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Boston vacation rentals

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Top-rated vacation rentals in Boston

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

Apartment in South End
Stylish Downtown Studio in the SouthEnd, C.Ave# 43
The unit is stylishly designed for comfort, value and convenience. Centrally located on the line Boston’s Back Bay and South End. Quaint and chic are just 2 words to describe Boston’s South End neighborhood. In the past few years, the South End has grown to be one of Boston’s hottest neighborhoods built with families and young professionals in mind. Loaded with restaurants (some of the best in the city), art galleries, and boasting a modern industrial vibe, the South End is an ideal destination.
$190 per night
Superhost
Private room in Fenway - Kenmore
Fenway Park Brownstone B&B-4B (one guest only)
*This is a single guest room, one guest only* --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. Guest rooms are on the 3rd or 4th floor.
$164 per night
Private room in Cambridge
Peaceful, mid-Cambridge room with private en suite
This quiet, peaceful room with private en-suite in Inman Square is a great choice for your next trip to Cambridge/Boston. It is centrally located—a 10 to 15 minute walk to Harvard, MIT, Central Square, and the tech companies around Kendall Square. Whole Foods, Koreana, S&S Deli, local microbreweries, and many more food options are within blocks. This room with en-suite is an excellent place to “get away” and yet be in the heart of Cambridge.
$97 per night

Stay near Boston's top sights

Fenway Park815 locals recommend
Boston Common567 locals recommend
TD Garden243 locals recommend
New England Aquarium399 locals recommend
Freedom Trail470 locals recommend
Boston Logan International Airport110 locals recommend

Boston oceanfront vacation rentals

Private room in East Boston
#3 Maverick MBTA clean, comfy private room
$109 per night
Superhost
Private room in East Boston
First floor room 1
$92 per night
Superhost
Private room in Charlestown
"Casita" on the Water - Harbor View
$230 per night
Superhost
Private room in Winthrop
Beautiful Victorian
$72 per night

Boston fishing vacation rentals

Superhost
Private room in Arlington
@3闪闪 sunny room near Tufts Cambridge Davis Sq.
$78 per night
Private room in Watertown
Private Room/Free Parking close to Harvard& Boston
$111 per night
Superhost
Private room in Brighton
Rogers Pk Ave, Queen Bed/private bath, Park free.
$126 per night
Superhost
Condo in Jamaica Central - South Sumner
Fully-Equipped, Private 2nd Floor 1-Bed 1-Bath Apt
$164 per night

Private Boston vacation rentals

Loft in Coolidge Corner
A Stylish Stay w/ a Queen Bed, Heated Floors; #29
$208 per night
Apartment in Downtown Boston
Modern 1BR Downtown Boston-Milk301
$287 per night
Superhost
Apartment in Back Bay
(C11) Newly Styled Back Bay Studio!
$281 per night
Apartment in South End
(T7) NEW Cozy South End Studio!
$264 per night

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.


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.


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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