Southport Rentals
From $1500 per night (USD)VRBO
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 ...
From $1500 per night (USD)VRBO
From $368 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 $368 per night (USD)Expedia
From $368 per night (USD)VRBO
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 ...
From $368 per night (USD)VRBO
From $468 per night (USD)Expedia
Three Lights Cottage by Sea Maine
- 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 $468 per night (USD)Expedia
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Charming Cottage on Ocean Point
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Your ideal Maine vacation begins in this classic cottage at Ocean Point. Sage Cottage welcomes you with open ocean view ...
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From $265 per night (USD)VRBO
3 BR, 1.5 BA home is perfect for your visit to Boothbay Harbor
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This spacious, comfortable one-level, 3 bedroom, 1 1/2 bath home has a large yard, views of the Sheepscot River and Indi ...
From $265 per night (USD)VRBO
From $165 per night (USD)VRBO
WINDSONG | 3 Bed, 1.5 Bath
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
THIS PROPERTY RENTS WITH A 3-NIGHT MINIMUM, JUNE - SEPTEMBER Cottage Connection is proud to offer one of the most uniqu ...
From $165 per night (USD)VRBO
From $260 per night (USD)Expedia
OAK POINT CABIN | WATERFRONT | 2 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
THIS HOME RENTS WITH A 4-NIGHT MINIMUM Stay for a week for a special rate! Get away from it all at this traditional Ma ...
From $260 per night (USD)Expedia
From $500 per night (USD)VRBO
Charming Boothbay Harbor cottage with elegant appointments and a private dock.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Town's End Cottage! Built in 1950, this charming cottage blends rustic knotty pine and elegant appointments f ...
From $500 per night (USD)VRBO
From $476 per night (USD)Expedia
Oceanfront, dog-friendly condo with Boothbay Harbor views & prime location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Whale's Tale Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $476 per night (USD)Expedia
From $291 per night (USD)VRBO
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 $291 per night (USD)VRBO
From $464 per night (USD)Expedia
Adirondack Feel With Ocean Appeal ... Yes Please!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Adirondack style cabin with large logs and original art will excite you when you open the front door, but wont you be su ...
From $464 per night (USD)Expedia
From $198 per night (USD)VRBO
Stunning log cabin with fireplace & nature views - near shopping & dining
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Hammond Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $198 per night (USD)VRBO
From $293 per night (USD)Expedia
Cozy & Pet-Friendly Log Cabin with Access to a Private Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Deer Creek Cabin is the best of both worlds - the cabin is close to Boothbay Harbor's wonderful restaurants and shopping ...
From $293 per night (USD)Expedia
From $159 per night (USD)VRBO
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 ...
From $159 per night (USD)VRBO
From $278 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 $278 per night (USD)Expedia
From $197 per night (USD)VRBO
Charming coastal cottage with high-speed WiFi, furnished deck, gas grill, & dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Blue Shutters Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $197 per night (USD)VRBO
From $189 per night (USD)Expedia
Prickly Hollow · Charming cottage in the woods easy walk into town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This pretty, shingled cottage is only minutes away from downtown Boothbay Harbor, yet so peaceful you can enjoy the soun ...
From $189 per night (USD)Expedia
From $351 per night (USD)VRBO
Charming Cottage Room with Porch | Hot Tub + Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Spend a relaxing stay in our Cottage Room in Boothbay Harbor! Whether you're traveling with friends or family, our space ...
From $351 per night (USD)VRBO
From $342 per night (USD)Expedia
Woodlandview Lodge with Fireplace + Spa Access
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Our relaxing ADA Lodge Room in Boothbay Harbor is the perfect getaway for you! Enjoy relaxing days lounging by the outdo ...
From $342 per night (USD)Expedia
From $442 per night (USD)VRBO
Bright Cottage Close to Waterfront! Private Porch
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
We can't wait to host you in our tranquil 2 Bedroom Cottage in Boothbay Harbor! Enjoy a relaxing stay with friends and f ...
From $442 per night (USD)VRBO
From $336 per night (USD)Expedia
Spa + Pool Access! Bright Woodland View Room
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Escape to Boothbay Harbor for a relaxing and tranquil escape! Enjoy days kayaking, whale watching, or paddle boarding on ...
From $336 per night (USD)Expedia
From $391 per night (USD)VRBO
Lodge Room with Partial Ocean View | Pool + Spa
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the rich heritage and peaceful atmosphere in Boothbay Harbor when you book a stay in our charming Lodge Room! I ...
From $391 per night (USD)VRBO
From $392 per night (USD)Expedia
Partial Ocean Views! ADA Room with Fireplace+Porch
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover the charm and picturesque atmosphere of Boothbay Harbor when you stay in our lovely ADA Lodge Room. Spend memor ...
From $392 per night (USD)Expedia
From $377 per night (USD)VRBO
Bright ADA Lodge Room with Partial Ocean Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Book a relaxing stay in our lovely ADA Lodge Room in Boothbay Harbor! Enjoy unforgettable days whale watching, kayaking, ...
From $377 per night (USD)VRBO
From $413 per night (USD)Expedia
Relaxing Escape! Partial Oceanview Lodge Room
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Ideally located between the ocean and the forest, our quiet escape is the perfect retreat for your group! Enjoy relaxing ...
From $413 per night (USD)Expedia
From $455 per night (USD)VRBO
Bright Oceanview Lodge Room | Private Porch + Spa
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Whether you're traveling with friends or family, our lovely Lodge Room in Boothbay Harbor is the perfect getaway for you ...
From $455 per night (USD)VRBO
From $435 per night (USD)Expedia
Beautiful Room + Porch | Shared Pool + Hot Tub
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Spend a relaxing stay in our bright Lodge Room in Boothbay Harbor! Whether you're traveling with friends or family, our ...
From $435 per night (USD)Expedia
From $650 per night (USD)VRBO
Oceanfront House on 2 acres, Sleeps 8, Use of SPI amenities-6 passes. Views!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Windjammer Week Available! (June 23-30). For June, July, and August stays of 7 nights minimum are required, with a Sund ...
From $650 per night (USD)VRBO
From $185 per night (USD)Expedia
Charming Cottage in Boothbay Harbor 5 minutes from Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 14
Enjoy an entire private cottage in Boothbay Harbor region and stay in a 1,200 square foot, 3BR/1.5BA private home on .5 ...
From $185 per night (USD)Expedia
From $788 per night (USD)VRBO
SPRUCE CABIN | OCEAN POINT | 3 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
THIS HOUSE RENTS WEEKLY, SATURDAY-SATURDAY, JUNE-OCTOBER ______________________________________________________________ ...
From $788 per night (USD)VRBO
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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 ...
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From $441 per night (USD)VRBO
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 $441 per night (USD)VRBO
From $2600 per night (USD)VRBO
Eastern Compass | 5 Bed, 4 Bath
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
THIS HOME RENTS WEEKLY, SATURDAY-SATURDAY, JUNE-SEPTEMBER ______________________________________________________________ ...
From $2600 per night (USD)VRBO
From $873 per night (USD)VRBO
SALT WATER LODGE | 4 Bed, 3.5 Bath
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
THIS HOUSE RENTS WEEKLY, SATURDAY-SATURDAY, JUNE-SEPTEMBER 4 NIGHT STAYS AVAILABLE IN THE FALL ________________________ ...
From $873 per night (USD)VRBO
From $407 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 $407 per night (USD)Expedia
From $300 per night (USD)VRBO
Original Cottage Of Spruce Point Inn - Special rate for June
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This appealing & cozy cottage is located in the desirable Spruce Point Colony and is one of the original cottages of Spr ...
From $300 per night (USD)VRBO
From $357 per night (USD)Expedia
Beautiful Summer Cottage on Iconic Ocean Point
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Ocean Point, East Boothbay, Maine. Ocean Point is a friendly community of seasonal, rental and year-round fa ...
From $357 per night (USD)Expedia
From $304 per night (USD)VRBO
Just one block from the Ocean!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Coastal cottage sits one block from the ocean and a short walk from the community center where there are tennis, pickleb ...
From $304 per night (USD)VRBO
From $368 per night (USD)Expedia
Stunning Views with Walks to the Beach
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 11
Located in East Boothbay on breathtaking Ocean Point sits this traditional cottage with three porches. Enjoy the view fr ...
From $368 per night (USD)Expedia
From $330 per night (USD)VRBO
Charming Home located on McKown Point , 5 min. drive to downtown Boothbay Harbor
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
You’ll enjoy peeks of the water from this charming home. One floor living with fully equipped kitchen including a microw ...
From $330 per night (USD)VRBO