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Holiday rentals in Boston

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Quick stats about holiday rentals in Boston

  • Total holiday rentals

    Explore 10,830 holiday rentals in Boston

  • Verified guest reviews

    Over 533,960 verified reviews to help you choose

  • Family-friendly holiday rentals

    3,750 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 2,930 rentals that welcome pets

  • Holiday rentals with a pool

    640 properties feature pools

  • Rentals with dedicated workspaces

    5,890 properties have a dedicated workspace

  • Wifi availability

    10,640 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

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
A grand staircase made of dark wood features intricately carved banisters and a rich, patterned carpet. The walls are adorned with floral wallpaper, enhancing the historic charm. Various wooden furniture pieces are arranged beside the staircase, contributing to the elegant atmosphere.
Private room in Fenway-Kenmore

Fenway Park Vintage Brownstone (3C)

This charming brownstone, built in 1896, is set on quiet, tree-lined Bay State road, one of the "10 Boston’s Best Secret Streets" by Travel and Leisure. It is under the Boston landmark Citgo Sign, within 5 minute walking distance to Fenway Park, Kenmore Sq, Charles River and Boston University. The property has been lovingly maintained as a private residence for two generations. All original architectural details have been preserved with Victorian charm. Guest rooms are on the 3rd or 4th floor.

FamilyValueAccess

4.96 out of 5 average rating, 553 reviews
Flat in Downtown

Kasa at Boston Common | Three Bedroom

Stellar location meets generous space at Kasa at Boston Common. Choose from 1, 2, 3, or 4-bedroom furnished apartments with full kitchens and in-unit laundry, giving you more reason to stay longer, and with more room for people you want to travel with. The feeling of home, with all of downtown Boston’s best dining, shopping and attractions right at your doorstep. Our tech-enabled rooms offer self check-in at 4pm, 24/7 guest support by text and Virtual Front Desk accessed via mobile device.

LocationWalkabilityCondition

5.0 out of 5 average rating, 4 reviews
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

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

LocationFamilyBathroom

4.94 out of 5 average rating, 169 reviews
Top guest favourite
A spacious living room features comfortable seating arranged around a central coffee table. A large television is mounted on a wooden cabinet, surrounded by shelves filled with books. Natural light filters through multiple windows, enhancing the bright and airy feel of the room.
Home in Roxbury

5-story Luxury Boston Brownstone

Bring lots of friends, or family, together to enjoy Boston in a home spread across 5 stories. This is an 1870s 6-bedroom single-family townhouse renovated in 2025. The basement boasts a pool table and a walkout patio, the entry level has a large kitchen with seating at the island, peninsula, and a 12-person dining table. The 2nd floor has a hangout-inspired living room with puzzles and games, a bedroom, and full bath. The 3rd and 4th floors both have bedrooms and full baths.

FamilyValueQuiet

4.98 out of 5 average rating, 60 reviews
Guest favourite
Hotel room in Back Bay

Walk to Fenway Park with 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.

ValueFamilyView

4.88 out of 5 average rating, 336 reviews
Guest favourite
A bright living area features floor-to-ceiling glass doors that frame scenic waterfront views. A cozy sofa is positioned alongside a wooden table with a potted plant. Sunlight streams in, highlighting the wood-paneled ceiling and warm oak flooring.
Home in East Boston

Waterfront Escape - Close to Airport & Downtown

Experience the best of Boston from the Harborview House. This stunning waterfront home is only 5 minutes from the airport and 15 minutes from downtown Boston - yet feels like a world away. Enjoy panoramic views of the water from every floor, a terraced backyard patio with fire pit, gas grill and Constitution Beach only 1 block away. If you’re looking for a unique, luxury home for your group or family while you’re in Boston, the Harborview House should be your destination!

ValueFamilyCheck-in

5.0 out of 5 average rating, 59 reviews
Superhost
Hotel room in South Boston Waterfront

In The Heart of Boston’s Seaport + Rooftop Bar

The Envoy Hotel connects Boston with food, drink, and skyline views that define the city. At Para Maria, Chopped champion Tatiana Rosana serves eclectic dishes inspired by French training, Cuban roots, her wife’s Korean heritage, and New England grit. Rooftop at The Envoy offers craft cocktails and fire pits with stunning harbor views. With art‑filled spaces, vibrant design, and Seaport originality, The Envoy delivers hospitality that rises above the ordinary.

LocationValueAccuracy

4.79 out of 5 average rating, 84 reviews
Hotel room in North End

Premier king water view

Premier king water view features a luxurious king bed, newly renovated decor, and expansive ocean views for a memorable stay. Enjoy a rain-forest shower, Nespresso coffee and tea maker, a 55 inch HD TV, and advanced wifi for ultimate comfort. Additional amenities include individually controlled air conditioning, a safe, desk, bathrobe, and environmentally friendly bath products, creating a relaxing and modern retreat.

LocationValueWalkability

4.75 out of 5 average rating, 20 reviews
Hotel room in Back Bay

Revere Hotel Boston Common, Superior room two que.

Superior room 2 queen beds features two queen beds and a private balcony with neighborhood views. Enjoy amenities like high speed wifi, a safe, smoke detectors, and a bathtub with shower combination for your comfort. The room includes a 55 inch LED TV and offers a view of the city for a relaxing atmosphere. Stylish design and modern conveniences make this a perfect choice for your stay.

ValueFamilyBathroom

4.82 out of 5 average rating, 95 reviewsA minimalist bedroom features a spacious bed with a dark blue accent. Two circular tables are positioned beside the bed, accompanied by stylish black chairs. Natural light enters through a large window, where a small plant is displayed on the sill, and a vibrant piece of artwork adorns the wall.
Flat in Fenway-Kenmore

Walk to Berklee, Fenway & Newbury St

Enjoy a stylish stay in the heart of Boston’s Fenway District at Maverick Suites’ 28 Fenway. This modern furnished unit is ideal for solo travelers or up to two guests looking for a convenient weekend getaway or short city stay. Located near restaurants, museums, public transit, and top Boston attractions, it offers a great home base for exploring the city.

ValueLocationRiver

4.77 out of 5 average rating, 380 reviews
Hotel room in Downtown

The Dagny, Standard King

- Recently renovated 1920s Art Deco gem, spectacularly located near all the biggies: Quincy Market, Faneuil Hall and Freedom Trail. - Comfy rooms rock high ceilings, crown molding – plus a 42" flat-screen and mini-fridge. - Feast on delicacies from the full raw bar and New England go-to’s (yes, chowdah) at the onsite Fin Point Oyster Bar and Grille.

ValueLocationDecor

4.74 out of 5 average rating, 62 reviews
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

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!

FamilyLocationAccess

5.0 out of 5 average rating, 61 reviews

Popular amenities for Boston holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Boston's top sights

Fenway Park

980 locals recommend

Boston Logan International Airport

152 locals recommend

Harvard University

673 locals recommend

Boston Seaport

6 locals recommend

Boston Common

721 locals recommend

New England Aquarium

933 locals recommend

Other great holiday rentals in Boston

Hotel room in Everett

enVision Hotel Boston - Everett, Executive boutiq.

ValueLocationIndoor spaces

4.89 out of 5 average rating, 18 reviews
Hotel room in South Boston Waterfront

Premier room king bed

LocationSleep qualityView

4.67 out of 5 average rating, 3 reviews
Hotel room in Allston

Studio Allston Hotel, Standard king room

LocationFamilyHospitality

4.53 out of 5 average rating, 15 reviews
Hotel room in Cambridge

Superior double queen ADA

Hospitality

5.0 out of 5 average rating, 3 reviews
Hotel room in Fenway-Kenmore

The Verb Hotel, Pool view king

ValueLocationBreakfast

4.75 out of 5 average rating, 4 reviews
Hotel room in Kendall Square

The Kendall Hotel, Classic queen

LocationAmenitiesCondition

5.0 out of 5 average rating, 6 reviews
Hotel room in Downtown

Club Quarters Hotel Faneuil Hall, Boston, Club ro.

ValueLocationGetting around

4.67 out of 5 average rating, 12 reviews
Hotel room in South Boston Waterfront

In the heart of revitalized South Boston

ValueLocationComfort

4.66 out of 5 average rating, 124 reviews

When is the best time to visit Boston?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$160 SGD$156 SGD$174 SGD$211 SGD$230 SGD$256 SGD$214 SGD$221 SGD$207 SGD$218 SGD$186 SGD$169 SGD
Avg. temp-1°C0°C4°C9°C15°C20°C23°C23°C19°C13°C7°C2°C

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.

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