Book Holiday Homes in Damariscotta

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Featured Holiday Homes in Damariscotta

Boothbay Harbor Woodland Retreat

Boothbay Harbor Woodland Retreat

Boothbay Harbor ME
With a stay at this vacation home in Boothbay Harbor, you'll be within a 5-minute drive of Boothbay Harbor Marina and Burnt Island Living Lighthouse.
Opens in a new windowBoothbay Harbor Woodland Retreat
Smuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE

Smuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE

East Boothbay ME
A stay at this vacation home places you in the heart of East Boothbay, within a 5-minute drive of Linekin Bay and Grimes Cove Beach.
Opens in a new windowSmuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE
Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston

Thomaston ME
The price is AU$364 per night from 16 May to 17 May
AU$364
16 May - 17 May
includes taxes & fees
With a stay at this vacation home in Thomaston, you'll be within a 5-minute drive of General Henry Knox Museum and Maine State Prison Store.
Opens in a new windowBright 2-Bedroom Apartment Near Downtown Thomaston
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In-town, coastal + relaxing in Rockland

In-town, coastal + relaxing in Rockland

Rockland ME
The price is AU$899 per night from 26 May to 27 May
AU$899
26 May - 27 May
includes taxes & fees
A stay at this vacation home places you in the heart of Rockland, steps from Sandy Beach and 5 minutes by foot from Coastal Children's Museum.
Opens in a new windowIn-town, coastal + relaxing in Rockland
Downtown Waterfront Cottage with shoreline sitting room

Downtown Waterfront Cottage with shoreline sitting room

Boothbay Harbor ME
With a stay at this vacation home, you'll be centrally located in Boothbay Harbor, just a 4-minute walk from Boothbay Harbor Memorial Library and 5 minutes by ...
Opens in a new windowDowntown Waterfront Cottage with shoreline sitting room
Captain's Guest Room w/private bath. Walk to everything.

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

Bath ME
The price is AU$204 per night from 16 May to 17 May
AU$204
16 May - 17 May
includes taxes & fees
With a stay at this vacation home in Bath, you'll be within a 10-minute walk of Chocolate Church Arts Center and Bath Center for the Arts.
Opens in a new windowCaptain's Guest Room w/private bath. Walk to everything.
Summer 2026 ! Kayak on the Kennebec " EVERYTHING you need "

Summer 2026 ! Kayak on the Kennebec " EVERYTHING you need "

Phippsburg ME
A stay at this vacation home places you in the heart of Phippsburg, a 1-minute drive from Casco Bay and 7 minutes from Maine Maritime Museum.
Opens in a new windowSummer 2026 ! Kayak on the Kennebec " EVERYTHING you need "
Downtown Boothbay Harbor, 2-Story Cottage

Downtown Boothbay Harbor, 2-Story Cottage

Boothbay Harbor ME
With a stay at this vacation home in Boothbay Harbor, you'll be within a 5-minute walk of Opera House at Boothbay Harbor and Boothbay Region Historical Society ...
Opens in a new windowDowntown Boothbay Harbor, 2-Story Cottage
Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach

Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach

Rockport ME
Located in Rockport, this vacation home is by the ocean, within a 5-minute drive of Oakland Park Bowling Lanes and Owls Head Lighthouse.
Opens in a new windowOceanfront,Unobstructed Views Private Onsite ocean access to a small sandy 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.

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

Holiday houses in Damariscotta 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 Damariscotta 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 Damariscotta adventures, obvs.

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

Damariscotta Holiday Homes essential information

Accommodation
545 Holiday Homes
Lowest Price
AU$185
Highest Price
AU$899
Popular accommodation
Boothbay Harbor Woodland Retreat, Smuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE, Bright 2-Bedroom Apartment Near Downtown Thomaston, In-town, coastal + relaxing in Rockland, Downtown Waterfront Cottage with shoreline sitting room, Captain's Guest Room w/private bath. Walk to everything., Summer 2026 ! Kayak on the Kennebec " EVERYTHING you need ", Downtown Boothbay Harbor, 2-Story Cottage, Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach

Top trending hotels in Damariscotta

Trade Winds on the Bay

Trade Winds on the Bay

3.5 out of 5
2 Park Dr Rockland ME
Fully refundableReserve now, pay when you stay
A stay at Trade Winds on the Bay places you in the heart of Rockland, steps from Maine Lighthouse Museum and Project Puffin Visitor Center.
Opens in a new windowTrade Winds on the Bay
Harborline Hotel

Harborline Hotel

3 out of 5
6 Park Drive Rockland ME
Fully refundableReserve now, pay when you stay
A stay at Harborline Hotel places you in the heart of Rockland, steps from Maine Lighthouse Museum and Buoy Park.
Opens in a new windowHarborline Hotel
Rockland Harbor Hotel

Rockland Harbor Hotel

2.5 out of 5
520 Main Street Rockland ME
Fully refundableReserve now, pay when you stay
The price is AU$185 per night from 25 May to 26 May
AU$185
25 May - 26 May
includes taxes & fees
With a stay at Rockland Harbor Hotel, you'll be centrally located in Rockland, steps from Rockland Ferry Terminal and within a 10-minute walk of Rockland Harbor ...
Opens in a new windowRockland Harbor Hotel
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Residence Inn Bath Brunswick Area

Residence Inn Bath Brunswick Area

3 out of 5
139 Richardson St. Bath ME
Fully refundableReserve now, pay when you stay
The price is AU$222 per night from 28 May to 29 May
AU$222
28 May - 29 May
includes taxes & fees
Located in Bath, Residence Inn Bath Brunswick Area is within a 5-minute drive of Casco Bay and Bath Visitor Information Center.
Opens in a new windowResidence Inn Bath Brunswick Area
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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.

Top Picks

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^Subject to availability and chosen travel dates.