Holiday rentals with a home theatre in Boothbay Harbor

Coastal Escape | Hot Tub Fire Pit Chef Kitchen

Welcome to your modern brand new custom built Coastal Escape! Relax in the private hot tub, gather at the fire pit, and cook like a pro in the fully equipped chef’s kitchen. Bedrooms: Four restful rooms with fresh linens and blackout shades. Outdoor perks: Spacious yard, grill, and Adirondack seating. SuperFast Fiber Optics Wi-Fi & Smart TVs Home Theater Washer/dryer Self-check-in Minutes to Portland’s Old Port, beaches, breweries, and hiking trails. Book now for year-round Maine adventure!

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.

Charming, Family-Friendly Historical In Town Home

STR25-25 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. Ask us about free delivery from Ruckus Donuts!

Luxe Eco Studio near Back Cove

2 miles from downtown, perfect for a couple or family looking for a restorative getaway. The owners, architect and landscaper, spent the last three years designing and building this light-filled spacious suite to meet the needs of the most discerning guest. Settle in with luxurious accommodations. Organic and down-topped king mattress, linen bedding, spacious marble rain shower, deep water soaking tub and heated slate floors are just a few amenities that will ensure a memorable Maine vacation!

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)

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.

Pine&Eagle Family&Dog Friendly Lake Sebago Access

Welcome to the Pine & Eagle, your relaxing retreat in Sebago. As you step into this charming property you will be greeted by beautiful views of the glistening lake waters that will instantly soothe your soul. This cozy retreat is perfect for the whole family, including the dogs. Grab a book and relax on the front porch by day and enjoy an outdoor movie with the family by night. 3 min to Nason's Beach 10 min Naples Causeway 10 min to Sebago State Park 15 min Point Sebago Golf Course

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.

HotTub, Game Room, LakeFront,Paddleboards & Kayaks

Follow us @anchorunwind Discover our retreat, designed for families and couples to escape the city and reconnect with nature. Enjoy nearby trails, winter skiing, or paddle boarding right from our private dock—this getaway has it all. Our cozy lake house offers a peaceful escape, with the soothing sounds of a stream between Trickey Pond and Sebago Cove as your backdrop. The home sleeps up to 6 adults and 2 children comfortably.

Luxury Lake House w/ Home Theater, Hot Tub & Gym

This modern 4-bedroom retreat offers a private lake escape with resort-style features just steps from the water. From a saltwater hot tub under the stars to a theater-style game room and a fully equipped home gym, every space is designed for comfort, style, and play. With exclusive lake access, premium amenities, and a quiet neighborhood setting, it's the perfect getaway for families, couples, or small groups.

Steps from the sandy beach! "Surf's Up"

This 275 sq ft studio condo is 100 yards from the beach in an area that is outside the busiest part of OOB, but yet close enough. The beach is flat and the sand is smooth and your sunrise views are amazing! This unit is side by side with "Seashell" if your family needs a second unit. We also know several unit owners in this building if you have a larger family and want to coordinate your trip.