Experience a bustling working waterfront, one of the nation's most exciting culinary epicenters, and easy access to the year-round beauties of Midcoast Maine by booking a getaway to one of our charming Portland vacation rentals! Founded by Great Britain as a trade and fishing settlement in 1632, Portland has seen its turn as a trade power, a shipping mecca, and the largest city in Maine, which today is home to nearly one-quarter of the state population in the city's greater metropolitan area.
View 2 more homes
Whether you're an outdoorsman, a food lover, a lighthouse enthusiast, or a foliage-watcher, you'll find the perfect home away from home in these Southern Maine vacation rentals.
Originally called Machigonne - or "Great Neck" - by the Native Americans who first lived in the region, the city of Portland occupies a peninsula in Southern Maine's Casco Bay. Although this coastal city is in the far northeastern reaches of New England, it is also an easy and scenic drive just 112 miles south to Boston and 52 miles south to Portsmouth, NH.
Leveled by a great fire in 1866 and almost entirely rebuilt in the Victorian Era, Portland is a city of 19th century architecture and historic charm. And perhaps nowhere are Portland's past and present better displayed than the Old Port, a revitalized warehouse district that connects the working waterfront to an eclectic collection of shops and restaurants.
Looking to sample the bounty of a city built upon the fishing industry? Guests at our Portland vacation homes will find a rapidly growing culinary scene, where chefs showcase the very best local ingredients to attract diners from all over the country. Fill your days with pastries from Standard Baking Co. and classic lobster rolls from Fisherman's Grill; end your evenings with delectable small plates at Central Provisions, the freshest local oysters at Eventide Oyster Co., and farm-to-table splurges at the legendary Fore Street.
Thanks to its scenic coastal location, Portland is also an ideal place to explore the outdoor beauties of Maine. Drive five miles through South Portland to reach Cape Elizabeth and the Portland Head Light, which is believed to be the most photographed lighthouse in the world. You can also stop by Portland Paddle to rent stand-up paddle boards and book guided kayaking tours of Casco Bay.
Whether you're planning a winter retreat, a summer beach vacation, or a search for New England's most glorious fall foliage, Portland is the perfect home base for excursions across coastal Maine.
In the warm summer months, head 28 miles south to Kennebunkport, the quaint community of beachgoers made famous by the Bush family compound.
A scenic drive east on Highway One will allow visitors to discover the picturesque towns, charming harbors, and pristine coastlines of Midcoast Maine. In search of history? Head 35 miles east to the Maine Maritime Museum, the renowned facility located between the shipbuilding city of Bath and its bucolic coastal neighbor, West Bath. Looking for lobster rolls? Join the summer crowds that rightfully line up outside Red's Eats in the waterfront town of Wiscasset. Yearning for natural beauty? Launch your kayak near Southport, Boothbay Harbor, or East Boothbay to explore the Sheepscot River, the Damariscotta River, or Damariscove Island just offshore.
Feel up to traveling a bit further? Spend the day 82 miles east of Portland in Camden Hills State Park, a collection of gorgeous hillside trails that overlook the serene Camden harbor. Just be sure to stop for dinner at Primo on the way home - this James Beard Award winner in the neighboring city of Rockland is one of the most beloved restaurants in Maine.
Experience the tastes, landscapes, and sights of New England as they were meant to be enjoyed - book one of our Portland vacation rentals today!