Holiday rentals with outdoor seating in Boothbay

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.

Peaceful Oasis by the Great Salt Bay - 3BR/2Ba

Waterfront Retreat with Gorgeous Views Stunning 3-bedroom, 2-bath home perfect for multi-generational gatherings. Features an open-concept layout, chef’s kitchen, 1st-floor bedroom and bath, 2nd floor with 2 bedrooms and 1 bath. Kayak from your backyard, hike nearby trails, or swim in Damariscotta Lake just a 5-minute walk away. Stay connected with high-speed fiber optic WiFi. Close to charming Newcastle and Damariscotta shops and restaurants. A true oasis for nature and relaxation lovers!

Cottage in the woods on Ocean Point

Secluded getaway in the woods close enough to see and hear the ocean and catch amazing sunsets. Charming 1BR + Loft, 1BA cottage situated among an acre of Ocean Point fir trees providing privacy and a quiet get away. Less than 100yd walk to the shore, beach and path at Grimes Cove, Ocean Point Inn Restaurant & Bar, and daily activities at the community "casino" building with playground, tennis, pickle ball, basketball, and Sunday softball. Harbor is 20 mins away for exploring.

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.

Near Beach+Cedar Sauna+Outdoor Shower+Pond+FirePit

Unwind at your own studio cabin with forest views, private sauna & pond! * New Private Cedar & Glass Barrel Sauna * Minutes to Reid State Park Beach & 5 Island🦞 * Fire Pit * Outdoor Shower * Rain Shower & Heated Bathroom Floor * AC/Heat * TV & Record Player w/Vinyl * Fast Wifi *Spruce Studio 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 & separated by a privacy screen and natural landscaping.

Captain Fuller House: Boat Builders Retreat - Main

Wake up to sweeping views of Linekin Bay at this pet-friendly coastal retreat . Nestled in a quiet neighborhood, the home sleeps 6–8 guests with three bedrooms and two full bathrooms, perfect for families or small groups. Enjoy peaceful waterfront scenery, fresh ocean air, and easy access to Boothbay Harbor. Modern comforts include an on-site EV charger, while classic Maine charm makes it an ideal place to relax, recharge, and enjoy life by the bay—paws included.

Farnham Point Retreat

New modern apartment over garage. Brand new patio and fire Pit area. Nestled in the woods. 10 minutes from downtown scenic Boothbay Harbor and Botanical Gardens. Near Carriage House Restaurant. Near Ocean Point. Large walk-in closet. Two large flat screen TVs. BBQ Grill, Fire Pit, and outdoor Dining area with table and chairs. Corn hole and ring toss games. Firewood in the shed for guests. Outlet for EV charger available for small fee, upon request.

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.

Coastal Cotton Cottage on Sheepscot Harbour

Coastal Cotton Cottage is on beautiful Davis Island in a peaceful setting by the sea. Open the French doors from the living room and step out onto the spacious front porch to watch the sun set across Wiscasset Harbor. This cottage features two bedrooms downstairs and one single bed in the loft. NEW UPDATES THIS SPRING! Our cottage has been recently updated with fresh paint, new towels and new coastal interior decor.

Lakeside 3 BR Cabin in Boothbay Harbor

This swanky mid-60's cabin sits on a hill overlooking West Harbor pond in the town of Boothbay Harbor. It offers privacy yet is close to everything downtown Boothbay Harbor has to offer. It is great for couples, solo adventurers, business travelers and families (with kids), and large enough to accommodate bigger groups. If you would like to bring along your canine pal feel free, they are welcome (sorry no cats).

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.

Harbor for Two

Absorbed in ship-building tradition, picturesque Boothbay Harbor is still about boats-boats from around the world bobbing in the harbor, lobster boats unloading the day's catch, sea-kayaks exploring the rocky shoreline. Paddle, shop or gallery-hop along the charming waterfront or discover some of the endless hiking trails.