Freeport Vacations from $340

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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.

The Latest Freeport vacation packages

Price found within the past 48 hours. Click for updated prices.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $452, price is now $340 per person
$340
per person
Jan 23 - Jan 25
found 8 hours ago
Roundtrip non-stop flight included
New York (LGA) to Portland (PWM)
19.2/10 Exceptional! (161 reviews)
Wish they had a liquor license and could do a cocktail hour in addition to a breakfast service. Wish they had just a tad more breakfast options. Really wish they had a key pad and front door access! LOVED the fire places in every room. Property manager was lovely and friendly. Loved the snacks available and variety.

Reviewed on Oct 27, 2025

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
Price was $584, price is now $456 per person
$456
per person
Jan 23 - Jan 25
found 8 hours ago
Roundtrip non-stop flight included
New York (LGA) to Portland (PWM)
19.2/10 Exceptional! (119 reviews)
Adorable spot in Portland, great location, really cool concept. Felt like an upgraded vacation rental. You don’t have the whole place to yourself but it basically feels like it. Check in and everything was seamless. The local recommendations, games, and snacks were a nice touch. We loved plays scrabble and drinking wine in the parlor. We do wish some items were a bit nicer given the cost. The bathroom could've had nicer facilities (cheap toilet seat, low water pressure) our bed was a rickety. The breakfast delivered was a nice touch but the contents itself kinda fell flat, not as curated as the website made it seem. Overall we still enjoyed our stay and the concept, but the website may have upsold it a bit.

Reviewed on Nov 11, 2025

The Docent's Collection - Boyd Block

The Docent's Collection - Boyd Block

2 out of 5
Downtown Portland
Price was $526, price is now $416 per person
$416
per person
Jan 23 - Jan 25
found 8 hours ago
Roundtrip non-stop flight included
New York (LGA) to Portland (PWM)
20/10 Exceptional! (2 reviews)
Really nice and clean new hotel!

Reviewed on Oct 27, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Price was $1,244, price is now $989 per person
$989
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
18.8/10 Exceptional! (1,001 reviews)
What an amazing experience! Definitely heading back there

Reviewed on Nov 18, 2025

The Kennebunk Inn

The Kennebunk Inn

2.5 out of 5
Price was $592, price is now $476 per person
$476
per person
Dec 26 - Dec 31
found 10 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
15.6/10 Exceptional! (745 reviews)
The room was very clean , the front staff was very helpful and sweet! Only thing that was a downside (but makes sense) due to the age of the building you can hear everything. If you are a light sleeper bring a fan to drown out some noise ! Hopefully will be back soon!

Reviewed on Nov 9, 2025

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Discover the most popular places to visit in Freeport

LL Bean Flagship Store featuring a pond and interior views as well as a family

LL Bean Flagship Store

4.5/5(578 reviews)

Explore almost limitless possibilities for outdoor adventure at this iconic Maine brand’s 24-hour outpost, with special attractions alongside abundant shopping opportunities.

LL Bean Flagship Store
Bradbury Mountain State Park featuring a small town or village, fall colors and landscape views

Bradbury Mountain State Park

Reach the summit of a mountain, have a picnic and count soaring hawks at this pretty park, one of Maine’s five original state parks.

Bradbury Mountain State Park
Harrington House

Harrington House

Delve into the history of southern Maine and life in the 19th century at this intriguing and well-preserved home in Freeport.

Harrington House

Freeport Hotel Deals

Holiday Inn Express Hotel & Suites Freeport by IHG

Holiday Inn Express Hotel & Suites Freeport by IHG

2.5 out of 5
450 U.S. Route 1 Freeport ME
Fully refundable
$94 nightly
The price is $102 total per night from Nov 23 to Nov 24
$102 total
Nov 23 - Nov 24
Total with taxes and fees
8.6/10 Excellent! (1,005 reviews)
Room was clean, staff were friendly - for the price a good spot to stay. The traffic on 295 can be loud but expected for a hotel along an interstate.

Reviewed on Nov 14, 2025

Holiday Inn Express Hotel & Suites Freeport by IHG
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
$109 nightly
The price is $119 total per night from Dec 14 to Dec 15
$119 total
Dec 14 - Dec 15
Total with taxes and fees
9.2/10 Wonderful! (856 reviews)
Cleanliness, friendliness and helpfulness of staff

Reviewed on Nov 18, 2025

The Harraseeket Inn & Event House Freeport Downtown
Hilton Garden Inn Freeport Downtown

Hilton Garden Inn Freeport Downtown

3 out of 5
5 Park St Freeport ME
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $95 total per night from Dec 14 to Dec 15
$95 total
Dec 14 - Dec 15
Total with taxes and fees
9/10 Wonderful! (1,003 reviews)
Great room and great staff.

Reviewed on Nov 12, 2025

Hilton Garden Inn Freeport Downtown
See all 1,765 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.

Find the Best Freeport Vacation Packages

Freeport Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)
Population
1,500
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Thomas Point Beach, Wolfes Neck Woods State Park and Maine State Music Theater

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Frequently asked questions

How much does a Freeport vacation package cost?
Offering great value package deals from $340 on Expedia, you'll be thrilled with how little a vacation to Freeport costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Freeport?
If you're looking to score a cheap Freeport vacation package, consider visiting in January, October and December. You'll typically find better prices on hotels and flights during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Freeport?
Generally, a handful of days is enough to tick off the top attractions during your Freeport vacation. However, if you want 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?
Popular for its shopping, nature and hiking, a Freeport vacation is a hit with all kinds of visitors. Be sure to check out key sights like Desert of Maine and Wolfe's Neck Woods State Park, and consider renting a car for day trips to experience even more.
How to find the best Freeport package deals?
Use Expedia's filters to help you find some unbeatable Freeport package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or browse for Freeport package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Freeport vacation as a package?
You can enjoy significant savings on your Freeport escape by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to see the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Freeport?
If you're considering a spur-of-the-moment Freeport getaway, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find awesome deals on your hotels and flights by booking ahead.
How to plan a trip to Freeport?

  1. Choose when to travel: Check your diary and get your bags packed. Your favorite season and the activities on offer will also help you decide when to escape to Freeport.
  2. Set a budget: Consider expenses like flights, food and transportation when working out how much to put aside for your trip to Freeport. Then, select a hotel that fits your budget, whether that's a wallet-friendly option or a lavish retreat.
  3. Organize your Freeport escape with our trip planning tool: Look for and book hotels and experiences all in one place. You can also collaborate with friends and family to plan an unforgettable trip to Freeport together.
  4. Work out your trip length: Consider how much time you want to spend exploring Freeport. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  5. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find a Freeport vacation package that brings all your bookings together.
  6. Book experiences or activities ahead of time: Whether it's entrance to a big attraction or a walking tour, you won't have to worry about missing out on Freeport's best offerings. Find all the incredible things to do in Freeport with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Freeport vacation packages?
Your Freeport break should be an escape from your busy life, not a reason for money worries. So to allow you a bit more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any 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.