Vacation rentals with a home theater 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.

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.

Chic Greenwood Chalet

You'll feel right at home when you walk through the doors of this Greenwood vacation rental. The 3-bedroom, 2.5-bath chalet-style house features 2,100 square feet of sleek living space complete with tasteful decor, 2 living areas, and a spacious wraparound deck with views of Mt. Abram and Mt. Washington. Overlooking the South Pond and surrounded by trees, this home offers families and groups plenty of outdoor recreation opportunities from boating and watersports to hiking, biking, and skiing!

Wellness Retreat~HotTub~Sauna ~Theater ~Yoga

Welcome to Ridgeline Retreat! 🏔️ 15 minutes to Sunday River & Mt. Abram 🏪 10 minutes to downtown Bethel 🌲 1.8 acres of privacy 🧖‍♀️ Hot tub & sauna 🍿 Home theater 🕹️ Game room w/ Arcade & Xbox 🧘🏼‍♂️ 3-season wellness room 💪🏼 Free weights 🎿 Boot room 👨🏼‍🍳 Chef’s kitchen, fully stocked 🍗 Outdoor deck w. 10-person table and grill (Spring - Fall) 🛜 1,000 mbps Fast WiFi ❄️ A/C 🐣 Kids toys, high chair, pack n’ play 🛏️ Linens, bathrobes, & soaps provided 🐕 Pet friendly

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.

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!

Hot Tub | Game Room | Dog-Friendly | Sleeps 14

Planning a ski trip, mountain biking weekend, or relaxing getaway? The Retreat by Just Happy Homes is meticulously crafted to offer an exceptional experience for family and friends seeking both outdoor adventure and relaxation. New construction, 5 bed/3.5 bath mountain home, 12 min to Sunday River, 7 min to Mt. Abram, and 5 min to downtown Bethel. Enjoy a private hot tub, huge game room, stocked kitchen, kid-friendly supplies, dog-friendly hospitality, and peaceful wooded views.

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.