Showing 69 Vacation Rentals from Southport, ME

Amenities:
Fireplace, Screened porch, Swimming Pool

Activities:
Surfing

Vacation Home Description:
description:This secluded retreat offers one floor living with a spectacular ocean view through its wall to wall, floor to ceiling windows, deck and screened porch.;

Amenities:
Fireplace, Woodburning Stove

Activities:
-

Vacation Home Description:
description:As the owner says - Fifty-five steps to Shangra La describes Wood's Roost to a T. The water views from this cottage are phenomenal and the property oozes charm. The living area is very open and boasts a gorgeous, antique wood stove. The master bedroom is cozy and romantic. The cottage has a large deck overlooking the water and a back yard with an old stone fireplace for barbeques. This cottage can sleep four people and is intended to pair with Blue Shutters to provide a second cottage at the same location to accommodate extended family groups of up to eight people. It can be rented only in conjunction with Blue Shutters. This cottage is suitable for adults or older children only because of the stairs and height of the deck. ;

Amenities:
Fireplace, Internet Access, Kitchenette, Laundry, Swimming Pool

Activities:
Biking, Board Games, Fishing, Kayaking

Vacation Home Description:
description:We welcome this cottage back! Newagen Cove Cottage is a three-bedroom cottage with a guest house (called Camp David) on Southport Island in the village of Cape Newagen. Built in 1928, this two-story, 2,500 square foot home is light and bright with lots of windows, a living room with cathedral ceiling and panoramic views. With 200+ feet on a beautiful and serene salt marsh that is fed by the tides, opens out to the ocean and includes tidal pools and a freshwater stream, your views will be constantly changing. Enjoy the ease of the open-concept living room, kitchen and dining room. Sit in the sunroom with deepset windows, skylights and Italian tile floors drinking tea, playing board games, or just reading a good book. The basement includes a laundry area with a washer and dryer. Stone patios and landscaped gardens provide opportunities to enjoy the sunshine all day long and spectacular sunsets. Even though this house sits close to the road, it is remarkably quiet and private. The separate guest house (Camp David) has a bath, kitchenette and is heated with a Vermont Castings gas fireplace. This property has many extras, including fishing poles and bicycles. A 5-minute walk will bring you to the harbor with a view of Margaret Hamilton's (best known as the Wicked Witch of the West in The Wizard of OZ) house. Bring your own kayak or rent one locally. Internet service is provided with this cottage. Linen is included as part of this package. ;

Amenities:
Fireplace

Activities:
Beach, Boating, Swimming

Vacation Home Description:
description:This quintessential cottage sits at the water's edge on a private beach and looks out at Little and Large Green Islands. Its living room boasts a wonderful and unusual stone fireplace. The beach can be used for swimming and beachcombing. All three bedrooms are located on the second floor. One of the single bedrooms is accessed through the master bedroom. Blue Shutters is a quiet spot to kick back, relax and enjoy the spectacular water views and fascinating boating activity. A private dock and float can be available with permission. This property is part of a compound of three cottages located at the end of Dog Fish Head Road. Blue Shutters can be combined with Wood's Roost and provide accommodations for four additional people. ;

Amenities:
Screened porch

Activities:
Boating, Hiking, Shopping, Swimming

Vacation Home Description:
description:Perched on a 50' cliff facing east on Southport Island, this estate sits on 3 acres, with its own private dock and float.;

Amenities:
Swimming Pool

Activities:
Ping Pong

Vacation Home Description:
description:Private setting, cheerfully and comfortably furnished throughout.;

Amenities:
Internet Access, TV

Activities:
Canoeing, Fencing, Fishing, Kayaking

Vacation Home Description:
description:You can't get any closer to the water than Dockside. This lovely Southport cottage sits directly on the water's edge of Townsend Gut and has incredible views of the busy waterway and little harbor. Relax on the deck with your coffee as you watch the sun rise. Enjoy watching fishermen and lobstermen return with their catch and then take a short stroll to Robinson's Wharf or the Lawnmere Inn to sample their wares. Bring your boat or use the dock and float for fishing, canoeing and kayaking. The dock and float are semi-private and shared only with Dockside's guest cottage, Shiloh at Dockside, which is also available for rent. This bright and sunny cottage was renovated in 1998 and features upscale furnishings and appliances, hardwood floors, floor to ceiling windows overlooking the water, and beautiful perennial gardens. The master bedroom on the 1st floor has a 3/4 bathroom with shower. The 2nd floor has two bedrooms and a full bathroom. There is also a den/playroom with a flatscreen TV, skylights, and futon. Although Dockside is quite close to the road, you won't feel it. There is brand new fencing along the road and almost all the windows overlook the water. High-speed internet is available. ;

Amenities:
Linens

Activities:
-

Vacation Home Description:
description:This modern style cottage is located at Cape Newagen on Southport Island. Bold ocean views overlook Damariscove, Fishermen's Island, and beyond. Scavenge the tidepools for marine life in the rocky backdrop that is your backyard. A large deck provides a front row seat to the working waterfront just outside your door. This two story cottage boasts oceanviews from every bedroom. A walkway takes you to the oceans edge for all types of water activity. This cottage can be paired with Stone or Sunshine for one large family or two families traveling together. Linens are included with this home. ;

Amenities:
Swimming Pool

Activities:
-

Vacation Home Description:
description:Glorious sunshine and ocean views welcome your family to the southern tip of Southport Island. Light and bright, inside and out, Sunshine Cottage takes advantage of every bit of sunlight, with outstanding views of open ocean through the expansive windows. Sit on the covered deck and watch the kids scramble on the rocks and explore enchanting tide pools just steps from the cottage. Crisp and cool inside, with a cheerful decor. May be paired with Stone Cottage for a memorable combined family gathering. This cottage is all one level. Linen included as part of this package. ;

Amenities:
Fireplace

Activities:
Beach

Vacation Home Description:
description:Don't sit home and pine for Maine. Piffi Biff is located in the Pine Cliff section of Southport Island, only a couple of miles from Boothbay Harbor. This classic Maine summer cottage has four bedrooms, two and a half bathrooms, a large living room with fireplace, a dining room, a breakfast room with ocean views, kitchen, and a covered wrap around porch from which to enjoy the panoramic ocean and island views. Watch the lobster boats pulling their traps just below your cottage, or enjoy the beautiful sailboats and other boats coming and going from the Harbor. Swim in the ocean if you are brave enough, or drive to the other side of the island and swim at Southport Beach. This cottage can accommodate someone in a wheelchair. There is a small step up into the cottage and a first floor bedroom and shower bath. Combine with other Pine Cliff cottages for extended family. Linen included as part of this package. ;

Amenities:
Playground

Activities:
Basketball, Beach, Tennis

Vacation Home Description:
description:New Capitol Island Listing! The Beach House is everything the name implies, located directly across the street from the Capitol Island Beach. Known once as the Capitol Island Restaurant, this older cape can accomodate six with three bedrooms and full bath upstairs and one half bath downstairs. Take in the views of the Atlantic from one of the two covered porches that this cottage boasts. In addition to the beach, island activites for the children include a basketball court, playground, and tennis courts for a fee. For the adults, the association dock and public boat ramp are found nearby. Relish a slice of island life for your next vacation. ;

Amenities:
-

Activities:
Boating, Fishing

Vacation Home Description:
description:Bright and newly furnished one bedroom cottage in the heart of Southport Village offers partial waterviews of the Townsend Gut and Southport swing bridge. Plenty of boating activity surrounds this busy working waterfront. Just a short walk to the local lobster pound for lunch or to pick up the nights lobster feast. Great fishing off the bridge just a short walk from the property. This cottage can be paired with Great Escape or Crosstrees. ;

Amenities:
-

Activities:
Kayaking

Vacation Home Description:
description:Check out the photos of this newly remodeled one story boathouse. Country nautical describes the decor. Lighting in this cottage comes from a local, well known pottery. The newly redone living/dining area has comfortable furnishings, an entertainment center, and more. Dine while watching the boats and water activities in the cove. One level living with a deck off the main living area providing an outside spot to read, relax or enjoy nature. You have a private dock and float so bring your own boat or kayak and enjoy the waters. Located on a quiet cove off Townsend Gut, about two and a half miles from Boothbay Harbor. ;

Amenities:
Fireplace

Activities:
Beach, Fishing, Swimming

Vacation Home Description:
description:This snug little cottage is situated on 10 acres of Southport Island with limited views of Deckers Cove. Conveniently located only a short walk to the local lobster pound, specialty foods store, and a short drive to Hendrick's Head Beach for swimming. Walk to one of the two bridges close by for fishing. Featuring a stone fireplace for those chilly nights. Access to all that Southport has to offer at a reasonable rate. ;

Amenities:
-

Activities:
Beach

Vacation Home Description:
description:This cozy bungalow by the sea is located just across the road from Hendrick's Head Beach on Southport Island with views of the lighthouse beyond. After a long day of soaking up the sun, dine waterside on the picnic table across the way while watching a spectacular Maine sunset over Sheepscot Bay. An ample lawn provides a great area for play. Just a short walk to the Southport General Store. Only a ten minute drive to downtown Boothbay Harbor. ;