
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.

801B New Luxury Studio King Bed Downtown By Subway
✨BRAND NEW✨ 1 King-Bed Luxury Studio with private upgraded bathroom & fully-stocked kitchen, located right at Boston Commons and Downtown! NO SHARING OF RESTROOMS OR KITCHEN! *No children under 12. 📍Centrally located to be able to walk anywhere needed and 200-400 ft. to multiple T stops 🚊 Perfect for traveling professionals, mid-term stays and more! ALL UTILITIES INCLUDED. 482 sq feet. 8th floor. 2 Elevators, no stairs! Need more space, different dates, or multiple rooms? Inquiry for more!

(N3F) Beautiful View, Back Bay, Brownstone Newbury
🌆 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.

Lux 2BR Apt w/ Pool and Gym
Welcome to your perfect getaway! Our space combines the comforts of home with luxurious amenities to make your stay truly special. Highlights: • Conveniently close to Downtown Boston • Meticulously deep-cleaned before every stay • Complimentary gourmet coffee, fresh linens, and premium bathroom essentials • 24/7 access to a state-of-the-art fitness center • Modern yoga studio and high-tech training equipment • Experience the charm of Somerville while enjoying hotel-quality amenities at home.

Harvard/MIT Bright 1 BR + Loft Parking Permit
This sun-filled spacious one-bedroom apartment is located in the perfect location between MIT and Harvard, in the heart of Central Square. It’s a 10 minute walk to MIT and an 18 minute walk to Harvard. The apartment has been owner occupied and just recently opened up for renting. It’s furnished with West Elm, Pottery Barn, and Room & Board furniture. It’s comes with a recently renovated bathroom and central AC. The apartment has a washer and dryer. There’s a second bed in the loft space.

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

Luxury Boston 2BR,Back Bay, Pru, Copley, Fenway
Stylish, newly renovated 2BR in a classic South End building: on a quiet street, walk to Copley Square, Boston Public Garden, Prudential Sq, Boston Common, and world class restaurants. Enjoy a king bed in the primary room, queen in the second bedroom, central air, 3 smart TVs, a fully stocked kitchen, and a dreamy bay window reading nook. Thoughtfully designed for relaxing after a day in the city. Walk to shops, cafes, and parks, everything Boston has to offer is right outside your door.

Cozy studio in Bay Village near Public Garden
This newly renovated private studio is ready to welcome you! This unit has 1 queen bed and 1 sleeper sofa, a desk, a kitchenette, a full bathroom, and a washer/dryer. It is the lower level of a historic 1800s Bostonian house, recently renovated. It has its own separate entrance. Great location! Conveniently located in Bay Village next to the Boston Public Garden, the studio is close to Downtown, Theater district, Chinatown, Beacon Hill, Back Bay, and South End!

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.

(W11) Vibrant Area, Pizza, Shopping, Parks W/D
🌆 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.

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!

Cambridge Cottage Retreat Near Harvard
Escape to a charming Cambridge cottage just a 15 minute walk (4 min drive) to Harvard Square. Enjoy the best of both worlds - steps from vibrant shops, cafes, and restaurants, yet tucked away as a peaceful retreat. Dine in a cozy nook overlooking a sun dappled garden oasis. This one-bedroom features a queen bed, plus a full pullout sofa in the open living area - perfect for someone travelling alone, couples or small families.

The Weiss : Modern Gallery • Historic Property!
Stay inside a historic restored monastery in Brighton. This spacious studio blends preserved historic architecture with modern comfort and features an expandable room divider for a one-bedroom feel. Just a 5-minute walk to the T with easy access to Boston College, Harvard, hospitals, and downtown Boston. Amenities Include: → Blazing-fast WiFi → 65” Smart TV → Fully stocked kitchen → Washer & dryer → Comfortable queen bed
Popular amenities for Boston holiday rentals
Other great holiday rentals in Boston

Steps from Fenway Park + Free Breakfast & Pool

Harvard Square Hotel Cambridge

Luxurious Fenway 2BR Penthouse w/ Roof Deck

The Dagny

Sunlit Modern Room near Airport & Subway

Steps to Charles River | Bar & Restaurant + Gym

Modern South End Stay, Stay Tonight!

Timeless Stay | Freedom Trail. Fitness Center
When is the best time to visit Boston?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $161 SGD | $157 SGD | $175 SGD | $200 SGD | $224 SGD | $223 SGD | $215 SGD | $223 SGD | $209 SGD | $219 SGD | $187 SGD | $170 SGD |
| Avg. temp | -1°C | 0°C | 4°C | 9°C | 15°C | 20°C | 23°C | 23°C | 19°C | 13°C | 7°C | 2°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.
Destinations to explore
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- Rentals with pools Boston
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- Family-friendly rentals Boston
- Rentals with a patio Boston
- Waterfront rentals Boston
- Rentals with a kayak Boston
- Fitness-friendly rentals Boston
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- Bed and breakfasts Boston
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- Rentals with a washing machine and dryer Boston
- Hotel rooms Boston
- Rentals with an EV charger Boston
- Rentals with lake access Boston
- Rentals with an accessible-height bed Boston
- Serviced apartment rentals Boston
- Boutique hotels Boston
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- Apartment rentals Boston
- Fenway Park
- Harvard University
- Hampton Beach
- TD Garden
- Boston Common
- Boston Seaport
- Gillette Stadium
- Revere Beach
- Brown University
- Boston University
- Boston Convention and Exhibition Center
- Freedom Trail
- New England Aquarium
- Onset Beach
- Canobie Lake Park
- MIT Museum
- Duxbury Beach
- North Hampton Beach
- Crane Beach
- Boston College
- Northeastern University
- Quincy Market
- Tufts University
- Harvard Square
- Things to do Boston
- Art and culture Boston
- Tours Boston
- Food and drink Boston
- Nature and outdoors Boston
- Sightseeing Boston
- Things to do Suffolk County
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- Art and culture Suffolk County
- Things to do Massachusetts
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- Nature and outdoors Massachusetts
- Tours Massachusetts
- Sports activities Massachusetts
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