Monhegan Island Vacations from $479

Book a Hotel + Flight or Car together to unlock savings

Photo by Jeffrey Offermann

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 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

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.
Harborline Hotel

Harborline Hotel

3 out of 5
Price was $569, price is now $479 per person
$479
per person
Sep 25 - Sep 28
found 11 hours ago
Roundtrip flight included
Nashville (BNA) to Rockland (RKD)
7.6/10 Good! (124 reviews)
Great location and friendly staff

Reviewed on Aug 22, 2025

Trade Winds on the Bay

Trade Winds on the Bay

3.5 out of 5
Price was $616, price is now $512 per person
$512
per person
Sep 25 - Sep 28
found 11 hours ago
Roundtrip flight included
Nashville (BNA) to Rockland (RKD)
8.4/10 Very Good! (250 reviews)
It was very hands off-- you go, retrieve your key from the lock box and let yourself in. But it is a gorgeous old building built like a fancy plantation - castle, in the middle of a small coastal town in pristine Maine, with a pool and a fitness center. I didn't realize it at first, but my room had a hallway to another living room area, with a balcony to sit and watch the sunrise from. Wow! Yeah, it's a great place.

Reviewed on Aug 14, 2025

Captain Sweetser's Inn

Captain Sweetser's Inn

2 out of 5
Price was $691, price is now $580 per person
$580
per person
Sep 27 - Oct 1
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Rockland (RKD)
10/10 Exceptional! (116 reviews)
Wonderful property decorated and cared for with love. Lori & Ginny were wonderful hosts who share the history of the area and property which was so interesting. It was spotless and the bed and housing very comfortable and spacious….and the breakfast was amazing! A real treasure for sure!

Reviewed on Aug 21, 2025

Homeport Inn and Tavern

Homeport Inn and Tavern

3 out of 5
Price was $822, price is now $715 per person
$715
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Rockland (RKD)
9.8/10 Exceptional! (283 reviews)
This beautiful antique mansion was the perfect place to begin exploring. Convenient to many attractions. Onsite tavern was a bonus. Breakfasts were perfect.hard to find charm and great hospitality.

Reviewed on Aug 13, 2025

The Craignair Inn & Restaurant

The Craignair Inn & Restaurant

3.5 out of 5
Price was $627, price is now $551 per person
$551
per person
Oct 9 - Oct 12
found 11 hours ago
Roundtrip flight included
Nashville (BNA) to Rockland (RKD)
9/10 Wonderful! (188 reviews)
Delightful, historical inn right next to Clark Island Preserve. Lovely wee walks on the shore and to the old quarry. Minimal light pollution at night allows for terrific stargazing. Rooms are on the small side, but thoughtfully designed. Included breakfast was delicious, with fresh made biscuits and a nice selection of offerings. Only slight negative is the slow WiFi, but maybe it's okay to take a break from streaming and read a book!

Reviewed on Jul 28, 2025

Don't see what you're looking for?
See all available trips from Columbus to Monhegan Island
View all trips

Discover the most popular places to visit in Monhegan Island

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.

Lupine Gallery

Monhegan Island Hotel Deals

Ocean Gate Resort

Ocean Gate Resort

3 out of 5
70 Ocean Gate Rd, Southport, ME
Fully refundableReserve now, pay when you stay
$177 nightly
The price is $191 total per night from Sep 1 to Sep 2
$191 total
Sep 1 - Sep 2
Total with taxes and fees
8.4/10 Very Good! (1,007 reviews)
"The property is amazing, amenities are great, the place is really relaxing, and nice views just above the ocean. We'll come back!"

Reviewed on Aug 18, 2025

Ocean Gate Resort
Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
200 Townsend Avenue, Boothbay Harbor, ME
$149 nightly
The price is $163 total per night from Sep 21 to Sep 22
$163 total
Sep 21 - Sep 22
Total with taxes and fees
8.2/10 Very Good! (1,011 reviews)
"It was a nice place to stay! Quiet and clean. Agreeable personnel!"

Reviewed on Aug 20, 2025

Flagship Inn and Suites
Bluebird Ocean Point Inn

Bluebird Ocean Point Inn

3 out of 5
191 Shore Road, East Boothbay, ME
$246 nightly
The price is $268 total per night from Aug 24 to Aug 25
$268 total
Aug 24 - Aug 25
Total with taxes and fees
8.6/10 Excellent! (486 reviews)
"Nice Place"

Reviewed on Aug 20, 2025

Bluebird Ocean Point Inn
See all 867 properties in Monhegan 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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Monhegan Island vacation package cost?
Offering excellent value package deals from $479 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.