Holiday rentals in Boston

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Top-rated holiday rentals in Boston

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Top guest favourite
An inviting living area features a navy blue sofa adorned with two patterned cushions, complemented by a round coffee table. Nearby, a dining set is visible beside a kitchen with stainless steel appliances, wood cabinetry, and ample counter space, illuminated by natural light from a window.
Flat in South Boston
4.99 out of 5 average rating, 122 reviews

Extraordinary 1-Bedroom Apartment in South Boston!

Cozy, comfortable, centrally-located one-bedroom unit in Southie. Unbeatable location, steps from Carson Beach, L Street Bathouse, BCEC, Sail Boston, World Cup 2026! This property presents endless possibilities for creating your perfect getaway! Convenient private entrance ensures hassle-free coming and going. Whether commuting to work, enjoying a concert/game/event/the vibrant local scene, or simply indulging in the beach and parks nearby, you are sure to enjoy it at this very special home!

Top guest favourite
Flat in Fenway-Kenmore
4.97 out of 5 average rating, 64 reviews

Fenway Park – Studio – Walk everywhere – Location!

Amazing location! WALK WALK WALK to Fenway Park! So close to Kenmore Square, Museum of Fine Arts, Northeastern University, Longwood Medical Area, Symphony Hall, LOTS of Universities, House of Blues, Isabella Stewart Gardner Museum, Kelleher Rose Garden, Berklee College of Music, New England Conservatory, theaters, Whole Foods, Target, bars, restaurants, and a few minutes from downtown! Includes everything you'll need for your stay. Public transportation is right there, super easy and safe!

Top guest favourite
Flat in Somerville
5 out of 5 average rating, 10 reviews

Penthouse Views / Near Boston + New Build

Where Boston Character Lives - Free parking for 4 vehicles - BONUS parking before сheck-in/after check-out is available - Walkable location near public transit, major attractions, restaurants, shops - Private balcony - Central A/C & Heating with SMART thermostat - TV in each room - FREE luggage STORAGE for early check-in/late check-out - Charming neighborhood near Foss Park - Third-floor unit Welcome to a modern 2-bedroom home! Enjoy living spaces, parking, and easy access to the T-station

Guest favourite
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, 262 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 contemporary living area features a large flat-screen TV mounted on a wooden panel. A light-colored sofa sits across from a glass coffee table, which is adorned with small potted plants. A floor lamp provides ambient lighting, while sheer curtains allow natural light to filter in.
Flat in Brighton
4.86 out of 5 average rating, 150 reviews

The Crawford: Spacious • Elegant • W/D

Enjoy Boston in an elegant 2 bedroom with sleek interior furnishing for long and short stays. Just a 5 min walk from the T and close to Boston College/Harvard, you can tastefully engage with all of Boston. Unit Features -> 24/7 Concierge -> Blazing Fast WiFi -> 65” Roku TV Living Room -> 50” Roku TV Bedroom -> Fully Stocked Kitchen -> Washer & Dryer -> 2 Comfortable Queen Bed -> 1 Twin Ideal for business travelers, couples, nurses, and everyone looking to experience Boston in style!

Top guest favourite
The exterior of a charming historic home is displayed, featuring pink shingle siding and white trim. Window boxes with flowers and small American flags adorn the windows, creating a festive and welcoming atmosphere, alongside patriotic decorations draped beneath each window.
Guest suite in South Boston
4.96 out of 5 average rating, 454 reviews

Paul Revere Suite PVT Entry/BATH QN Bed History

*5 STAR ★★★★★ **No Chores! No To-Do List!** Yes, Private Bathroom! Cleaned and Sanitized *Luxury and Comfort *Historic and charming home. *South Boston trendy neighborhood *Beach two blocks *National Historic Sites *Dedicated Luxury Suites *Key-less Coded Access *Queen Pillow Top Bed *Private bath with shower *Great Bath Amenities *Workstation Free WIFI *Minutes to Airport/Downtown/Convention Center *Netflix Limited street parking. Check the photos for free overnight street parking.

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.
Flat in Fenway-Kenmore
4.84 out of 5 average rating, 249 reviews

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.

Top guest favourite
Guest house in Melrose
4.96 out of 5 average rating, 52 reviews

Cozy Private Loft, Easy Access to Boston

Welcome to your cozy, sunlit private loft—your perfect home away from home! This modern Boston retreat features a private entrance, kitchenette, chic full bathroom, dedicated office area, gardens, and a comfy queen bed plus a joybird sofa bed for additional guests. Enjoy a peaceful morning Nespresso located just a few steps to the commuter rail, restaurants, downtown Melrose and Gillette. A comfortable, stylish home base to relax, recharge, and experience it all together.

Guest favourite
A comfortable sitting area features a blue upholstered armchair and a patterned ottoman, providing a cozy space for relaxation. An antique-style chair adds character, while soft natural light streams in through the large windows, illuminating the warm-toned walls and inviting ambiance.
Flat in Danvers
4.78 out of 5 average rating, 37 reviews

Danvers Port Studio

Charming little studio with queen bed in a 1800's home in downtown Danvers. Perfect alternative to hotel living. The studio is located in the back of the house- its entrance is also a lovely deck with chairs to enjoy a coffee or read a book. Walk to restaurants, marina and even a little park and "beach". Close to major highways, shopping, 35 minutes to Boston or New Hampshire, Salem is next door, and Cape Ann with all the beaches is 15- 20 minutes up Rt 128.

Superhost
Flat in Everett
4.91 out of 5 average rating, 33 reviews

Sterling 1BR at Everett | Pool & Gym

Enjoy contemporary comfort in this bright and inviting 1BR/1BA apartment in Everett. The home features a modern kitchen with stainless steel appliances, convenient in-unit laundry, and a naturally lit living space designed for relaxation. Make the most of the community’s outdoor courtyard pool, 24/7 fitness center, and cozy lounge areas with fire pits. Located minutes from Encore, Assembly Row, and key highways, it offers easy access to all of Greater Boston.

Superhost
Flat in Everett
4.77 out of 5 average rating, 13 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.

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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