Mansion holiday rentals in Portland

Luxurious 5 bedroom on the ocean, w/ dock & kayaks

Historic 1735 home on a spacious one-acre property overlooking the ocean. Enjoy swimming from the dock in Cape Porpoise’s protected cove. Two kayaks provided for exploring the lighthouse & picnicking on nearby islands. Stroll past picturesque lobster boats to the town pier, where restaurants serve fresh local lobster & drinks. Walk to morning coffee, pastries, a local grocery store, athe renowned Nunan’s Lobster Hut. Just two miles from Kennebunkport and a nine-minute drive to Goose Rocks Beach.

Charming Historic Freeport House

Bring the whole family to this historic house just minutes from downtown Freeport and the LL Bean flagship stores. The cozy central kitchen and dining are flanked by two separate living rooms making plenty of room for fun and relaxation! With two twin beds, toddler bed and full-sized crib we can accomodate any family. Catch glimpses of the Harraseeket River from this updated 1840s home on a half acre. A wonderful jumping off point for both Portland and the natural beauty of Mid-coast Maine!

Creative comfort. Coziness refined. Artist's home.

Hip, sun-filled Portland landmark lovingly restored by artist/writer. This classic 1870s four-square was the original Oakhurst dairy, in the prestigious Deering Highlands neighborhood, 5 minutes from PWM airport, Portland's downtown, Old Port, and renowned foodie and music scene, and walking/running distance to the village of Deering Center and the trails of Back Cove, Baxter Woods, and Evergreen Cemetery. Modern amenities, funky charm, and plenty of room, inside and out. Cows not included.

4br2ba House+parking@PeacefulOasis on Munjoy Hill

This standalone 1500sf 3-story cottage is set in an ideal location, close to the Eastern Prom, cafes, award-winning restaurants, breweries and the Old Port. -Main floor: well-equipped kitchen + open concept living/dining room -Upper floor: 3BR (1 queen, 1 full, 1 twin) + bath -Garden level: 1BR/1 bath (queen) with private entrance - Off-street parking for 1 car This charming home @ A Peaceful Oasis offers plenty of space, privacy & comfort, making it the perfect home base for your stay.

Classic, calm river view & centrally located home

We are happy to share with you our coastal, colonial home set on eight acres along the Kennebunk River. Enjoy our quaint, warm home just 5 min to the beach and 3 minutes to Cape Arundel Golf Club. Our 4 bdrm, 2.5 bathroom suits short or long term stays. The location is ideal: 6 min from Kennebunkport, 15 min from Biddeford, and 30 min from Portland or Portsmouth! We hope to make you feel at home with the morning birds chirping and the calmness of the river just in back of the property.

Edgewater Retreat - Lakefront w/Sauna & EV Charger

Welcome to Edgewater Retreat! This custom-built cottage features lakefront views and access to three beaches: secluded pocket beach in front of cottage, boaters beach with docks, and a full sun sandy bottom swim beach. Enjoy an unforgettable Maine vacation. Paddlecraft on the water, lounge in the hammocks, S'mores by the campfire, canoe to nearby island for offshore yoga, and gril with friends & family. In winter, enjoy ice fishing and kids enjoy snow sledding on adjacent hill.

Easy Old Port Access & Casco Bay View Craftsman

Experience classic New England charm in this beautifully restored Craftsman-style home with sweeping water views of Casco Bay and the Presumpscot River. Just minutes from Portland’s Old Port, this spacious six-bedroom, three-bath retreat offers easy access to shops, dining, and waterfront attractions. Enjoy hardwood floors, original trim, and modern updates for comfort, plus a hot tub, private patio, yard, and plenty of parking. Perfect for families, groups, and gatherings year-round.

Waterfront 5 BR Home | On Casco Bay in Freeport!

Spacious waterfront 5BR coastal retreat on Harraseeket Cove and South Freeport Harbor, perfect for kayaking, wildlife, and relaxing coastal Maine getaways. Set on 3.5 private wooded acres, the home features fast WiFi, smart TVs, outdoor dining, grills, firepit, kayaks, and peaceful water views throughout the property. Enjoy the tranquility of Maine’s coast while being only 3 minutes from Freeport’s shops, restaurants, breweries, and LLBean, with Wolfe’s Neck Woods State Park nearby.

Blueberry Hill

Beautiful property located on Watchic Lake in Standish Maine. Clear clean spring fed lake. 25 minutes to Portland with access to shopping, restaurants and entertainment. 45 minutes to North Conway New Hampshire. Where you wil find plenty of shopping, restaurants and winter skiing. Property includes use of Main Chalet home year round and two additional cabins each sleeping 4 are available from May-Oct. Great for extended families and friends.

House Your Group - 5 Minutes to Everything!

Our goal is to ensure our guests have a comfortable place to stay so they can focus on making the most of their visit. With four bedrooms, a large living room for everyone to gather, and an eat-in kitchen, this house is the ideal place to host your group. The kitchen is stocked with the essentials: dishes, cooking basics, and plenty of coffee. In addition, you can enjoy the private back deck and fenced in yard. Dogs are welcome as well!

Drakes Island Beach Front Breathtaking Property !

Ocean views from Kennebunkport to Cape Neddick and a gorgeous half mile sandy beach right outside your door! Watch the sunrise and the sunset over the sandy Drakes Island shores. Enjoy daily walks on the beach or take a walk on the peaceful trails nearby alongside the Rachel Carson Wildlife Refuge & Laudholm Farm, and go to town for restaurants, arcades and more fun. It doesn’t get better than this !

CHowder Cabin Dog Oasis Fenced Yard

🐾 Dog Welcoming Cabin with Fully Fenced Yard Escape to a peaceful, cozy cabin tucked away in the woods — the perfect balance of private seclusion and close proximity to town. Kick your feet up on the deck, breathe in the pine, listen to the birds and frogs, or take a gentle stroll down Bufflehead Cove Lane. Walk quietly and you may spot a heron or egret on the pond!