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$Two-Story Family-Friendly Home w\/Free WiFi, Deck, and Partial Ocean Views$
From $360 per night (USD)
VRBO
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 $360 per night (USD)
VRBO
From $582 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 $582 per night (USD)
Expedia
From $283 per night (USD)
VRBO
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 $283 per night (USD)
VRBO
From $541 per night (USD)
Expedia
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 $541 per night (USD)
Expedia
From $583 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 $583 per night (USD)
VRBO
From $473 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 $473 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 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)
VRBO
From $200 per night (USD)
Expedia
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)
Expedia
From $744 per night (USD)
VRBO
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 $744 per night (USD)
VRBO
From $1216 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 $1216 per night (USD)
Expedia
From $358 per night (USD)
VRBO
Seawood Sunset Cottage: Southport Island
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Seawood Sunset Cottage – Southport Island, Maine. Hosted by Of Sea and Pine, Maine Vacation Rentals Built by an artist ...
From $358 per night (USD)
VRBO
From $379 per night (USD)
Expedia
Cottage at Island Point
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Cottage at Island Point – Southport Island, Maine. Hosted by Of Sea and Pine, Maine Vacation Rentals Come experienc ...
From $379 per night (USD)
Expedia
From $591 per night (USD)
VRBO
Gracious 4-bedroom house in Southport on Townsend Gut with a private pond.
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
This Southport Island house boasts 4 inviting bedrooms with 2 queen beds, 1 full bed, and 1 twin (convertible to king) i ...
From $591 per night (USD)
VRBO
From $202 per night (USD)
Expedia
Charming Two-Bedroom Ocean-View Cottage in Quiet Southport
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located on Southport Island, this cottage is a dream for travelers looking to enjoy the slower pace of life. Sip your mo ...
From $202 per night (USD)
Expedia
From $353 per night (USD)
VRBO
Charming 3-bedroom cottage in Southport with water views and close to Boothbay.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to a fabulous 3-bedroom cottage in Southport. This welcoming retreat features a queen bed, bunk bed, twin bed, an ...
From $353 per night (USD)
VRBO
From $412 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 $412 per night (USD)
Expedia
From $286 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 $286 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 Dockside Cottage is located on Decker's Cove overlooking a busy waterway with lots of boat traffic. Lobster wharf + ...
From $174 per night (USD)
Expedia
From $181 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 $181 per night (USD)
VRBO
From $427 per night (USD)
Expedia
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 $427 per night (USD)
Expedia
From $291 per night (USD)
VRBO
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 $291 per night (USD)
VRBO
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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 ...
Click For Pricing
Expedia
From $768 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 $768 per night (USD)
VRBO
From $841 per night (USD)
Expedia
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)
Expedia
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 $164 per night (USD)
Expedia
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)
Expedia
From $164 per night (USD)
VRBO
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)
VRBO
From $336 per night (USD)
Expedia
Cozy Waterfront Cottage with Dock
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Step into the charm of coastal Maine at The Lilly Pad, a lovingly restored 1940s cottage nestled on the tranquil shores ...
From $336 per night (USD)
Expedia
From $935 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 $935 per night (USD)
VRBO
From $628 per night (USD)
Expedia
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 $628 per night (USD)
Expedia
From $948 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 $948 per night (USD)
VRBO
From $809 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 $809 per night (USD)
Expedia
From $1130 per night (USD)
VRBO
Miradon Ocean Estate
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Miradon Ocean Estate affectionately known as “Ole Gusty”, is an extraordinary oceanfront retreat. Designed to showcase p ...
From $1130 per night (USD)
VRBO
From $215 per night (USD)
Expedia
Enjoyable 1-bedroom rustic cottage in Southport.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Get ready to relax in this welcoming 1-bedroom rustic cottage in Southport. This gorgeous retreat features a cozy queen ...
From $215 per night (USD)
Expedia
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VRBO
Cedarbush Cabin - Waterfront Cottage - walk to Robinson's Wharf!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Mid-Century Modern Charm on the Waterfront! Discover the charm of coastal Maine at Cedarbush Cabin, a classic mid-centu ...
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VRBO
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Expedia
Osprey Perch Cottage - Water Views
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cozy Getaway with Water Views - Southport! Nestled in a peaceful spot with beautiful water views, Osprey Perch Cottage ...
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Expedia
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VRBO
Osprey Perch - Large Family Cottage - Waterfront
Bedrooms:
3
Bathrooms:
6
Sleeps:
11
Stunning Cliffside Cottage with Harbor Views! Perched on a 50-foot cliff with breathtaking views of the harbor, Mouse I ...
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VRBO
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Expedia
Colburn Cottage - Whole Home
Bedrooms:
1
Bathrooms:
7
Sleeps:
12
Perfect Family Vacation Spot on Capitol Island – Spacious Waterfront Retreat! Gather your loved ones and escape to this ...
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Expedia
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VRBO
Colburn Cottage - Downstairs - Waterfront + Beach!!
Bedrooms:
0
Bathrooms:
2
Sleeps:
4
Perfect Family Vacation Spot – Beachfront Bliss! This charming seaside retreat offers everything you need for a relaxin ...
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VRBO
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Expedia
Cove Point House - Water Views of Decker's Cove!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Waterfront Retreat with Stunning Views of Decker's Cove - Southport! Relax and unwind at Cove Point House, a beautiful ...
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Expedia
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VRBO
Colburn Cottage - Upstairs
Bedrooms:
0
Bathrooms:
5
Sleeps:
7
Perfect Family Vacation Spot – Coastal Comfort Awaits! Looking for the perfect place to unwind with the family? Welcome ...
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VRBO
From $598 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 $598 per night (USD)
Expedia
From $475 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 $475 per night (USD)
VRBO
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Expedia
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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Expedia
From $1144 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 $1144 per night (USD)
VRBO
From $641 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. STAY THE WEEK FOR A SPECIAL RATE! ____ ...
From $641 per night (USD)
Expedia
From $989 per night (USD)
VRBO
CLIFF COTTAGE | TOWNSEND GUT | 4 Bed, 2.5 Bath
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
THIS PROPERTY RENTS WEEKLY, SATURDAY - SATURDAY, JUNE - SEPTEMBER 4 NIGHT STAYS AVAILABLE IN THE SHOULDER SEASON. Welco ...
From $989 per night (USD)
VRBO
From $371 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 $371 per night (USD)
Expedia
From $449 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 $449 per night (USD)
VRBO
From $230 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 $230 per night (USD)
Expedia
From $518 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 $518 per night (USD)
VRBO
From $701 per night (USD)
Expedia
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 $701 per night (USD)
Expedia
From $1402 per night (USD)
VRBO
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 $1402 per night (USD)
VRBO
From $173 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 $173 per night (USD)
Expedia
From $354 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 $354 per night (USD)
VRBO
From $382 per night (USD)
Expedia
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)
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 $246 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 $246 per night (USD)
Expedia
From $487 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 $487 per night (USD)
VRBO
From $244 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 $244 per night (USD)
Expedia
From $554 per night (USD)
VRBO
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 $554 per night (USD)
VRBO
From $243 per night (USD)
Expedia
'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 $243 per night (USD)
Expedia
From $337 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 $337 per night (USD)
VRBO
From $865 per night (USD)
Expedia
Oceanfront home & guesthouse w/ 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 $865 per night (USD)
Expedia
From $685 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 $685 per night (USD)
VRBO
From $377 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 $377 per night (USD)
Expedia
From $663 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 $663 per night (USD)
VRBO
From $455 per night (USD)
Expedia
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 $455 per night (USD)
Expedia
From $455 per night (USD)
VRBO
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 $455 per night (USD)
VRBO
From $506 per night (USD)
Expedia
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 $506 per night (USD)
Expedia
From $395 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 $395 per night (USD)
VRBO
From $363 per night (USD)
Expedia
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)
Expedia
From $2743 per night (USD)
VRBO
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 $2743 per night (USD)
VRBO
From $344 per night (USD)
Expedia
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)
Expedia
From $384 per night (USD)
VRBO
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 $384 per night (USD)
VRBO
From $839 per night (USD)
Expedia
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 $839 per night (USD)
Expedia
From $571 per night (USD)
VRBO
New Listing: Five Islands Waterfront Retreat
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Enjoy this quintessential Maine, newly renovated home in Five Islands! The home is equipped with a custom kitchen, spaci ...
From $571 per night (USD)
VRBO
From $524 per night (USD)
Expedia
Oceanfront 2Q Rm | Coastal Vibe | No Hidden Fees
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Seabreeze 1 offers serene ocean views and upscale comfort in a split-level layout designed for relaxation. With two quee ...
From $524 per night (USD)
Expedia
From $647 per night (USD)
VRBO
Oceanfront King Rm | Sunset View | No Hidden Fees
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Set along the ocean’s edge, Sunset A delivers timeless Boothbay elegance with panoramic water views. This cottage-style ...
From $647 per night (USD)
VRBO
From $573 per night (USD)
Expedia
King Rm | Fireplace + Water View | No Hidden Fees
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Seabreeze 2 welcomes you with a tranquil, upscale layout that captures Boothbay's nautical charm. From its king bed and ...
From $573 per night (USD)
Expedia
From $612 per night (USD)
VRBO
Queen Suite | Harbor View + Porch | No Hidden Fees
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Windward Suite welcomes you with western-facing harbor views from its enclosed third-floor porch. A queen bedroom and in ...
From $612 per night (USD)
VRBO
From $548 per night (USD)
Expedia
Woodland Cottage | Fireplace | No Hidden Fees
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Step into Little Spruce Cottage, a nostalgic woodland retreat tucked among towering trees. With cathedral ceilings and a ...
From $548 per night (USD)
Expedia
From $488 per night (USD)
VRBO
Ocean Deck Rm | Lighthouse View | No Hidden Fees
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Holland Room 2 honors Spruce Point’s legacy with serene ocean views and timeless style. Featuring two queen beds and a p ...
From $488 per night (USD)
VRBO
From $540 per night (USD)
Expedia
Top Floor Queen Rm | Panorama View |No Hidden Fees
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Sail into panoramic bliss at the Crow’s Nest, perched at the top of the historic Inn. Though intimate in size, its third ...
From $540 per night (USD)
Expedia
From $796 per night (USD)
VRBO
Cozy Forest Cottage + 2 Porches | No Hidden Fees
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Tucked along the woodland edge, Tanager Cottage welcomes families or groups with three bedrooms, 2.5 baths, and charming ...
From $796 per night (USD)
VRBO
From $556 per night (USD)
Expedia
Harborview Suite | Private Deck | No Hidden Fees
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Admiral’s Quarters crowns the historic Main Inn with harbor-facing views and rich maritime character. Anchored by brass ...
From $556 per night (USD)
Expedia
From $1014 per night (USD)
VRBO
Boothbay Cottg | Oceanfront+Deck | No Hidden Fees
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Discover the Osprey Cottage, perched above the Atlantic with a front-row seat to Boothbay’s coastal charm. With vaulted ...
From $1014 per night (USD)
VRBO
From $495 per night (USD)
Expedia
Cozy Forest Cottage | Stone FP | No Hidden Fees
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Set in a peaceful woodland corner, the Oriole Suite welcomes you with pine-paneled walls, a vaulted ceiling, and cozy st ...
From $495 per night (USD)
Expedia
From $409 per night (USD)
VRBO
Classic 2Q Rm | Bright Charm | No Hidden Fees
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Named for the visionary who helped shape Spruce Point's golden years, Harold Room 8 offers vintage Maine charm and sunli ...
From $409 per night (USD)
VRBO
From $602 per night (USD)
Expedia
Coastal King | Ocean Deck | No Hidden Fees
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A favorite since the 1950s, the Druce Room pairs nostalgic elegance with sweeping sea views from its second-floor perch. ...
From $602 per night (USD)
Expedia
From $571 per night (USD)
VRBO
Seaside King Cotg | Split Lvl | No Hidden Fees
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Tucked between iconic coastal cottages, Sunset B presents a luxurious waterfront stay with sweeping ocean views. This re ...
From $571 per night (USD)
VRBO
From $357 per night (USD)
Expedia
Sail Loft - Upscale Oceanfront on a Pier near BBH!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to Sail Loft, a one-of-a-kind vacation destination in Boothbay Harbor! You can't get any closer to the water tha ...
From $357 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 $382 per night (USD)
Expedia
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)
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 $278 per night (USD)
Expedia
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 $278 per night (USD)
Expedia
From $1183 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 $1183 per night (USD)
VRBO
From $327 per night (USD)
Expedia
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)
Expedia
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 $296 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 $296 per night (USD)
Expedia

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