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 area showcases a green couch with a scalloped white base, accompanied by a red accent chair. A small dining table is positioned nearby. Natural light filters through windows with red curtains, while a large mirror reflects the space and enhances its openness.
Flat in Fenway-Kenmore
4.85 out of 5 average rating, 59 reviews

(F22) Charming Boho-Inspired Studio in Fenway!

In the heart of the city’s 🏟️ sports and cultural hub, steps from iconic Fenway Park. This lively neighborhood offers easy access to Back Bay and its upscale shopping along Newbury Street, as well as countless dining and entertainment options. Top hospitals like Brigham & Women’s and Beth Israel Deaconess 🏥 are nearby, making this a convenient choice for both leisure and medical stays. With excellent transit connections, you’ll enjoy a well-connected Boston experience right outside your door.

Superhost
A private patio features two hanging egg chairs adorned with green patterned cushions, positioned on a wooden deck. A small round planter sits in the center, adding a touch of greenery. The backdrop showcases urban buildings with a clear blue sky above.
Flat in Back Bay
4.82 out of 5 average rating, 261 reviews

(N2R) Private Deck, Styled Studio, Prime Location!

🌆 Stay on Iconic Newbury Street, Back Bay Experience Boston at its most stylish on Newbury Street, famous for its historic brownstones, tree-lined sidewalks, and vibrant atmosphere. 🛍️ Stroll right outside your door to explore designer boutiques, local shops, art galleries, and some of the city’s best cafés and restaurants. You’ll be just steps from Copley Square, the Prudential Center, and the Charles River Esplanade, with easy access to the Green Line T for exploring the rest of the city.

Guest favourite
Flat in Beacon Hill
4.96 out of 5 average rating, 25 reviews

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

Superhost
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
4.95 out of 5 average rating, 138 reviews

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

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
4.91 out of 5 average rating, 242 reviews

Steps from Fenway Park + Free Breakfast & Pool

Stay steps from Fenway Park in a hotel that lives and breathes rock ‘n’ roll. At The Verb, you’re not just checking into a room—you’re stepping into a retro-cool experience with a vinyl library, record players in every room, and a year-round outdoor pool. Whether you’re catching a game, exploring Boston’s iconic music scene, or sipping cocktails poolside, this stay is anything but ordinary. It’s fun, loud (in a good way), and full of personality—just like the city around it.

Guest favourite
Flat in Brighton
4.85 out of 5 average rating, 46 reviews

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.

Superhost
Hotel room in Cambridge
4.78 out of 5 average rating, 285 reviews

Steps from the T & Museum of Science

The Fairfield Inn and Suites Cambridge is the perfect location for guests visiting both Cambridge and Boston. Close to MIT and Harvard Universities, the TD Garden and a short walk to the T for subway rides into Downtown Boston. - 24/7 Front Desk support - Free Wi-Fi - Free breakfast buffet daily - Housekeeping service - Mini-refridgerator/Microwave/Private Bathroom in each room - Market on-property for anything you forgot or need - Fitness Room - Parking (daily fee)

Guest favourite
Flat in Fenway-Kenmore
4.95 out of 5 average rating, 21 reviews

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.

Top guest favourite
Flat in South End
5 out of 5 average rating, 12 reviews

South End Historic Rowhouse | Reunions + World Cup

In the heart of Boston’s South End is this newly finished, design-forward 3 bedroom, 2.5 bath historic brick rowhouse. Stay in a legacy neighborhood with classic architecture, tree lined streets, and true character. This home is high-end with thoughtful finishes and furnishings. Laundry, fireplace, and private outdoor space. Surrounded by green parks, cafes and restaurants, and one block from Boston’s only Michelin-star. Accessible to the best of the city.

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
4.75 out of 5 average rating, 658 reviews

Stay in the Heart of Fenway & Berklee

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.

Top guest favourite
Home in Roslindale
5 out of 5 average rating, 9 reviews

Your own cottage in the city

Whether you need to relax, be productive, or have a safe home base for your adventures, the Sowden cottage has you covered. Nestled near the heart of Roslindale, the cottage is a short walk to shopping and dining and is near easy transportation to every part of Boston. It's the perfect place to call home while you work, visit family, or experience the city we love. Whatever brings you to Boston, we look forward to welcoming you at the cottage!

Guest favourite
Flat in Back Bay
4.87 out of 5 average rating, 145 reviews

The Ellie House 5- Cozy Back Bay Getaway!

The Ellie House is ideally located on St. Botolph Street, where Back Bay meets the South End. Surrounded by classic brownstones and leafy streets, you’re steps from Newbury Street, the Prudential Center, and Copley Square. Walk to top universities like Northeastern, Berklee, and BU, and access world-renowned hospitals including Mass General and Brigham & Women’s. Enjoy endless dining, shopping, and cultural landmarks right outside your door.

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.

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.

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