29374+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Massachusetts pickleball Stays, Resort Rentals, & Homes

About Massachusetts Vacation Rentals

Discover over 29374 amazing vacation rental options in Massachusetts 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 Massachusetts.

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 932.54 ft², with prices averaging US $598 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 Massachusetts.

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Top Pickleball-Ready Accommodation Types in Massachusetts

Type Count
Vacation Homes 16535
Holiday Apartments 6024
Cottages 1957
Villas 70

Use these Quick Filters to Find a Vacation Rental in Massachusetts

★ 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 Massachusetts with PickleTrip™.

Weather in Massachusetts, US

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

December - February
High 45°F       Low 20°F
March - May
High 63°F       Low 22°F
June - August
High 80°F       Low 57°F
September - November
High 74°F       Low 30°F

Top Attractions Around Massachusetts, US

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


Fenway Park
Boston University
Harvard University
TD Garden
Boston Common
Faneuil Hall Marketplace
Boston Convention and Exhibition Center
Gillette Stadium
New England Aquarium
Northeastern University
Boston Museum of Fine Arts
Copley Square
Harvard Square
Massachusetts General Hospital
Museum of Science
Hynes Convention Center
University of Massachusetts-Amherst
Massachusetts Institute of Technology
Copley Place
Boston Children's Museum
Xfinity Center
Salem Witch Museum
Boston College
Black Falcon Cruise Terminal
Boston Opera House
Jiminy Peak Mountain Resort
Boston Harbor
Quincy Market
Prudential Tower
Old Sturbridge Village

Other Places to Stay in Massachusetts, US


Barnstable County 8,120 Properties
Cape Cod 8,055 Properties
Boston 4,588 Properties
Suffolk County 2,263 Properties
Middlesex County 1,469 Properties
North Shore 1,292 Properties
Essex County 1,280 Properties
Dukes County 1,102 Properties
Martha's Vineyard 1,101 Properties
Berkshire County 1,016 Properties
The Berkshires 1,016 Properties
Yarmouth 840 Properties

Frequently Asked Questions About Massachusetts?

What are the top vacation rentals, resorts, and hotels in Massachusetts 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 Massachusetts. 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 Massachusetts!

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

Discover 1400 accommodations with private or nearby pickleball courts in Massachusetts. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in Massachusetts? 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 Massachusetts?

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 29374 properties listed in Massachusetts in 2026, 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.


People Also Ask

There are 29374 Massachusetts, US Vacation Rentals

Recently Booked Vacation Rentals in Massachusetts