
Monhegan Island Vacations from $676
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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.
The Latest Monhegan Island vacation packages
Price found within the past 48 hours. Click for updated prices.

Trade Winds on the Bay
$676
per person
Oct 27 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Rockland (RKD)
8.6/10 Excellent! (444 reviews)
The room was clean, parking was easy with the parking pass, and the hospitality was amazing. The other thing I would change about my stay would be staying longer.
Reviewed on Aug 18, 2026


The Craignair Inn & Restaurant
$989
per person
Oct 27 - Nov 1
found 23 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Rockland (RKD)
9.2/10 Wonderful! (200 reviews)
We love the Craignair and this was our second visit. The staff are all wonderful and so accommodating. Our arrival was a bit rough because there was private event taking place, so we had to wait until the bartender found someone to check us in and then it felt a bit like we weren't supposed to be in the common areas until the event concluded. No big deal, but we might have planned differently had we known ahead of time that this was the case. Wait staff were a bit loud one night after dinner service, but quieted down when we asked. Still, I am impressed at how relaxed and homey the place feels even in high summer when tourists are everywhere. We had previously stayed in November and kind of had it to ourselves, so we were definitely spoiled by that experience, but were amazed at how peaceful it was even during the busy season. Loved hiking Craig Island and watching the birds and the waves every morning and evening from our balcony or the dining area. This place is truly a gem.
Reviewed on Aug 9, 2026


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View all tripsStay near popular Monhegan Island attractions
Monhegan Lighthouse
Perched atop Lighthouse Hill since 1824, this historic beacon offers panoramic Atlantic Ocean views. Visit the keeper's quarters housing the Monhegan Museum of Art & History to discover the island's artistic legacy.
Lupine Gallery
Discover Monhegan Island's artistic legacy at Lupine Gallery, featuring works from over 50 contemporary artists. Browse original paintings and prints while learning about Maine's coastal beauty from knowledgeable staff.
Cathedral Woods
Cathedral Woods enchants with its fairy houses—tiny structures made from natural materials along pine-needle paths. Wander beneath the natural canopy where dappled light creates a magical, cathedral-like atmosphere.
White Head Trail
This dramatic coastal trail winds through forests before revealing Maine's highest cliffs and Atlantic panoramas. Bring sturdy boots and pause at the summit to spot seabirds soaring above the rugged shoreline.
Monhegan Museum of Art & History
Perched in a historic lighthouse, the Monhegan Museum showcases the island's artistic legacy and maritime history. Explore the intimate galleries where art and island culture intertwine against dramatic coastal views.
Fish Beach
Fish Beach showcases Monhegan Island's authentic working waterfront where fishermen tend their daily catch. Visitors can observe maritime traditions up close and purchase fresh lobster straight from the boats.
Monhegan Island Hotel Deals

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

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

Flagship Inn and Suites
200 Townsend Avenue Boothbay Harbor ME
$153 nightly
$167 total
Aug 23 - Aug 24
Total with taxes and fees
8/10 Very Good! (1,032 reviews)
"Pool and hot tub. Breakfast. Great ac"
Reviewed on Aug 18, 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.
Find the Best Monhegan Island Vacation Packages
Monhegan Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Knox County Regional Airport (RKD) |
Max Temp Winter | 30ºF |
Max Temp Summer | 70ºF |
Top Sights | Fish Beach, Pemaquid Point Lighthouse Park and Lupine Gallery |
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Frequently asked questions
How much does a Monhegan Island vacation package cost?
Offering excellent value package deals from $676 on Expedia, you'll be thrilled with how little a vacation to Monhegan Island costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Monhegan Island?
If you'd like to book a cheap Monhegan Island vacation package, consider planning a trip in October, November and December. You'll usually find lower rates on accommodations and flights during these quieter months — ideal for budget-conscious travelers.
How many days is enough for Monhegan Island?
With a well-planned schedule, you can easily hit the main Monhegan Island attractions in a few days. But if you'd like to discover hidden spots or go on day trips, think about booking your Monhegan Island vacation for longer.
Is it worth booking a vacation package to Monhegan Island?
Well known for its culture, nature and a host of other highlights, you can be assured Monhegan Island is a good vacation destination. Some of the top attractions to add to your itinerary? Don't miss Lupine Gallery and Fish Beach during your Monhegan Island vacation.
How to find the best Monhegan Island package deals?
Landing a cheap Monhegan Island package deal is easy with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply a couple of filters and browse what's available. You can personalize your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to discover the most affordable Monhegan Island package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are typically lower.
Is it cheaper to book a Monhegan Island vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll generally land a better deal than booking each component separately. And you'll still enjoy the flexibility to create a customized Monhegan Island vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Monhegan Island?
If you've got your Monhegan Island vacation dates finalized, book as soon as you can to score some unbeatable deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are ideal for traveling on a whim.
Does Expedia offer Book Now, Pay Later Monhegan Island vacation packages?
Your Monhegan Island trip should be a relaxing escape from your daily routine, not a source of money worries. So to give you a bit more flexibility, we've teamed up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.
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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.



















