Southport Rentals
From $841 per night (USD)VRBO
Saltwater farmhouse on 2+ acres of waterfront with private dock
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Hartwell House has origins in the 1770s and expanded in the 1800s and 1970s. It is in a protected cove off Ebenecook Ba ...
From $841 per night (USD)VRBO
From $319 per night (USD)VRBO
Oceanfront Cottage Southport 3 BR 2BA, Handicapped Accessible
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Snowman Cottage -- Southport Enjoy water views of Cape Harbor and the open ocean from nearly every room in this 3-bedroo ...
From $319 per night (USD)VRBO
From $95 per night (USD)VRBO
Boothbay Harbor, Maine Beautiful Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This room has a personal key. Spacious Bedroom with a firm Queen Bed, a love seat, and a comfortable chair, a refrigera ...
From $95 per night (USD)VRBO
From $375 per night (USD)Expedia
Classic Boathouse - 2BD Waterfront Cottage - Dock & Float Access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Classic Waterfront Cottage on Townsend Gut - Southport! Perched right at the water’s edge on scenic Townsend Gut, Class ...
From $375 per night (USD)Expedia
From $164 per night (USD)VRBO
Charming Plumpoint Cottage On Southport Island
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy the serenity of beautiful Southport Island in a classic Maine cottage with a peek at Decker's Cove. Walk to Robins ...
From $164 per night (USD)VRBO
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Pennoyer Point Cottage - 4 BR Waterfront Cottage B- Mooring Access + Shared Dock
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 13
Ultimate Classic Maine Waterfront Cottage – Perfect for Family Fun! Welcome to the ultimate Maine vacation spot, where ...
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From $483 per night (USD)VRBO
Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Spruce Ledge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $483 per night (USD)VRBO
From $501 per night (USD)Expedia
Cottage Room | Porch+HotTub+Pool | No Hidden Fees
- 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 $501 per night (USD)Expedia
From $495 per night (USD)VRBO
Woodland ADA Lodge | Spa Access | No Hidden Fees
- 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 $495 per night (USD)VRBO
From $635 per night (USD)Expedia
Bright Cottage| Porch+Waterfront | No Hidden Fees
- 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 $635 per night (USD)Expedia
From $475 per night (USD)VRBO
Woodland View Rm | Spa & Pool | No Hidden Fees
- 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 $475 per night (USD)VRBO
From $475 per night (USD)Expedia
Ocean Peek Lodge | Pool+Spa | No Hidden Fees
- 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 $475 per night (USD)Expedia
From $440 per night (USD)VRBO
ADA Rm | Ocean Peek+Porch+FP | No Hidden Fees
- 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 $440 per night (USD)VRBO
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Bright ADA Lodge Rm | Ocean Peek | No Hidden Fees
- 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, ...
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From $505 per night (USD)VRBO
Relaxing Lodge Rm | Ocean Peek | No Hidden Fees
- 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 $505 per night (USD)VRBO
From $542 per night (USD)Expedia
Lodge Rm | Oceanview+Spa+Porch | No Hidden Fees
- 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 $542 per night (USD)Expedia
From $473 per night (USD)VRBO
Beautiful Rm | Porch+HotTub+Pool | No Hidden Fees
- 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 $473 per night (USD)VRBO
From $164 per night (USD)Expedia
3 Bedroom Classic Maine Cottage, Close To Beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Open floor plan cottage, on wooded, private lot, less than 5 minute walk to beautiful, perfect-for-kids beach. Well equ ...
From $164 per night (USD)Expedia
From $275 per night (USD)VRBO
Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Come enjoy the peaceful tranquility of this lakefront retreat just 5 minutes from the quaint seaside shops and restauran ...
From $275 per night (USD)VRBO
From $649 per night (USD)VRBO
Oceanfront House on 2 acres, Sleeps 8, incredible property. Views!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
For June, July, and August stays of 7 nights minimum are required, with a Sunday check in, but we will try to accommodat ...
From $649 per night (USD)VRBO
From $491 per night (USD)VRBO
Historic riverfront home with boathouse & private dock - dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Captain Kent's Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $491 per night (USD)VRBO
From $451 per night (USD)Expedia
Stunning oceanfront cottage w/ private deck and Atlantic views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Serene Newagen House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $451 per night (USD)Expedia
From $363 per night (USD)VRBO
Enjoy the stunning views while relaxing on the deck at East Ledge Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Treat yourself to a Maine Classic! East Ledge Cottage in Georgetown is a beautiful property with stunning water views fr ...
From $363 per night (USD)VRBO
From $311 per night (USD)VRBO
Charming cottage overlooking picturesque Five Islands Harbor
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
3 Bedroom cottage overlooking the quintessential Maine working harbor of Five Islands. Watch lobster boats come and go ...
From $311 per night (USD)VRBO
From $184 per night (USD)VRBO
Waterfront Cottage With An Awesome View Of Capital And Burnt Island
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Two story home, with 3 bedrooms upstairs and Bathroom down stairs.Large living area with a beautiful view of the ocean a ...
From $184 per night (USD)VRBO
From $382 per night (USD)VRBO
Oceanfront Juniper Point Cottage with dock, screened porch, close boat traffic
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Fun, unique spot with lots of diverse boats traveling right by property. Seasonal cottage with great views, private doc ...
From $382 per night (USD)VRBO
From $477 per night (USD)VRBO
Steamboat Landing Cottage
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Steamboat Landing - Southport Island, Maine. Nestled between Sheepscot Bay and Boothbay, Southport Island is connected ...
From $477 per night (USD)VRBO
From $255 per night (USD)Expedia
A Cozy Retreat on Southport Island
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This cute-as-a-button waterfront cottage is located on Southport Island across the swing bridge from Boothbay Harbor. "P ...
From $255 per night (USD)Expedia
From $444 per night (USD)VRBO
Coastal Island Retreat - Privacy and Convenience. Boat rental available.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Bird's Nest sits high on a secluded ledge immediately on the rocky shore of the mouth of the Sheepscot River. Fall is th ...
From $444 per night (USD)VRBO
From $350 per night (USD)VRBO
Sea Haven at Ocean Point
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Located in the heart of the Ocean Point Colony this three-bedroom summer cottage offers the experience of a true Maine v ...
From $350 per night (USD)VRBO
From $438 per night (USD)VRBO
Ocean Point home, large porch, picturesque views, beach access
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
Ocean Point Cottage With Waterfront Access Our calendar is updated in real-time & our nightly rates are accurately disp ...
From $438 per night (USD)VRBO
From $355 per night (USD)Expedia
Coastal bungalow with large yard, beautiful kitchen, & great location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Captains Cottage on Atlantic Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $355 per night (USD)Expedia
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A Picturesque Cottage on Capitol Island, Maine
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Capitol Island is the epitome of quintessential Maine! Capitol with a Sea cottage is situated just above the docks at t ...
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From $938 per night (USD)VRBO
Newly Restored 1920's Vintage Boathouse.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Impeccably restored former boathouse. Very unique property that features a spectacular view of Boothbay Harbor and the o ...
From $938 per night (USD)VRBO
From $327 per night (USD)VRBO
Ocean Point, Maine Cottage Weekly Rental
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
A beautiful Ocean Point Cottage! This charming cottage, rarely rented, is privately located at the end of a long drivewa ...
From $327 per night (USD)VRBO
From $461 per night (USD)Expedia
Oceanfront 2 bedroom unit on The Harbor
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to the Barnacle! Located right in the heart of Boothbay Harbor and is a short walk to the downtown area. This ne ...
From $461 per night (USD)Expedia
From $690 per night (USD)VRBO
Stunning Renovated Waterfront Home with Private Deepwater Dock; Windows Galore!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
On the water with expansive views and a private deepwater dock on the property for your boat. This location cannot be be ...
From $690 per night (USD)VRBO
From $329 per night (USD)Expedia
Historical New England home, outdoor shower , Dog-friendly
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Firehouse Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $329 per night (USD)Expedia
From $636 per night (USD)VRBO
Ocean Point Colony Home w/ Sunroom & Sweeping Ocean Views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Ocean Point Colony House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $636 per night (USD)VRBO
From $258 per night (USD)Expedia
Romley House | Deck & New Luxe Kitchen | Near Boothbay Harbor
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Romley House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $258 per night (USD)Expedia
From $504 per night (USD)VRBO
Beachfront Delight with detached guesthouse, sunset views & private beach access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Deep Cove Cabin Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $504 per night (USD)VRBO
From $624 per night (USD)Expedia
Oceanfront home incredible ocean views, deck & location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Tranquil Ocean Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $624 per night (USD)Expedia
From $627 per night (USD)VRBO
Decker Cove Southport Paradise with Central Air Conditioning
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Brand new construction in 2019. 3 bed, 3 bath home. Partial view of Decker Cove from all bedrooms, walking distance to R ...
From $627 per night (USD)VRBO
From $273 per night (USD)VRBO
Boothbay Harbor Cabin w/ Spacious Deck & Yard!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Now is the time to escape to peaceful surroundings, spend summer days hiking beneath bright blue skies, and enjoy starga ...
From $273 per night (USD)VRBO
From $323 per night (USD)VRBO
Relax over looking the quaint Five Islands Harbor in Georgetown Maine
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This 3 bedroom cottage sits right on the picturesque harbor of Five Islands with views out to the Sheepscot River and be ...
From $323 per night (USD)VRBO
From $210 per night (USD)VRBO
'Sprucewold' Boothbay Harbor Cottage w/ Deck
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy the northeast wilderness effortlessly with this intimate 2-bed, 1-bath vacation rental. Whether you're here with f ...
From $210 per night (USD)VRBO
From $432 per night (USD)VRBO
Prickly Hollow by Rocky Coast Rentals
- 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 $432 per night (USD)VRBO
From $333 per night (USD)Expedia
Secluded Dog-Friendly Getaway w/ Free WiFi, Private Washer/Dryer, Furnished Deck
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Island Pines Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $333 per night (USD)Expedia
From $496 per night (USD)VRBO
Wiggleswick Cottage; A Dogs Welcome Certified Property!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come experience the magic of Midcoast Maine at Wiggleswick Cottage on the island of Georgetown (accessible by car) owned ...
From $496 per night (USD)VRBO
From $311 per night (USD)VRBO
Updated Cottage on Water’s Edge with Deepwater Boat Dock!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
On the water with deepwater dock for your boat - this location cannot be beat. This cottage is located on Southport Isla ...
From $311 per night (USD)VRBO
From $174 per night (USD)VRBO
3 one-bedroom fully equipped cottages with free WIFI /weekly rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Dockside Cottage is located on Decker's Cove overlooking a busy waterway with lots of boat traffic. Lobster wharf + ...
From $174 per night (USD)VRBO
From $174 per night (USD)Expedia
3 one-bedroom fully equipped cottages with free WIFI /weekly rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Tan Cottage is located on Decker's Cove overlooking a busy waterway with lots of boat traffic. Lobster wharf + resta ...
From $174 per night (USD)Expedia
From $174 per night (USD)VRBO
3 one-bedroom fully equipped cottages with free WIFI /weekly rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The White Cottage is located on Decker's Cove overlooking a busy waterway with lots of boat traffic. Lobster wharf + res ...
From $174 per night (USD)VRBO
From $315 per night (USD)Expedia
Remodeled Cottage with AC, Private W/D, Full Kitchen, and High-Speed WiFi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Little Cottage in the Woods Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply e ...
From $315 per night (USD)Expedia
From $453 per night (USD)VRBO
Water's Edge - Waterfront Cottage on Southport - Wrap-Around Porch!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Charming Waterfront Cottage with Stunning Views of Townsend Gut - Southport! Nestled right on the waterfront of Townse ...
From $453 per night (USD)VRBO
From $384 per night (USD)Expedia
Gorgeous Views of Harbor Entrance!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Cottage at Roads End, situated on one of the most desirable streets in all of Boothbay Harbor. This one-story ...
From $384 per night (USD)Expedia
From $377 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 $377 per night (USD)VRBO
From $547 per night (USD)VRBO
Oceanfront home
- Bedrooms:
- 1
- Bathrooms:
- 5
- Sleeps:
- 9
Beautiful oceanfront home with large outdoor deck facing the water for dining and relaxing, Great sunsets. Private sand ...
From $547 per night (USD)VRBO
From $322 per night (USD)VRBO
Harborview Perch... spacious & open floorplan, privacy, harbor view, amenities
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
"Harborview Perch": comfortable & inviting with spectacular, elevated views of Boothbay Harbor! "Harborview Perch" a ...
From $322 per night (USD)VRBO
From $441 per night (USD)VRBO
Waterfront cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Beautiful Cottage on Southport Island with access to dock and kayaks. Cozy, the perfect getaway. Gorgeous sunsets. Priv ...
From $441 per night (USD)VRBO
From $341 per night (USD)VRBO
Decker Cove Cottage, new in 2020!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our cottage is brand new, built in 2020, Radiant Heat on both 1st and 2nd floor. Enjoy the tranquility of a cozy cottage ...
From $341 per night (USD)VRBO
From $292 per night (USD)Expedia
Breathtaking Water Views on Southport Island
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The sound of the waves will greet you even before you can lay eyes on the ocean. It will call you to the front porch wh ...
From $292 per night (USD)Expedia
From $490 per night (USD)VRBO
SALT WATER MAINE COTTAGE WITH DOCK - MINUTES TO BOTANICAL GARDENS
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Morning Star Cottage is the perfect year-round Maine vacation rental! This Victorian custom-built home is situated on a ...
From $490 per night (USD)VRBO
From $211 per night (USD)Expedia
Vintage, Log Cabin in the Woods with Beach Club Access About One Mile Away
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Sebenoa Retreat at Sprucewold Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $211 per night (USD)Expedia
From $508 per night (USD)VRBO
Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 4
The moment you arrive at this bright 4-bedroom, 2-bathroom cottage you are sure to be enchanted by its historic New Engl ...
From $508 per night (USD)VRBO
From $448 per night (USD)Expedia
Classic Maine Cottage with Ocean Views and Beach
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Stuart Little is a wonderful place to slow down and just breathe. It's a perfect place for making summer memories. The b ...
From $448 per night (USD)Expedia
From $382 per night (USD)VRBO
Come and enjoy our Boothbay Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Boothbay Harbor Region is considered one of the perfect Maine destinations. Rich in history, awash in local color an ...
From $382 per night (USD)VRBO
From $713 per night (USD)Expedia
Sunset Lodge by Rocky Coast Rentals
- 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 $713 per night (USD)Expedia
From $118 per night (USD)VRBO
Boothbay Harbor Maine, Beautiful private Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Spacious Living room / kitchenet , comfy couch, Queen Ann chair, bar style table with stools seating. Refrigerator, micr ...
From $118 per night (USD)VRBO
From $192 per night (USD)Expedia
Boothbay Open Plan 1- Bedroom Apt. Woods & Water. Southport.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Located on Southport Island, we are near the water, and adjacent to Capitol Island. This detached garage apartment is sp ...
From $192 per night (USD)Expedia
From $271 per night (USD)VRBO
Stunning log cabin with fireplace & nature views - near shopping & dining
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
Hammond Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $271 per night (USD)VRBO
From $260 per night (USD)Expedia
Cozy & Pet-Friendly Log Cabin with Access to a Private Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Deer Creek Cabin is the best of both worlds - the cabin is close to Boothbay Harbor's wonderful restaurants and shopping ...
From $260 per night (USD)Expedia
From $375 per night (USD)VRBO
Thrush Cottage - Cozy 2BDR with Water Views -Original Spruce Point Inn Cottage!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy Harbor-View Retreat in Spruce Point Welcome to Thrush Cottage, a charming one-level getaway tucked within the desi ...
From $375 per night (USD)VRBO
From $393 per night (USD)VRBO
Southport ME Waterfront - Cozy Harbor
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Enjoy an island getaway on a private island off Southport, ME yet only 10 minutes to Boothbay Harbor. The house sits on ...
From $393 per night (USD)VRBO
From $787 per night (USD)VRBO
Charming Waterfront Cottage with Private Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Established in 1844 and rich with history and charm, The Boathouse is the perfect little getaway spot for couples and fa ...
From $787 per night (USD)VRBO
From $1292 per night (USD)Expedia
Stunning Ocean Front Estate with a Private Dock
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
Relax and unwind in this spacious and peaceful oceanfront setting just minutes from fine dining, hiking trails, shopping ...
From $1292 per night (USD)Expedia
From $413 per night (USD)VRBO
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 $413 per night (USD)VRBO
From $391 per night (USD)Expedia
Just one block from the Ocean!
- Bedrooms:
- 1
- 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 $391 per night (USD)Expedia
From $654 per night (USD)VRBO
Stunning Views with Walks to the Beach and a short walk to pay and play tennis
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 8
Located in East Boothbay on breathtaking Ocean Point sits this traditional cottage with three porches. Enjoy the view fr ...
From $654 per night (USD)VRBO
From $140 per night (USD)Expedia
A Sweet Little Guest Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked away on Southport Island is this little guest house for two. Located just across the swing bridge from Boothbay H ...
From $140 per night (USD)Expedia
Click For PricingVRBO
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 ...
Click For PricingVRBO
From $410 per night (USD)Expedia
Samoset Cottage - 3 BR Water View Home, Boothbay Harbor
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Riverside Retreat – Spacious, Peaceful Home with Water Views & Private Dock! Settle into comfort and tranquility at thi ...
From $410 per night (USD)Expedia
From $708 per night (USD)VRBO
Boothbay area -- Newly renovated, near ocean, short drive to Botanical Gardens
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
Welcome to this modern architectural gem tucked among the spruces on Southport Island, serenely peaceful and yet just a ...
From $708 per night (USD)VRBO
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Charming Southport Island Cottage on Cozy Harbor with Sunny Deck - Sleeps 6!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Enjoy the spectacular natural beauty of Cozy Harbor and delight in watching all the harbor activity from the privacy of ...
Click For PricingExpedia
From $554 per night (USD)VRBO
Solitude abounds at this idyllic Southport OCEANFRONT home-5 mins from the beach
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Let it all go! Come here for peace and respite. Welcome to quintessential Maine summer living! Enjoy stunning ocean v ...
From $554 per night (USD)VRBO
From $274 per night (USD)Expedia
Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
THIS HOME RENTS WITH A 3-NIGHT MINIMUM, JUNE - SEPTEMBER Cottage Connection is proud to offer one of the most unique va ...
From $274 per night (USD)Expedia
From $380 per night (USD)VRBO
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 $380 per night (USD)VRBO
From $568 per night (USD)Expedia
PINE CLIFF DWELLER | 2 Bed, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
THIS PROPERTY RENTS WEEKLY, SATURDAY - SATURDAY, JUNE - SEPTEMBER 4 NIGHT STAYS AVAILABLE IN THE SHOULDER SEASON. STAY ...
From $568 per night (USD)Expedia
From $902 per night (USD)VRBO
Unforgettable Oceanfront: Panoramic Ocean Views Await at Ledgemere Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
THIS HOME RENTS WEEKLY, SATURDAY - SATURDAY, JUNE - SEPTEMBER _________________________________________________________ ...
From $902 per night (USD)VRBO
From $708 per night (USD)Expedia
Piffi Biff: Watch Whales & Lobster Boats from This Classic Oceanfront Gem!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
THIS HOME RENTS WEEKLY, SATURDAY - SATURDAY, JUNE - SEPTEMBER 4 NIGHT STAYS AVAILABLE IN THE SHOULDER SEASON. STAY THE ...
From $708 per night (USD)Expedia
Click For PricingVRBO
Coastal Cottage - Panoramic Views - Pond & Nature
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our family's favorite Maine coastal cottage! Although small in size, 600 SF - Gull Cottage is overflowing w ...
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From $1360 per night (USD)Expedia
A SLICE OF HEAVEN | 4 Bed, 3 Bath
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
THIS PROPERTY RENTS WEEKLY, FRIDAY - FRIDAY, JUNE, JULY, AND SEPTEMBER ONLY ___________________________________________ ...
From $1360 per night (USD)Expedia
From $1036 per night (USD)VRBO
Ocean front cottage on a drive-on island in Boothbay Harbor, Maine
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Exquisitely maintained 5 bedroom/2 bathroom cottage right on the ocean. Family owned since 1891. Step back in time into ...
From $1036 per night (USD)VRBO
From $487 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 $487 per night (USD)Expedia
From $341 per night (USD)VRBO
Charming cottage near the beach with balcony, deck, grill, fireplace - dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
North Star Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $341 per night (USD)VRBO
From $2725 per night (USD)Expedia
Oceanfront Serenity: Exclusive Waterfront Estate with Private Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Introducing a magnificent waterfront getaway presented by Legacy Properties Sotheby’s International Realty, set against ...
From $2725 per night (USD)Expedia
From $420 per night (USD)VRBO
Cedar Cove: a tranquil retreat on the water just minutes from Boothbay Harbor
- Bedrooms:
- 2
- 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 $420 per night (USD)VRBO
From $332 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 $332 per night (USD)Expedia
Click For PricingVRBO
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 ...
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From $484 per night (USD)Expedia
Breathtaking Oceanfront Views, Private Dock & Osprey Nest at Merwick Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
THIS HOME RENTS WEEKLY, SATURDAY - SATURDAY, JUNE - SEPTEMBER 4 NIGHT STAYS AVAILABLE IN THE SHOULDER SEASON. WEEKLY SP ...
From $484 per night (USD)Expedia