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
4.87 out of 5 average rating, 112 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.

Guest favourite
Flat in Boston
5 out of 5 average rating, 9 reviews

Red Sox 09.7 - Fenway Park. Longwood Medical. NEU.

Enjoy a stylish experience at this centrally-located place. Perfect location in the Fenway neighborhood (Home of the historic Fenway Park and the legendary Boston Red Sox) Beautiful Brownstone home with small elevator, and the perfect location to get anywhere else in Boston. Fenway Subway station is a five minute walk. Museum of fine Arts subway station is a ten minute walk. You can walk to the Boston Red Sox game in less than ten minutes. Fast wifi. Smart TV. Quarter operated laundry.

Top guest favourite
A modern living area showcases a grey sectional sofa, complemented by a geometric area rug. A small coffee table sits in front, and a desk with a chair is positioned nearby. Large windows provide natural light, and a cityscape photograph adorns the wall.
Flat in East Boston
4.88 out of 5 average rating, 129 reviews

1 BR Gem 5min to Train & Airport explore the city

This modern stylish place to stay is perfect to explore the city of Boston. It’s a hidden gem 1 block away from the Blue Line T station, two stops away from downtown, the aquarium, TD Garden, Faneuil Hall, and multiple museums. 2 mins walking distance from the apartment to Piers Park and spectacular views of Boston Harbor and the skyline.Hop on the ferry to explore Seaport restaurants and bars close by with differing cultures and cuisines. Only 2 min from Logan Airport via train or car.

Top guest favourite
A well-lit sleeping area features a spacious bed adorned with white linens and a soft gray blanket. An artistic wall hanging adds a splash of color above the bed. Sheer curtains frame the window, enhancing the serene ambiance of the room.
Flat in Roslindale
4.97 out of 5 average rating, 32 reviews

Cozy 1BR suite in Boston's Roslindale Village

This is a 1BR suite on the 2nd floor of our newly renovated home in Boston's Roslindale, which is about 6 miles or 20 min away from downtown (please look up the neighborhood to have a clear idea where it is). Our place is close to restaurants & bars in Rozzy Village and West Roxbury. There is a connection via bus at the corner to the subway at the Forest Hills Orange Line T-stop that will get you to downtown in about 20 min, and there is commuter rail in Roslindale Village.

Guest favourite
Wooden pilings extend vertically from the calm water, their reflections creating a series of vertical lines. In the background, sailboats are visible moored gently, while a clear blue sky complements the serene atmosphere of the harbor.
Houseboat in Downtown
4.96 out of 5 average rating, 45 reviews

Endless Summer: Oceanside Views

Stay a weekend. Stay a week! All of the amenities of home are included in this spectacular apartment-on-the-water in the heart of Boston's North End. Enjoy amazing harbor views and cool ocean breezes in the light-filled stateroom. Prepare breakfast in the fully stocked chef's kitchen, complete with stainless steel appliances and a granite island. Invite friends over for drinks on the enormous deck. This is truly Boston's most unique and memorable vacation experience.

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, 345 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
Flat in South End
4.8 out of 5 average rating, 98 reviews

(W5) Spacious Studio, Location! Dining & Shopping+

🌆 Welcome to Boston’s South End! Stay in one of Boston’s most historic and culturally rich neighborhoods, known for its brownstones, tree-lined streets, and vibrant local scene. From Worcester St, you’re just a short walk to Tremont St’s acclaimed restaurants, cozy cafés, art galleries, and boutique shops. Perfectly situated for exploring the rest of Boston—whether for leisure, business, or medical stays. Charming, convenient, and well-located.

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

Central Penthouse & balcony in Boston Chinatown

This special place is close to everything, making it easy to plan your visit. Bedroom with Queen bed and en-suite full bathroom. Living room comes with day bed (2 twin beds). Desk and chair, TV, side chair and couch. Walking distance to Boston Common, many restaurants, TUFTS T-station, South Station and other public transportation. Grocery store in the same building, three elevators, Pool Table and Lounge on the 11th floor!

Superhost
Flat in Everett
4.8 out of 5 average rating, 5 reviews

Luxurious Open-Concept Home with Roof Skyline View

Enjoy a luxurious stay at this centrally located home, just minutes from the airport, downtown, and Encore Casino. Featuring an open-concept design with high ceilings and stunning views of Everett’s city skyline, this home is perfect for both relaxation and adventure. • Prime Location: Close to key attractions and entertainment. • Modern Comforts: Rooftop deck, Spacious, stylish, and equipped with everything you need.

Top guest favourite
A cozy living room is depicted, featuring a brown sofa, two accent chairs in light blue, and a dark coffee table. A textured area rug anchors the seating area. Exposed brick walls provide a warm backdrop, while soft lighting enhances the inviting ambience.
Flat in North End
4.95 out of 5 average rating, 374 reviews

Large 1-Bed. Condo in the Heart of the North End

Perfectly appointed, clean and comfy 1 bedroom condo unit steps from the Old North Church in Boston's historic North End. A full kitchen, a full bathroom with shower & washer/dryer, one bedroom with a comfy queen bed, a living room with one sofa bed, and a dining room with ample room all make this the perfect place to plop down during your visit to Boston. Centrally located, quiet and private.

Guest favourite
The living area features a spacious, modern sectional sofa in a bold pink hue, paired with a geometric coffee table in a deep green color. Large windows allow natural light to fill the room, highlighting the exposed brick wall and nearby dining space with multicolored chairs.
Flat in Back Bay
4.98 out of 5 average rating, 46 reviews

Stunning Penthouse, Private Deck & River Views

📍 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. 🏛️

Guest favourite
A motor yacht is docked at a marina, featuring a spacious upper deck with a canopy. The exterior showcases a cream-colored hull with large windows and a comfortable layout. A wooden walkway leads to the boat, surrounded by additional boats in the marina.
Boat in Charlestown
4.91 out of 5 average rating, 32 reviews

Serenity - 36’ Aft Cabin Carver

At Constitution Marina's Bed & Breakfast Afloat you can enjoy the ambiance, the comfort, the romance of staying ON THE WATER with all the amenities of a modern hotel, at rates as low as you'll find anywhere in Boston! For boats with 2 staterooms, there is an additional fee of $100.00 plus tax/night if the 2nd room is rented. The 2nd room is booked directly through the host.

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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