Holiday rentals in South Bristol

Waterfront Guest House on the Maine Coast

Bright open four-season guest house with fantastic view of Jones Cove and the open ocean in beautiful South Bristol, Maine. The guest house offers privacy and independence. The top floor has an open space with kitchen, sleeping area with queen bed, bathroom. The ground floor has a desk, Smart TV, seating area and French doors that open onto a stone patio. Includes Kohler generator, fiber optic wifi, outdoor grill & fire pit. The water is tidal Owner lives on property (150 ft from guest house)

The Sail Loft - Pastoral, Coastal South Bristol

Lovely 2-bedroom apartment offered by Superhosts John and Kina. A short walk to lovely South Bristol harbor, 15 minute drive to Pemaquid Beach, with parking and amenities. Surrounded by lush woodland, birds galore, deer and foxes, the spacious second-floor apartment has a roomy living area with sofa, TV and ample kitchen with dining. One large bedroom with queen bed and a second bedroom with twin beds, full bath with shower. Balcony overlooks extensive woods. Private entrance, plenty of parking.

Moss House: A Modern Waterfront Cabin in the Woods

Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

Hermit Thrush House

The 1 bedroom, 1 and 1/2 bathroom with laundry apartment is located at: 19 POORHOUSE COVE ROAD in South Bristol, Maine 04568. The apartment has skylights in the living room and kitchen and is located on a private property as a stand alone guest house. Close to Christmas Cove, Wawenock public/private golf course and 15 miles from scenic Damariscotta and the Pemaquid peninsula with a public white sand beach. Our waterfront is Poorhouse Cove, an estuary off of the Gulf of Maine, Atlantic Ocean.

Sauna+Near Beach+Pond+Outdoor Shower+Fire Pit

Relax at your own private forest retreat! * Private Cedar Glass Sauna * Minutes Reid State Park Beach & 5 Island🦞 * Private Outdoor Shower * Private Fire Pit w/S'mores * 100% Cotton sheets/towels * Rain Shower & Heated Bathroom Floor * AC/Heat * SmartTV & Record Player w/Vinyl * Fast Broadband Wifi *Pine Cabin is one of two cabins on 8 acres right down the road from one of the best beaches in Maine! The cabins are 150ft. apart and separated by a privacy screen and natural landscaping.

Twin Ponds Guest House

Be it Spring & flowers, Summer living on the water, Winter's Gardens of Light Festival or the Lush colorful Fall, this guest house is the quintessential Maine experience. Twin Ponds Guest House boasts an open-floor-plan overlooking the historic Saw & Gristmill on Mill Pond and Marsh's fresh water Pond. Stone walls, lavender walkways & day lilies will welcome you. Relax & read the day away or in moments you can be in the midst of the most wonderful sailing, shops, food and fun imaginable.

Clarks Cove Farm - Orchard Apartment

The Orchard Apartment with Private Deck and Water Views. Welcome to your peaceful getaway overlooking the Apple orchard and cove. Walk to the water, enjoy bird watching, or launch into canoeing, kayaking, and coastal water activities. Explore nearby scenic hiking trails, then unwind on your private deck with beautiful sunset views or relax in a comfortable, air-conditioned space with fast WiFi. Visit our friendly Donkeys 🫏 chicken🐔 and sheep 🐑 . Perfect for adventure and relaxation.

Charming Coastal Maine Cottage

This Charming Maine cottage is nestled between the Damariscotta river and Jones cove in the quaint village of South Bristol. It is minutes away from the Town of Damariscotta, Pemaquid Beach, the Pemaquid lighthouse and many other fun and relaxing activities like: kayaking, golfing, fishing, hiking, a relaxing bicycle ride, or simply laying on the hammock while enjoying the sounds of nature and the ocean breeze. Of course there's plenty of lobster or "Lobstah" close by too. Enjoy!!

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.

Serenity, Privacy, Clean and Bright

This large studio can be rented by the week only June - September. A high ceiling, many windows and skylights give this space a feeling of spaciousness. On a private road. A short walk takes you to the Damariscotta River. Perfect for artists, writers and those looking for a retreat space. 10 miles away are great cafes, stores, a movie theater, a health food store "better than Whole Foods", a lighthouse and a beautiful beach. Close by are countless spectacular walking trails.

Cottage on an island on the end of a peninsula W

Compass Rose Way Cottages are on Rutherfords Island in South Bristol, Maine. There are four cottages, we rent two 9f the four, North and West, both are two bedroom, one bathroom, both with an open concept living room and kitchen cottages We are less than 1/3 mile from downtown South Bristol and the ocean. We are about 14 miles from Damariscotta, Pemaquid Point, and other mid coast Maine towns. Our electricity is provided by our solar array that is grid connected.

Chic 1-Bedroom at the Heart of Boothbay Harbor

Come and Stay in Oak Ledge! Oak Ledge is a beautifully-renovated 2-storey 1-bedroom apartment in the heart of Boothbay Harbor. Bedroom and Bathroom on the upper level. 2-night minimum 5-night maximum This is an adults only listing. Sorry, no pets. Our friendly rescue dog "Oscar" roams freely on the property. Off-street parking for one car. Self check-in. Smart TV with streaming - remember to have your log-ins.