Book Holiday Homes in Woolwich

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Featured Holiday Homes in Woolwich

Fantastic Waterfront Views

Fantastic Waterfront Views

Phippsburg ME
The price is AU$557 per night from 5 Jan to 6 Jan
AU$557
5 Jan - 6 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
Newly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH.

Newly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH.

Boothbay Harbor ME
A stay at this vacation home places you in the heart of Boothbay Harbor, within a 5-minute walk of Boothbay Region Land Trust and Boothbay Region Historical ...
Opens in a new windowNewly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH.
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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Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

Boothbay Harbor ME
With a stay at this vacation home in Boothbay Harbor, you'll be on the beach, just a 4-minute walk from Boothbay Harbor Memorial Library and 6 minutes by foot ...
Opens in a new windowDowntown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
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
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
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Bailey Island ME
With a stay at this vacation home in Bailey Island, you'll be on the beach, just a 1-minute walk from Casco Bay and 14 minutes by foot from Mackerel Cove.
Opens in a new windowNew Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
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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.

Woolwich 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 Woolwich vacation homes are the perfect way for you to wing it.

Holiday houses in Woolwich 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 Woolwich 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 Woolwich adventures, obvs.

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

Woolwich Holiday Homes essential information

Accommodation
532 Holiday Homes
Lowest Price
AU$146
Highest Price
AU$557
Popular accommodation
Fantastic Waterfront Views, Newly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH., Captain's Guest Room w/private bath. Walk to everything., Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views, Windward Lodge- stunning, dog-friendly private waterfront retreat. Seasonal dock, Beautiful house on the Harpswell Peninsula over looking Casco Bay, Lone Pine Cottage Maine - Chef’s Kitchen, Spectacular Oceanfront Estate with Beautiful Sunsets on 8 acres, New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Top trending hotels in Woolwich

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$156 per night from 22 Dec to 23 Dec
AU$156
22 Dec - 23 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
Comfort Inn Brunswick

Comfort Inn Brunswick

2.5 out of 5
199 Pleasant St Brunswick ME
Fully refundableReserve now, pay when you stay
The price is AU$146 per night from 18 Dec to 19 Dec
AU$146
18 Dec - 19 Dec
includes taxes & fees
With a stay at Comfort Inn Brunswick, you'll be centrally located in Brunswick, within a 15-minute drive of LL Bean Flagship Store and Casco Bay.
Opens in a new windowComfort Inn Brunswick
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$154 per night from 18 Dec to 19 Dec
AU$154
18 Dec - 19 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
Save an average of 15% on thousands of hotels when you're signed in
The Brunswick Hotel

The Brunswick Hotel

3 out of 5
4 Noble St Brunswick ME
Fully refundableReserve now, pay when you stay
The price is AU$193 per night from 22 Dec to 23 Dec
AU$193
22 Dec - 23 Dec
includes taxes & fees
A stay at The Brunswick Hotel places you in the heart of Brunswick, steps from Maine Street and Casco Bay.
Opens in a new windowThe Brunswick Hotel
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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.