Southport Rentals
From $509 per night (USD)VRBO
Oceanfront, dog-friendly condo with Boothbay Harbor views & prime location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Whale's Tale Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $509 per night (USD)VRBO
From $470 per night (USD)Expedia
Charming cottage near the beach with balcony, deck, grill, fireplace - dogs OK
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
North Star Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $470 per night (USD)Expedia
From $2725 per night (USD)VRBO
Oceanfront Serenity: Exclusive Waterfront Estate with Private Dock
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Introducing a magnificent waterfront getaway presented by Legacy Properties Sotheby’s International Realty, set against ...
From $2725 per night (USD)VRBO
From $405 per night (USD)VRBO
Cedar Cove: a tranquil retreat on the water just minutes from Boothbay Harbor
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Cedar Cove was completed in 2023 and designed for tranquility: find yourself surrounded by woods and water, in a beauti ...
From $405 per night (USD)VRBO
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Dog-friendly forest cottage with HOA beach on Linekin Bay, walk to dining\/spa
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 4
Cooper Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
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From $346 per night (USD)Expedia
Newly renovated modern guest cottage across from Spruce Point Inn Pet Friendly!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps away from the ocean, across the street from the Spruce Point Inn and alongside an acre of wooded land, smell the s ...
From $346 per night (USD)Expedia
From $4925 per night (USD)VRBO
Generational Southport Property w\/ Private Beach Newly Available for Rent!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
**CONTACT US TO SEE RENTING AVAILABILITY** Get ready to enjoy amazing afternoon sun on your own private sandy beach, lo ...
From $4925 per night (USD)VRBO
From $721 per night (USD)Expedia
SPRUCE CABIN | OCEAN POINT | 3 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
THIS HOUSE RENTS WEEKLY, SATURDAY-SATURDAY, JUNE-OCTOBER ______________________________________________________________ ...
From $721 per night (USD)Expedia
From $421 per night (USD)VRBO
OWL HOUSE | SCREEN PORCH | 4 Bed, 2.5 Bath
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
THIS HOUSE RENTS WITH A 4-NIGHT MINIMUM, JUNE-OCTOBER This charming newly-built, year-round 3BR, 2.5 Bath Cape Cod-styl ...
From $421 per night (USD)VRBO
From $692 per night (USD)Expedia
MERWICK COTTAGE | GEORGETOWN | 3 Bed, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
THIS PROPERTY RENTS WEEKLY, SATURDAY - SATURDAY, JUNE - SEPTEMBER 4 NIGHT STAYS AVAILABLE IN THE SHOULDER SEASON. Due ...
From $692 per night (USD)Expedia
From $556 per night (USD)VRBO
Remodeled for 2024! Immaculate Southport Island home. 5 minutes to Boothbay!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Newly remodeled for the 2024 season, this charming and bright cottage features 5 bedrooms and will house 7 to 8 people. ...
From $556 per night (USD)VRBO
From $202 per night (USD)Expedia
The Ticket Office - Just the ticket for a Private & Romantic Getaway!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Why pay more per night for a noisy hotel room, when you can enjoy the privacy and charm of this one room cottage? Locat ...
From $202 per night (USD)Expedia
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Exclusive oceanfront location in Boothbay Harbor! Walk to town.
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Imagine waking up to the sunrise at your own oceanfront property. Take in the morning sounds and sights from the patio o ...
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From $398 per night (USD)Expedia
TERRAPIN COTTAGE | 2 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
THIS HOME RENTS WEEKLY, SATURDAY-SATURDAY, JUNE-SEPTEMBER 4 NIGHT MINIMUM IN THE FALL THE HOUSE (pictures are after the ...
From $398 per night (USD)Expedia
From $3225 per night (USD)VRBO
Eastern Compass | 5 Bed, 4 Bath
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
THIS HOME RENTS WITH A 4-NIGHT MINIMUM, JUNE-SEPTEMBER STAY FOR A WEEK FOR A SPECIAL RATE! ____________________________ ...
From $3225 per night (USD)VRBO
From $637 per night (USD)Expedia
NEW FOR 2024 | SEA MIST | 4 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
THIS HOME RENTS WITH A 7-NIGHT MINIMUM, JUNE-LABOR DAY 4 Night Minimum in Fall _______________________________________ ...
From $637 per night (USD)Expedia
From $1466 per night (USD)VRBO
SALT WATER LODGE | 4 Bed, 3.5 Bath
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
THIS HOUSE RENTS WITH A 4-NIGHT MINIMUM STAY FOR A WEEK OR LONGER FOR A SPECIAL RATE! _________________________________ ...
From $1466 per night (USD)VRBO
From $678 per night (USD)Expedia
Edge Of The Sea | 3 Bed, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
THIS PROPERTY RENTS WEEKLY, SATURDAY - SATURDAY, JUNE - SEPTEMBER ______________________________________________________ ...
From $678 per night (USD)Expedia
From $1119 per night (USD)VRBO
CLIFF COTTAGE | TOWNSEND GUT | 4 Bed, 2.5 Bath
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
THIS PROPERTY RENTS WEEKLY, SATURDAY - SATURDAY, JUNE - SEPTEMBER 4 NIGHT STAYS AVAILABLE IN THE SHOULDER SEASON. Welco ...
From $1119 per night (USD)VRBO
From $635 per night (USD)Expedia
THE LEDGE ON SOUTHPORT ISLAND | 3 Bed, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
THIS PROPERTY RENTS SATURDAY - SATURDAY, TWO WEEKS MINIMUM _____________________________________________________________ ...
From $635 per night (USD)Expedia
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An enchanting Maine cottage, where timeless charm meets modern luxury!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
This charming Maine cottage offers the best of both worlds – classic charm and modern amenities! Perfectly located on th ...
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From $379 per night (USD)Expedia
Beautiful Ocean Point Escape
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Greyview Cottage was built in 1895 and is located in the heart of a thriving summer community where kids still ride thei ...
From $379 per night (USD)Expedia
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Beautiful Ocean Point Escape
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Greyview Cottage was built in 1895 and is located in the heart of a thriving summer community where kids still ride thei ...
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From $602 per night (USD)Expedia
Charming Cottage with Panoramic Views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to our charming shingle style cottage nestled on Shore Road! As you step inside, the bright and airy atmosphere ...
From $602 per night (USD)Expedia
From $438 per night (USD)VRBO
Seawood Sunset Cottage: Southport Island
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Seawood Sunset Cottage is located on the beautiful island of Southport. Built by an artist and displaying much of her wo ...
From $438 per night (USD)VRBO
From $830 per night (USD)VRBO
Waterfront Home on Decker Cove
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Sit out on the covered porch or open deck and enjoy the boating activity out on Townsend Gut and across the protected co ...
From $830 per night (USD)VRBO
From $344 per night (USD)VRBO
Cozy Ocean Side Cottage with screened in Sun room! 5 minutes from Private beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
TheCottageAtFiveIslands.com The Cottage is a fully furnished 900 sq ft two bedroom with full kitchen, bathroom and livi ...
From $344 per night (USD)VRBO
From $590 per night (USD)VRBO
Birdsong Landing: Luxurious Coastal Farmhouse with Stunning Views and Dock!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This stunning, spacious coastal farmhouse has just completed a gut renovation. With only the finest fixtures and finishe ...
From $590 per night (USD)VRBO
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Woodlandview Lodge with Porch and Garden|Fireplace
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover the rich heritage and peaceful atmosphere in Boothbay Harbor when you book a stay in our lovely Lodge Room! Ide ...
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From $374 per night (USD)VRBO
Charming coastal home in idyllic Southport, Maine
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come enjoy coastal Maine island living at this comfortable Southport cottage. This peaceful Newagen retreat will make yo ...
From $374 per night (USD)VRBO
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Tranquil Ocean view home with a washer & dryer and a relaxing Deck
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Peaceful Waters Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
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From $377 per night (USD)Expedia
Oceanfront, dog-friendly condo with Boothbay Harbor views & prime location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Ocean Breeze Condo Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $377 per night (USD)Expedia
From $855 per night (USD)VRBO
Elegant Oceanfront Condo with Stunning Harbor Views & Spectacular Sunsets
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sunset Sanctuary Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $855 per night (USD)VRBO
From $643 per night (USD)Expedia
3-bedroom house- Sprucewold Boothbay Harbor. GARDENS AGLOW
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Discover this 3-bedroom gem in the highly desired Sprucewold area of Boothbay Harbor. This newly built house features ...
From $643 per night (USD)Expedia