Book Holiday Homes in Damariscove Island

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Featured Holiday Homes in Damariscove Island

Stunning oceanfront cottage w/ private deck and Atlantic views

Stunning oceanfront cottage w/ private deck and Atlantic views

Southport
A stay at this vacation home places you in the heart of Southport, just a 3-minute walk from Southport Memorial Library and within a 5-minute drive of Hendricks ...
Stunning oceanfront cottage w/ private deck and Atlantic views
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces

Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces

Westport
Located in Wiscasset, this vacation home is by the ocean, a 4-minute drive from Long Ledge and 6 minutes from Brooks Point.
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
Spacious Waterfront Summer Home with Swimming, Kayaking, and Sunsets

Spacious Waterfront Summer Home with Swimming, Kayaking, and Sunsets

Phippsburg
Located in Phippsburg, this vacation home is on the waterfront, within a 15-minute drive of Casco Bay and Kennebec River.
Spacious Waterfront Summer Home with Swimming, Kayaking, and Sunsets
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Sunrise Catcher with a Panoramic View!

Sunrise Catcher with a Panoramic View!

Harpswell
Located in Harpswell, this vacation home is by the ocean, within a 15-minute drive of Casco Bay and Paddleworks.
Sunrise Catcher with a Panoramic View!
325 Year OldWaterfront Fully Renovated Loaded with Amenities
Bring Your Boat!

325 Year OldWaterfront Fully Renovated Loaded with Amenities Bring Your Boat!

Arrowsic
With a stay at this vacation home in Bath, you'll be on the waterfront, just steps from Kennebec River and a 2-minute drive from Sewell Pond Conservation ...
325 Year OldWaterfront Fully Renovated Loaded with Amenities Bring Your Boat!
Boothbay Harbor Home with Water Views | Near Dining & Whale Watching

Boothbay Harbor Home with Water Views | Near Dining & Whale Watching

Boothbay Harbor
With a stay at this vacation home in East Boothbay, you'll be by the sea, just steps from Linekin Bay and a 2-minute drive from Grimes Cove Beach.
Boothbay Harbor Home with Water Views | Near Dining & Whale Watching
New home at Popham Beach

New home at Popham Beach

Phippsburg
When you a stay at this vacation home in Phippsburg, you'll be by the ocean, just steps from Casco Bay and Popham Beach State Park.
New home at Popham Beach
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor

Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor

Boothbay Harbor
With a stay at this vacation home in Boothbay Harbor, you'll be a 4-minute walk from Boothbay Harbor Memorial Library and 5 minutes by foot from Boothbay Harbor ...
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor
Dog-friendly home with deck, pool table, & firepit - walk to downtown Boothbay

Dog-friendly home with deck, pool table, & firepit - walk to downtown Boothbay

Boothbay Harbor
Located in Boothbay Harbor, this vacation home is by the sea, within a 5-minute walk of Linekin Bay and Barrett Park.
Dog-friendly home with deck, pool table, & firepit - walk to downtown Boothbay
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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.

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

Holiday houses in Damariscove Island 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 Damariscove Island 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 Damariscove Island adventures, obvs.

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

Top trending hotels in Damariscove Island

Tugboat Inn

Tugboat Inn

3 out of 5
80 Commercial St., Boothbay Harbor, ME
The price is AU$246 per night from 9 Jun to 10 Jun
AU$246
per night
9 Jun - 10 Jun
With a stay at Tugboat Inn in Boothbay Harbor, you'll be within a 5-minute walk of Burnt Island Living Lighthouse and Boothbay Harbor Marina.
Tugboat Inn
Boothbay Harbor Inn

Boothbay Harbor Inn

2.5 out of 5
31 Atlantic Ave, Boothbay Harbor, ME
The price is AU$213 per night from 30 May to 31 May
AU$213
per night
30 May - 31 May
When you a stay at Boothbay Harbor Inn in Boothbay Harbor, you'll be on the waterfront, within a 5-minute walk of Boothbay Railway Village and Fisherman's Memorial ...
Boothbay Harbor Inn
Days Inn by Wyndham Brunswick Bath Area

Days Inn by Wyndham Brunswick Bath Area

2 out of 5
224 Bath Rd, Brunswick, ME
Fully refundableReserve now, pay when you stay
The price is AU$184 per night from 30 May to 31 May
AU$184
per night
30 May - 31 May
With a stay at Days Inn by Wyndham Brunswick Bath Area in Brunswick, you'll be within a 5-minute drive of Bowdoin College and Casco Bay.
Days Inn by Wyndham Brunswick Bath Area
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Best Western Plus Brunswick Bath

Best Western Plus Brunswick Bath

2.5 out of 5
71 Gurnet Road, Brunswick, ME
Fully refundableReserve now, pay when you stay
The price is AU$184 per night from 2 Jun to 3 Jun
AU$184
per night
2 Jun - 3 Jun
With a stay at Best Western Plus Brunswick Bath in Brunswick, you'll be in a shopping district, within a 5-minute drive of Bowdoin College and Casco Bay.
Best Western Plus Brunswick Bath
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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.