Mansion holiday rentals in Portland

C-Howder Cabin Dog Oasis Fenced Yard

Don’t forget your dogs! Enjoy the peacefulness of this cozy tranquil cabin tucked away in the woods. The cabin has the best of both worlds; private & secluded, while being close to town. Kick your feet up on the deck. Breathe in the pine, listen to the birds & frogs. Or take a lovely stroll down Bufflehead Cove Lane, walk quietly you may see a heron or egret on the pond. Left at Port Rd. & continue down to Western Ave. Lots of stairs. Driveway very steep, requires 4-wheel drive in winter.

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.

Schoolhouse*Hot Tub*Game Room*King Beds*Firepit*Ne

MAKE MEMORIES together in the school's large classroom which is an impressive gathering spot for the whole group with the modern kitchen, massive dining table and comfy living room. Endless entertainment in the brand new barn game room! This lovingly restored schoolhouse is a unique mixture of historic charm, warmth, character and modern ease. Gather outside on the 7 acre property for a cookout, chat by the fire or relax in the hot tub after hiking, swimming, boating, skiing, dining or shopping

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.

Perched atop the Coast of the Atlantic Ocean

Enjoy sweeping vistas of the Atlantic Ocean from this 2002 home perched among spruce trees above the rocky coast. Watch for bald eagles and seals. Fall asleep to the sound of crashing waves. Walk down to the edge of the ocean to lounge or picnic. The intrepid visitor can scramble along the shore. Walk 6 minutes or drive the 0.1 miles to the park entrance. Hike the Little River Trail. The house has vaulted ceilings, panoramic views, fully equipped kitchen, and whirlpool bath.

Bay View Craftsman with Easy Old Port Access

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.

Adorable Beach House Across the Street From Beach!

Time for a beach vacation! Cozy home right across the street from Pine Point! Stroll the seven miles of quiet, sandy, residential beach, or bring your bike for a quick ride to the Pier at Old Orchard Beach. Located within a block are several restaurants and a gift shop. Just 20 minutes drive to the heart of Portland, you won't want to miss the local breweries and shopping in Old Port. Kayak rental nearby. Be sure to check out our other listings!

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!