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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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
An open living and dining area is highlighted by a wooden dining table set with decorative plates. The space features grey upholstered chairs and a cozy seating arrangement with light-toned furniture. A circular chandelier hangs above, while exposed brick accents add texture to the room.
Flat in Dorchester
4.96 out of 5 average rating, 171 reviews

🎖The Ashmont Suite | Close to Subway + Downtown🎖

This high end & unique 3 bed / 2 bath unit is brand new, along with all the furnishings. It includes 1 King, 1 Double, & 1 Single size private bedrooms. The unit is extremely clean and remarkably decorated. Only a 5 minute walk to Ashmont station (red line), which takes you directly into Downtown Boston, Harvard Square, South Boston, Kendall/MIT, U Mass. There’s also plenty of parking available in front of the property. As well as a local coffee shop & a Dunkin just across Ashmont T station.

Guest favourite
Flat in Brighton
4.92 out of 5 average rating, 85 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 kitchen layout features a wooden dining table at the center and sleek cabinetry adorned with simple hardware. Sunlight illuminates various houseplants placed on the windowsill, with a patterned backsplash adding visual interest. A pendant light hangs above the table, enhancing the space.
Apartment in Somerville
4.97 out of 5 average rating, 61 reviews

2 BR apt near subway w/ parking

Colorful, modern, and convenient! This is my primary residence, and I usually share the space with guests while I'm in town. But the entire place is for rent while I'm away in July/August. The apartment has 2 bedrooms and 1.5 bathrooms. You may park up to 2 cars in the driveway next to the house. The Gilman Square subway station is only a 4-minute walk away. Only a few quick stops to Boston! Coffee, tea, and basic cooking items (sugar, oil, spices etc.) will be provided for you.

Top guest favourite
Flat in Fenway-Kenmore
4.91 out of 5 average rating, 126 reviews

Brownstone Luxury Penthouse Condo

Beautiful and sunny 2 bed 2 bath renovated 3rd floor penthouse condo with access to all that Boston has to offer! Walking distance to shops, groceries, and entertainment, including Fenway Park!, Immediate access to Green Line subway as well as other local transportation! Enjoy our primary bedroom with king size bed and ensuite bathroom, 2nd bedroom with full bed, additional full bathroom, full kitchen with dining area, living room with fireplace, and balcony with sitting area!

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 Somerville
4.91 out of 5 average rating, 78 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 living area displays a light-colored sofa adorned with patterned pillows, accompanied by two blue armchairs. A sleek work desk and a television are positioned near an elegant marble fireplace. Natural light fills the room, highlighting the wooden flooring and soft color palette.
Apartment in Charlestown
4.98 out of 5 average rating, 152 reviews

Large 1+bed in historic Charlestown, Boston!

Large 1 BR condo. This is a brick 3 story home & the rental condo is on the 1st floor only. KING bed, work desk area, living room w/queen pull out bed, fully equipped kitchen & private deck/courtyard. Washer/dryer. Convenient walk to cafes & restaurants, Whole Foods, MBTA, Freedom Trail, Bunker Hill Monument, USS Constitution. Courtyard is broken down Dec-March & NO smoking in house and NO smoking in courtyard. Not suitable for children under 6 years old.

A well-lit bedroom features a spacious bed adorned with neatly arranged pillows and a navy blue throw. Natural light enters through multiple windows with gray shades, and a cozy seating area is provided by a light gray chair positioned beside the bed.
Loft in Coolidge Corner
4.74 out of 5 average rating, 322 reviews

Steps to the Green Line & Minutes from Boston! #28

In the heart of Coolidge Corner right off the Green Line, our picturesque studio apartment is a quick train ride to Fenway, Faneuil Hall and the Back Bay. Our space is perfect for solo adventures, business travel, or visiting students at the many neighboring universities. Sleep comfortably on pillow-top mattresses. Other features include heated bathroom floors and shared beautiful stainless steel full kitchens with crafted Italian Granite counter tops.

Top guest favourite
A spacious living area features an exposed brick wall, wooden flooring, and ample natural light from skylights above. A small dining table and two bar stools are positioned near the modern kitchen, which includes essential appliances. Unique pendant lighting adds character to the room.
Flat in Cambridge
4.91 out of 5 average rating, 119 reviews

Renovated 1-Bed w/ private deck

Newly-renovated, modern apartment located directly 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.

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.

Top guest favourite
A secluded patio area is visible, featuring a brick pathway and two metal chairs positioned for relaxation. The entrance to the guest unit is framed by a set of steps, accompanied by leafy trees that provide shade and a sense of serenity.
Guest suite in Jamaica Plain
4.94 out of 5 average rating, 113 reviews

Peaceful Garden Apartment

Your beautiful garden guest unit is a tranquil getaway. The layout is ideal - a bedroom with an ensuite bath; living room with a pull out couch and a door that transforms the living room into a private bedroom; a second full bath; and a kitchen/dining area. Best of all, it's less than a ten minute walk to 500 acres of parkland and "JP" center with great restaurants, pubs, bakeries and shops.

Top guest favourite
A pair of large, double doors with a rich, textured surface stands prominently in the background. The doors are flanked by warm, wooden floors and a light-colored sofa adorned with decorative pillows. A vibrant area rug adds color to the setting.
Apartment in Downtown
4.97 out of 5 average rating, 191 reviews

Downtown Loft Boston - Close to everything

Spacious loft in Downtown Boston, Historic District, with high ceilings, large windows, original wooden floors, private bedroom area-queen bed, also sofa in living room can become a pull-out double size bed. The bathroom is with shower and tub, a complete kitchen, and laundry room. The unit also offers the highest speed available in the area -1 gig internet access and 55" smart TV.

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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