel)

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to P 3,118 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Squirrel Island

Ocean Gate Resort

Ocean Gate Resort

3 out of 5
70 Ocean Gate Rd, Southport, ME
Fully refundableReserve now, pay when you stay
The price is P7,906 per night from Sep 1 to Sep 2
P7,906
P10,045 total
Sep 1 - Sep 2
includes taxes & fees
8.4/10 Very Good! (1,008 reviews)
"Perfect place for a little getaway. Nice property, absolutely wonderful breakfast - close to everything. Harbor views were incredible!"

Reviewed on Aug 7, 2025

Ocean Gate Resort
Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
200 Townsend Avenue, Boothbay Harbor, ME
The price is P7,620 per night from Aug 26 to Aug 27
P7,620
P9,751 total
Aug 26 - Aug 27
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"The free breakfast was great and convenient to town"

Reviewed on Aug 8, 2025

Flagship Inn and Suites
Fishermans Wharf Inn

Fishermans Wharf Inn

2.5 out of 5
22 Commercial St, Boothbay Harbor, ME
Fully refundableReserve now, pay when you stay
The price is P13,131 per night from Sep 7 to Sep 8
P13,131
P14,313 total
Sep 7 - Sep 8
includes taxes & fees
8.6/10 Excellent! (786 reviews)
"Right in the heart of the harbor and parking on sight"

Reviewed on Aug 6, 2025

Fishermans Wharf Inn
See all 1,357 properties in Squirrel 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.

Frequently asked questions

How much does a Squirrel Island vacation package cost?
You can grab a vacation package to this top destination on Expedia. But how much your vacation to Squirrel Island costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Squirrel Island?
You can typically find lower rates and better availability in January, February and March. Browse our cheap Squirrel Island vacation packages and you could land some great off-season deals.
How many days is enough for Squirrel Island?
With a well-planned itinerary, you can easily hit the most popular Squirrel Island attractions in a handful of days. But if you'd like to venture off the beaten track or take day trips, think about booking your Squirrel Island vacation for longer.
How to find the best Squirrel Island package deals?
Begin your search for a Squirrel Island package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Squirrel Island package deal straight away, just play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Squirrel Island escape underway.
Is it cheaper to book a Squirrel Island vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component separately. And you'll still have the freedom to create a personalized Squirrel Island vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Squirrel Island?
If you're planning an impromptu Squirrel Island adventure, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can score awesome deals on your hotels and flights by booking ahead.
How to plan a trip to Squirrel Island?

  1. Pick the right time to travel: Your schedule, favorite season and the type of weather you enjoy can all influence your decision on when to travel to Squirrel Island.
  2. Budget wisely: In addition to the cost of your hotel, you'll need to factor in other expenses too. These include transportation, food and flights. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Squirrel Island.
  3. Decide your trip length: Think about how long you want to spend exploring Squirrel Island. Plan your days so you can get to all the activities and attractions you're interested in without rushing.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Squirrel Island vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.