Holiday rentals with outdoor seating in Boothbay Harbor

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.

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.

Sunny Downtown Apartment with Views of the Harbor

The views of the Boothbay Harbor and the new footbridge are spectacular! This spot is walking distance to bars, shops, restaurants and the grocery store. If you want to stay home, you can hang out on the deck that has comfy outdoor furniture and a dining table. Enjoy your coffee on this sunny deck with an amazing breakfast sandwich from the bakery next door. Downtown Boothbay can get loud but we are just far enough away to have a restful place within walking distance to all of the fun.

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

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.

Chic 1-Bedroom at the Heart of Boothbay Harbor

Welcome to Oak Ledge! Stay for Windjammer 2026: June 21-27! 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.

Battersea Cottage - quintessential Maine! ALL new!

Everything about this cottage is brand new! This quaint Boothbay Harbor cottage has been completely renovated. Fresh and new without sacrificing the charm of a Maine coastal village home. Located in the area of West Harbor, this cottage is within walking distance of the rocky shore of Mill Cove as well as the village center. Nestled in the trees on an ample lot, Battersea has everything you could need for a perfect getaway!

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.

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.

Adorable Year Round Cottage - Walk to Town!

You will love our waterfront cottage located on Mill Cove in downtown Boothbay Harbor which is a few minute walk to the center of town! Our cottage is a quaint, comfortable home with all the amenities that you could want. Our goal is to ensure that you have a most wonderful vacation. A new heating and air conditioning system guarantees comfort any time of year.