Southport Rentals
From $816 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 $816 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 $465 per night (USD)Expedia
Two-Story Family-Friendly Home w\/Free WiFi, Deck, and Partial Ocean Views
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 6
Cape Newagen Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $465 per night (USD)Expedia
From $297 per night (USD)VRBO
Waterfront Cottage with a dock & float on Townsend Gut w\/one floor living
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This charming 2 bedroom, 1 bath cottage sits right at the water's edge of Townsend Gut. Boats galore can be seen from th ...
From $297 per night (USD)VRBO
From $160 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 $160 per night (USD)VRBO
From $977 per night (USD)VRBO
The ultimate vacation spot, 4 BR waterfront cottage overlooking the open ocean
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 13
The ultimate Maine vacation spot! Enjoy the open ocean and boating activity from this 4 bedroom, 2 bath waterfront cotta ...
From $977 per night (USD)VRBO
From $792 per night (USD)Expedia
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 $792 per night (USD)Expedia
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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 ...
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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 ...
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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 ...
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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 ...
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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 ...
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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 ...
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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, ...
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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 ...
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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 ...
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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 ...
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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 ...
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From $330 per night (USD)Expedia
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 $330 per night (USD)Expedia
From $727 per night (USD)VRBO
Oceanfront House on 2 acres, Sleeps 8, Use of SPI amenities-6 passes. 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 $727 per night (USD)VRBO
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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 ...
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From $591 per night (USD)VRBO
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 $591 per night (USD)VRBO
From $363 per night (USD)Expedia
Enjoy the stunning views while relaxing on the deck at East Ledge Cottage
- Bedrooms:
- 3
- 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)Expedia
From $323 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 $323 per night (USD)VRBO
From $176 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. Large living area with a beautiful view of the ocean and dining area all in on ...
From $176 per night (USD)VRBO
From $322 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 $322 per night (USD)VRBO
From $452 per night (USD)Expedia
Steamboat Landing Cottage
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Steamboat Landing is a large cottage overlooking the Sheepscot River on Southport Island. Hosted by Of Sea and Pine; Mai ...
From $452 per night (USD)Expedia
From $274 per night (USD)VRBO
A Cozy Retreat on Southport Island
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This cute-as-a-button newly renovated waterfront cottage is located on Southport Island across the swing bridge from Boo ...
From $274 per night (USD)VRBO
From $444 per night (USD)VRBO
Coastal Island Retreat - Privacy and Convenience. Boat rental available.
- Bedrooms:
- 2
- 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 $296 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 $296 per night (USD)VRBO
From $556 per night (USD)Expedia
Boothbay - Ocean Point home w\/ screened porch, amazing view & water access
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
Best View in ME Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $556 per night (USD)Expedia
From $448 per night (USD)VRBO
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 $448 per night (USD)VRBO
From $448 per night (USD)Expedia
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 ...
From $448 per night (USD)Expedia
From $152 per night (USD)VRBO
Newly Restored 1920's Vintage Boathouse.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Impeccably restored former boathouse. Very unique property that features a spectacular view of Boothbay Harbor and the o ...
From $152 per night (USD)VRBO
From $327 per night (USD)VRBO
Ocean Point, Maine Cottage Weekly Rental
- Bedrooms:
- 2
- 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 $307 per night (USD)VRBO
Newly Renovated Upstairs Suite in 1790's Sea Captain's House on Deckers Cove
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Coveside - This newly renovated upstairs suite in a Sea Captain's style home sits directly across the street from Decke ...
From $307 per night (USD)VRBO
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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 ...
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From $665 per night (USD)VRBO
Stunning Renovated Waterfront Home with Private Deepwater Dock; Windows Galore!
- Bedrooms:
- 3
- 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 $665 per night (USD)VRBO
From $654 per night (USD)VRBO
Oceanfront Log Cabin with Dock on Southport Island - 7 acres with westerly views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Log cabin on Love's Cove and looking west over Ebenecook Bay on Southport Island. Built and furnished in 1909 by the sa ...
From $654 per night (USD)VRBO
From $380 per night (USD)VRBO
Historical New England home with outdoor shower - near downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Firehouse Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $380 per night (USD)VRBO
From $724 per night (USD)Expedia
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 $724 per night (USD)Expedia
From $362 per night (USD)VRBO
Southport Island Cottage | Deck & New Luxe Kitchen | Near Boothbay Harbor
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Southport Island Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $362 per night (USD)VRBO
From $691 per night (USD)Expedia
Beachfront Delight with detached guesthouse, sunset views & private beach access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Deep Cove Cabin Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $691 per night (USD)Expedia
From $627 per night (USD)VRBO
Oceanfront home & guesthouse w\/ incredible ocean views, deck & location
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Tranquil Ocean Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $627 per night (USD)VRBO
From $551 per night (USD)VRBO
Decker Cove Southport Paradise with Central Air Conditioning
- Bedrooms:
- 3
- Bathrooms:
- 4
- 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 $551 per night (USD)VRBO
From $268 per night (USD)VRBO
Boothbay Harbor Cabin w\/ Spacious Deck & Yard!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Now is the time to escape to peaceful surroundings, spend summer days hiking beneath bright blue skies, and enjoy starga ...
From $268 per night (USD)VRBO
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Luxury Cabin on Linekin Bay
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This quant cabin sits on Linekin Bay nestled amongst the spruce trees and is the perfect couples getaway. Enjoy the spec ...
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From $433 per night (USD)VRBO
Newly Renovated 3 B\/2.5B Suite in 1790's Sea Captains House
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Coveside – This newly renovated 3 bedroom, 3 bath main floor suite in a Sea Captain’s style home sits directly across th ...
From $433 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 $284 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 $284 per night (USD)VRBO
From $288 per night (USD)Expedia
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 $288 per night (USD)Expedia
From $356 per night (USD)VRBO
Secluded Dog-Friendly Getaway w\/ Free WiFi, Private Washer\/Dryer, Furnished Deck
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Island Pines Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $356 per night (USD)VRBO
From $424 per night (USD)Expedia
Wiggleswick Cottage;Voted BEST Pet Friendly rental in Maine! 2024 Holidays!
- 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 $424 per night (USD)Expedia
From $230 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 $230 per night (USD)VRBO
From $164 per night (USD)Expedia
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 $164 per night (USD)Expedia
From $164 per night (USD)VRBO
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 $164 per night (USD)VRBO
From $164 per night (USD)Expedia
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 $164 per night (USD)Expedia
From $232 per night (USD)VRBO
Remodeled Cottage with AC, Private W\/D, Full Kitchen, and High-Speed WiFi
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Little Cottage in the Woods Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply e ...
From $232 per night (USD)VRBO
From $370 per night (USD)VRBO
Waterfront Cottage Sitting On The Water's Edge Of Townsend Gut
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This 2 bedroom, 2 bath cottage sits waterfront on Townsend Gut. Sit out on the wrap-around porch and enjoy the abundant ...
From $370 per night (USD)VRBO
From $409 per night (USD)VRBO
Gorgeous Views of Harbor Entrance!
- Bedrooms:
- 2
- 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 $409 per night (USD)VRBO
From $282 per night (USD)Expedia
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 $282 per night (USD)Expedia
From $576 per night (USD)VRBO
Oceanfront home
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 9
Beautiful oceanfront home with large outdoor deck facing the water for dining and relaxing, Great sunsets. Private sand ...
From $576 per night (USD)VRBO
From $357 per night (USD)Expedia
Harborview Perch... spacious & open floorplan, privacy, harbor view, amenities
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
"Harborview Perch": comfortable & inviting with spectacular, elevated views of Boothbay Harbor! "Harborview Perch" a ...
From $357 per night (USD)Expedia
From $490 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 $490 per night (USD)VRBO
From $200 per night (USD)VRBO
Brand new in 2020 Cozy Cottage
- Bedrooms:
- 2
- 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 $200 per night (USD)VRBO
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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 ...
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From $465 per night (USD)Expedia
SALT WATER MAINE COTTAGE WITH DOCK - MINUTES TO BOTANICAL GARDENS
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Morning Star Cottage is the perfect year-round Maine vacation rental! This Victorian custom-built home is situated on a ...
From $465 per night (USD)Expedia
From $355 per night (USD)VRBO
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 $355 per night (USD)VRBO
From $569 per night (USD)Expedia
Oceanfront Cottage w\/ Deck 2 Mi to Boothbay Harbor
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 5
The moment you arrive at this bright 4-bedroom, 2-bathroom cottage you are sure to be enchanted by its historic New Engl ...
From $569 per night (USD)Expedia
From $506 per night (USD)VRBO
Classic Maine Cottage with Ocean Views and Beach
- Bedrooms:
- 2
- Bathrooms:
- 6
- 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 $506 per night (USD)VRBO
From $316 per night (USD)VRBO
Rustic Chic Cottage in Ocean Point! Water Views, Fireplace and Great Linens!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Ship's Wheel in Ocean Point! An awesome place to chill! Combine an authentic Maine camp with great amenities ...
From $316 per night (USD)VRBO
From $380 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 $380 per night (USD)VRBO
From $610 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 $610 per night (USD)Expedia
From $98 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 $98 per night (USD)VRBO
From $179 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 $179 per night (USD)Expedia
From $366 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 $366 per night (USD)VRBO
From $292 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 $292 per night (USD)Expedia
From $348 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 $348 per night (USD)VRBO
From $358 per night (USD)VRBO
Pratts Island Get Away
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Enjoy an island living getaway with this three bedroom two two-bathroom home located across a wooden bridge from Southpo ...
From $358 per night (USD)VRBO
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Spectacular Ocean Front Estate on Southport
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Prepare to be captivated by this extraordinary oceanfront retreat, boasting breathtaking panoramic views of the open oce ...
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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 ...
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From $1560 per night (USD)VRBO
Stunning Ocean Front Estate with a Private Dock
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 14
Relax and unwind in this spacious and peaceful oceanfront setting just minutes from fine dining, hiking trails, shopping ...
From $1560 per night (USD)VRBO
From $508 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 $508 per night (USD)Expedia
From $437 per night (USD)VRBO
Just one block from the Ocean!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Coastal cottage sits one block from the ocean and a short walk from the community center where there are tennis, pickleb ...
From $437 per night (USD)VRBO
From $677 per night (USD)Expedia
Stunning Views with Walks to the Beach
- 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 $677 per night (USD)Expedia
From $149 per night (USD)VRBO
A Sweet Little Guest Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Tucked away on Southport Island is this little guest house for two. Located just across the swing bridge from Boothbay H ...
From $149 per night (USD)VRBO
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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 $315 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 $315 per night (USD)VRBO
From $545 per night (USD)Expedia
Boothbay area -- Newly renovated, near ocean, short drive to Botanical Gardens
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 13
Welcome to this modern architectural gem tucked among the spruces on Southport Island, serenely peaceful and yet just a ...
From $545 per night (USD)Expedia
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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 ...
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From $631 per night (USD)Expedia
Solitude abounds at this idyllic Southport OCEANFRONT home-5 mins from the beach
- Bedrooms:
- 2
- 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 $631 per night (USD)Expedia
From $465 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 $465 per night (USD)VRBO
From $534 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 $534 per night (USD)Expedia
From $625 per night (USD)VRBO
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. FALL ...
From $625 per night (USD)VRBO
From $1537 per night (USD)VRBO
LEDGEMERE ON SOUTHPORT ISLAND | 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. _____ ...
From $1537 per night (USD)VRBO
From $841 per night (USD)VRBO
PIFFI BIFF ON SOUTHPORT ISLAND | 5 Bed, 3 Bath
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
THIS PROPERTY RENTS WEEKLY, SATURDAY - SATURDAY, JUNE - SEPTEMBER 4 NIGHT STAYS AVAILABLE IN THE SHOULDER SEASON. _____ ...
From $841 per night (USD)VRBO
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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 $1097 per night (USD)VRBO
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 $1097 per night (USD)VRBO
From $1121 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 $1121 per night (USD)VRBO