Holiday rentals in Southport

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Top-rated holiday rentals in Southport

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Top guest favourite

Guest house in Southport

5 out of 5 average rating, 49 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

Superhost

Home in Southport

4.92 out of 5 average rating, 100 reviews

Maine Stowaway Cottage/Your Year-Round Destination

Awe Inspiring Maine Cottage! The Stowaway is located on a secluded 5.5 acres with a hilltop location possessing stunning water views at every level. Our pet friendly home is a 3-story, 4 BR, 3 Bath Seaside Estate that sleeps 8. It is a luxury home making great memories guaranteed! Great work from home/study areas and plenty of space to spread out! Travel to Maine during the beautiful summer, in the Fall for the Foliage Fair and Winter for your Snowy Holiday festivities and all it's beauty!

Guest favourite

Home in Boothbay Harbor

4.93 out of 5 average rating, 128 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, 106 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

4.56 out of 5 average rating, 9 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, 101 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, 418 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.

Top guest favourite

Cabin in Georgetown

4.99 out of 5 average rating, 146 reviews

Sauna+3min to Beach+Pond+Screen Porch+FirePit+A/C

Come relax at Pine Cabin, one of two cabins on 8 wooded acres with a pond. Unwind in your private cedar glass sauna w/forest views. Designed & Built by local craftsmen. * Minutes Reid State Park & 5 Island🦞 * Maine Family Run * Gas Grill * Outdoor Shower * Private Bedroom w/Queen Bed * Loft w/Queen Bed & Record Player * Cotton sheets/towels * Rain Shower Heads * Custom cabinets & couch * Screen porch * AC/Heat * EV charger * Fast Wifi * Beach Gear * SmartTV * Generator

Top guest favourite

Flat in Boothbay Harbor

5 out of 5 average rating, 120 reviews

Sail Loft - Upscale Oceanfront on a Pier near BBH!

Welcome to Sail Loft, a one-of-a-kind vacation destination in Boothbay Harbor! You can't get any closer to the water than this! Imagine relaxing in style and comfort, right over the ocean, and having views from every window. It's like being on a boat but better! Our newly updated, spotless loft has all the amenities you could want, and is only a short walk to downtown. You will find a great mattress, with cozy bedding and fluffy towels.

Superhost

Home in Southport

5 out of 5 average rating, 4 reviews

Miradon Ocean Estate

Miradon Ocean Estate - Southport Island, Maine. Affectionally known as “Ole Gusty” this home is an extraordinary oceanfront retreat. Designed to showcase panoramic sunsets, the home boasts ocean views that are best enjoyed from the expansive deck. Miradon is located on the enchanting island of Southport, just a stone’s throw from Boothbay Harbor. This home is truly an oasis for family and friends to gather. Sleeps 8 adults.

Top guest favourite

Guest house in Boothbay Harbor

5 out of 5 average rating, 257 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.

Top guest favourite

Cottage in Southport

5 out of 5 average rating, 12 reviews

Cottage at Island Point

The Cottage at Island Point – Southport Island, Maine. Come experience the charm of coastal island living at this serene Southport cottage. Nestled in the peaceful Newagen community, The Cottage at Island Point feels like stepping into an Edward Hopper painting—where life slows down, sea breezes fill the air, and the soothing sound of buoy bells will be your evening soundtrack.