House holiday rentals in Southport

Southport, views of Christmas cove (Boothbay area)

Set on a hill above Christmas cove, enjoy water views from the deck or launch kayaks from the cove. Inside is a refreshed kitchen and full bath. Bedroom 1 has a Queen bed and half bath, bedroom 2 has a bunk and a twin bed and the loft has a king bed with half bath. Nearby are the Southport general store, Hendricks head beach, and Cozy’s dockside/Robinson’s wharf restaurants. Tour the Alpaca farm or drive to nearby Boothbay for a boat tour or the botanical gardens. Great for families and friends!

Maine Cottage/Your Year-Round Destination

The Stowaway sits on 5.5 private acres atop a hill with breathtaking waterviews from every level. This pet-friendly, 3 story home offers 4 bedrooms, 3 baths & sleeps 8. Perfect for family getaways, milestone celebrations or relaxing escapes, the cottage combines comfort & style! The carriage house sleeps 4 more & together the property can host events of 50-150 guests (event fee $9000). Explore Maine's beauty year-round from summer by the sea, to colorful fall foliage, to snowy winter holidays.

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.

Oak Leaf

Welcome to our charming 1940s cottage, nestled in the banks of the beautiful New Meadows River. This cozy getaway boasts stunning river views and vintage charm with all the modern comforts. With two bedrooms and a bright, airy living space, you’ll feel right at home. Conveniently located just off Route 1, you’re only 10 to 20 minutes from Maine’s top beaches, fine dining, and unique shopping experiences. Enjoy beautiful sunsets by the fire pit, unwind and make lasting memories by the river.

Modern home on Southport Island

Modern 3 bed, 3 bath home sleeps 6 comfortably. Water views of Decker Cove from all bedrooms, easy walking distance to Robinson's Wharf & Restaurant. Luxury indoor/outdoor space with fire pit, gas grill, hard top gazebo, and 40 foot Farmers porch overlooking Decker Cove. Bring a boat and launch at the public launch 1/2 mile away! Central Air Conditioning, Radiant Heat, Gas Fireplace, Open Concept Living Dining and Kitchen with gas range, dishwasher, built in microwave and coffee station.

Cozy Harbor Waterfront

This historic home was once the lightkeeper’s house and has been beautifully renovated with four bedrooms and three bathrooms. Located on idyllic Southport Island, the home feels peaceful and tucked away while still being easily accessible by a swing bridge, so you are never truly isolated. It is a short walk down to Cozy’s Dockside Restaurant where you have a perfect view of all the boats in the harbor. It’s a 10-minute walk to the Southport General Store which has great coffee and food.

Waterfront cottage with private dock Southport, ME

Enjoy an island getaway on a private island off Southport, ME yet only 10 minutes to Boothbay Harbor. The house sits on an acre of waterfront property with views of cozy harbor. House comes with a private dock (seasonal) and 2 kayaks. Master on first floor with King bed. Two additional bedrooms have a bunk and 2 twin beds. Enjoy a fully stocked kitchen so you can feel at home. Close to everything - Hendricks Head Beach, The Southport General store, restaurants, and Botanical Gardens.

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). We accept either one dog or one cat.

Pinkham Cove - Water Front Cottage

Authentic oceanfront Maine home, with stunning views and amazing sunsets. Located on Pinkham Cove at the mouth of Boothbay Harbor. Experience the village of BBH , hiking trails, Botanical Gardens and explore the tranquility of Maine. This is the perfect getaway cottage. Enjoy the deck and beach access. The home was recently remodeled. The kitchen is a gem with quartz countertops and Bosch appliances. Curl up by the cozy fireplace, enjoy the amazing harbor view!!

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. 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.

The Rowe House

Charming Coastal Cottage Walk to Harbor – Perfect Couples Escape w/ Private Setting The entire house is yours! 2 bedrooms, full bathroom, washer/dryer, a fully furnished living room, kitchen and dining room. Hardwood floors downstairs and carpet upstairs. Perfect for couples, solo adventurers, business travelers, small families and pets. NOTE: WE DO CHARGE $40 NON REFUNDABLE PET FEE PER PET DURING YOUR STAY.

Victorian Charm in Wiscasset, Maine: Acorn Cottage

A TRULY NOSTALGIC MAINE VACATION STAY. This spacious 1903 Masonic Victorian home in the “Prettiest Village” in Midcoast Maine offers 3 bedrooms, 1.5 baths, and is steps from local landmarks like world famous “Red’s Eats” for a lobster roll, boutique shops, antiques, art galleries, and restaurants. Just up the road is the award-nominated “Alna Store”!