Vacation rentals in Boston

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Top-rated vacation rentals in Boston

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Private room · Fenway - Kenmore
Fenway Park Vintage Brownstone B&B - 3B
This charming brownstone, built in 1896, is set on quiet, tree-lined Bay State road, one of the "10 Boston’s Best Secret Streets" by Travel and Leisure. It is under the Boston landmark Citgo Sign, within 5 minute walking distance to Fenway Park, Kenmore Sq, Charles River and Boston University. The property has been lovingly maintained as a private residence for two generations. All original architectural details have been preserved with Victorian charm. Guest rooms are on the 3rd or 4th floor.
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Private room · Chelsea
Private, Intimate Ocean Blue Room @ The Washburn!
The intimate Ocean Blue Room is perfect for the single traveler seeking a one night stopover or an extended stay in a very affordable property that is close to Logan Airport and easily accessible to Greater Boston!
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Entire rental unit · Fenway - Kenmore
Chic Studio, Affordable & Simple
Bay Village Suites welcomes you to stay in one of our recently renovated high efficiency micro-apartments. At just 180 square feet the suite is beautifully furnished and because of its size we are able to offer exceptional prices! For all locals & stays 7+ nights, a copy of your license and proof of work in town is required within 24 hours of booking.

Vacation rentals for every style

Get the amount of space that is right for you

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Stay near Boston's top sights

Photo of Fenway Park
Fenway Park316 locals recommend
Photo of Boston Common
Boston Common232 locals recommend
Photo of Freedom Trail
Freedom Trail154 locals recommend
Photo of Harvard Square
Harvard Square127 locals recommend
Photo of Public Garden
Public Garden190 locals recommend
Photo of Museum of Science
Museum of Science175 locals recommend

Weekend vacation rentals in Boston

Private room · Brighton
Clean room with Free parking
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Private room · Cambridge
Modica Estate, Room #2
Private room · East Boston
Shelly's Place Cozy
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Private room · Brighton
Sunny Room #2 Free Parking
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Private room · Cambridge
The Modica Estates #4
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Private room · Chelsea
Private cozy, Green Room @ The Washburn!
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Private room · Roxbury
The Jazzy Airbnb
Hotel room · Fenway - Kenmore
Staypineapple Boston, Back Bay King
Private room · East Boston
Shelly's Bunk Room
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Entire rental unit · Downtown Boston
Perfect Location to Explore Boston
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Private room · East Boston
XL 1BR 24hr SelfCheck-In on Blue Line Free Parking
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Private room · MIT
Private bedroom close to MIT & BU
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Boston summer vacation rentals

Private room · Cambridge
The Modica Estates apartment 3 room A
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Private room · Brighton
Sunny room with Free parking
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Private room · Cambridge
The Modica Estates #5
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Private room · Cambridge
The Modica Estates Apartment 4 Room 1
Private room · East Boston
Shelly's Garden Room
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Private room · Cambridge
High-class private room next to MIT/Harvard 1
Private room · Cambridge
joyful private room next to central sq/MIT 2
Private room · Somerville
Sunny 1-bedroom unit w/ pvt bath, parking & deck
Private room · Quincy
Room2
Private room · Cambridge
Private bedroom close to MIT & Central Sq
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Private room · Cambridge
keyless private room near MIT,Central Sq 3
Entire rental unit · Fenway - Kenmore
Gorgeous Beacon Hills Studio next to State house
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Your guide to Boston

Welcome to Boston

One of America’s oldest and most important cities, Boston intertwines quaint New England charm with well-preserved history. The Massachusetts state capital’s scenic and strategic location, where Boston Harbor meets the Charles River, imbues it with a natural beauty while keeping the city thriving economically for almost four centuries.

The bay, and the Atlantic Ocean from which it’s fed, shapes Boston’s seafood-focused culinary scene, and also keeps the city center small, making it an easy place to navigate; you can hardly walk a few blocks without running into historic Revolutionary War sites. But even squeezed into the peninsula, the city’s “Emerald Necklace,” with 1,100 acres of linked parks, holds plenty of wide open space. Meanwhile, Boston’s dozens of colleges and universities attract a sophisticated crowd that upholds the long traditions of cultural entities like the Boston Public Library and the Boston Symphony Orchestra.


When is the best time to stay in a vacation rental in Boston?

Autumn in Boston paints the city in classic New England fall colors while threading the needle between hot, humid summer and chillingly cold winter. Late spring offers similarly pleasant weather, though the thaw from winter and slightly rainier months can turn things muddy. April’s marathon weekend, officially a state holiday called Patriots’ Day, draws huge crowds on the third Monday of the month. Average low temperatures in the winter rarely climb above freezing, but armed with plenty of warm clothing, you can take advantage of the off-season to book your vacation rental and visit high-traffic tourist sites without the crowds. Warm days with humidity make Boston summers sticky, but staying close to the many waterways around the city will help you stay cool.


What are the top things to do in Boston?

Boston Common

The country’s oldest city park remains a jewel of public space in downtown Boston. Its 50 historic acres began as communal grazing grounds for livestock, then hosted British soldiers in the Revolutionary War. The park now offers open greenspace, lined with trees and dotted with fountains and statues, forming the southern terminus of the Freedom Trail, and bordering the stunning Boston Public Garden.

Black Heritage Trail

Where Boston’s Freedom Trail gives you a window into the city’s role in the Revolutionary War, this lesser-known but equally important 1.6-mile walk shows off what happened next. Take one of the free guided tours that tells the story of Boston’s large free Black community between the Revolutionary and Civil wars through 14 national historic sites, including the African Meeting House, built in 1806 and the oldest surviving Black church in the United States.

Boating

Boston’s harbor and rivers have shaped the city, so seeing it from the water offers the best way to both learn about and enjoy it. Choose from one of the many harbor tours, scenic sunset excursions, and fascinating architecture cruises offered to visitors, or rent a boat to paddle the Charles River or sail to the Harbor Islands.

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