Vacation rentals in Southport

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Top-rated vacation rentals in Southport

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Top guest favourite

Cabin in Georgetown

4.99 out of 5 average rating, 141 reviews

Sauna+Near Beach+Pond+Outdoor Shower+FirePit+A/C

Come relax at Pine Cabin, one of two cabins on 8 acres with a pond minutes from one of the best beaches in Maine. Unwind in your private outdoor cedar glass sauna w/forest views & refresh in our seasonal outside shower! * Minutes to Reid State Park & 5 Island🦞 * Fire Pit * Family Own & Run * Gas Grill * Private Bedroom w/Queen Bed * Loft w/Queen Bed & Record Player * Rain Shower * Custom cabinets & couch * Screen porch * AC/Heat * EV charger * Fast Wifi * Beach Gear * Smart TV * Generator

Top guest favourite

Guesthouse in Southport

5 out of 5 average rating, 45 reviews

THE COVE’s Anchor New England Nautical charm

THE COVE’S ANCHOR : A charming romantic guest cottage attached to Main House. A Serene start : Peace, calm, tranquility. Hit the reset button & Gain a new perspective. Created with my own hands for Loved ones & wonderful Guest. Perfect for a couple or a friends getaway. Children always welcomed. Designed W/ New England Charm W/ splash of Nautical. Quality, Classic, simplicity at its finest. Tv / Internet Provided as convenience only not integral to stay nor loss of power due to Mother Nature

Guest favourite

Home in Southport

5 out of 5 average rating, 11 reviews

Maine Stowaway Carriage House

Welcome to the Maine Stowaway Carriage House, a coastal retreat nestled on 5.5 acres overlooking Cozy Harbor. Enjoy breathtaking sunsets and beautiful views from this brand new coastal home. The nearby General Store and Hendricks Head Beach are within walking distance and make it the perfect place to unplug and unwind. Boothbay is a short ride away for restaurants, shopping & music. Whether you are seeking a peaceful escape or a scenic spot to relax, this property offers an ideal getaway.

Guest favourite

Home in Boothbay Harbor

4.93 out of 5 average rating, 125 reviews

Renovated home with amazing waterfront views

Welcome to Dancing Pines Cottage! We are located across from West Harbor Pond with beautiful water views in each room. Relax on the deck or bbq on the patio or take a short drive into charming Boothbay Harbor town for lobster rolls. We have three bedrooms and a den/office and 2 full bathrooms and can accommodate up to 7 guests. The house is private and has ample parking. One week rentals for June, July, and August (Saturday-Saturday). Starting January 2025 we will no longer allow pets.

Top guest favourite

Home in Georgetown

5 out of 5 average rating, 101 reviews

Perched atop the Coast of the Atlantic Ocean

Enjoy sweeping vistas of the Atlantic Ocean from this 2002 home perched among spruce trees above the rocky coast. Watch for bald eagles and seals. Fall asleep to the sound of crashing waves. Walk down to the edge of the ocean to lounge or picnic. The intrepid visitor can scramble along the shore. Walk 6 minutes or drive the 0.1 miles to the park entrance. Hike the Little River Trail. The house has vaulted ceilings, panoramic views, fully equipped kitchen, and whirlpool bath.

Superhost

Cabin in Southport

4.86 out of 5 average rating, 7 reviews

Charming Seaside Cottage

Escape to a tranquil haven with our charming seaside cottage on Capitol Island. Nestled along Maine's pristine coastline, this idyllic retreat offers a perfect blend of relaxation and adventure. Step into a world of serenity as you wake up to the soothing sound of waves and the gentle caress of ocean breezes. Our cozy cottage is designed for your utmost comfort, featuring 4 bedrooms, a fully equipped kitchen, a quaint living area with panoramic views, and a porch directly on the ocean.

Superhost

Cottage in Southport

4.77 out of 5 average rating, 98 reviews

Custom Built Quaint Knotty Pine Cottage

Quaint cottage tucked away in the woods, minutes away from the ocean and the charming town of Boothbay Harbor. Two bedrooms and one bathroom with beautiful knotty pine interior, gas fireplace and open floorplan. Screen-in porch for enjoying the peaceful evenings watching the fireflies and an outdoor deck to enjoy the summer days. All basics amenities including a washer/dryer, coffee maker, TV/Wifi are available for a comfortable stay. Come and have a wonderful vacation in Maine!

Top guest favourite

Cottage in Boothbay Harbor

4.98 out of 5 average rating, 416 reviews

The Cottage at the McCobb House

Freshly renovated inside and out, the cottage is your private Maine camp. Located on an acre and a half of wooded grounds, and surrounded by forest, the cottage feels secluded, but it’s only a mile to the restaurants, shops, and waterfront attractions of bustling Boothbay Harbor. With hiking trails in the Pine Tree Preserve that adjoins the property and the Lobster Cove Meadow Preserve a five minute walk up the road, you can also explore nature and enjoy the solitude of the woods.

Superhost

Guesthouse in Southport

4.71 out of 5 average rating, 7 reviews

Ticket Office: Charming Coastal Couples Retreat

Situated in the heart of midcoast Maine, the “Ticket Office” is the perfect stay for a quick coastal stay. This tiny house provides a unique blend of modern comfort, new amenities, and New England charm. Local seafood restaurants and attractions are within a quick drive - or even walk - ensuring that you have a memorable stay. Spend time in the harbor experiencing the breathtaking beauty of a breezy coastal summer day. We invite you to relax and unwind at the “Ticket Office”.

Top guest favourite

Cottage in Southport

5 out of 5 average rating, 7 reviews

Seawood Sunset Cottage: Southport Island

Seawood Sunset Cottage – Southport Island, Maine. Built by an artist and adorned with her original works, Seawood Sunset Cottage is a magical, light-filled oasis nestled among the pines. Just a stone’s throw from the water, the cottage was designed as a gathering place for loved ones—and it's sure to inspire your own cherished family memories. Please Note: This cottage does not offer water views or direct water access.

Top guest favourite

Guest suite in Boothbay

4.96 out of 5 average rating, 134 reviews

Linekin Guest Suite

Tucked away guest studio attached to main home that you will have all to yourself with basic amenities and a sky lighted bathroom. A few minutes to Ocean Point and hiking trails and less than 10 minutes to Boothbay Harbor. **Please note there are stairs that need to be climbed on the front deck in order to access the property. Use the directions provided as your GPS sometimes puts you in a circle around Boothbay!

Top guest favourite

Guesthouse in Boothbay Harbor

5 out of 5 average rating, 253 reviews

The Sparrow’s Nest Charming Country Cottage

The Sparrow's Nest is located on a country road approximately 5 miles from downtown Boothbay Harbor. The Sheepscot River, it's coves and nature trails are close by. Enjoy the beautiful country surroundings, gardens, and the miracle of nature. What a delight to wake up to the sound of birdsong while enjoying a cup of local coffee, or sitting by the outdoor fire sipping wine and taking in the beautiful night sky.