Freeport Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Your Freeport Vacation

From its laid-back lifestyle to its spectacular views and beyond, there's loads to like about Freeport. Uncover the wonders of this fascinating city with a Freeport vacation package that's tailored to you. Make your trip to Freeport even more fun by including some sightseeing. LL Bean Flagship Store, Wolfes Neck Woods State Park and Desert of Maine are some of the big attractions you'll want to explore. Whoever you're going away with and whatever the size of your budget, your ultimate Freeport vacation is just clicks away with Expedia.

Top Freeport Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was CA $1,346, price is now CA $1,026 per person
CA $1,026
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)
We were in the clover, the room was well decorated but not so spacious. We loved all the possibilities there is to do at the resort. The free breakfast is croissants, danishes, fruits and coffee near the lobby. Loved how walkable it was to the the heart of Ogunquit and the beach.

Reviewed on Jul 30, 2026

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Price was CA $1,746, price is now CA $1,117 per person
CA $1,117
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9/10 Wonderful! (1,008 reviews)
Pros: Quiet , clean pool , clean grounds , balcony , close to beaches and shopping areas, nice staff. Cons: terrible internet connection , TVs kept freezing, carpet, mold in bathroom, breakfast was not good, 10-15 min waits to both check in and check out.

Reviewed on Jul 30, 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $2,139, price is now CA $1,525 per person
CA $1,525
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,781 reviews)
The property is in a great location minutes walk away from stores, great food and sights and trips. But as a property itself it lacks amenities and maintenance levels to fully justify the high seasonal pricing

Reviewed on Jul 28, 2026

Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Price was CA $2,611, price is now CA $2,015 per person
CA $2,015
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Portland (PWM)
10/10 Exceptional! (6 reviews)
The accommodations were perfect for a family of 4. The 2 bedroom/2 bath was very spacious, very well laid out and in an excellent location. We really enjoyed our stay!

Reviewed on Jul 28, 2026

Driftaway Hotel and Pool

Driftaway Hotel and Pool

2 out of 5
Price was CA $1,496, price is now CA $1,164 per person
CA $1,164
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
8.6/10 Excellent! (1,002 reviews)
Retro vibe. The whole family enjoyed it.

Reviewed on Jul 29, 2026

Ready to book your vacation to Freeport?

 

Choose your dates

Freeport Hotel Deals

Best Western Freeport Inn

Best Western Freeport Inn

3 out of 5
31 US Route 1 Freeport ME
Fully refundableReserve now, pay when you stay
The price is CA $209 per night from Aug 2 to Aug 3
CA $209
CA $228 total
Aug 2 - Aug 3
includes taxes & fees
7.8/10 Good! (1,000 reviews)
"If you want a place to rest your head and don't mind the tenor so minute drive into Freeport this place hits the spot"

Reviewed on Jul 30, 2026

Best Western Freeport Inn
The Freeport Hotel, an Ascend Collection Hotel

The Freeport Hotel, an Ascend Collection Hotel

2 out of 5
506 Us Route 1 Freeport ME
Fully refundable
The price is CA $135 per night from Aug 13 to Aug 14
CA $135
CA $147 total
Aug 13 - Aug 14
includes taxes & fees
The Freeport Hotel, an Ascend Collection Hotel
The Harraseeket Inn & Event House Freeport Downtown

The Harraseeket Inn & Event House Freeport Downtown

3.5 out of 5
162 Main St Freeport ME
Fully refundableReserve now, pay when you stay
The price is CA $336 per night from Aug 3 to Aug 4
CA $336
CA $366 total
Aug 3 - Aug 4
includes taxes & fees
9.4/10 Exceptional! (978 reviews)
"Super clean, friendly staff and stunning hotel! We loved our stay!"

Reviewed on Jul 28, 2026

The Harraseeket Inn & Event House Freeport Downtown
See all 1,944 properties in Freeport
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

Stay near popular Freeport attractions

A building with 'L.L. Bean Inc.' signage, a large boot sculpture, and outdoor seating.

LL Bean Flagship Store

9.2/10 (1,289 reviews)
During your trip to Freeport, you can enjoy retail therapy at LL Bean Flagship Store. Stroll along the area's waterfront or simply enjoy its seafood restaurants.
See properties

Frequently asked questions

How much does a Freeport vacation package cost?
Offering great value package deals from CA $1,026 on Expedia, you'll be surprised at how little a vacation to Freeport costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Freeport?
January, February and March are the best times to look for cheap Freeport vacation packages. Choosing to travel in less busy months means you'll typically find reduced prices on flights and accommodations.
How many days is enough for Freeport?
Usually, a handful of days is enough to see the main sights during your Freeport vacation. But if you prefer to have time to kick back or go on day tours, think about extending your itinerary.
Is it worth booking a vacation package to Freeport?
Whether you'd like to check out major attractions like Desert of Maine and Wolfe's Neck Woods State Park on your Freeport vacation, or coming for its excellent shopping, hiking and nature, there's something for everyone here. With so many things to see and do, you'll quickly learn why so many people think Freeport is a good vacation destination.
How to find the best Freeport package deals?
Landing a cheap Freeport package deal is easy with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, add some filters and see what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most pocket-friendly Freeport package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Freeport vacation as a package?
You can enjoy significant savings on your next Freeport getaway by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to view some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Freeport?
Score fantastic discounts by booking your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Freeport trip.
How to plan a trip to Freeport?

  1. Choose when to go: Check your schedule and get packing. Your preferred season and the activities available will also help you decide when to vacation in Freeport.
  2. Set your budget: Consider costs like food, flights and transportation when working out how much to set aside for your trip to Freeport. Then, select a property that matches your budget, whether that's an economical option or a deluxe getaway.
  3. Work out your trip length: Think about how much time you'd like to spend discovering Freeport. Plan your itinerary so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to choose a Freeport vacation package that brings all your bookings together.

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.