Holiday rentals with a home theatre in Boothbay

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

New Luxury Seaside w/ 8 Person Hot Tub + Firepit

Escape to Portland’s Coastal Maine ‘s Seaside Sanctuary—a brand-new, custom-built luxury retreat just built. Nestled in heart of Portland, this award-winning design offers sleek open-concept elegance with high ceilings, floor-to-ceiling windows, and a gourmet kitchen. Unwind in the 8 person hot tub under a gazebo, cozy up to large linear fireplace, or explore nearby beaches, trails, ski, and dining. Perfectly blending luxury with adventure, this retreat promises an unforgettable Maine getaway.

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!

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

This modern 4-bedroom home offers a private lake escape with resort-style amenities, just steps from the water. You'll enjoy exclusive lake access, a saltwater hot tub, and a movie theater-style game room. Key Amenities: • Private lake access • 4 bedrooms + queen air mattress • 2 kayaks + 2 paddleboards w/ life vests • Outdoor saltwater hot tub • Game room w/ big screen + theater seating • Home gym • Fully equipped kitchen • Outdoor fire pit • Quiet neighborhood • Free on-site parking

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

Steps from the sandy beach! "Seashell"

This studio apartment 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 "Surfs Up" if your family needs a second unit (pictures shown are of Surf’s Up next door which is a mirror image layout). We also know several unit owners in this building if you have a larger family and want to coordinate your trip.