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Featured Holiday Homes in Freeport

Sunny Modern Oasis in Portland’s Trendy East End

Sunny Modern Oasis in Portland’s Trendy East End

Portland ME
With a stay at this vacation home, you'll be centrally located in Portland, within a 10-minute drive of Maine Mall and Casco Bay.
Opens in a new windowSunny Modern Oasis in Portland’s Trendy East End
Fantastic Waterfront Views

Fantastic Waterfront Views

Phippsburg ME
The price is AU$476 per night from 11 Jan to 12 Jan
AU$476
11 Jan - 12 Jan 2026
includes taxes & fees
With a stay at this vacation home in Phippsburg (West Point), you'll be within a 15-minute drive of Casco Bay and Popham Beach State Park.
Opens in a new windowFantastic Waterfront Views
Captain's Guest Room w/private bath. Walk to everything.

Captain's Guest Room w/private bath. Walk to everything.

Bath ME
With a stay at this vacation home in Bath, you'll be within a 10-minute walk of Chocolate Church and Markings Gallery.
Opens in a new windowCaptain's Guest Room w/private bath. Walk to everything.
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Large, light filled 4 bedroom house - walk to ocean and ferry

Large, light filled 4 bedroom house - walk to ocean and ferry

Peaks Island ME
With a stay at this vacation home in Peaks Island, you'll be by the ocean, just a 1-minute walk from Casco Bay and 7 minutes by foot from Umbrella Cover ...
Opens in a new windowLarge, light filled 4 bedroom house - walk to ocean and ferry
Windward Lodge- stunning, dog-friendly private waterfront retreat. Seasonal dock

Windward Lodge- stunning, dog-friendly private waterfront retreat. Seasonal dock

Woolwich ME
Located in Woolwich, this vacation home is within a 5-minute drive of Kennebec River and Markings Gallery.
Opens in a new windowWindward Lodge- stunning, dog-friendly private waterfront retreat. Seasonal dock
Beautiful house on the Harpswell Peninsula over looking Casco Bay

Beautiful house on the Harpswell Peninsula over looking Casco Bay

Harpswell ME
With a stay at this vacation home in Harpswell, you'll be by the ocean, just steps from Casco Bay and a 4-minute drive from Mitchell Field.
Opens in a new windowBeautiful house on the Harpswell Peninsula over looking Casco Bay
Private 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi

Private 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi

Scarborough ME
With a stay at this vacation home in Scarborough, you'll be on the waterfront, within a 10-minute drive of Maine Mall and Nonesuch River Golf Club.
Opens in a new windowPrivate 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi
Lone Pine Cottage Maine - Chef’s Kitchen

Lone Pine Cottage Maine - Chef’s Kitchen

Bath ME
When you stay at this vacation home in Bath, you'll be by the sea, within a 15-minute walk of Maine Maritime Museum and Kennebec River.
Opens in a new windowLone Pine Cottage Maine - Chef’s Kitchen
Spectacular Oceanfront Estate with Beautiful Sunsets on 8 acres

Spectacular Oceanfront Estate with Beautiful Sunsets on 8 acres

Harpswell ME
With a stay at this vacation home in Harpswell, you'll be on the waterfront, just steps from Casco Bay and a 5-minute drive from Lower Goose Island.
Opens in a new windowSpectacular Oceanfront Estate with Beautiful Sunsets on 8 acres
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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.

Freeport Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Freeport vacation homes are the perfect way for you to wing it.

Holiday houses in Freeport let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Freeport in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Freeport adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Freeport with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Freeport vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Freeport Holiday Homes essential information

Accommodation
515 Holiday Homes
Lowest Price
AU$154
Highest Price
AU$476
Popular accommodation
Sunny Modern Oasis in Portland’s Trendy East End, Fantastic Waterfront Views, Captain's Guest Room w/private bath. Walk to everything., Large, light filled 4 bedroom house - walk to ocean and ferry, Windward Lodge- stunning, dog-friendly private waterfront retreat. Seasonal dock, Beautiful house on the Harpswell Peninsula over looking Casco Bay, Private 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi, Lone Pine Cottage Maine - Chef’s Kitchen, Spectacular Oceanfront Estate with Beautiful Sunsets on 8 acres

Top trending hotels in Freeport

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
The price is AU$155 per night from 23 Dec to 24 Dec
AU$155
23 Dec - 24 Dec
includes taxes & fees
With a stay at Holiday Inn Express Hotel & Suites Freeport by IHG in Freeport, you'll be within a 5-minute drive of LL Bean Flagship Store and Casco Bay.
Opens in a new windowHoliday Inn Express Hotel & Suites Freeport by IHG
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
The price is AU$161 per night from 30 Dec to 31 Dec
AU$161
30 Dec - 31 Dec
includes taxes & fees
With a stay at Hilton Garden Inn Freeport Downtown, you'll be centrally located in Freeport, within a 10-minute walk of LL Bean Flagship Store and Harrington ...
Opens in a new windowHilton Garden Inn Freeport Downtown
The Harraseeket Inn & Event House Freeport Downtown

The Harraseeket Inn & Event House Freeport Downtown

3.5 out of 5
162 Main St Freeport ME
The price is AU$180 per night from 1 Jan to 2 Jan
AU$180
1 Jan - 2 Jan 2026
includes taxes & fees
The Harraseeket Inn & Event House Freeport Downtown is in the heart of Freeport, within a 10-minute walk of Casco Bay and LL Bean Flagship Store.
Opens in a new windowThe Harraseeket Inn & Event House Freeport Downtown
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Hampton Inn Freeport/Brunswick

Hampton Inn Freeport/Brunswick

2.5 out of 5
194 Lower Main St Freeport ME
Fully refundableReserve now, pay when you stay
The price is AU$154 per night from 4 Jan to 5 Jan
AU$154
4 Jan - 5 Jan 2026
includes taxes & fees
With a stay at Hampton Inn Freeport/Brunswick in Freeport, you'll be within a 5-minute drive of LL Bean Flagship Store and Casco Bay.
Opens in a new windowHampton Inn Freeport/Brunswick
Don't see what you're looking for?
See all available properties in Freeport
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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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^Subject to availability and chosen travel dates.