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.
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Portland
A stay at this vacation home places you in the heart of Portland, steps from Casco Bay and 3 minutes by foot from University of Southern Maine.
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Lakefront House

Lakefront House

Windham
Located in Windham, this vacation home is on the waterfront, within a 10-minute drive of Maine Wildlife Park and Mercy Primary Care.
Lakefront House
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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
A stay at this vacation home places you in the heart of Portland, steps from Casco Bay and 3 minutes by foot from Maine Jewish Museum.
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
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
Private 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi

Private 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi

Scarborough
Located in Scarborough, this vacation home is on the waterfront, within a 10-minute drive of Gorham Country Club and Sable Oaks Golf Course.
Private 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi
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
Dog-friendly bay view home - water views, dock access & Linekin Bay Resort fun

Dog-friendly bay view home - water views, dock access & Linekin Bay Resort fun

Boothbay Harbor
When you a stay at this vacation home in Boothbay Harbor, you'll be by the sea, just steps from Cabbage Island and Linekin Bay.
Dog-friendly bay view home - water views, dock access & Linekin Bay Resort fun
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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
493 Holiday Homes
Lowest Price
AU$161
Highest Price
AU$259
Popular accommodation
Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown., Spacious & Sunny 4 Bedroom Close to Downtown, hot tub, Lakefront House, Beautiful Combo Home Located in Downtown Portland - Close to the Beach, Private Oceanfront Cottage, Private Sand Beach -Lighthouse one mile away, Oceanfront Cabin-Castle in Maine Woods, Private 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi, Bayfront home with 270-degree views, large deck & porch - near Popham Beach, Dog-friendly bay view home - water views, dock access & Linekin Bay Resort fun

Top trending hotels in Harpswell

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 AU$161 per night from 27 Jan to 28 Jan
AU$161
includes taxes & fees
27 Jan - 28 Jan
With a stay at The Westin Portland Harborview, you'll be centrally located in Portland, steps from State Theatre and Portland Museum of Art.
The Westin Portland Harborview
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$166 per night from 8 Jan to 9 Jan
AU$166
includes taxes & fees
8 Jan - 9 Jan
Located in Portland (Nasons Corner), Ramada Plaza by Wyndham Portland is within a 5-minute drive of Happy Wheels Skate Center and Fore River Sanctuary.
Ramada Plaza by Wyndham Portland
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$259 per night from 8 Jan to 9 Jan
AU$259
includes taxes & fees
8 Jan - 9 Jan
A stay at Portland Harbor Hotel places you in the heart of Portland, steps from Casco Bay and 3 minutes by foot from Cross Insurance Arena.
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$256 per night from 12 Jan to 13 Jan
AU$256
includes taxes & fees
12 Jan - 13 Jan
With a stay at Canopy by Hilton Portland Waterfront in Portland (Downtown Portland), you'll be steps from Casco Bay and 3 minutes by foot from Cross Insurance ...
Canopy by Hilton Portland Waterfront
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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.