
Holiday rentals in Boston
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Quick stats about holiday rentals in Boston

Total holiday rentals
Explore 10,280 holiday rentals in Boston

Verified guest reviews
Over 514,260 verified reviews to help you choose

Family-friendly holiday rentals
3,930 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 2,850 rentals that welcome pets

Holiday rentals with a pool
450 properties feature pools

Rentals with dedicated workspaces
5,640 properties have a dedicated workspace

Wifi availability
10,090 of Boston holiday rentals include wifi access

Popular amenities for guests
Guests love Self check-in, Monthly stays and Waterfront across Boston rentals

4.7 Average rating
Boston stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
Boston’s top spots include Fenway Park, Boston Common and TD Garden
Top-rated holiday rentals in Boston
Guests agree: these stays are highly rated for location, cleanliness and more.

Romantic Boston Harbor Houseboat -Waterfront Suite
Enjoy sunrise on the deck, unwind by the water and experience Boston from your floating retreat. Stay in Boston Harbor minutes from the North End, Faneuil Hall, Freedom Trail and downtown. The Green Turtle Ste 2 is perfect for 2 people looking for a unique waterfront escape with beautiful views and easy access to everything Boston has to offer. Relax after a day of sight seeing in your comfortable dock chair. The houseboat includes two separate private suites and a reservation is for one suite.

Astonishing 1 Bed South End Boston's Best Location
Clean, unique, bright, inviting, 1-bedroom on the 1st floor. Newly renovated with astonishing ceilings, new tall custom windows, new appliances. The best of Boston outside your door Located half a block to Restaurant Row, where you’ll find some of the best dining in the city. Famous bakeries, coffee shops are all near, a super effortless walk to the very BEST Boston has to offer. Complimentary Keurig coffee, snacks, Netflix, movie channels, high speed internet. It doesn't get better than this!

Extraordinary 1-Bedroom Apartment in South Boston!
Cozy, comfortable, centrally-located one-bedroom unit in Southie. Unbeatable location, steps from Carson Beach, L Street Bathouse, BCEC, Sail Boston, World Cup 2026! This property presents endless possibilities for creating your perfect getaway! Convenient private entrance ensures hassle-free coming and going. Whether commuting to work, enjoying a concert/game/event/the vibrant local scene, or simply indulging in the beach and parks nearby, you are sure to enjoy it at this very special home!

Fenway Park! – Walk to all! – 1bedroom/1bathroom!
Amazing and cozy 1 bedroom apartment! WALK WALK WALK to Fenway Park. Close to Kenmore Square, Museum of Fine Arts, Northeastern University, Longwood Medical Area, Symphony Hall, LOTS of Universities, House of Blues, Isabella Stewart Gardner Museum, Kelleher Rose Garden, Berklee College of Music, New England Conservatory, theaters, Whole Foods, Target, bars, restaurants, and a few minutes from downtown! Includes everything you'll need for your stay. Public transportation is walking distance!

Beacon Hill - Historic Elegance
Step into 40 Hancock Street, a grand Beacon Hill brownstone suite with soaring ceilings, ornate fireplaces, and elegant bay windows that flood the space with light. This historic yet modern retreat blends timeless Boston charm with upscale finishes. Just steps from Boston Common, the Charles River, and the city’s finest dining, this luxury unit offers an unforgettable stay in one of the city’s most iconic neighborhoods. Entire apartment. No shared spaces. 100% private. 🚫 No pets allowed

Luxurious Fenway 2BR Penthouse w/ Roof Deck
This luxurious penthouse is nestled in the Fenway area and just a walk from everything you need. This multi-floor penthouse has something for everyone! Enjoy the reading nook, with a selection of board games! Relax on the roof deck, with views of both the Boston Skyline, and the Charles River! Get work done with the unique loft desk over looking the floor to ceiling windows! And fully equipped with utensils, glasses, and everything you need for a full short or long term stay.

Quaint studio apartment! Back Bay Area
Discover serenity at the South End Sanctuary, a charming first-floor studio nestled between the desirable Back Bay and South End neighborhoods. This quaint hideaway offers a private bathroom, mini fridge, oven, cabinets, and closet, all meticulously arranged within its 326 sqft of space. Immerse yourself in the fascinating history of this early 1900s Lodging House while savoring its timeless charm in a central location. Indulge in a tranquil experience in this hidden treasure.

Brownstone Luxury Penthouse Condo
Beautiful and sunny 2 bed 2 bath renovated 3rd floor penthouse condo with access to all that Boston has to offer! Walking distance to shops, groceries, and entertainment, including Fenway Park!, Immediate access to Green Line subway as well as other local transportation! Enjoy our primary bedroom with king size bed and ensuite bathroom, 2nd bedroom with full bed, additional full bathroom, full kitchen with dining area, living room with fireplace, and balcony with sitting area!

The Cori: Elegant • Airy • W/D
Experience Boston with classic warm furnishing near the heart of Boston. Just a 5 min walk from the T and close to Boston College/Harvard/MIT, you can tastefully engage with all of Boston. Additional sleeping arrangements provided on request! Unit Features -> Blazing Fast WiFi -> 65” Roku TV Living Room -> 55” Roku TV Bedroom -> Fully Stocked Kitchen -> Washer & Dryer -> Comfortable Queen Bed Ideal for and anyone looking to experience Boston in peace and comfort.

Kasa Boston at Fenway | Two Bedroom
With its prime location and exceptional amenities, Kasa Boston at Fenway is the ideal home in the heart of the city. Enjoy our fully furnished apartments with kitchens, in-unit laundry, and access to the fitness center. Just steps from Fenway Park, the Longwood Medical Area, restaurants and attractions, it’s perfect for short visits or extended stays. Our tech-enabled apartments offer 24/7 guest support through our Virtual Front Desk accessed via mobile device.

Walk to Berklee, Fenway & Newbury St
Experience a unique and comfortable stay in Boston at Maverick Suites' 28 Fenway. Located in the heart of the Fenway District, this modern studio apartment provides luxury and style with a hint of rebellion. Enjoy the convenience of being close to the city's best restaurants, museums, and attractions. With comfortable furnishings, stylish decor, and a spirit of exploration, Maverick Suites' 28 Fenway is the perfect place to experience life in Boston.

Renovated 1-Bed w/ private deck
Newly-renovated, modern apartment located directly above Remnant Brewing Satellite, in the vibrant and culturally diverse neighborhood of Wellington-Harrington. The location is perfect for someone who wants quick access to: Inman Square, East Cambridge, Harvard Square, Kendall Square, Union Square, Central Square, Davis Square, Charlestown, and Downtown Boston. Easy access to Fenway, TD Bank North, theaters, venues, and the hospitals.
Popular amenities for Boston holiday rentals
Other great holiday rentals in Boston

"Top of the Hub" - SecretAgent Room

A Lovely Private Room in the heart of Cambridge

Bold & Spacious Studio | Back Bay

Bright & Private Suite Steps from Davis Sq

(Mlb7) Charming and Cozy Back Bay Studio

Constellation 3

Charming 2BR in Boston

Luxurious King Size Bed in Boston with Amenities
When is the best time to visit Boston?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £95 | £92 | £103 | £117 | £132 | £131 | £127 | £131 | £123 | £129 | £110 | £100 |
| Avg. temp | -1°C | 0°C | 4°C | 9°C | 15°C | 20°C | 23°C | 23°C | 19°C | 13°C | 7°C | 2°C |
Frequently Asked Questions
What are the best places to stay in Boston?
Boston has vibrant neighborhoods like Beacon Hill, Back Bay, and the South End, each celebrated for distinct architecture and dining scenes. Families and groups often look to areas near the waterfront or around Fenway for parks and easy access to attractions.
What are the best things to do in Boston with kids?
Families often explore the New England Aquarium, Boston Children’s Museum, and Franklin Park Zoo. Green spaces like Boston Common provide play areas and spots for outdoor activities.
What are some of the best things to do in Boston?
Boston has the Freedom Trail for historic walks, the Museum of Fine Arts for world art, and lively markets around Faneuil Hall. Fenway Park draws baseball fans, and the waterfront invites strolls along the harbor.
How is the weather in Boston?
Boston winters have cold temperatures from 23 to 37°F (-5 to 3°C) with frequent snow. Summers are warm, with afternoon highs near 80°F (27°C) and humidity; spring and autumn see milder days and vibrant foliage.
What are the best places to visit in Boston?
Boston has historic sites like Paul Revere House and Old North Church, art collections at the Isabella Stewart Gardner Museum, and lively green spaces like the Boston Public Garden. The North End is popular for its Italian eateries and old-world atmosphere.
What are some hiking trails in Boston?
Emerald Necklace park system features walking trails through scenic urban nature. Forest Hills and the Arnold Arboretum are frequently suggested for gentle trails surrounded by botanical collections.
What are some family activities we can do in Boston?
Families can explore hands-on exhibits at science museums, ride the Swan Boats in the Boston Public Garden, or watch a Boston Red Sox game at Fenway Park. Aquarium and zoo visits are also frequently suggested for a day of discovery.
What are some of the best day trip ideas from Boston?
Day trips from Boston often include visiting historic Salem, scenic Cape Cod beaches, or Concord’s literary landmarks. Those looking for nature might explore nearby state parks or coastal villages.
Are there any pet friendly accommodations available in Boston?
Many vacation rentals in Boston welcome pets, especially in neighborhoods like South Boston, Jamaica Plain, and Beacon Hill. Urban parks and walking paths nearby help make it easy to explore the city with companion animals.
What are some local tips for visiting Boston?
Locals often walk or use public transit to get around, as historic streets can be busy. Try visiting markets early for fresher selections, and dress in layers to adapt to shifting weather, even in summer.
What is Boston known for?
Boston is recognized for its Revolutionary War history, renowned universities, and a sports legacy with teams like the Red Sox and Celtics. The city’s neighborhoods blend centuries-old architecture with diverse culinary scenes.
What are the best hidden gems to explore in Boston?
Explore hidden gardens in Beacon Hill, murals in Jamaica Plain, and the literary history at the Boston Athenaeum. The South End’s art galleries and community markets reveal creative local energy.
What are the best foods to try in Boston?
Locally rooted classics in Boston include clam chowder, lobster rolls, and Boston cream pie. Italian pastries are popular in the North End, and food markets showcase New England seafood and international flavors.
What should I bring for a trip to Boston?
Bring comfortable shoes for walking, layered clothing for changing temperatures, and a light rain jacket year-round. A reusable water bottle and sunscreen help, especially during outdoor city activities.
What is the nightlife in Boston like?
Boston’s nightlife has lively music venues in Allston, cocktail bars in the South End, and late-night eateries around Fenway. Some neighborhoods host comedy clubs and performances, drawing a mix of locals and visitors.
What are the most popular events or festivals in Boston?
The Boston Marathon, held each spring, is internationally recognized, and Independence Day celebrations feature fireworks along the Charles River. Boston Calling draws music fans in late spring, while Head of the Charles Regatta is often highlighted for rowing competitions in autumn.
Are there family friendly vacation rentals in Boston?
Boston has family-friendly vacation rentals in neighborhoods like Back Bay, South Boston, and Jamaica Plain. Many locations are near parks, museums, and playgrounds for easy access to activities.
When is the best time to visit Boston?
Late spring and autumn are often recommended for pleasant temperatures and colorful city parks. Summer draws visitors for festivals, outdoor concerts, and waterfront activities.
All about Boston
As one of the United States' oldest settlements, the New England city of Boston is thick with history. Downtown's mazelike map of one-way streets alludes to a time when travel meant horseback, and you can still wander the well-worn cobblestone pathways that ribbon through Beacon Hill — Acorn Street is an especially popular photo op. Harvard University in Cambridge has been around since 1636, and Boston Harbor still hosts reenactments of its infamous Boston Tea Party.
But history isn’t the only reason to visit the capital of Massachusetts. There are baseball games at Fenway Park, exhibits to explore at the Museum of Fine Art, and picnic opportunities at Boston Common. Next to the Common, the Public Garden features leisurely rides on the paddle-operated Swan Boats, operating on the pond since 1877.
Cocktail bars and creative cafes serve up drinks on both sides of the Charles River. For freshly shucked oysters and Boston clam chowder, downtown is hard to beat.
What are the top things to do in Boston?
Isabella Stewart Gardner Museum
This museum houses more than 7,500 paintings, ceramics, sculptures, and other works of art, plus thousands of rare books and archival objects — all curated by its original owner, Victorian collector Isabella Stewart Gardner. Upon her death, she dedicated the building and its exhibitions “for education and enjoyment of the public forever.”
Boston Public Market
Quincy Market may get more press, but the Boston Public Market is arguably more intimate, with tens of shops instead of hundreds. As an indoor market, it’s also open year-round, with independent sellers hawking chocolates, doughnuts, fish, and honey — all grown, caught, or made locally in Massachusetts.
Blue Hills Hiking
Just 15 minutes from downtown, the Blue Hills Reservation offers 200 kilometres of trails through Massachusetts hills and meadows. Hikes run the gamut from gentle walks like Houghton’s Pond Loop — an especially gorgeous route in autumn — to mountain climbs up to Buck Hill and Skyline. You’ll also find cross-country ski routes available in winter.
Destinations to explore
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- Fenway Park
- Harvard University
- Hampton Beach
- TD Garden
- Gillette Stadium
- Boston Common
- Boston Seaport
- Revere Beach
- Brown University
- Boston University
- Boston Convention and Exhibition Center
- Freedom Trail
- New England Aquarium
- Onset Beach
- MIT Museum
- Canobie Lake Park
- Crane Beach
- Duxbury Beach
- North Hampton Beach
- Boston College
- Roxbury Crossing Station
- Northeastern University
- Quincy Market
- Tufts University
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