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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Guest favourite
A spacious living room features exposed brick walls and large windows allowing natural light to fill the space. A comfortable sofa is complemented by a rocking chair. A coffee table sits on a patterned area rug, and a TV is positioned on a modern entertainment unit.
Flat in South End
4.89 out of 5 average rating, 385 reviews

Charming South-End condo with large outdoor patio

Elegant and spacious 1BR loft on the 1st floor of a classic South End brownstone. Features a large private deck with outdoor seating, washer and dryer, fully equipped stainless steel and granite countertop kitchen. Located in the heart of Boston’s historic South End—just steps from great restaurants, major landmarks, iconic tourist attractions, top universities, and public transit. Thoughtfully designed for comfort, style, and a warm welcome. Please see Policies and House Rules for more details

Guest favourite
A cozy studio space features a spacious bed with colorful pillows and a stylish gray sofa. Natural light floods in through three large windows adorned with dark curtains. A small dining table is positioned nearby, enhancing the inviting layout.
Flat in Fenway-Kenmore
4.93 out of 5 average rating, 153 reviews

Walk! Location! Steps from the T! 1 bed 1st floor!

Beautiful apartment in the middle of everything with Queen size bed! Located right in Kenmore Square, steps from subway station and Famous Citgo Sign. Walking distance to Fenway Park, Back Bay, restaurants, and bars. Walk everywhere! Next to Boston University and in front of Charles River Esplanade. Very close to Downtown, Cambridge, Longwood Medical Area, supermarkets, and way so many cool places! Includes everything you'll need for your stay. Super safe and convenient neighborhood! :)

Guest favourite
Flat in Brighton
4.9 out of 5 average rating, 69 reviews

The Clark : Aesthetic • Clean • Amenities!

Experience Boston in this incredibly stylish 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.

Guest favourite
A modern dining area features a round table surrounded by four white chairs, with light wood flooring continuing into the space. Glass pocket doors provide a view of the bedroom, where a spacious bed is visible. A decorative light fixture complements the contemporary design.
Flat in Cambridge
4.91 out of 5 average rating, 543 reviews

Luxury 1BR APT w/ parking by MIT/Harvard/BU/Fenway

Stunning private one bedroom apartment! Newly renovated, luxury retreat, with free off-street parking, queen sized memory foam bed, 55'' TV with free cable & WIFI, heated flooring, A/C, keyless entry for self-checkin. Also includes your own full, modern kitchen with new, high-end appliances. Next to MIT, Harvard, BU, Kendall Sq, Boston, Fenway Park, Red & Green lines, Charles River, Flour Bakery, Whole Foods & Trader Joe's. This garden-level unit is immaculate and professionally cleaned.

Guest favourite
A modern kitchen is seen, featuring sleek white cabinets and a gray stone island with seating for three. Stainless steel appliances, including a refrigerator and microwave, are positioned thoughtfully. Natural light pours in through large windows, illuminating the warm wooden flooring.
Home in Prospect Hill
4.93 out of 5 average rating, 69 reviews

Beautiful appartement - quiet location - downtown

"Latest News" - The new Green line station, direct to Boston just opened 10min walk from the house. Soon it will also access to Tufts University Enjoy one of the best Somerville location, very quiet, central air conditioning, 5 min from Union Square restaurants, take-out, coffee shop, donuts places. 2 min from Prospect Hill Park and 2 min from bus stops. Very quiet, safe and nice neighborhood. 15min drive to Boston, 5min to Cambridge and easy access to future Green line

Top guest favourite
A modern living area features a black leather sofa paired with decorative pillows. A white area rug lies beneath a coffee table, complemented by an accent chair with a geometric pattern. Natural light filters through the two windows, creating a bright and inviting space.
Apartment in Cambridge
4.92 out of 5 average rating, 851 reviews

Spacious 2 bedrooms Apt -Roof deck NO Cleaning fee

A brand new spacious 3rd floor apartment over 1,000 sq ft centrally locate, near 2 subway stations/bus line, 4 grocery stores within 10 mins walk. The apt has a big kitchen, roof top deck and a huge yard. All brand new furnitures from Crate & Barrel, Pottery Barn and West Elm. Bed sheet sets from Crate & Barrel. NO Cleaning fee. We offer a great atmosphere, high quality amenities and cleanliness are utmost importance. Please read the reviews from prior guests.

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.
Apartment in Fort Hill
4.94 out of 5 average rating, 343 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!

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

802B HUGE New Downtown Boston Studio Walk to T

✨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. 494 sq. feet. 8th floor. Elevator access, no stairs.

Guest favourite
An open living area showcases wooden furniture, including two sofas and a dining table with chairs. Light wood flooring is complemented by natural light from multiple windows. A floor lamp adds warmth, while exposed ductwork accents the modern design.
Flat in Cambridge
4.89 out of 5 average rating, 356 reviews

Newly-Renovated, Stunning Cambridge 1BR

Newly-renovated, modern apartment located 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.

Guest favourite
Flat in South End
5 out of 5 average rating, 19 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.

Superhost
Apartment in Cambridge
4.97 out of 5 average rating, 176 reviews

Phil's Harvard Home - Harvard Set

Right at the heart of Harvard University, we are seconds away from university facilities and key attractions, making it a perfect place to stay if you are interested in exploring Harvard. This room will have a private bathroom. The house is in traditional Victorian style with a lot of history while the interior was renovated in 2016.

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
5 out of 5 average rating, 36 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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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 9,960 holiday rentals in Boston

  • Verified guest reviews

    Over 508,020 verified reviews to help you choose

  • Family-friendly holiday rentals

    3,540 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 2,900 rentals that welcome pets

  • Holiday rentals with a pool

    480 properties feature pools

  • Rentals with dedicated workspaces

    5,630 properties have a dedicated workspace

  • Wifi availability

    9,830 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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