Vacation Rentals in Portland

Portland has a good network of roads and bridges, plus a convenient airport for those traveling by air. Commercial flights coming from different parts of the country arrive at Portland International Jetport, located 2 miles west of the city. There are quick non-stop flights from major East Coast cities like New York and Philadelphia.

Train and bus services to Portland from major cities in the northeast US are also plentiful, through companies such as Amtrak and Greyhound. The extensive interstate freeway network also has numerous connections to Portland if you're looking to combine your stay with a road trip. Portland is served by I-95, with connections to cities like Boston and New York.

Portland has a food culture that guests will love, with some of the best restaurants in the US. The options are abundant, whether the focus on the local seafood or international cuisine.

1. Central Provisions: Sample decadent small plates of tuna, suckling pig, cheese, oysters, and fish prepared by detail-oriented chefs.

2. Eventide Oyster Co.: At this oyster bar, fill up on local oysters, lobsters, ceviche, and other New England-centric dishes.

3. Fore Street Restaurant: Fore Street is known for its upscale, typical American fare. The menu changes daily, with selections such as wood oven-roasted seafood and artisan-quality desserts.

4. Emilitsa: Traditional Greek food is the focus here, with a variety of small and large plates using fresh local ingredients.

5. Empire Chinese Kitchen: This combined restaurant and music hall offers delicious Chinese dishes, especially its dim sum.

6 . The Honey Paw: Grab tasty noodles and local craft beer at this eatery known for its Asian fusion cuisine.

7. Boda: Thai food lovers should check out the exquisite veggie skewers and meat here.

8. Evo Kitchen + Bar: This stylish venue serves modern takes on Middle Eastern and Mediterranean food. There's an open kitchen for curious diners to watch.

9. Piccolo: Book a table at this cozy bistro, and savor southern and central Italian dishes and wines.

10. Street & Co: Scrumptious seafood preparations are the house specialties here, located in a cobblestoned alley.

Portland's Old Port is a lively historic district-cum-tourist strip. A multitude of shops, bars, and restaurants line the winding alleys amid cobblestone streets and historic architecture. Best explored on foot, this part of town is great for a sunny day.

The best views in the city can be captured from the Portland Observatory. The tower has a fascinating history, dating back to 1807. Guided tours are available daily and a sunset photo tour is available during summer months.

The Fort Williams Park makes an outstanding day trip. You can enjoy hours of hiking trails including a cliffside loop, arboretum, and a rocky beach, all in one park. The adjacent Portland Head Light lighthouse is one of the most photographed in the nation, and the oldest in Maine.

For some of Maine's best scenery, a ferry tour of the Casco Bay Islands is perfect. Photographers can capture lighthouses, civil war forts, and lovely coastal scenes, as well as seals, eagles, and the occasional whales. Most ferries allow you to bring a picnic lunch and alcoholic drinks.

1. Pride Portland!

One of Portland's most interesting annual events is this 10-day festival celebrating the local LGBTQ community, including a parade through town.

2. Maine Restaurant Week

This is an event that dining aficionados can't miss, where you can dine at some of Portland's best restaurants offering multi-course menus at attractive prices.

3. Maine Lobster Festival

This celebration is held every August at Rockland’s Harbor Park, northeast of Portland. Enjoy fresh Maine lobster and a variety of events, including a seafood cooking contest, wine tasting, arts and crafts, and the Big Parade.

4. Summer Kickoff Weekend

This weekend-long event is a great start to summer, including its Square Hop with live concerts in city parks, a waterfront walking tour, and events highlighting local businesses.

5. Bug Light Park Kite Festival

Fly a kite, attend crafting workshops, enjoy a fundraiser barbecue, and watch the sky fill up with colorful flying creations. This fun-filled, family-friendly event is a must-do activity on the third weekend every May.

1. The Maine Brew Bus

Craft beer is a local favorite, so don't forget to book a brewery tour with these folks. Hop in one of the green brew buses for one of many great tour options. You’ll stop at local breweries and distilleries, where you can chat with the brewmasters and sample different ales and lagers.

2. City Walking Tour

Experienced tour guides provide valuable insights on the history and culture of both Portland and Maine, showing you where the most notable sights are, including top dining and shopping areas. Walk along the Old Port, visit historic mansions, or climb up the hill to the Portland Observatory.

3. Lighthouse Tour

Maine is also known for its pretty coastline and lovely lighthouses, six of which are located in Portland. Arrange a lighthouse tour to admire these amazing beacons, including the Portland Head Light and Ram Island Light.