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Squirrel Island Holiday Rentals

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50 rentals in Squirrel Island.
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Darling Rustic Ocean Point Cottage, holiday rental in Squirrel Island

Darling Rustic Ocean Point Cottage

4 bedrooms
2 bathrooms
Sleeps 9
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Dog-friendly, bayfront home w/ gorgeous ocean views & a full kitchen, holiday rental in Squirrel Island

Dog-friendly, bayfront home w/ gorgeous ocean views & a full kitchen

4 bedrooms
3 bathrooms
Sleeps 10
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Water Views, Wrap Around Porch, 3 BR Coastal Home, holiday rental in Squirrel Island

Water Views, Wrap Around Porch, 3 BR Coastal Home

3 bedrooms
2 bathrooms
Sleeps 6
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Ocean front cottage with spectacular view, holiday rental in Squirrel Island

Ocean front cottage with spectacular view

2 bedrooms
2 bathrooms
Sleeps 6
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A Unique Experience!!, holiday rental in Squirrel Island

A Unique Experience!!

2 bedrooms
1 bathroom
Sleeps 5
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Stunning Renovated Waterfront Home with Private Deepwater Dock; Windows Galore!, holiday rental in Squirrel Island

Stunning Renovated Waterfront Home with Private Deepwater Dock; Windows Galore!

4 bedrooms
3 bathrooms
Sleeps 8
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Lobster Cove Lookout, holiday rental in Squirrel Island

Lobster Cove Lookout

3 bedrooms
1 bathroom
Sleeps 6
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Year Round Luxury Waterfront Condo, Heart of Boothbay Harbor, holiday rental in Squirrel Island

Year Round Luxury Waterfront Condo, Heart of Boothbay Harbor

3 bedrooms
2 bathrooms
Sleeps 6
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Boothbay/Ocean Point 1/1 Air conditioned Oceanfront apartment, holiday rental in Squirrel Island

Boothbay/Ocean Point 1/1 Air conditioned Oceanfront apartment

1 bedroom
1 bathroom
Sleeps 2
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Updated Cottage on Water’s Edge with Deepwater Boat Dock!, holiday rental in Squirrel Island

Updated Cottage on Water’s Edge with Deepwater Boat Dock!

1 bedroom
1 bathroom
Sleeps 2
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Waterfront Cottage!  2 Bedroom, 2 Bath  **Walk to Town*  1/2 Mile to the Harbor, holiday rental in Squirrel Island

Waterfront Cottage! 2 Bedroom, 2 Bath **Walk to Town* 1/2 Mile to the Harbor

2 bedrooms
2 bathrooms
Sleeps 4
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Historic House Featured in March 2015 House Beautiful Magazine!, holiday rental in Squirrel Island

Historic House Featured in March 2015 House Beautiful Magazine!

5 bedrooms
3 bathrooms
Sleeps 13
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Cozy Boothbay Harbor Cottage, holiday rental in Squirrel Island

Cozy Boothbay Harbor Cottage

1 bedroom
2 bathrooms
Sleeps 2
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Relax & Enjoy Beautiful Views From This 2BR with Loft Cottage On the Sea, holiday rental in Squirrel Island

Relax & Enjoy Beautiful Views From This 2BR with Loft Cottage On the Sea

2 bedrooms
1 bathroom
Sleeps 4
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Classic Maine Waterfront Cottage w/ Deepwater Dock, holiday rental in Squirrel Island

Classic Maine Waterfront Cottage w/ Deepwater Dock

4 bedrooms
2 bathrooms
Sleeps 7
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Oceanfront Cottage On Linekin Bay Boothbay Harbor, holiday rental in Squirrel Island

Oceanfront Cottage On Linekin Bay Boothbay Harbor

1 bedroom
1 bathroom
Sleeps 2
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Vintage Victorian Oceanfront with Deep Water Dock and Pool, holiday rental in Squirrel Island

Vintage Victorian Oceanfront with Deep Water Dock and Pool

6 bedrooms
5 bathrooms
Sleeps 10
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Cedar Log Cabin in Boothbay Harbor, Maine, holiday rental in Squirrel Island

Cedar Log Cabin in Boothbay Harbor, Maine

3 bedrooms
2 bathrooms
Sleeps 5
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Cozy, dog-friendly cabin w/ a wood burning fireplace & a full kitchen, holiday rental in Squirrel Island

Cozy, dog-friendly cabin w/ a wood burning fireplace & a full kitchen

2 bedrooms
1 bathroom
Sleeps 6
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Quiet family and pet friendly home, holiday rental in Squirrel Island

Quiet family and pet friendly home

2 bedrooms
1 bathroom
Sleeps 4
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Pointed Fir Cove: Stunning Ocean Front Maine Retreat for Discerning Vacationers!, holiday rental in Squirrel Island

Pointed Fir Cove: Stunning Ocean Front Maine Retreat for Discerning Vacationers!

6 bedrooms
5 bathrooms
Sleeps 12
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Charming water view home overlooking Mill Cove w/ a large deck - near town, holiday rental in Squirrel Island

Charming water view home overlooking Mill Cove w/ a large deck - near town

2 bedrooms
2 bathrooms
Sleeps 4
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Landings East...Classic Waterfront Coastal Home, holiday rental in Squirrel Island

Landings East...Classic Waterfront Coastal Home

2 bedrooms
2 bathrooms
Sleeps 4
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Lovely waterfront home, harbour-side setting, holiday rental in Squirrel Island

Lovely waterfront home, harbour-side setting

2 bedrooms
2 bathrooms
Sleeps 4
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Inviting & rustic cabin w/wood-burning fireplace & grill- Enjoy a private beach!, holiday rental in Squirrel Island

Inviting & rustic cabin w/wood-burning fireplace & grill- Enjoy a private beach!

1 bedroom
1 bathroom
Sleeps 4
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Oceanfront  Cottage Southport 3 BR 2BA, Handicapped Accessible, holiday rental in Squirrel Island

Oceanfront Cottage Southport 3 BR 2BA, Handicapped Accessible

3 bedrooms
2 bathrooms
Sleeps 7
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Sea Haven at Ocean Point, holiday rental in Squirrel Island

Sea Haven at Ocean Point

3 bedrooms
1 bathroom
Sleeps 8
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Decker Cove Southport Paradise with Central Air Conditioning, holiday rental in Squirrel Island

Decker Cove Southport Paradise with Central Air Conditioning

3 bedrooms
3 bathrooms
Sleeps 6
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Century-old oceanfront home w/ wrap-around porch - walk downtown, dogs OK!, holiday rental in Squirrel Island

Century-old oceanfront home w/ wrap-around porch - walk downtown, dogs OK!

4 bedrooms
2 bathrooms
Sleeps 12
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New listing! Beautiful, dog-friendly home w/ water views, deck, & gas fireplace, holiday rental in Squirrel Island

New listing! Beautiful, dog-friendly home w/ water views, deck, & gas fireplace

4 bedrooms
3 bathrooms
Sleeps 9
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Rustic bayfront cottage with fantastic views - just minutes to downtown!, holiday rental in Squirrel Island

Rustic bayfront cottage with fantastic views - just minutes to downtown!

3 bedrooms
1 bathroom
Sleeps 6
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Pointed Fir Cove - Ocean Manor Home, holiday rental in Squirrel Island

Pointed Fir Cove - Ocean Manor Home

4 bedrooms
4 bathrooms
Sleeps 8
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New listing! Woodsy home w/ a cottage feel plus furnished decks & ocean view, holiday rental in Squirrel Island

New listing! Woodsy home w/ a cottage feel plus furnished decks & ocean view

3 bedrooms
2 bathrooms
Sleeps 6
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Family home w/ wood stove, game room, gas grill & garden views - 2 dogs OK!, holiday rental in Squirrel Island

Family home w/ wood stove, game room, gas grill & garden views - 2 dogs OK!

3 bedrooms
3 bathrooms
Sleeps 6
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Open Plan 1- Bedroom Apt. Woods & Water. Southport., holiday rental in Squirrel Island

Open Plan 1- Bedroom Apt. Woods & Water. Southport.

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Boothbay Harbor Beach House by Park & Restaurants!, holiday rental in Squirrel Island

Boothbay Harbor Beach House by Park & Restaurants!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Ocean Point, Maine Cottage Weekly Rental, holiday rental in Squirrel Island

Ocean Point, Maine Cottage Weekly Rental

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful waterfront home, holiday rental in Squirrel Island

Beautiful waterfront home

2 bedrooms
2 bathrooms
Sleeps 4
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Beautiful Ocean Point Community, holiday rental in Squirrel Island

Beautiful Ocean Point Community

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Destination estate with exclusive views, privacy, and convenience, holiday rental in Squirrel Island

Destination estate with exclusive views, privacy, and convenience

6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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The Hilltop Boothbay Harbor Steps from the Footbridge and in town dog friendly, holiday rental in Squirrel Island

The Hilltop Boothbay Harbor Steps from the Footbridge and in town dog friendly

3 bedrooms
1 bathroom
Sleeps 5
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Tiny House Cottage, holiday rental in Squirrel Island

Tiny House Cottage

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Boothbay Harbor Cabin w/Spacious Deck & Yard!, holiday rental in Squirrel Island

Boothbay Harbor Cabin w/Spacious Deck & Yard!

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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2 bedroom  1 bath, large deck and dock, on the water in peaceful cove,   Year, holiday rental in Squirrel Island

2 bedroom 1 bath, large deck and dock, on the water in peaceful cove, Year

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming East Boothbay Cottage w/ Large Yard!, holiday rental in Squirrel Island

Charming East Boothbay Cottage w/ Large Yard!

1 bedroom
1 bathroom
Sleeps 6
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Pointed Fir Cove Cottage - Maine, holiday rental in Squirrel Island

Pointed Fir Cove Cottage - Maine

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Classic Home on Saltwater Pond in Secluded Oceanfront Neighborhood, holiday rental in Squirrel Island

Classic Home on Saltwater Pond in Secluded Oceanfront Neighborhood

3 bedrooms
2 bathrooms
Sleeps 8
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NEW! ‘Sprucewold’: Boothbay Harbor Cottage w/Deck, holiday rental in Squirrel Island

NEW! ‘Sprucewold’: Boothbay Harbor Cottage w/Deck

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor, holiday rental in Squirrel Island

Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Luxury Carriage House In Beautiful Spruce Point, Pets Welcome, holiday rental in Squirrel Island

Luxury Carriage House In Beautiful Spruce Point, Pets Welcome

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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