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Harpswell Holiday Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
85 rentals in Harpswell.
Beautiful house on the Harpswell Peninsula over looking Casco Bay, holiday rental in Harpswell
Beautiful house on the Harpswell Peninsula over looking Casco Bay, holiday rental in Harpswell
Beautiful house on the Harpswell Peninsula over looking Casco Bay, holiday rental in Harpswell

Beautiful house on the Harpswell Peninsula over looking Casco Bay

Holiday Rental House
8 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly., holiday rental in Harpswell
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly., holiday rental in Harpswell
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly., holiday rental in Harpswell

Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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1 room luxury ocean front studio cottage, holiday rental in Harpswell
1 room luxury ocean front studio cottage, holiday rental in Harpswell
1 room luxury ocean front studio cottage, holiday rental in Harpswell

1 room luxury ocean front studio cottage

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Osprey's Nest. Waterfront unit with boat and kayak access. Pet Friendly!, holiday rental in Harpswell
Osprey's Nest. Waterfront unit with boat and kayak access. Pet Friendly!, holiday rental in Harpswell
Osprey's Nest. Waterfront unit with boat and kayak access. Pet Friendly!, holiday rental in Harpswell

Osprey's Nest. Waterfront unit with boat and kayak access. Pet Friendly!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Centerview cottage, holiday rental in Harpswell
Centerview cottage, holiday rental in Harpswell
Centerview cottage, holiday rental in Harpswell

Centerview cottage

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Spectacular 8 Acre Oceanfront Property with Beautiful Sunsets, holiday rental in Harpswell
Spectacular 8 Acre Oceanfront Property with Beautiful Sunsets, holiday rental in Harpswell
Spectacular 8 Acre Oceanfront Property with Beautiful Sunsets, holiday rental in Harpswell

Spectacular 8 Acre Oceanfront Property with Beautiful Sunsets

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Dog-friendly home with high-speed WiFi, washer/dryer, & private dock, holiday rental in Harpswell
Dog-friendly home with high-speed WiFi, washer/dryer, & private dock, holiday rental in Harpswell
Dog-friendly home with high-speed WiFi, washer/dryer, & private dock, holiday rental in Harpswell

Dog-friendly home with high-speed WiFi, washer/dryer, & private dock

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Private Ocean Front property with bathing cove and deep water swimming, holiday rental in Harpswell
Private Ocean Front property with bathing cove and deep water swimming, holiday rental in Harpswell
Private Ocean Front property with bathing cove and deep water swimming, holiday rental in Harpswell

Private Ocean Front property with bathing cove and deep water swimming

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sea Forever! Waterfront, Seasonal dock, Pet friendly,  20 min to Bowdoin College, holiday rental in Harpswell
Sea Forever! Waterfront, Seasonal dock, Pet friendly,  20 min to Bowdoin College, holiday rental in Harpswell
Sea Forever! Waterfront, Seasonal dock, Pet friendly,  20 min to Bowdoin College, holiday rental in Harpswell

Sea Forever! Waterfront, Seasonal dock, Pet friendly, 20 min to Bowdoin College

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Morningside. Waterfront home with seasonal dock and float, Pet friendly!, holiday rental in Harpswell
Morningside. Waterfront home with seasonal dock and float, Pet friendly!, holiday rental in Harpswell
Morningside. Waterfront home with seasonal dock and float, Pet friendly!, holiday rental in Harpswell

Morningside. Waterfront home with seasonal dock and float, Pet friendly!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bay-View. Waterfront Log cabin on the bay. Pet Friendly., holiday rental in Harpswell
Bay-View. Waterfront Log cabin on the bay. Pet Friendly., holiday rental in Harpswell
Bay-View. Waterfront Log cabin on the bay. Pet Friendly., holiday rental in Harpswell

Bay-View. Waterfront Log cabin on the bay. Pet Friendly.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Breathtaking Oceanfront Views with Deep-Water Dock and Mooring, holiday rental in Harpswell
Breathtaking Oceanfront Views with Deep-Water Dock and Mooring, holiday rental in Harpswell
Breathtaking Oceanfront Views with Deep-Water Dock and Mooring, holiday rental in Harpswell

Breathtaking Oceanfront Views with Deep-Water Dock and Mooring

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Quaint antique island home, holiday rental in Harpswell
Quaint antique island home, holiday rental in Harpswell
Quaint antique island home, holiday rental in Harpswell

Quaint antique island home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Lofty cottage, holiday rental in Harpswell
Lofty cottage, holiday rental in Harpswell
Lofty cottage, holiday rental in Harpswell

Lofty cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Sunrise Catcher with a Panoramic View!, holiday rental in Harpswell
Sunrise Catcher with a Panoramic View!, holiday rental in Harpswell
Sunrise Catcher with a Panoramic View!, holiday rental in Harpswell

Sunrise Catcher with a Panoramic View!

Holiday Rental House
3 bedrooms
5 bathrooms
Sleeps 6
Match: Sleeps
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Charming Maine cottage overlooking the working waterfront., holiday rental in Harpswell
Charming Maine cottage overlooking the working waterfront., holiday rental in Harpswell
Charming Maine cottage overlooking the working waterfront., holiday rental in Harpswell

Charming Maine cottage overlooking the working waterfront.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Harpswell, Maine, Seascape, Honeymoon Retreat, Writer's Paradise, On the Water, holiday rental in Harpswell
Harpswell, Maine, Seascape, Honeymoon Retreat, Writer's Paradise, On the Water, holiday rental in Harpswell
Harpswell, Maine, Seascape, Honeymoon Retreat, Writer's Paradise, On the Water, holiday rental in Harpswell

Harpswell, Maine, Seascape, Honeymoon Retreat, Writer's Paradise, On the Water

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Quintessential oceanfront Maine cottage on the shore of picturesque Cundy`s, holiday rental in Harpswell
Quintessential oceanfront Maine cottage on the shore of picturesque Cundy`s, holiday rental in Harpswell
Quintessential oceanfront Maine cottage on the shore of picturesque Cundy`s, holiday rental in Harpswell

Quintessential oceanfront Maine cottage on the shore of picturesque Cundy`s

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Oceanfront Cottage with Spectacular Sunset Views, holiday rental in Harpswell
Charming Oceanfront Cottage with Spectacular Sunset Views, holiday rental in Harpswell
Charming Oceanfront Cottage with Spectacular Sunset Views, holiday rental in Harpswell

Charming Oceanfront Cottage with Spectacular Sunset Views

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy cottage, holiday rental in Harpswell
Cozy cottage, holiday rental in Harpswell
Cozy cottage, holiday rental in Harpswell

Cozy cottage

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Sunny Cottage on Private Oceanfront Point, holiday rental in Harpswell
Sunny Cottage on Private Oceanfront Point, holiday rental in Harpswell
Sunny Cottage on Private Oceanfront Point, holiday rental in Harpswell

Sunny Cottage on Private Oceanfront Point

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy Waterfront Cottage in Harpswell, Maine, holiday rental in Harpswell
Cozy Waterfront Cottage in Harpswell, Maine, holiday rental in Harpswell
Cozy Waterfront Cottage in Harpswell, Maine, holiday rental in Harpswell

Cozy Waterfront Cottage in Harpswell, Maine

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Camp Forever cottage, holiday rental in Harpswell
Camp Forever cottage, holiday rental in Harpswell
Camp Forever cottage, holiday rental in Harpswell

Camp Forever cottage

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Oceanfront cottage with dock and float on beautiful Quahog Bay, holiday rental in Harpswell
Oceanfront cottage with dock and float on beautiful Quahog Bay, holiday rental in Harpswell
Oceanfront cottage with dock and float on beautiful Quahog Bay, holiday rental in Harpswell

Oceanfront cottage with dock and float on beautiful Quahog Bay

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Hopkin's view. Water's edge living in this 1 BR/1 BA first floor unit., holiday rental in Harpswell
Hopkin's view. Water's edge living in this 1 BR/1 BA first floor unit., holiday rental in Harpswell
Hopkin's view. Water's edge living in this 1 BR/1 BA first floor unit., holiday rental in Harpswell

Hopkin's view. Water's edge living in this 1 BR/1 BA first floor unit.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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ON the Water in Harpswell Maine, holiday rental in Harpswell
ON the Water in Harpswell Maine, holiday rental in Harpswell
ON the Water in Harpswell Maine, holiday rental in Harpswell

ON the Water in Harpswell Maine

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Cozy oceanfront cottage on Orr's Island, holiday rental in Harpswell
Cozy oceanfront cottage on Orr's Island, holiday rental in Harpswell
Cozy oceanfront cottage on Orr's Island, holiday rental in Harpswell

Cozy oceanfront cottage on Orr's Island

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Oceanfront Property, holiday rental in Harpswell
Oceanfront Property, holiday rental in Harpswell
Oceanfront Property, holiday rental in Harpswell

Oceanfront Property

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Dockside Cottage ~ A Quiet Coastal Waterfront Setting With Breathtaking Sunsets, holiday rental in Harpswell
Dockside Cottage ~ A Quiet Coastal Waterfront Setting With Breathtaking Sunsets, holiday rental in Harpswell
Dockside Cottage ~ A Quiet Coastal Waterfront Setting With Breathtaking Sunsets, holiday rental in Harpswell

Dockside Cottage ~ A Quiet Coastal Waterfront Setting With Breathtaking Sunsets

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy Waterfront Home, holiday rental in Harpswell
Cozy Waterfront Home, holiday rental in Harpswell
Cozy Waterfront Home, holiday rental in Harpswell

Cozy Waterfront Home

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Waterfront home on scenic cove., holiday rental in Harpswell
Waterfront home on scenic cove., holiday rental in Harpswell
Waterfront home on scenic cove., holiday rental in Harpswell

Waterfront home on scenic cove.

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Bayview Cottage with Deck, Firepit, Garden - 200' from the Water, holiday rental in Harpswell
Charming Bayview Cottage with Deck, Firepit, Garden - 200' from the Water, holiday rental in Harpswell
Charming Bayview Cottage with Deck, Firepit, Garden - 200' from the Water, holiday rental in Harpswell

Charming Bayview Cottage with Deck, Firepit, Garden - 200' from the Water

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Classic Maine House, wrap around deck,  water activity a walk away., holiday rental in Harpswell
Classic Maine House, wrap around deck,  water activity a walk away., holiday rental in Harpswell
Classic Maine House, wrap around deck,  water activity a walk away., holiday rental in Harpswell

Classic Maine House, wrap around deck, water activity a walk away.

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Watch The Sun Set, The Tide Change On A Beautiful And Peaceful Salt Water Inlet, holiday rental in Harpswell
Watch The Sun Set, The Tide Change On A Beautiful And Peaceful Salt Water Inlet, holiday rental in Harpswell
Watch The Sun Set, The Tide Change On A Beautiful And Peaceful Salt Water Inlet, holiday rental in Harpswell

Watch The Sun Set, The Tide Change On A Beautiful And Peaceful Salt Water Inlet

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Waterfront log cabin nestled in the woods providing unparalleled privacy, holiday rental in Harpswell
Waterfront log cabin nestled in the woods providing unparalleled privacy, holiday rental in Harpswell
Waterfront log cabin nestled in the woods providing unparalleled privacy, holiday rental in Harpswell

Waterfront log cabin nestled in the woods providing unparalleled privacy

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Charming summer cottage with all the comforts of home. Fabulous covered porch, holiday rental in Harpswell
Charming summer cottage with all the comforts of home. Fabulous covered porch, holiday rental in Harpswell
Charming summer cottage with all the comforts of home. Fabulous covered porch, holiday rental in Harpswell

Charming summer cottage with all the comforts of home. Fabulous covered porch

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Amazing Oceanfront Private Cottage Deep H2O Dock, holiday rental in Harpswell
Amazing Oceanfront Private Cottage Deep H2O Dock, holiday rental in Harpswell
Amazing Oceanfront Private Cottage Deep H2O Dock, holiday rental in Harpswell

Amazing Oceanfront Private Cottage Deep H2O Dock

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Old Farm Cottage  - Harpswell, Maine, holiday rental in Harpswell
Old Farm Cottage  - Harpswell, Maine, holiday rental in Harpswell
Old Farm Cottage  - Harpswell, Maine, holiday rental in Harpswell

Old Farm Cottage - Harpswell, Maine

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Thorburn - Experience a classic ME vacation at this beautiful summer cottage, holiday rental in Harpswell
Thorburn - Experience a classic ME vacation at this beautiful summer cottage, holiday rental in Harpswell
Thorburn - Experience a classic ME vacation at this beautiful summer cottage, holiday rental in Harpswell

Thorburn - Experience a classic ME vacation at this beautiful summer cottage

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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This cozy Maine cottage is the perfect location enjoying sunrises!, holiday rental in Harpswell
This cozy Maine cottage is the perfect location enjoying sunrises!, holiday rental in Harpswell
This cozy Maine cottage is the perfect location enjoying sunrises!, holiday rental in Harpswell

This cozy Maine cottage is the perfect location enjoying sunrises!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful timber framed home with comfortable furnishings, on the ocean and, holiday rental in Harpswell
Beautiful timber framed home with comfortable furnishings, on the ocean and, holiday rental in Harpswell
Beautiful timber framed home with comfortable furnishings, on the ocean and, holiday rental in Harpswell

Beautiful timber framed home with comfortable furnishings, on the ocean and

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious single-story cottage with ocean views, large screen porch, and a quiet, holiday rental in Harpswell
Spacious single-story cottage with ocean views, large screen porch, and a quiet, holiday rental in Harpswell
Spacious single-story cottage with ocean views, large screen porch, and a quiet, holiday rental in Harpswell

Spacious single-story cottage with ocean views, large screen porch, and a quiet

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Rose Cottage Oceanfront with Private Dock, holiday rental in Harpswell
Rose Cottage Oceanfront with Private Dock, holiday rental in Harpswell
Rose Cottage Oceanfront with Private Dock, holiday rental in Harpswell

Rose Cottage Oceanfront with Private Dock

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Ocean  Front  House with large wharf and dock, holiday rental in Harpswell
Ocean  Front  House with large wharf and dock, holiday rental in Harpswell
Ocean  Front  House with large wharf and dock, holiday rental in Harpswell

Ocean Front House with large wharf and dock

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Water-view retreat with beach access, deck, grill, EV charger & lawn games, holiday rental in Harpswell
Water-view retreat with beach access, deck, grill, EV charger & lawn games, holiday rental in Harpswell
Water-view retreat with beach access, deck, grill, EV charger & lawn games, holiday rental in Harpswell

Water-view retreat with beach access, deck, grill, EV charger & lawn games

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterledge Cottage - Orrs Island, Maine, holiday rental in Harpswell
Waterledge Cottage - Orrs Island, Maine, holiday rental in Harpswell
Waterledge Cottage - Orrs Island, Maine, holiday rental in Harpswell

Waterledge Cottage - Orrs Island, Maine

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Relax in the serenity of this accommodating waterfront home!, holiday rental in Harpswell
Relax in the serenity of this accommodating waterfront home!, holiday rental in Harpswell
Relax in the serenity of this accommodating waterfront home!, holiday rental in Harpswell

Relax in the serenity of this accommodating waterfront home!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Spectacular waterfront home with panoramic views on 4 private acres !, holiday rental in Harpswell
Spectacular waterfront home with panoramic views on 4 private acres !, holiday rental in Harpswell
Spectacular waterfront home with panoramic views on 4 private acres !, holiday rental in Harpswell

Spectacular waterfront home with panoramic views on 4 private acres !

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Windward - Enjoy privacy, comfortable living spaces, and easy water access, holiday rental in Harpswell
Windward - Enjoy privacy, comfortable living spaces, and easy water access, holiday rental in Harpswell
Windward - Enjoy privacy, comfortable living spaces, and easy water access, holiday rental in Harpswell

Windward - Enjoy privacy, comfortable living spaces, and easy water access

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Cottage located on the Shore of Quahog Bay - Spacious deck and, holiday rental in Harpswell
Beautiful Cottage located on the Shore of Quahog Bay - Spacious deck and, holiday rental in Harpswell
Beautiful Cottage located on the Shore of Quahog Bay - Spacious deck and, holiday rental in Harpswell

Beautiful Cottage located on the Shore of Quahog Bay - Spacious deck and

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Showing results 1-50 of 85
Frequently Asked Questions about Harpswell