Holiday rentals in Boston

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Top-rated holiday rentals in Boston

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

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Superhost
A bright living space is furnished with a light-colored sofa and a wooden coffee table. A large wall-mounted TV is positioned above a light wood sideboard. A round mirror and a floor lamp add to the decor, while a dining area with a wooden table and benches is situated near a window adorned with natural light.
Flat in Brighton
4.86 out of 5 average rating, 114 reviews

The Franklin: Wellness • Aesthetic • W/D • Gym

Experience Boston in this incredible eye-catching studio. Comes with a room divider for 1 bedroom like feel! Just a 5 min walk from the T and close to Boston College/Harvard, you can engage with all of Boston tastefully. Unit Features -> Blazing Fast WiFi -> 65” SmartTV with Streaming -> Fully Stocked Kitchen -> Washer & Dryer -> Comfortable Queen Bed Ideal for business travelers, couples, nurses, those in hospital treatment and everyone looking to experience Boston in comfort and peace.

Top guest favourite
A spacious room is presented with wooden flooring and light-colored walls. A queen size bed is arranged with decorative pillows and a soft blanket. A small gray sofa, accented with colorful cushions, is placed nearby. Shelves with plants and decor items are mounted on the walls.
Flat in Fenway-Kenmore
4.96 out of 5 average rating, 57 reviews

Fenway Park – Studio – Walk everywhere – Location!

Amazing location! WALK WALK WALK to Fenway Park! So 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 right there, super easy and safe!

Top guest favourite
A spacious bedroom features a large bed with decorative cushions, a cozy seating area, and an ornate fireplace. Natural light streams through the tall windows, highlighting the soft wall colors and the intricate ceiling fixture. A mirror reflects the room's inviting atmosphere.
Loft in East Cambridge
4.95 out of 5 average rating, 279 reviews

Charming, spacious gem in heart of City

Amazing location with this 1st floor airy and serene, fully furnished apartment in a two family, historic, recently renovated Greek Revival row-house with a private entrance. Located in a quiet, family-friendly location close to the Charles River, Kendall Square, Cambrideside Mall, Kendall Theater, Harvard Square, MIT, groceries, cafes, restaurants and more. Close to red line (Kendall), green line (Lechmere) and multiple convenient bus lines as well as a quick drive from Logan Airport.

Top guest favourite
A bright and airy living area features large windows with natural light streaming in. A white sectional sofa with a yellow decorative pillow faces a modern entertainment unit. The exposed brick wall adds character to the space, which is complemented by warm bamboo flooring.
Apartment in South End
4.94 out of 5 average rating, 246 reviews

SouthEnd Penthouse

Centrally located penthouse unit in the heart of Boston SouthEnd. Abundance of sunlight, spacious living area, and open kitchen will make your stay a unique and charming experience in a historically preserved area. Ideal to explore the local neighborhood restaurants or walk to Boston commons, the ballpark, downtown or Newbury Street. The neighborhood is historic to Boston with classical brick stone look and the place itself is quite a gem, very quiet and open dining+living room style.

Guest favourite
A wooden deck surrounded by vibrant red foliage and lush greenery creates a serene outdoor space. The deck is framed by wooden posts, with chairs visible on one side, inviting relaxation among the seasonal colors.
Flat in Cambridge
4.89 out of 5 average rating, 375 reviews

Harvard/MIT/BU Riverside Studio w/parking

Discover historic charm in our 1880s studio that opens up to a beautiful backyard and patio. Right in the heart of Harvard University, just steps from student dorms Mather house & Dunster House, and key attractions like the Charles River and eclectic shops. Walking distance to HBS, HLS, MIT, Harvard Sq, Central Sq. Easy access to the rest of Boston via Red Line, car, or bike - this is the perfect place to immerse yourself in the essence of Harvard, Cambridge, and Boston.

Guest favourite
A comfortable living room is showcased, featuring a light-colored L-sectional sofa with decorative pillows. A dark coffee table sits in front, while a dining table for four is positioned nearby. Large windows allow natural light to brighten the space, complemented by warm hardwood floors.
Flat in Back Bay
4.86 out of 5 average rating, 50 reviews

Renovated One Bedroom in Back Bay

Newly renovated 1 Bedroom | 1 Bath located on Marlborough St in Boston's historic Back Bay. This spacious 550 sqft condo is located on the third floor and offers brand new kitchen, updated bath, 10'+ high ceilings, high speed internet, premium cable, and new hardwood floors! Located on Marlborough Street in Boston's historic Back Bay between Charlesgate East and Massachusetts Avenue, we are just a quick walk to Newbury Street, Hynes Convention Center, and Fenway Park.

Top guest favourite
The living room features a dark sofa with teal accent pillows, complemented by a wooden coffee table. A light fixture hangs from the ceiling, and natural light fills the space through large windows. A small dining table with two chairs is visible, enhancing the cozy layout.
Apartment in Beacon Hill
4.97 out of 5 average rating, 355 reviews

Gorgeous Beacon Hill 1BR | 1BA

Come stay at our lovely condo in the heart of Boston's most desirable neighborhood, Beacon Hill! Our newly renovated 1 bedroom | 1 bathroom condo comfortably sleeps three adults and comes with everything you need for an enjoyable stay. Whether you want to walk the Freedom Trail, visit a relative at Mass General, or shop on Newbury St, you will find it all within walking distance. You could not be more centrally located to take in all the city has to offer.

Top guest favourite
A living area features a contemporary black sofa and two matching armchairs arranged around a round glass coffee table, all placed on a vibrant blue rug. A large artwork hangs on the wall, and a window allows natural light to enter the space.
Apartment in South End
4.99 out of 5 average rating, 107 reviews

1 Bedroom Apartment in Boston/South End

One bedroom condo on parlor level on quiet South End street. Convenient to all the restaurants, Back Bay, Financial District, Downtown. There are stairs leading to the building. Full size bed, full-size tub with shower in bathroom. Wi-Fi. Listing is for the full apartment. Two guests only. No one under 18. No visitors or parties. There is no street or designated parking. Best for one or two people visiting and enjoying the city.

Top guest favourite
A spacious living area features an exposed brick wall, wooden flooring, and ample natural light from skylights above. A small dining table and two bar stools are positioned near the modern kitchen, which includes essential appliances. Unique pendant lighting adds character to the room.
Flat in Cambridge
4.9 out of 5 average rating, 111 reviews

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.

Superhost
Apartment in Boston
5 out of 5 average rating, 4 reviews

803B HUGE Boston Studio King Bed Downtown Subway

✨BRAND NEW✨ 1 King-Bed Luxury Studio with private upgraded bathroom & fully-stocked kitchen, located right at Boston Commons and Downtown! NO SHARING OF RESTROOMS OR KITCHEN! *No children under 12. 📍 Centrally located to be able to walk anywhere needed and 200-400 ft. to multiple T stops 🚊. Perfect for traveling professionals, mid-term stays and more! ALL UTILITIES INCLUDED. 452 sq. feet. 8th floor. Elevator access, no stairs.

Guest favourite
Flat in Boston
5 out of 5 average rating, 26 reviews

Stylish Boston Getaway | Rooftop & Fireplace

Welcome to your Boston retreat! This stylish 1-bedroom on a charming cobblestone street offers comfort and unbeatable walkability. Enjoy the quiet Bay Village residential feel while being just steps from the Back Bay, South End, Chinatown and Theater District. Start your day with coffee on the shared rooftop or unwind by the fireplace after exploring the city.

Guest favourite
A waterfront view captures the skyline of Boston, showcasing various high-rise buildings under a partly cloudy sky. A bench faces the water, while decorative railings border the pathway, inviting peaceful moments by the harbor.
Flat in East Boston
5 out of 5 average rating, 39 reviews

Boston Skyline Stay | 1BR + City Views

Enjoy skyline views at Casa Blanca, a cozy 1BR on the Boston Harbor. Full kitchen, Smart TV, WiFi, in-unit laundry, and remote work setup. Walk to Piers Park, the Harborwalk, or ride the Ferry downtown. Quick access to Blue Line T, Logan Airport, Downtown Boston, Seaport, and Charlestown. Boutique hotel feel in the heart of the city!

Popular amenities for Boston holiday rentals

When is the best time to visit Boston?

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Avg. price$153 SGD$153 SGD$172 SGD$198 SGD$222 SGD$221 SGD$213 SGD$221 SGD$207 SGD$217 SGD$185 SGD$168 SGD
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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.

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

Destinations to explore

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  2. United States
  3. Massachusetts
  4. Suffolk County
  5. Boston