Vacation rentals with a home theater in Boothbay Harbor

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.

Panoramic Lake-View Retreat | Hot Tub & Game Room

✨ Private Lake-View Cabin | Hot Tub | Near Sunday River & Mt. Abram ✨ 🌲 Secluded lake-view cabin with panoramic mountain scenery 🎿 Minutes from world-class skiing & hiking, Mt. Abram – 7 min Sunday River – 18 mins 💑 Ideal for couples, families, or friends looking to unplug & recharge 🛁 Private hot tub under the stars after skiing or hiking adventures 🪵 Warm up by the fireplace with hot cocoa on snowy nights 🌄 Wake up to peaceful lake and mountain views and crisp alpine air 🦮 Dog friendly

Sunset & Lake View, Theater, HTub, Xbox, Mini Golf

Welcome to the Sunday River retreat in our luxury chalet with the best views in Maine. Our sanctuary can comfortably sleep 12 and boasts Lake Christopher panoramic views with Mt. Abram sights. Minutes from Sunday River Resort, a public boat launch and other area attractions. Private hot tub, fire pit, wood stove and deck await your arrival. Enjoy arcade games, Xbox, a movie theatre room, BBQ grill and speakeasy theme bar setup. Don't forget to take a picture in the gondola and to catch a sunset!

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.

Lakefront Retreat, Boating, Groups & Dogs Welcome!

A Beautiful Home on pristine Flying Lake, Amazing Views, a Private Boat Dock & Lounge Area, Perfect for a family/friends getaway! Located on 200+ ft of PRIVATE, pristine Lakefront property with Kayaks, a Hot Tub, Theatre Room, Two Kitchens, and so much more! 2026: Sleeps 18-20, assuming mostly 2/bed, Tiny House Optional in Summer, Outdoor Hot Tub, Jetted Spa, Theatre Room, Fire Pit, 26 Acres *AWD in winter months. Plenty of parking, snowmobiling & ITS Trails, Lake front parking, Ice fishing

NEW Luxury Retreat Hot Tub+Swim Lake+Firepits

Award-winning 2025 custom-built design estate Near Sunday River ⛷️ —a serene 15-acre mountain oasis! Enjoy a gourmet kitchen, open-concept living, and Samsung 8K OLED theater plus 4 other SMART 4K TVs to accomodate guest with other interest. Game room! Unwind on spacious porches with a hot tub or gather by the fire pit for s’mores, stargazing, fish, swim pond, and unforgettable moments. Where luxury meets tranquility, this retreat is your perfect escape. Create memories that last a lifetime!!

The Stilt House

Once the island Trading Post (in the 1820's) now serves as a private retreat on Westport Island. The whole property has been listed on the National Register of Historic Places since 1982. The building is nestled at the water's edge, half on land and half on stilts over the tidal waters of the Sheepscot River. The property has its own private deck, island, rocky beach, trails and hammock. This is an old structure - over 200 years old! A great piece of history and an absolute oasis.

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

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!

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.