Vacation Rentals in Portland (ME)

Set on a peninsula in Maine’s Casco Bay, Maine is a quintessential slice of New England on the US Atlantic Coast. The town has all the trappings of a nostalgic coastal town where seagulls cry and the smell of fish & chips waft through the salty air. The Old Port district is quite reminiscent of an old European town thanks to its 19th century streets, bookstores, and intimate pubs. When you tire of all those historic landside distractions and museums, take off on a lobster-hunting excursion, a sunset cruise or a boat ride to the nearby islands. Maine’s largest city is best enjoyed with a vacation rental as your base.

A true four-season destination, Portland is easily accessible from Boston – it’s just a 2 hour drive up north. Vacation rentals in Portland are well-equipped with amenities such as high-speed Wi-Fi, television, sunny patios, and fully-functional kitchens. The best part is you can choose from a range of sea-facing rentals with divine Atlantic Ocean views. Families with kids and dogs, solo travelers, and honeymooners will feel right at home here. With regards to the best area to live in, the Old Port district in Downtown Maine is quite popular owing to its proximity to popular lobster houses, bars, and museums – it’s also right by the Casco Bay waterfront. The Arts District will appeal to museum-goers as Portland’s Museum of Art and the Children’s Museum are both located here. For cheaper prices on accommodation, look for vacation rentals around the Portland International Airport, and those off the highway.

Maine’s history has been wonderfully preserved through its historic parks, mansions, and lighthouses. Rent a car and set about exploring the coast. Hard to miss is the picturesque Portland Head Light which is America’s most photographed lighthouse having guided ancient mariners since 1791! While it is closed to the public, visitors can certainly enjoy views of the craggy coastline and working harbor from here. Nearby is the Fort Williams Park, a historic artillery base where you can stroll through the ruins and check out the WWII bunkers on the lawns. Food trucks at the park sell tasty lobster rolls. Finally, on a nice day consider kayaking out to Fort Gorges on Hog Island Ledge where you can explore the ruins of the former US military fort.

Start at the Portland Museum of Art (PMA) opened in 1882 in the iconic Arts District. This is Maine’s oldest and largest public art institution, and it houses important European, American, and Contemporary art – look out for Renoir and Monet’s works, as well as those of local Maine artists. The Maine Jewish Museum in the East End district offers visitors a crash course in the contribution of Jewish immigrants to the region – there are art exhibitions to be enjoyed here as well. Finally, don’t miss the immersive and thoroughly engaging Children’s Museum & Theater where kids can milk fake cows, navigate replica lobster boats, and even try some dress-up theater! If possible, catch a show at Maddy’s Theater, America’s oldest continuously operating theater for children.

Fuel yourself with a hearty breakfast at Becky’s Diner, local favorite since 1991. Their luscious chocolate chip pancakes, pastrami omelets, and sausage patties are highly sought after and the prices are honest too. Bang on the pier is DiMillo's On The Water, a bit of a Portland institution, opened in 1954 by Tony DiMillo. Their Lobster Mac & Cheese, fried clams, and Angus beef preparations are excellent. Five minutes away is another heavyweight on the town’s culinary scene – the Portland Lobster Company. Enjoy their famous steamed lobster dinners, and mussels in romantic waterfront setting. A memorable meal in a lighthouse setting awaits at The Lobster Shack at Two Lights. Savor their classic warm clam chowder to the sounds of the crashing surf. What about drinks? Don't forget Portland’s brewery of choice since 1988, the award-winning Gritty’s Portland Brew Pub – you’ll love their classic pale ales and pub fare.

A booming performing arts scene

One of the best ways to experience the famed New England coastline is with a Maine coastal cruise. Knowledgeable captains will regale you with tidbits of information on the islands, lighthouses, and historic districts of coastal towns you’ll cruise by!

Fifteen minutes south of Portland lies the town of Scarborough whose top attraction is the Prouts Neck Cliff Walk – make sure to photograph the genteel old homes en route. You can also visit the erstwhile home of one of America’s greatest landscape artists, Winslow Homer.

Set on the pristine Saco Bay, Ferry Beach State Park merits mention for its sweeping vistas of white sand beaches along the Saco River. Well-marked natural trails and guided programs are a fun and informative way to reconnect with nature.

Having tried all those tasty lobsters at Maine’s coastal cafes, how about catching some of your own? A lobster cruise is a fantastic way to get acquainted with local lobster men and pick up some hunting skills.

Get in touch with your inner child at New England’s only beachfront amusement park where over 250 games await. Classic rides such as Tilt-a-Whirl, Dodgem Cars, and carousels make this a mandatory stop for the family.