Where to stay around Wakefield, MA?

Our 2019 property listings offer a large selection of 2,188 vacation rentals near Wakefield. From 1,160 Condos/Apartments to 991 Studios, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Wakefield for a holiday or a weekend are on VRBO.

What is the best area to stay when traveling to Wakefield?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Wakefield:

  • North End: 453 vacation rentals
  • Back Bay: 1,046 vacation rentals
  • Beacon Hill: 571 vacation rentals
  • Charlestown: 74 vacation rentals
  • Dorchester: 1,511 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

Can I rent Condos/Apartments in Wakefield?

Yes, of course. VRBO has 1,160 Condos/Apartments in Wakefield. Our other popular types of vacation rentals in Wakefield include:

  • Studios: 991 rentals available
  • Hotels: 817 rentals available
  • Houses: 141 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Townhouses and more.

Can I find a vacation rental with pool in Wakefield?

Yes, you can select your prefered vacation rental with pool among our 549 vacation rentals with pool available in Wakefield. Please use our search bar to access the selection of vacation rentals available.

    Wake up to storybook life in Wakefield

    When you’re here, you’re home. The friendly locals in Wakefield will make sure of that. And how can you not feel a little of that down-home goodness in a place that looks like something straight out of a New England storybook? Abundant trees, lush lawns, and sparkling lakes lend the town its scenic beauty. No matter the location of your Wakefield vacation rental, you’re only minutes away from something special: a pretty park, a shimmering waterfront, a vibrant town common. It’s quaint, it’s peaceful, it’s home (at least for a short spell).

    Facing the music in Wakefield

    Fancy a night out on the town? The Wakefield Repertory Theatre is perfect for catching a musical on date night with your honey. There are countless annual festivals, too, including the July 4th parade, Art Week Wakefield, the springtime egg hunt, and even Local Eats Week devoted to the area’s best grub. Of course, booking a Wakefield vacation rental is meaningless if you don’t brush up on your area history. Take a self-guided walking tour of historic downtown Wakefield to see the area’s oldest structures, including churches and the OG YMCA building.

    Waking up to history in Wakefield

    If you’re a history buff, the museum at Wakefield Historical Society has all of the answers to all of your burning Wakefield queries. A combination of fixed and fresh exhibits delves deep into the area’s fascinating past. The town is also home to the Soldiers and Sailors Monument, a granite statue dedicated to the memory of war heroes. There’s also a single schoolhouse remaining: West Ward School, built in 1847, which now serves as a museum. The city is dotted with legendary 19th-century homes, many of which are listed on the National Register of Historic Places.

    The time of the season(s) for loving

    If ever you’ve dreamed of the true meaning of the 4 seasons then you’ve come to the right place. Wakefield boasts 4 distinct seasons, and each promises exactly what you might expect. Winter is a brisk and snowy affair, with January lows approaching 15 degrees. Summer is hot and humid. Spring, Mother Nature’s gift to New England, is exuberant in its sunshine and pleasant temperatures—that said, you might meet an April shower or 2. Autumn is typically cool, but the sun beats down all day long.

    Heartbreakingly breathtaking beauty in Wakefield

    In Middlesex County, part of greater Boston, Wakefield is home to popular Lake Quannapowitt. Its 3.3-mile trail is considered one of the best in the area for a leisurely hike or jog. Man-made Crystal Lake is also here. If you happen to book a Wakefield vacation rental in the spring, make some time to walk the Floral Way. It’s a pretty path along Church Street that brightens the town with its perennial pink and white blooms. Stunning Breakheart Reservation is, well, heartbreakingly beautiful, what with its dense forest that casts shadows over river waters.