Southport Rentals
From $845 per night (USD)VRBO
Ambleside in Boothbay Harbor Maine! Perfect for Fall Foliage and Gardens Aglow!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Situated on the Eastside of the quintessential Maine harbor town of Boothbay Harbor, this home is just a short walk acro ...
From $845 per night (USD)VRBO
From $275 per night (USD)VRBO
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 $275 per night (USD)VRBO
From $229 per night (USD)VRBO
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 $229 per night (USD)VRBO
From $499 per night (USD)VRBO
Enchantingly beautiful with views of Five Islands Harbor and Ocean
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful new home nestled in Five Islands with views of the harbor and ocean. Open concept kitchen/living room with a s ...
From $499 per night (USD)VRBO
From $578 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 $578 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 $279 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 $279 per night (USD)VRBO
From $613 per night (USD)Expedia
Spruce Ledge by Sea Maine
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Nestled amidst the quaint charm of Boothbay Harbor, Maine, sits a picturesque house that exudes timeless elegance and mo ...
From $613 per night (USD)Expedia
From $663 per night (USD)VRBO
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 $663 per night (USD)VRBO
From $581 per night (USD)Expedia
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 $581 per night (USD)Expedia
From $667 per night (USD)VRBO
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 $667 per night (USD)VRBO
From $525 per night (USD)Expedia
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 $525 per night (USD)Expedia
From $569 per night (USD)VRBO
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 $569 per night (USD)VRBO
From $383 per night (USD)Expedia
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 $383 per night (USD)Expedia
From $478 per night (USD)VRBO
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 $478 per night (USD)VRBO
From $822 per night (USD)Expedia
3BR Cottage | Near Main Inn | No Hidden Fees
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Cardinal Cottage offers a peaceful woodland setting just behind the historic Main Inn. With three cozy bedrooms, 2.5 bat ...
From $822 per night (USD)Expedia
From $931 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 $931 per night (USD)VRBO
From $538 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 $538 per night (USD)Expedia
From $766 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 $766 per night (USD)VRBO
From $1644 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 $1644 per night (USD)Expedia
From $383 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 $383 per night (USD)VRBO
From $563 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 $563 per night (USD)Expedia
From $679 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 $679 per night (USD)VRBO
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Moss House: A Modern Waterfront Cabin in the Woods
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A modern cabin set above a native spruce forest, offering calm water views out to the Atlantic. Featured in Maine Home + ...
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From $428 per night (USD)VRBO
Oceanfront Retreat with Dock, Boothbay Harbor
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront 3BR/3BA retreat where the road ends in Boothbay Harbor. Enjoy stunning harbor views, a private dock, and a la ...
From $428 per night (USD)VRBO
From $2466 per night (USD)Expedia
Ocean Point Luxury on Shore Road
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Set against the backdrop of Maine’s rocky coastline and backed by pine forests sits a dream coastal escape in idyllic Oc ...
From $2466 per night (USD)Expedia
From $385 per night (USD)VRBO
Serene Seaside Getaway
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to The Patch House by Sea Maine, a charming and spacious coastal retreat nestled in the serene area of Boothbay ...
From $385 per night (USD)VRBO
From $437 per night (USD)Expedia
Waterfront Retreat on Southport Island - Pet-Friendly, Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Welcome to your coastal escape! This 3-bedroom, 1.5-bath waterfront home is tucked away on Southport Island, a hidden ge ...
From $437 per night (USD)Expedia
From $355 per night (USD)VRBO
Tranquil Woodland Retreat + Private Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Tranquil Forest Cabin Retreat Near Boothbay Harbor & Private Beach Escape to serenity at this charming, treehouse-sty ...
From $355 per night (USD)VRBO