Book Holiday Homes in Harpswell

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Featured Holiday Homes in Harpswell

Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

Cumberland
Book a stay at this family-friendly vacation home in Cumberland Center. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Capt Lyman Stuart, ...
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!
The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries

Portland
Book a stay at this family-friendly vacation home in Portland. Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Thompson's Point and ...
The Globe House on Munjoy Hill - Walk to Breweries
Rent a room in the gorgeous Holt House

Rent a room in the gorgeous Holt House

Portland
Stay at this vacation home in Portland. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Thompson's Point and Maine Mall are located ...
Rent a room in the gorgeous Holt House
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Beautifully renovated home w/ prime location - walk to the footbridge & downtown

Beautifully renovated home w/ prime location - walk to the footbridge & downtown

Boothbay Harbor
Book a stay at this family-friendly vacation home in Boothbay Harbor. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Boothbay Harbor ...
Beautifully renovated home w/ prime location - walk to the footbridge & downtown
Elegant home right in town with gorgeous water view, deck & interior

Elegant home right in town with gorgeous water view, deck & interior

Wiscasset
Stay at this vacation home in Wiscasset. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Castle Tucker and Lincoln County Jail Museum ...
Elegant home right in town with gorgeous water view, deck & interior
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
Book a stay at this beach vacation home in Boothbay Harbor. Enjoy a beach locale, a garden, and patios. Our guests praise the helpful staff in our reviews. Popular ...
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

Bailey Island
Book a stay at this family-friendly vacation home in Bailey Island. Enjoy free WiFi, a garden, and patios. Popular attractions Bailey Island Bridge and Cobwork ...
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Home In Boothbay - Holiday Getaway

Home In Boothbay - Holiday Getaway

Boothbay
Stay at this vacation home in Boothbay. Enjoy free WiFi, a garden, and patios. Popular attractions The Boothbay Playhouse and Dolphin Mini Golf are located ...
Home In Boothbay - Holiday Getaway
Welcome to Owl House - Your Coastal Retreat in East Boothbay!

Welcome to Owl House - Your Coastal Retreat in East Boothbay!

Boothbay
Stay at this vacation home in East Boothbay. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Grimes Cove Beach and Linekin Bay are located ...
Welcome to Owl House - Your Coastal Retreat in East 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.

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
645 Holiday Homes
Lowest Price
NZ$239
Highest Price
NZ$376
Popular accommodation
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!, The Globe House on Munjoy Hill - Walk to Breweries, Rent a room in the gorgeous Holt House, Beautifully renovated home w/ prime location - walk to the footbridge & downtown, Elegant home right in town with gorgeous water view, deck & interior, Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views, Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary, Home In Boothbay - Holiday Getaway, Welcome to Owl House - Your Coastal Retreat in East Boothbay!

Top trending hotels in Harpswell

1 room luxury ocean front studio cottage

1 room luxury ocean front studio cottage

Harpswell
Stay at this apartment in Harpswell. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Paddleworks and Bailey Island Bridge are located ...
1 room luxury ocean front studio cottage
Beautiful House just a step from ocean

Beautiful House just a step from ocean

Harpswell
Stay at this vacation home in Harpswell. Enjoy a fitness center, in-room jetted tubs, and air conditioning. Popular attractions Thomas Point Beach and Brunswick ...
Beautiful House just a step from ocean
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is NZ$239 per night from 11 May to 12 May
NZ$239
includes taxes & fees
11 May - 12 May
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the bar and the helpful staff in ...
The Westin Portland Harborview
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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 NZ$376 per night from 29 Apr to 30 Apr
NZ$376
includes taxes & fees
29 Apr - 30 Apr
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the bar and the ...
Portland Harbor 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.