Less than fifty miles north of Boston waits one of New England’s quaintest small towns: Manchester-by-the-Sea, Massachusetts.
Videos by TravelAwaits
The town sits on the coast of Cape Ann, which is known for its stretching, sandy beaches and scenic outlooks. (One of them, Singing Beach, even squeaks when you walk on the sand.) Along the coast, you can also find dozens of grand mansions that were built by affluent visitors over the last century.
The small town is home to less than six thousand residents, but the area comes alive during summer as families pack into the seaside town. It’s a quintessential summer escape—one that’s more accessible and affordable than nearby spots like Cape Cod. You can reach it via the MBTA Commuter Rail from Boston, or drive up in less than an hour.
Here are the best Airbnbs in Manchester-by-the-Sea, Massachusetts, whether you’re a first-time visitor or you’ve been vacationing in the area for years. I’ve also included a few highly rated Vrbos in the area.
[This article is part of TravelAwaits new Airbnb and Vrbo recommendation series. We dig into listings to identify the crème de la crème of Guest Favorites, Superhost listings, and hidden gems to make finding the perfect rental for your next trip a breeze.]
Best Vrbos & Airbnbs in Manchester-by-the-Sea, Massachusetts
- Most walkable: Downtown 2BR
- Best for couples: Coastal 1BR
- Best host support: Serendipity Suite
- Best for families: 3BR Getaway
- Coziest stay: North Shore Townhome
- Most historic rental: Spacious Captain’s Estate
- Best for small groups: Bluebird
- Best for large groups: 9BR Home
Best Vrbos & Airbnbs in Manchester-by-the-Sea, Massachusetts
Downtown 2BR
If you want to stay in the heart of Manchester-by-the-Sea, this two-bedroom offers an unbeatable location. You’re just ten minutes from Singing Beach, and even closer to the town’s shops, restaurants, and train station. That means you can reach this rental via public transportation—no car rental needed. Plus, the home comes with all the beach gear you’ll need, from a cooler to beach chairs.
Coastal 1BR
You can technically sleep three guests in this apartment, but it’s ideal for couples who want some peace and quiet. The unit comes with a private yard, including a cozy sitting area with a fire pit feature. It’s also located close to town, meaning you can reach shops, restaurants, and cafes just five minutes away. Singing Beach is fifteen minutes walking—although this unit comes with two parking spots.
Serendipity Suite
This quaint two-bedroom suite is located on the host’s property but has a private entrance and yard space. Though you can bank on privacy, this host has added a few personal touches that make this Airbnb special. First, you can expect suggestions on places to eat and shops to explore. Second, you know that the host is available in case anything comes up during your stay. Lastly, you’ll have two off-street parking spots at your disposal.
3BR Getaway
There are multiple Airbnbs in Manchester-by-the-Sea with more than two bedrooms, but this home is great for families thanks to its spaciousness. Even with eight guests staying in all three bedrooms, you won’t feel crowded thanks to the large yard, large patio, living room, and full kitchen. The kitchen is also fully stocked, making group meals a breeze. Lastly, there’s something extra for mom and dad, as the master suite has large windows and a private balcony, along with a jacuzzi tub.
North Shore Townhome
Who doesn’t want a bit of charm with their New England rental? This three-bedroom townhome has a hyper-cozy interior with a blend of vintage and modern furniture throughout. There’s also a backyard and garden with plenty of flowers and greenery, along with a grill setup for group meals. The driveway fits two vehicles, as well, for both a cozy and comfortable stay.
Spacious Captain’s Estate
This sprawling, 3.5-acre estate was built back in 1790. The exterior has a large outdoor pool, a fancy gazebo where you can find outdoor gear, an outdoor dining area, a lawn with cherry blossom trees, and other fantastical features. With five bedrooms that can sleep twelve guests, you won’t be short on space to roam. Just know that the interior has been updated, but still has a very old-school, rustic feel thanks to its vintage pieces.
Bluebird
The Bluebird is a townhome rental with four bedrooms and other features that make it great for small group visits. First, it’s a true four-bedroom—no sofa sleepers involved. Second, it’s close enough to town that you can walk in case you don’t want to drive. Third, the rental comes with extras like beach passes and access to pickleball courts. The only drawback is that there’s only one full bathroom.
9BR Home
The Spacious Captain’s Estate listed above has plenty of room for large groups—but this nine-bedroom home is the true palace. It also has five bathrooms, meaning you don’t need to wait when you want to shower. The home is also beautiful in its own right thanks to its midcentury modern design and bonus features, including a large outdoor pool, massive playroom, and the stone fireplace in the living room. It’s also a ten-minute walk to town, assuming your large group can fit onto the sidewalks. Just know that there’s no central AC—instead, the home has individual units throughout.
[Just a heads-up: We may earn an affiliate commission when you make a purchase from a link in our articles.]