Why go to Portland?
The two things I get the most excited about when I travel are 1.) Food and 2.) Nature— Portland, Maine has both of those in spades. The city has a reputation for being a foodie paradise, and is rumored to have more restaurants per capita than other city in the U.S. after San Francisco (including a surprising amount of Thai restaurants). For nature, simply get in your car and drive in either direction on the coastal Route 1: going south will take you the most photographed lighthouse in America and seaside lobster rolls at Cape Elizabeth, as well as the dog-friendly beaches of Kennebunkport. Head north and do a little shopping at L.L. Bean HQ before continuing on your way to Bar Harbor and Acadia National Park. August also marks blueberry season— and you'll find the sweet wild Maine blueberries jammed or embedded into baked goods all along the coast.
Where to Stay
In addition to places to stay near Downtown Portland, we've included recommendations in Kennebunkport because their lodging game is on point. Kennebunkport is a 20 minute drive away from Portland and ideal for those who prefer more of a small seaside town feel as opposed to Portland's urban New England vibes. Rates are based on a one-night search for August 2018. The InnBox may collect a share of sales from booking links on this page.
The Press Hotel Starting at $290/Night
Portland's current boutique hotel darling (think the east coast equivalent of Portland, Oregon's Ace Hotel). The hotel occupies the former Portland Press Herald Building and channels its publishing past into the decor— with gorgeous desks and leather writing chairs (perfect for work-from-hotel types), herringbone textures, and letterpress references abound which should please aspiring writers and typography nerds alike. The hotel is a part of Marriott's Autograph collection and if you book directly through their site you can take advantage of their 'flexible booking' feature which shows you the lowest rate for each month.
The Press Hotel has elevators and in-room accessibility.
"Antique Chic Decor in South Portland" Starting at $91/Night — 1 Bedroom
Sophie's South Portland apartment is a case study in doing Airbnb right. An affordable, unique, dog-friendly space in a convenient location with a friendly and communicative host who even drops off bagels for guests. This was where we stayed during our trip to Portland and I highly recommend it. Sophie's place comes in three different configurations— large groups can book the whole place while couples can book the individual floors. We opted to stay on the second floor which was more spacious and next to the gorgeous, shared kitchen space (we actually never encountered any other guests while using the kitchen so it felt very private to us). What I loved about the space was that even though the kitchen was technically shared our space had its own private living and dining area outside of the bedroom. Street parking was free and readily available right behind the apartment, and it was only a 5-10 minute drive across the bridge to anywhere we wanted to go in Downtown Portland. Your stay also comes with a free yoga class at the studio on the first floor but we were too busy to take advantage of it!
This airbnb is located on the second and third floor of a building and only accessibly by a stairway.
Mercury Inn Starting at $165/Night — Studio
The Mercury Inn is a modern take on the classic bed and breakfast with a focus on sustainability. It's operated by a pair of charming husbands who channeled their combined interests in Greco-Roman mythology, food, and hospitality into this project. It's also pretty cool that the philosophy for the Mercury Inn was informed by one of the owner's experiences working as an intern in homeless shelter communities, "learning what people require fundamentally to feel safe and comfortable in a space that is not their own".
All rooms are located on the second and third floor of the building, with no elevator access.
Pomegranate Inn Starting at $279/Night
I'll admit— I'm not the biggest fan of the traditional bed-and-breakfast aesthetic. They can sometimes feel a bit stuffy and outdated. However, Pomegranate Inn manages to take the classic Victorian vibe and make give it a fresh twist thanks to bold wallpaper, painted walls, and playful pattern mixing. The Inn is located in downtown Portland's West End neighborhood, which has been called "one of the best preserved Victorian neighborhoods in the country" by the Minnesota Star Tribune. It is also one of the most gay-friendly neighborhoods in the city.
There doesn't appear to be elevator access at Pomegranate Inn, but we recommend contacting the hotel directly for more accessibility details.
Cottages at Cabot Cove Starting at $249/Night
The perfect place for living out your fantasy of shacking up in a charming seaside cottage à la Diane Lane in Nights in Rodanthe. Okay, her inn was a lot bigger, but you get the idea. These petite cottages are embued with tons of charm, dreamy robin's egg blue exteriors, and the small size will feel right at home to urban dwellers. Cabot Cove, itself a body of water, inspired the name of the fictional "Cabot Cove" seaside town setting in the famous series Murder, She Wrote. But don't worry, unlike its fictional counterpart the real Cabot Cove is actually safe and idyllic. Book three months out for the best rates.
All of the cottages are located on the ground floor.
Captain Jefferds Inn Starting at $259
This is our top pick for dog owners! While Maine is generally very dog-friendly, there are many hotels who simply tolerate your pup's presence in exchange for a hefty fee— but it seems like the staff at Captain Jeffers truly love dogs and get that our pups are part of our family. The Inn has a carriage house with five dog friendly units, and an additional fee of $35 per dog per day which is actually very reasonable as many other hotels are in the $50-75 range. The fee covers cleaning but also some bonuses for your pet: a personalized dog treat, doggy bowls, towels/sheets, and as many pick up bags as you need. The hotel also offers in-room dog-sitting at $15/hour.
There are ground floor units at Captain Jefferds Inn.
Kennebunkport Inn Starting at $279/Night
This picturesque port town hotel will make you feel like you're crashing at your friend's rich New England parent's house. The hotel has an amazing outdoor patio space for entertaining, and a very tasteful application of a nautical color scheme. There are older, more traditional bed-and-breakfast style rooms available as well as rooms with a more modern interpretation of the theme. Your stay also comes with complimentary use of the beach cruiser bicycles on site, which you can use to navigate around Dock Square, the central area in Kennebunkport where the hotel is located.
Kennebunkport Inn has in-room accessibility and roll-in showers.