Holiday rentals with a home cinema in Boothbay

Damariscotta Lakefront 3BR+

PLEASE REACH OUT IF YOUR DATES IN MAY & JUNE NOT AVAILABLE. We want to host you during this gorgeous time of year & may have more flexibility. This tastefully updated family cottage w/ private dock on Damariscotta Lake was built for year round enjoyment. Nestled in a cove w/ resident beaver, spring peepers, late summer bullfrogs, and frequent visits by bald eagles, osprey, owls & loons, this is a phenomenal retreat for nature lovers & anglers. Sleeps 3 couples or 2 families with kids & friends.

Entire Home 5 mins from Downtown

5 minute walk to downtown. 5 beds (2 queens, 2 doubles, one large daybed) 3 bedrooms, 2.5 baths, home theater with blackout shades, built in bar, large yard and driveway, detached home gym with full weight sets and built in audio, and laundry room. This 3 story home is a 5 minute walk to downtown and local beaches and has air conditioning and heat in every room. Comes with a beach cart filled with chairs, umbrella, towels and all you’ll need for your trip to the sandy shores of OOB. Pet Friendly

Coastal Vibes in Boothbay Harbor

Fabulous and rare opportunity to enjoy both waterfront & in-town living in this custom home on Mills Cove. The property offers classic design with a blend of contemporary stylings. Enjoy the broad westerly views across the water and amazing sunsets. All rooms are light-filled w/ large windows and open concept floor plan. Equipped a with tidal dock and float. An original 2-story boat house has been retrofitted for the the ultimate unique theater experience. Just a short stroll to downtown!

Captain's House near Henry Allen's Lobster Shack

This spacious, comfortable house is your home away from home to explore the beautiful coast of Maine! Famous Lookout Point is just a stroll down the road - you can swim at the public beach or walk to two small islands. Be sure to stop by Allen’s Seafood market and pick up clams or lobsters for your evening feast. Big rooms, beautiful windows with lots of light, and even a pool table for raucous games in the evening make this a perfect place for family and friend gatherings through the seasons.

Modern lakefront log cabin with sunset views.

3 bedroom- 1 king, 1 queen, one double Oversized couch-single Pullout Queen in media room Single futon media roo 2 full bath log cabin. Outdoor shower **Fitness room** Media Room*** Hot Tub- Brand new...amazing jets! located on 6 acres private land with 200+ feet of lake frontage. **New dock** 4 kayaks 2 Paddle-boards Exclusive design propane heat with Jotul "wood burning stove look" radiant floor heat in bathroom edge-less shower hiking, fishing, snowmobiling **PETS** $50/night each

Modern, luxury newly renovated home right in town

Enjoy a stylish experience at this centrally-located house in quiet beautiful neighborhood in the heart of Camden. Newly renovated, air-conditioned in every room, tasteful & modern decors, high end chef kitchen. Leave your car and stroll to downtown attractions: harbor, restaurants and shops. Enjoy comfortable memory foam mattress (2 kings, 1 Queen), luxurious linen beddings, and plush towels. Essentials provided for your comfortable stay (picnic supplies ,paper goods, kitchen staples)

Brand-New Luxe Retreat | Hot Tub + Fire Pit

Brand-new luxury coastal home minutes from Portland’s Old Port. Relax in the 8-person hot tub, gather around the fire pit, and enjoy a beautifully appointed chef’s kitchen designed for memorable group getaways. A private deck overlooks the garden with a play area, play kitchen, crib, pak n play and fire pit, while a covered gazebo shelters the year-round spa. Perfect for families, friends, or remote work, with easy access to beaches, Portland’s dining scene, and waterfront attractions.

The Hill's on Buttonwood

We are out of the baby stage and ready to share our home while away. Our home is a great house for entertaining or just relaxing without feeling cramped. There are places for everyone, from the heated pool, the patio, or outdoor activities, to the many living/sitting rooms, gym or theater/game room. Located just minutes from the airport and minutes from downtown in the historic Stroudwater district or Portland. Sitting on nearly an acre on a small cul-de-sac of similar stately homes.

Luxury Retreat In Back Cove | 10 Min to Downtown

Bike to downtown just 2 miles away. Ideal for a couple or family looking for a restorative getaway in a quiet, locals neighborhood. The architect owner designed and built this light-filled spacious eco-suite to meet the needs of the most discerning guest with luxurious accommodations. Organic and down-topped king mattress, linen bedding, spacious marble rain shower, deep soaking tub, fenced in backyard with deck, hammock, and pool - everything you need for a memorable Maine vacation!

Oceanfront home in Owls Head with sweeping water v

Views of the Breakwater Lighthouse. **With new living and dining furniture, as well as painting, furniture and decor planned for Spring 2026** Welcome to your coastal retreat in Owls Head, where sweeping views of Rockland Harbor set the tone for an unforgettable Maine escape. This beautifully positioned three-bedroom, one-and-a-half-bath home offers a front-row seat to life on the water, from lobster boats heading out at dawn to sailboats and ferries gliding by throughout the day.

Robinhood Cove home - Georgetown

Welcome to your Maine coastal escape in Georgetown! This spacious 6BR, 2BA home sits directly on Robinhood Cove with a wraparound porch and seasonal dock for kayaking, paddleboarding, or relaxing by the water. Inside, enjoy a full kitchen, dining room, two living rooms, and a kids’ room/office. Outside, gather around the firepit, grill on the BBQ, or unwind by the cove—all just 5 minutes from Reid State Park and the charm of Georgetown’s classic MidCoast beauty.

Charming, Family-Friendly Historical In Town Home

STR26-48 Sadler House is an in-town historic home located just blocks from Main Street. We have made it truly convenient for families, with flexible sleeping arrangements in three cozy upstairs bedrooms, two full baths, a fully equipped kitchen, large dining table, living room, and sun room. Walk to shops, restaurants, museums and the harbor in minutes. Our house is the perfect home base for exploring all that the beautiful midcoast has to offer.