Holiday rentals with outdoor seating in Boothbay

Rosie's Hideaway By the Sea

Rosie's Hideaway By The Sea is in a lovely turn of the century Victorian farm house filled with paintings by Maine artists and beautiful hardwood floors. The front yard has gorgeous shade trees and a stone wall. Fabulous views of the harbor is a short walk away. . Follow the road along the harbor and you'll end up downtown Boothbay Harbor where all the shops and restaurants are. While we love children and animals, the space is not appropriate / safe for children under 8 or pets of any kind.

BREEZE, in a tree The Appleton Retreat

BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE guests may reserve the wood fired cedar hot tub and the sauna, which are close by and private, at an additional charge. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

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.

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.

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.

Chic 1-Bedroom at the Heart of Boothbay Harbor

Welcome to 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. 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 (Amazon Prime/Disney+/Max/Hulu/Netflix)

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

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.

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!!

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.

The Highland Cottage on Sheepscot

NO HIDDEN FEES THE PRICE IS THE PRICE + CLEANING! Charming, updated, 1920's cottage directly on the banks of the Sheepscot bay. Cottage has - one bedroom with queen bed, bistro table for two, sitting area with sofa and cable television, small convenience kitchen area (no stove), full bath, linens