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Holiday rentals in Boston

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Quick stats about holiday rentals in Boston

  • Total holiday rentals

    Explore 10,830 holiday rentals in Boston

  • Verified guest reviews

    Over 533,960 verified reviews to help you choose

  • Family-friendly holiday rentals

    3,750 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 2,930 rentals that welcome pets

  • Holiday rentals with a pool

    640 properties feature pools

  • Rentals with dedicated workspaces

    5,890 properties have a dedicated workspace

  • Wifi availability

    10,640 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.

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Guest favourite
Houseboat in North End

The Wave

Your scenic waterfront vacation awaits! This charming houseboat offers a unique blend of comfort, relaxation, and adventure. Wake up to the gentle sway of the water and enjoy your morning coffee on the deck as the sun rises over the horizon. With a fully stocked kitchen you can prepare meals just like at home and enjoy them in the cozy living space. Thoughtfully designed with modern furnishings and amenities, this two bedroom houseboat is offers a one-of-a-kind experience you won’t forget.

LocationBathroomNearby

4.91 out of 5 average rating, 11 reviews
Top guest favourite
A small dining area features a round white table with two yellow chairs. A simple floral arrangement sits atop the table. Overhead lighting brightens the space, while a colorful artwork adorns the wall. Bench seating is available along the nearby wall.
Flat in Coolidge Corner

A Brookline Sanctuary

You're in the heart of Brookline! LOCAL: Minutes away from a French bakery , Thai restaurant, taqueria, liquor store and small grocery store. More restaurants, cafes and bars down the street in Coolidge Corner and Washington Sq. BOSTON: 5-minute walk to subway stop. 10-min subway ride to Fenway Park. Direct subway to tourist spots! Easy transfer to Cambridge . Perfect for visiting Boston, a friend, a student or colleges. Enjoy the entire floor to yourself with a private entrance!

ValueLocationDecor

4.98 out of 5 average rating, 92 reviews
Guest favourite
A luxurious hotel entrance is visible, featuring a grand awning adorned with lights and elegant planters filled with flowers. Large glass windows showcase nearby upscale shops, including Tiffany & Co. High ceilings and classic architectural details contribute to the distinguished atmosphere.
Hotel room in Back Bay

Timeless Stay | Freedom Trail. Fitness Center

Explore a beautifully reimagined luxury hotel, The Newbury Boston, where the bustle of the Back Bay is your playground and the idyllic Boston Public Garden your front yard. Attractions just nearby: ✔Boston Expressionist paintings and Chinese ceramics at Museum of Fine Arts ✔Deep dive into history at Boston’s Tea Party Museum ✔Sharks, rays, penguins at New England Aquarium ✔400 years of Boston’s history and the story of nation’s pursuit of liberty, Freedom Trail ✔Downtown Boston

LocationValueAccess

4.94 out of 5 average rating, 169 reviews
A bright living area features large windows that fill the space with natural light, offering views of the outside. A sectional sofa is positioned near a round coffee table, complemented by two accent chairs. A simple fireplace is seen along the wall, enhancing the room's comfort.
Serviced apartment in Fenway-Kenmore

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.

FamilyLocationRiver

4.84 out of 5 average rating, 258 reviews
Flat in Fenway-Kenmore

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.

LocationFamilyAmenities

4.91 out of 5 average rating, 46 reviews
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

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.

LocationValueCheck-in

4.9 out of 5 average rating, 135 reviews
Superhost
Flat in Brighton

The Weiss : Modern Gallery • Historic Property!

Stay inside a historic restored monastery in Brighton. This spacious studio blends preserved historic architecture with modern comfort and features an expandable room divider for a one-bedroom feel. Just a 5-minute walk to the T with easy access to Boston College, Harvard, hospitals, and downtown Boston. Amenities Include: → Blazing-fast WiFi → 65” Smart TV → Fully stocked kitchen → Washer & dryer → Comfortable queen bed

ValueFamilyNearby

4.87 out of 5 average rating, 112 reviews
Superhost
Flat in South End

(T6) Boho Retreat, Prime Location, Food, Walkable!

🌆 Welcome to Boston’s South End! Stay in the heart of a historic and culturally diverse neighborhood, right on Tremont Street. Step outside and explore a vibrant mix of 🍽️ restaurants, art galleries, and unique boutiques—all within walking distance. The South End is the perfect base for discovering Boston, offering a blend of charm, convenience, and local culture that makes every stay unforgettable.

ValueLocationWifi

4.7 out of 5 average rating, 79 reviews
Guest favourite
Flat in Back Bay

(Mlb5) Bright Big Studio, Open Concept, Back Bay!

📍 Stay in the heart of Back Bay, just steps from Newbury Street, the Prudential Center, and Copley Square. This inviting space is close to Boston’s top hospitals—Mass General, Brigham and Women’s, Boston Children’s—prestigious universities like 🎓 Harvard, MIT, BU, and Northeastern, and iconic landmarks such as Boston Common, the Freedom Trail, and the Museum of Fine Arts.

ValueLocationKitchen

4.81 out of 5 average rating, 21 reviews
A bright sleeping area is presented, featuring a spacious bed with crisp white linens and a navy blue accent. A modern bedside table holds a lamp and a small plant. Natural light enters through a large window, illuminating the area.
Flat in Fenway-Kenmore

Stay in the Heart of Fenway & Berklee

Enjoy a stylish stay in the heart of Boston’s Fenway District at Maverick Suites’ 28 Fenway. This modern furnished unit is ideal for solo travelers or up to two guests looking for a convenient weekend getaway or short city stay. Located near restaurants, museums, public transit, and top Boston attractions, it offers a great home base for exploring the city.

FamilyLocationAir conditioning

4.76 out of 5 average rating, 686 reviews
Top 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

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!

FamilyLocationBreakfast

5.0 out of 5 average rating, 61 reviews
Top guest favourite
A spacious living area features a high wood-beamed ceiling and large windows overlooking greenery. A comfortable couch and plush chairs are arranged around a coffee table. A staircase leads to a loft area, and a flat-screen TV is visible in the background.
Flat in Roxbury

Light-Filled Luxury Apartment with View

Beautiful top floor luxury apartment in stately Victorian home. Extraordinary views of historic park as your front yard! Your own entrance through a private garden. Apartment is a studio-style open living space with full kitchen, living area, and bedroom bay with queen bed. Also includes loft bedroom with 2 twin beds.

FamilyValueCondition

4.97 out of 5 average rating, 436 reviews

Popular amenities for Boston holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Boston's top sights

Fenway Park

976 locals recommend

Boston Logan International Airport

151 locals recommend

Harvard University

670 locals recommend

Boston Seaport

6 locals recommend

Boston Common

717 locals recommend

New England Aquarium

931 locals recommend

Other great holiday rentals in Boston

Top guest favourite
A grand staircase made of dark wood features intricately carved banisters and a rich, patterned carpet. The walls are adorned with floral wallpaper, enhancing the historic charm. Various wooden furniture pieces are arranged beside the staircase, contributing to the elegant atmosphere.
Private room in Fenway-Kenmore

Fenway Park Vintage Brownstone (3C)

FamilyLocationHospitality

4.96 out of 5 average rating, 552 reviews
Guest favourite
A vibrant exterior view of The Verb Hotel showcases a retro red bus alongside the building's large 'Verb' mural. Lush greenery surrounds the area, and Fenway Park's stadium lights are visible in the background, highlighting the connection to the iconic ballpark.
Hotel room in Back Bay

Steps from Fenway Park + Free Breakfast & Pool

FamilyValuePool

4.89 out of 5 average rating, 310 reviews
Superhost
A cozy bedroom features a Queen Size bed with grey bedding and a plush white throw at the foot. Natural light enters through two large windows, framed by sheer white curtains, illuminating the warm wood flooring and simple wooden side table.
Private room in Medford

Bedroom in Cozy 1st Floor Tufts /Green Line Train

ValueFamilyHeating

4.89 out of 5 average rating, 279 reviews
Guest favourite
A cozy lofted bedroom features a spacious bed with white bedding and a low ceiling with angled walls. Natural light enters through a nearby window. A small nightstand stands beside the bed, while a minimalist shelf holds personal items along the wall.
Private room in Roxbury

AKBrownstone: Loft w/neighborhood views by T

LocationValueCleanliness

4.92 out of 5 average rating, 661 reviews
Guest favourite
A spacious bedroom features a dark wood bedframe with a light blue bedding set. A ceiling fan is visible above, and a television is positioned on a wooden dresser. Artwork adorns the walls, and a basket is placed in the corner next to a bedside table.
Private room in South Boston

Large Private Bedroom & Bathroom by the Seaport

ValueLocationDecor

4.87 out of 5 average rating, 695 reviews
Superhost
Hotel room in South Boston Waterfront

In The Heart of Boston’s Seaport + Rooftop Bar

LocationValueSleep quality

4.79 out of 5 average rating, 84 reviews
Guest favourite
Private room in Belmont

Constellation 3

ValueFamilyAccuracy

4.85 out of 5 average rating, 40 reviews
Private room in East Boston

Cozy Private Bedroom close to Logan & Subway

LocationGetting aroundComfort

5.0 out of 5 average rating, 4 reviews

When is the best time to visit Boston?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$160 SGD$156 SGD$174 SGD$211 SGD$230 SGD$255 SGD$213 SGD$221 SGD$207 SGD$217 SGD$185 SGD$168 SGD
Avg. temp-1°C0°C4°C9°C15°C20°C23°C23°C19°C13°C7°C2°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.

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