Monhegan Island Vacation Packages

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Your Monhegan Island Vacation

When you book a Monhegan Island vacation package, you can relax and enjoy your escape to the fullest. Uncover the highlights of this unique city knowing that all your travel arrangements have been taken care of before you go. Up for a bit of sightseeing? A trip to Monhegan Island wouldn't be complete without visiting Lupine Gallery, Fish Beach and other leading attractions. A couple of clicks is all it takes to build a customized Monhegan Island vacation on Expedia.

Top Monhegan Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Trade Winds on the Bay

Trade Winds on the Bay

CA $760
per person
Oct 17 - Oct 23
found 9 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Rockland (RKD)
8.6/10 Excellent! (468 reviews)
The room was very clean. Patio should be pressure washed to get rid of the bold and mildew on the railings. Pool area was nice. we were very satisfied with the hotel.

Reviewed on Sep 13, 2026

Harborline Hotel

Harborline Hotel

CA $828
per person
Oct 17 - Oct 23
found 9 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Rockland (RKD)
7.4/10 Good! (367 reviews)
The staff was super friendly and helpful, they let me borrow a hair dryer and they always said hello when I entered the building. The water pressure in this hotel is on another level, amazing shower. The hotel is literally a two minute walk from Main Street, super walkable. Had a great stay, will be back!

Reviewed on Sep 14, 2026

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Monhegan Island Hotel Deals

Monhegan Island Retreat - Spacious with 4 bedrooms and gorgeous ocean views.<br>

Monhegan Island Retreat - Spacious with 4 bedrooms and gorgeous ocean views.<br>

Monhegan ME
9.6/10 Exceptional! (50 reviews)
"The Magnolia House was the perfect location for ocean views and proximity to trails and “town.” The house was comfy and we felt very at home with our kids and dog. The host was responsive and helpful. We loved the porch off the main bedroom upstairs for watching sunsets, chatting, and playing ..."

Reviewed on Jul 25, 2026

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Monhegan Island Retreat - Spacious with 4 bedrooms and gorgeous ocean views.<br>
Sunsets Galore Peace & Quiet Beautiful 3-bedroom home on Monhegan Island.

Sunsets Galore Peace & Quiet Beautiful 3-bedroom home on Monhegan Island.

Monhegan Island ME
10/10 Exceptional! (4 reviews)
"We had a fabulous 4-night visit on Monhegan. The house is comfortable and has a great kitchen including a really nice water filter. The porch looking out over the water and Manana island is amazing—we spent hours sitting out there gazing at the view. We would love to come back!"

Reviewed on Jun 15, 2026

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Sunsets Galore Peace & Quiet Beautiful 3-bedroom home on Monhegan Island.
Flagship Inn and Suites

Flagship Inn and Suites

200 Townsend Avenue Boothbay Harbor ME
CA $137
CA $202 total
Oct 8 - Oct 9
includes taxes & fees
8/10 Very good! (1,004 reviews)
"We had two rooms .One room was old but ok. The other room should be offline (I advised the hotel as much)as it needed a deep cleaning in the bathroom. Faucets were old, handles didn’t work on toilet, drain guard on sink missing, refrigerator handle was broken. Staff was okay as they took notes on ..."

Reviewed on Sep 14, 2026

Flagship Inn and Suites
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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.
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Stay near popular Monhegan Island attractions

Lupine Gallery

You can spend time exploring the galleries in Lupine Gallery during your travels in Monhegan Island. Amble around the area's parks or experience its art scene.
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Monhegan Lighthouse

After visiting Monhegan Lighthouse, make a plan to see the other sights and activities in Monhegan Island. Take in the art scene while you're in the area.
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Fish Beach

Why not spend a lazy afternoon at Fish Beach during your trip to Monhegan Island? Take in the art scene while you're in the area.
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White Head Trail

You can take time to visit White Head Trail during your travels to Monhegan Island. Take in the art scene while you're in the area.
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Cathedral Woods

Commune with nature and explore the great outdoors at Cathedral Woods during your travels in Monhegan Island. Take in the art scene while you're in the area.
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Monhegan Museum of Art & History

You can spend an afternoon exploring the galleries in Monhegan Museum of Art & History during your trip to Monhegan Island. Take in the art scene while you're in the area.
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Frequently asked questions

How much does a Monhegan Island vacation package cost?
Offering excellent value package deals from CA $760 on Expedia, you'll be thrilled with how little a vacation to Monhegan Island costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Monhegan Island?
If you're looking to snag a cheap Monhegan Island vacation package, consider travelling in January, February and March. You'll typically find better prices on flights and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for Monhegan Island?
With a well-planned schedule, you can easily hit the most popular Monhegan Island sights in a few days. But if you want to discover hidden spots or go on day tours, think about booking your Monhegan Island vacation for longer.
Is it worth booking a vacation package to Monhegan Island?
During your Monhegan Island vacation, you can look forward to enjoying some top-notch nature and culture. Leave enough time in your itinerary to discover leading sights like Lupine Gallery and Fish Beach.
How to find the best Monhegan Island package deals?
Use Expedia's filters to help you find some fabulous Monhegan Island package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Monhegan Island package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Monhegan Island vacation as a package?
You can enjoy significant savings on your next Monhegan Island break by booking a customized vacation package. Click on the "Package" heading, then select your travel dates and destination to see some great flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Monhegan Island?
If you've got your Monhegan Island vacation dates confirmed, book as early as you can to score some fantastic deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Monhegan Island?
  1. Choose your travel dates: What you plan to do in Monhegan Island and your favourite season can help you decide when to travel.
  2. Set your budget: Consider expenses such as food, flights and transportation when working out how much to save for your trip to Monhegan Island. Then, choose a property that fits your budget, whether that's a low-cost option or a more luxurious getaway.
  3. Decide how many days away: Start by listing all the attractions and activities you'd like to get to in Monhegan Island. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a customized Monhegan Island vacation package.

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