6961+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Boston pickleball Stays, Resort Rentals, & Homes

About Boston Vacation Rentals

Discover over 6961 amazing vacation rental options in Boston with pickleball courts or nearby facilities. From resorts to hotels, villas to condos, PickleTrip connects you with a vast selection of pickleball-ready amenities at great prices, providing you with the perfect spot to base your next pickleball vacation. Stay and Play pickleball When You Travel and uncover great stays in Boston.

Find exclusive last-minute deals on vacation rentals, resorts, and hotels with private courts and nearby facilities with PickleTrip™, whether you're traveling solo or with a group. Our platform offers a variety of stay options, from vacation rentals to Airbnb-style properties, all with private pickleball courts or nearby facilities. Compare options from multiple suppliers with a single click to find the perfect stay that fits your budget and style. Places to stay near pickleball courts are an average of 629.26 ft², with prices averaging US $412 per night.

With PickleTrip™, you can easily search for and book your next pickleball vacation rental with courts or nearby facilities. Our platform connects you with the ideal holiday rental to create a lifetime of travel memories. Prices listed are often discounted versus rack rates, so you can secure your perfect place to stay today and get ready to play pickleball in Boston.

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Top Pickleball-Ready Accommodation Types in Boston

Type Count
Holiday Apartments 3989
Vacation Homes 1660
Cottages 27
Villas 12

Use these Quick Filters to Find a Vacation Rental in Boston

★ Pro Tip: PickleTrip™ is a travel platform, connecting avid pickleball players and enthusiasts with a variety of vacation rentals, resorts, and hotels featuring private pickleball courts or nearby facilities. We curate a vast selection of properties from trusted sources, providing you with unbeatable options and pricing to find the perfect pickleball getaway. Experience unforgettable pickleball matches in Boston with PickleTrip™.

Weather in Boston, MA

View the weather forecast for Boston before booking your Boston Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Boston, MA

PickleTrip offers a large selection of top attractions around Boston . Research things to do on your vacation before you visit Boston.


Fenway Park
Boston University
Harvard University
TD Garden
Boston Common
Faneuil Hall Marketplace
Boston Convention and Exhibition Center
New England Aquarium
Northeastern University
Boston Museum of Fine Arts
Copley Square
Harvard Square
Massachusetts General Hospital
Museum of Science
Hynes Convention Center
Massachusetts Institute of Technology
Copley Place
Boston Children's Museum
Salem Witch Museum
Boston College

Other Places to Stay in Boston, MA


Suffolk County 2,595 Properties
Middlesex County 1,612 Properties
Norfolk County 613 Properties
Cambridge 520 Properties
Downtown Boston 368 Properties
Back Bay 305 Properties
Fenway–Kenmore 223 Properties
The Freedom Trail 217 Properties
South End 199 Properties
West Fens 197 Properties
Brookline 184 Properties
Dorchester 184 Properties

Frequently Asked Questions About Boston?

What are the top vacation rentals, resorts, and hotels in Boston with Courts?

Experience the ultimate pickleball vacation with PickleTrip™. We offer a variety of premium rental properties, resorts, and hotels with private pickleball courts or nearby facilities in Boston. Whether you're a beginner or a seasoned player, we have the perfect destination for you to stay and play. Book now and discover the best pickleball vacation spots in Boston!

How many pickleball-ready properties have private pools in Boston?

Discover 147 accommodations with private or nearby pickleball courts in Boston. Some of the best destinations to stay and play pickleball are:

Which vacation rentals, resorts, or hotels in Boston is best for families looking for a pickleball-getaway?

Looking for a fun and active getaway with pickleball courts in Boston? With PickleTrip™, you'll have access to a wide selection of top-rated properties that offer private pickleball courts or nearby facilities. Make the most of you getaway and ace your A-game while you travel.

How many PickleTrip vacation rentals or resorts are available in Boston?

PickleTrip™ offers a diverse selection of properties with private pickleball courts or nearby facilities to enhance your pickleball experience on your next trip. With a combination of established great stays and new options in top locations, PickleTrip™ has over 6961 properties listed in Boston in 2025, and the number only continues to grow. By consolidating listings from various providers, PickleTrip™ brings you the best luxury stays for a sporty, professional, and fun travel experience.

Nearby Neighborhood (16) 
Neighborhood Property Count
Downtown Boston Vacation Rentals in Boston, Massachusetts 368
Back Bay Vacation Rentals in Boston, Massachusetts 305
Fenway–Kenmore Vacation Rentals in Boston, Massachusetts 223
South End Vacation Rentals in Boston, Massachusetts 199
Dorchester Vacation Rentals in Boston, Massachusetts 184
Boston Financial District Vacation Rentals in Boston, Massachusetts 173
Seaport District Vacation Rentals in Boston, Massachusetts 153
Brighton Vacation Rentals in Boston, Massachusetts 135
Roxbury Vacation Rentals in Boston, Massachusetts 93
Allston Vacation Rentals in Boston, Massachusetts 93
East Boston Vacation Rentals in Boston, Massachusetts 75
Theatre District Vacation Rentals in Boston, Massachusetts 72
Beacon Hill Vacation Rentals in Boston, Massachusetts 71
North End Vacation Rentals in Boston, Massachusetts 69
Jamaica Plain Vacation Rentals in Boston, Massachusetts 53
South Boston Vacation Rentals in Boston, Massachusetts 48

People Also Ask

There are 6961 Boston, MA Vacation Rentals

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