Holiday houses 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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Top Guest favourite
The spacious living area features large windows that allow natural light to fill the space. A modern black sofa and an orange couch provide comfortable seating. A wall with wooden panels adds texture, while a dining area with white chairs and a sleek table is visible in the background.
Apartment in East Somerville
4.98 out of 5 average rating, 118 reviews

Top Floor luxury Condo

Kick back and relax in this calm, stylish space with skyline views of Boston. This sun filled top floor condo is fully equipped for short- or long-term rentals. This spacious 850sq foot apartment features one bedroom with a queen size bed, dresser and spacious closets throughout. A workspace with high speed 800BPS internet and stylish furnishings throughout. A full kitchen features gorgeous marble counter tops and high-end appliances. Off-street parking - small and medium cars only. Rear patio

Top Guest favourite
The exterior of a Victorian home is showcased, featuring a light-colored facade with decorative trim. A welcoming porch area is accented by potted plants, and steps lead up to a wooden front door flanked by tall windows. Lush greenery surrounds the property.
Apartment in Newtonville
4.87 out of 5 average rating, 551 reviews

Country Charm minutes from the Hub - 1st Floor Apt

Private, smoke/pet-free 1st floor efficiency apartment with independent access for ONE PERSON ONLY at back of family home. Includes full bathroom, refrigerator, microwave, coffee maker + WiFi. All basic supplies provided. Driveway parking. Mins from MBTA transit including commuter rail. Laundry-room access for rentals of 7 nights ore more. Sorry, no vaping and no smokers - even if you smoke outside - because smoke odor on you or your clothes can be left in your wake in the room. No open flame.

Top Guest favourite
A modern living area features a comfortable gray sofa with an orange cushion, complemented by a sleek coffee table. Natural light enters through the glass door leading outside, and framed artworks adorn the walls, enhancing the minimalist aesthetic.
Apartment in East Cambridge
4.92 out of 5 average rating, 362 reviews

Newly Renovated & Oh-So-Convenient!

On the lower level of a beautiful Victorian home, this one-bedroom apartment is completely new construction with loads of amenities and a fun, modern vibe. Excellent location in trendy, quaint East Cambridge. Get anywhere fast! Short walks to MIT/Kendall Square/Biotech, the Museum of Science, the Charles River, and the red and green subway lines, which allow quick access to Harvard, MGH, and historic Boston. The neighborhood is full of life with restaurants and cafes, yet our street is serene.

Guest favourite
A spacious living area with a plush sectional couch in a neutral tone, centered around a coffee table, invites relaxation. Large sliding glass doors frame panoramic ocean views and provide natural light. A modern gas fireplace and stylish decor enhance the cozy atmosphere.
Apartment in Beachmont
4.96 out of 5 average rating, 167 reviews

Beachmont Guest Suite

Experience tranquility in our modern guest suite with stunning ocean views and a private deck overlooking the Atlantic. Wake up to breathtaking sunrises and relax by the cozy gas fireplace. Features a fully equipped kitchen with island seating, a comfortable queen bed, a plush sectional couch, and a luxurious bathroom. Just minutes from Boston, enjoy beachfront living—ideal for romantic getaways, peaceful retreats, or business travelers. Book now to experience the best of beachfront living!

Guest favourite
A micro studio space features a wall-mounted television positioned near a built-in bookcase. Natural light enters through two large windows, illuminating the minimalist decor and a cozy, spacious bed with crisp white bedding. A small white table and chair enhance the functionality of the room.
Apartment in Fort Hill
4.9 out of 5 average rating, 922 reviews

AKBrownstone: cozy private studio by T

🏠 Live like a local: designed micro studio, in a classic Boston Brownstone 🌳 Your very own cozy 170sqft (15sqm) pied-à-terre on the ground level, overlooking Victorian homes on a tree lined street 🚇 5 mins walk to the T (subway), 3rd stop to Back Bay city center or go on bike & walking path 👣 Walk to Longwood Medical Area (Harvard Medical, etc), Museums (MFA, Gardner), Northeastern, & Fenway Park 🇺🇸 Located in residential & historic Fort Hill/Highland Park, free street parking

Top Guest favourite
Condo in Beacon Hill
4.96 out of 5 average rating, 119 reviews

Charming and Historic Apartment

Located in the heart of the historic Beacon Hill neighborhood, this cozy apartment is on the first two floors of a four-story brick townhouse. Tucked away on a European-style gated courtyard, the apartment is incredibly quiet and private, and only steps away from the shops, restaurants and public transportation of Charles Street and Cambridge Street. The well equipped kitchen has been recently renovated with free in unit laundry, bar, adjacent patio. Also WFH station and gas fireplace.

Top Guest favourite
An inviting outdoor seating area features a dark wicker sectional sofa and a round, patterned area rug. Potted plants add a touch of greenery. The entrance is marked by a black door with a window, and a sign indicates the listing number.
Guest suite in Winthrop
4.95 out of 5 average rating, 990 reviews

Cozy studio, near beaches and city skyline views

The Boston Skyline sunsets are beautiful during the summer, just a minute down the street from your Airbnb. This cozy studio, with private entrance, and bathroom includes FREE off-street parking, high-speed internet access, comfy and cozy queen bed with premium linens, nespresso, fridge, with complimentary munchies and NO cleaning fee. Check out the beaches and restaurants. Relax watching your favorite show on the HD smart television or catch up on work with the spacious desk area.

Top Guest favourite
The private rooftop deck features a shaded seating area with sectional sofas adorned with cushions. Potted plants add greenery, while views of neighboring buildings and trees are visible in the background under a partially cloudy sky.
Condo in Fort Hill
4.94 out of 5 average rating, 340 reviews

Boston Rooftop Retreat

A beautiful, fully renovated historic brownstone with a private rooftop deck overlooking the city. Come be inspired by this colorful and romantic artist studio filled with books, records, art and all the comforts of home in a quiet neighborhood with lovely views. Conveniently located a short walk from public transportation, world class universities, medical institutions and museums. About a 22 minute walk to Fenway Park, MGM Music Hall and other great attractions!

Guest favourite
Apartment in Beacon Hill
4.82 out of 5 average rating, 377 reviews

Beacon Hills Studio next to State house 3

Come stay at our lovely studio in the heart of Boston's most desirable neighborhood, Beacon Hill! Whether you want to walk the Freedom Trail, or shop on Newbury St, Surrounded by brownstones, coffee shops, and locals, you’ll feel right at home in this community. Steps away from the State House, MGH, and the Boston Common, You could not be more centrally located to take in all the city has to offer.Take it easy at this unique and tranquil getaway.

Top Guest favourite
A spacious living area is furnished with a dark sofa, a decorative wall art piece, and a round coffee table. Bar stools are positioned near the kitchen, which is visible in the background. Natural light enters through windows covered by green curtains.
Apartment in Dorchester
4.93 out of 5 average rating, 427 reviews

Apartment 1BR mins from JFK/UMASS free parking

Airbnb Superhost offering meticulous and spacious 1 bedroom 1 bath, queen bed plus sleep sofa and airbed (please request it when booking). Free street parking or in the driveway, free laundry, full kitchen, hardwood and tile floors. Wireless internet, smart TV. 10 min walk to Red Line JFK/UMass station and Savin Hill station. Free parking on the street or in our driveway. Well kept front yard and back yard with porch, chairs and table.

Top Guest favourite
A cozy living space features a light-colored sectional sofa in front of a wall-mounted television. A framed artwork decorates the white walls, and a small round table sits between a patterned area rug and the sofa, adding comfort to the setting.
Apartment in Stoneham
4.87 out of 5 average rating, 365 reviews

Entire guest suite in Stoneham

Come enjoy this quiet and comfy home in the heart of Stoneham—your perfect getaway just 20 minutes from the airport and the historic city of Boston. Conveniently located near shopping malls, restaurants, coffee shops, grocery stores, and the natural beauty of Middlesex Fells Reservation and Stone Zoo, this peaceful retreat is designed to make your trip relaxing, enjoyable, and stress-free.

Top Guest favourite
A historic brick brownstone is shown from the street, featuring a classic architectural style with bay windows. The building is framed by vibrant green trees and neatly trimmed bushes, contributing to the residential charm of the neighborhood.
Condo in Jamaica Plain
4.89 out of 5 average rating, 571 reviews

Historic JP Brownstone with Parking. Pets Welcome!

Located in one of Boston's best neighborhoods, this 1200 square foot bright sun filled corner unit in a 120 year old historic Brownstone is the perfect retreat. Its excellent location is just steps from the T and a short walk to Centre Street shops and restaurants. Good for couples, solo adventurers, business travelers, and furry friends (pets).

Popular amenities for Boston holiday rentals

When is the best time to visit Boston?

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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 9,430 holiday rentals in Boston

  • Verified guest reviews

    Over 487,040 verified reviews to help you choose

  • Family-friendly holiday rentals

    3,500 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 2,700 rentals that welcome pets

  • Holiday rentals with a pool

    500 properties feature pools

  • Rentals with dedicated workspaces

    5,290 properties have a dedicated workspace

  • Wi-Fi availability

    9,310 of Boston holiday rentals include Wi-Fi 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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