Book Holiday Homes in Harpswell

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Featured Holiday Homes in Harpswell

Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.

Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.

Boothbay Harbor
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 ...
Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.
Oceanfront Cabin-Castle in Maine Woods

Oceanfront Cabin-Castle in Maine Woods

Georgetown
Located in Georgetown, this vacation home is by the ocean, a 1-minute drive from Reid State Park and 8 minutes from Georgetown Historical Society.
Oceanfront Cabin-Castle in Maine Woods
Charming 110-year former Inn 10' from the Ocean!

Charming 110-year former Inn 10' from the Ocean!

South Portland
With a stay at this vacation home in South Portland (Willard Beach), you'll be within a 15-minute drive of Thompson's Point and Maine Mall.
Charming 110-year former Inn 10' from the Ocean!
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The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries

Portland
With a stay at this vacation home, you'll be centrally located in Portland, within a 10-minute drive of Thompson's Point and Maine Mall.
The Globe House on Munjoy Hill - Walk to Breweries
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, a 3-minute drive from Thompson's Point and 8 minutes from Maine Mall.
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Oceanfront home & guesthouse w/ incredible ocean views, deck & location

Oceanfront home & guesthouse w/ incredible ocean views, deck & location

Boothbay
With a stay at this vacation home, you'll be centrally located in East Boothbay, just a 3-minute walk from Grimes Cove Beach and 13 minutes by foot from Linekin ...
Oceanfront home & guesthouse w/ incredible ocean views, deck & location
Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR

Harpswell
When you a stay at this vacation home in Bailey Island, you'll be on the waterfront, just steps from Casco Bay and Cobwork Bridge.
Orchid Harbor, Bailey Island 3BR
Single-family home situated on the waterfront in the beautiful midcoast Maine

Single-family home situated on the waterfront in the beautiful midcoast Maine

Bristol
With a stay at this vacation home in New Harbor (Pemaquid Beach), you'll be a 3-minute walk from Colonial Pemaquid State Historic Site and within a 5-minute ...
Single-family home situated on the waterfront in the beautiful midcoast Maine
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

Bailey Island
A stay at this vacation home places you in the heart of Bailey Island, steps from Casco Bay and Bailey Island Bridge.
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
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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
492 Holiday Homes
Lowest Price
AU$115
Highest Price
AU$272
Popular accommodation
Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown., Oceanfront Cabin-Castle in Maine Woods, Charming 110-year former Inn 10' from the Ocean!, The Globe House on Munjoy Hill - Walk to Breweries, Spacious & Sunny 4 Bedroom Close to Downtown, hot tub, Oceanfront home & guesthouse w/ incredible ocean views, deck & location, Orchid Harbor, Bailey Island 3BR, Single-family home situated on the waterfront in the beautiful midcoast Maine, Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

Top trending hotels in Harpswell

1 room luxury ocean front studio cottage

1 room luxury ocean front studio cottage

Harpswell
Located in Harpswell, this apartment is by the ocean, a 1-minute drive from Casco Bay and 6 minutes from Lower Goose Island.
1 room luxury ocean front studio cottage
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 16 Mar to 17 Mar
AU$272
includes taxes & fees
16 Mar - 17 Mar
With a stay at Portland Harbor Hotel, you'll be centrally located in Portland, a 5-minute drive from Thompson's Point and 9 minutes from Maine Mall.
Portland Harbor Hotel
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$163 per night from 26 Feb to 27 Feb
AU$163
includes taxes & fees
26 Feb - 27 Feb
Located in Portland (Nasons Corner), Ramada Plaza by Wyndham Portland is within a 10-minute drive of Maine Mall and Thompson's Point.
Ramada Plaza by Wyndham Portland
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DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4 out of 5
363 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$115 per night from 2 Mar to 3 Mar
AU$115
includes taxes & fees
2 Mar - 3 Mar
When you stay at DoubleTree by Hilton Hotel Portland in South Portland, you'll be near the airport, a 1-minute drive from Maine Mall and 8 minutes from Thompson's ...
DoubleTree by Hilton Hotel Portland
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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.