Destination guide

Charming cobblestoned streets and storied pasts

As the oldest American city, Boston is immensely proud of its history, and the role it played in the Revolution. Today, the city pays homage to its past with an array of monuments to former residents and national heroes, cobblestoned streets that lead to designated historical sites, and, perhaps most notably, the Freedom Trail. This 2.5-mile walk introduces visitors to 16 truly historic spots, while weaving among some of the city's best restaurants, bars, and markets. Book a Boston vacation rental on the harbor or in the heart of downtown, and prepare to learn about the city without even realizing it.

Activities

B is for Beacon Hill, Back Bay, and Beantown

From Beacon Hill to Back Bay, Boston's neighborhoods are perfect for shopping, so be sure to leave plenty of space in your suitcase for bringing home souvenirs. Though the city does offer a comprehensive public transit system, you'll get to know the streets so much better on foot or by bike, so consider a walking or bike tour to take you around. The city shines when the weather warms up, which means a picnic on Boston Common, al fresco dining by the harbor, or a Boston vacation rental with guaranteed outdoor space are a must.

Weather

From pleasant summers to less pleasant winters

Summers in Boston are an absolute delight, with sunny days and warm evenings. Naturally, this also lines up with peak travel season and, as such, peak prices. Instead, consider booking your Boston vacation rental in late spring or early fall for similar weather and lower prices. Late autumn is also a dream in New England, when the leaves turn from green to vibrant reds, yellows, and oranges. Winters in Boston are notoriously harsh, but if you don't mind the heaps of snow and ice, then you're most likely to find a deal.

Natural features

Water is for more than just tossing in tea

Situated on Massachusetts Bay and around the Charles River, more than one quarter of Boston is comprised of water. It's the only state capital in the contiguous lower 48 states that shares a border with the ocean. As an already active and outdoorsy city, the large amounts of water encourage plenty of water sports, from sailing to rowing to fishing. A variety of parks and gardens are scattered throughout the city, full of wild birds, small wildlife, and flowers that bloom when the weather allows.

Transport

Transportation to and around Boston

Fly into Boston, MA (BOS-Logan Intl.), the closest airport, located 2.2 mi (3.5 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Norwood, MA (OWD-Norwood Memorial), which is 13.3 mi (21.5 km) away.

If you're traveling by train, Boston North Station, Boston South Station and Boston-Back Bay Station are the main stations in the city. You can get around Boston by jumping on the metro at Government Center Station, State St. Station or Bowdoin Station.

Where to stay around Boston, MA?

Our 2019 property listings offer a large selection of 1,587 vacation rentals near Boston. From 1,186 Condos/Apartments to 280 Houses, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Boston for a holiday or a weekend are on Vrbo.

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

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 Boston:

  • Jamaica Plain: 62 vacation rentals
  • South Boston: 833 vacation rentals
  • Charlestown: 67 vacation rentals
  • Seaport District: 616 vacation rentals
  • Dorchester: 905 vacation rentals

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

What are the popular point of interests near where I can stay when traveling to Boston?

Vrbo offers a large selection of vacation rentals near lovely places in Boston. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Fenway Park: 1,202 vacation rentals
  • Boston Convention and Exhibition Center: 1,718 vacation rentals
  • Boston University: 1,324 vacation rentals
  • Harvard Square: 1,343 vacation rentals
  • Boston College: 1,609 vacation rentals

But there are many other points of interest around Boston listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Condos/Apartments in Boston?

Yes, of course. Vrbo has 1,186 Condos/Apartments in Boston. Our other popular types of vacation rentals in Boston include:

  • Houses: 280 rentals available
  • Boats: 9 rentals available
  • Cottages: 6 rentals available

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

Can I find a vacation rental with pool in Boston?

Yes, you can select your prefered vacation rental with pool among our 55 vacation rentals with pool available in Boston. Please use our search bar to access the selection of vacation rentals available.

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