Experience rich history and a classic seafaring vibe in Portland, Maine. From the cobblestones of the Old Port neighborhood to the grand brick homes of the West End, this classic city wins over visitors with its undeniable beauty. Spend your days biking along the Greenbelt, enjoying farm-to-table cuisine on Fore Street, or watching the boats on the waterfront. Book a stay at a Portland vacation rental today, and be situated within walking distance from the city’s best attractions. With that said, here are the most charming places in Portland to stay.

1. Old Port

In the Old Port, Portland, Maine
Source: Flickr/Phillip Capper

Easily the most picturesque neighborhood in Portland, the Old Port places you in the center of the city’s history. Here, red brick buildings rise above cobblestone streets, and warmly lit boutiques at street level create a welcoming feeling. Vacation rentals in this area sit within a few minutes of Portland’s best restaurants and just minutes from beautiful Casco Bay. Feel free to leave your car behind; the Old Port is highly walkable.

2. Portland Harbor

Maine State Pier
Source: Flickr/Corey Templeton

Stay close to the water with a vacation rental in Portland Harbor. Working piers jut out into the ocean, providing a thrilling view of fishing boats, ferries and personal watercraft. Catch a concert on the Maine State Pier, or hop on a ferry to explore the nearby islands. If you’re bringing the kids, don’t miss a visit to the Portland Science Center. Many local wharves feature restaurants and bakeries, so you can enjoy a meal with a view of the water.

3. West End

State Street Sidewalk
Source: Flickr/Corey Templeton

Step into the Victorian era in the West End, one of Portland’s most luxurious neighborhoods. Vacation rentals here range from perfectly restored carriage houses to enormous mansions, so you can find a historic home for groups of all sizes. Stay near Congress Street for quick access to the city’s most popular restaurants, or if you’re bringing the family, look for rentals near the beautiful McIntyre Park.

4. East End

Misty Morning On the East End
Source: Flickr/eric obery

Tucked on the tip of the peninsula, the East End neighborhood provides unparalleled water access. Largely residential, this area offers quiet, family-friendly vacation rentals just a short walk from Portland’s bustling downtown. The end of the peninsula is taken up by a large green space, where you can swim at East End Beach, ride or run along the waterfront path or watch the boats from Fish Point.

5. Arts District

A view of some Arts District buildings on Congress Street
Source: Flickr/Corey Templeton

Enjoy Portland’s best performing and fine arts in the Arts District. Culture is king in this historic neighborhood; within its boundaries, you can visit the Portland Museum of Art, the State Theatre and the Museum of African Culture. Learn about local lore at the Maine Historical Society, or bring the little ones to the Children’s Museum. The neighborhood hosts a variety of excellent restaurants and live music venues, so you’re never far from a great evening out within minutes from your vacation rental.

6. East Bayside

East Bayside Community Mural at Anderson and Fox Streets
Source: Flickr/Corey Templeton

Experience one of Portland’s funkiest, most up-and-coming neighborhoods in East Bayside. Once an industrial district, this revitalized area now houses a slew of craft breweries, new restaurants and custom murals. Vacation rentals here range from ultra-modern condos to warehouses that have been converted into stunning lofts. Start your day as the hip locals do, with a coffee at the legendary Coffee By Design, and explore the area by bike on the convenient Bayside Trail.

7. West Bayside

Source: Pixabay/Arcaion

Take advantage of Portland’s best views and green spaces with a vacation rental in West Bayside. Homes near Back Cove Park provide beautiful vistas across the water and quick access to the popular Back Cove Trail. Pack a picnic and head to Deering Oaks Park, where you can explore the extensive trail system, enjoy the playground or relax by the pond. When you’re ready for some action, downtown lies just a few minutes away.

8. Back Cove

Source: Pixabay/Oldiefan

Blend in with the Portland locals in Back Cove. This popular residential neighborhood lies across the Back Cove from the downtown core, making it a great home base for exploring the city. If you’re traveling without a car, rent a bike and pedal along the well-used trail that runs along the waterfront and connects to downtown. Vacation rentals in this area range from ranch homes to sprawling Victorians, so it’s a breeze to find accommodations that suit your style.

9. Parkside

Deering Oaks Bridge, Spring
Source: Flickr/Corey Templeton

Dominated by the sprawling Deering Oaks Park, the Parkside neighborhood offers quiet streets and beautiful open spaces. Here, families stroll under old-growth trees, and beautiful brick buildings pop up on every corner. Stay near the park and enjoy morning strolls by the pond, or look for vacation rentals in the southern end of the neighborhood to stay just steps from the downtown restaurants and galleries.

10. Peaks Island

Peaks Island, Maine
Source: Flickr/Angela Clare Morrow

Embrace ocean living on Peaks Island, a beautiful island that lies less than 20 minutes from downtown Portland by ferry. A popular summer destination for city-dwellers, this lovely community provides 360-degree ocean views and a relaxed, artistic vibe. Once you’re checked in to your vacation rental, do as the locals do and rent a golf cart to get around the island. Stop by the Fifth Maine Museum, rent a kayak for an afternoon of paddling and refuel with ice cream from the popular Down Front.

11. Knightville

Source: Pixabay/Pexels

Tucked into a curve at the end of the Casco Bay Bridge, Knightville is one of South Portland’s most welcoming up-and-coming neighborhoods. Newly revitalized, this area boasts a wide variety of independent businesses and a friendly, small-town vibe. Spend your days wandering into funky coffee shops, taking seaside yoga classes or testing the menu at the many hip eateries. Whether you want a modest bungalow or a modern condo, this cozy, walkable neighborhood has a vacation rental to meet your needs.

12. Ferry Village

Bug Light Park
Source: Flickr/Roger H. Goun

Wake up to beautiful views of downtown Portland in Ferry Village, a compact neighborhood in South Portland. With its wide selection of vacation rentals, it’s easy to find everything from sleek apartments to nautical-inspired bungalows. Head down to the Sunset Marina for a pleasant stroll, or explore the lighthouse and grounds at Bug Light Park. If you’re visiting in the summer, visit the park after dark to enjoy the summer movie series.