Book Holiday Homes in Harpswell

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Featured Holiday Homes in Harpswell

 New Well Built Elegant Home on the Water 2 miles to Freeport, 9  to Portland!

New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!

South Freeeport
A stay at this vacation home places you in the heart of Freeport, steps from Casco Bay and a 3-minute drive from Bradbury Mountain State Park.
New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Portland
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.
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Bayfront home with 270-degree views, large deck & porch - near Popham Beach

Bayfront home with 270-degree views, large deck & porch - near Popham Beach

Phippsburg
With a stay at this vacation home in Phippsburg, you'll be on the beach, just steps from Casco Bay and a 3-minute drive from Kennebec River.
Bayfront home with 270-degree views, large deck & porch - near Popham Beach
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Beautiful Combo Home Located in Downtown Portland - Close to the Beach

Beautiful Combo Home Located in Downtown Portland - Close to the Beach

Portland
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.
Beautiful Combo Home Located in Downtown Portland - Close to the Beach
Private Oceanfront Cottage, Private Sand Beach -Lighthouse one mile away

Private Oceanfront Cottage, Private Sand Beach -Lighthouse one mile away

Permaquid Point
With a stay at this vacation home in New Harbor (Pemaquid Point), you'll be within a 5-minute drive of Pemaquid Point Lighthouse Park and Pemaquid Craft ...
Private Oceanfront Cottage, Private Sand Beach -Lighthouse one mile away
Lofty cottage

Lofty cottage

Harpswell
The price is AU$566 per night from 26 Nov to 27 Nov
AU$566
includes taxes & fees
26 Nov - 27 Nov
Located in Harpswell, this vacation home is by the ocean, a 1-minute drive from Casco Bay and 9 minutes from Paddleworks.
Lofty cottage
Charming ocean-view cottage just 10 minutes from downtown Freeport shops

Charming ocean-view cottage just 10 minutes from downtown Freeport shops

2 out of 5
Freeport
Located in Freeport, Charming ocean-view cottage just 10 minutes from downtown Freeport shops is a 1-minute drive from Casco Bay and 7 minutes from Wolfe's Neck ...
Charming ocean-view cottage just 10 minutes from downtown Freeport shops
More then a Motel With Garden , Renovated Rooms at heart of Boothbay

More then a Motel With Garden , Renovated Rooms at heart of Boothbay

2 out of 5
Boothbay
With a stay at this vacation home in Boothbay, you'll be a 3-minute walk from Boothbay Railway Village and 7 minutes by foot from Dolphin Mini Golf.
More then a Motel With Garden , Renovated Rooms at heart of Boothbay
Newly Renovated Haven w/ Deck, Near Downtown: Walk to Shops, Dining &  Marina

Newly Renovated Haven w/ Deck, Near Downtown: Walk to Shops, Dining & Marina

Boothbay Harbor
With a stay at this vacation home, you'll be centrally located in Boothbay Harbor, just a 5-minute walk from Boothbay Harbor Memorial Library and 6 minutes by ...
Newly Renovated Haven w/ Deck, Near Downtown: Walk to Shops, Dining & Marina
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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.

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

Holiday houses in Harpswell 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 Harpswell 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 Harpswell adventures, obvs.

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

Harpswell Holiday Homes essential information

Accommodation
516 Holiday Homes
Lowest Price
AU$119
Highest Price
AU$566
Popular accommodation
New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!, Spacious & Sunny 4 Bedroom Close to Downtown, hot tub, Bayfront home with 270-degree views, large deck & porch - near Popham Beach, Beautiful Combo Home Located in Downtown Portland - Close to the Beach, Private Oceanfront Cottage, Private Sand Beach -Lighthouse one mile away, Lofty cottage , Charming ocean-view cottage just 10 minutes from downtown Freeport shops, More then a Motel With Garden , Renovated Rooms at heart of Boothbay, Newly Renovated Haven w/ Deck, Near Downtown: Walk to Shops, Dining & Marina

Top trending hotels in Harpswell

La Quinta Inn & Suites by Wyndham Portland

La Quinta Inn & Suites by Wyndham Portland

2.5 out of 5
340 Park Ave, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$136 per night from 9 Dec to 10 Dec
AU$136
includes taxes & fees
9 Dec - 10 Dec
Located in Portland, La Quinta Inn & Suites by Wyndham Portland is a 5-minute walk from Portland Exposition Building and 5 minutes by foot from Hadlock ...
La Quinta Inn & Suites by Wyndham Portland
Casco Bay Hotel, Ascend Hotel Collection

Casco Bay Hotel, Ascend Hotel Collection

3.5 out of 5
80 John Roberts Rd., South Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$119 per night from 9 Dec to 10 Dec
AU$119
includes taxes & fees
9 Dec - 10 Dec
With a stay at Casco Bay Hotel, Ascend Hotel Collection in South Portland, you'll be in a shopping district, just a 3-minute walk from Maine Mall and within ...
Casco Bay Hotel, Ascend Hotel Collection
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$272 per night from 1 Dec to 2 Dec
AU$272
includes taxes & fees
1 Dec - 2 Dec
With a stay at Portland Harbor Hotel, you'll be centrally located in Portland, within a 10-minute drive of Maine Mall and Casco Bay.
Portland Harbor Hotel
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Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
9 Center Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$216 per night from 2 Dec to 3 Dec
AU$216
includes taxes & fees
2 Dec - 3 Dec
With a stay at Canopy by Hilton Portland Waterfront in Portland (Downtown Portland), you'll be within a 10-minute drive of Maine Mall and Casco Bay.
Canopy by Hilton Portland Waterfront
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See all available properties in Harpswell
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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.