967+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Worcester County pickleball Stays, Resort Rentals, & Homes

About Worcester County Vacation Rentals

Discover over 967 amazing vacation rental options in Worcester County 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 Worcester County.

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 740.42 ft², with prices averaging US $375 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 Worcester County.

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Top Pickleball-Ready Accommodation Types in Worcester County

Type Count
Vacation Homes 495
Holiday Apartments 185
Cottages 53
Villas 6

Use these Quick Filters to Find a Vacation Rental in Worcester County

★ 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 Worcester County with PickleTrip™.

Weather in Worcester County, MA

View the weather forecast for Worcester County before booking your Worcester County 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 Worcester County, MA

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


Old Sturbridge Village
Wachusett Mountain Ski Area
DCU Center
Worcester Polytechnic Institute
College of the Holy Cross
Clark University
Union Station
Brimfield Antique Show
Coco Key Water Resort at Courtyard by Marriott Fitchburg
Auburn Mall
Fitchburg State University
Southwick's Zoo
Indian Ranch
Worcester Art Museum
Cushing Academy
Tower Hill Botanic Garden
Solomon Pond Mall
Nashoba Valley Winery
Green Hill Park
Cummings School of Veterinary Medicine at Tufts University
Northborough Crossing
Elm Park
EcoTarium
Lake Webster
Mechanics Hall
The Hanover Theatre for the Performing Arts
Franklin D. Roosevelt American Heritage Center
Blissful Meadows Golf Club
Gilbertville Covered Bridge
Lake Dennison State Recreation Area

Other Places to Stay in Worcester County, MA


Massachusetts 18,785 Properties
Milford 283 Properties
Worcester 235 Properties
West Wareham 195 Properties
Central Business District 123 Properties
Minot 101 Properties
Leominster 67 Properties
Glendale 50 Properties
Westborough 50 Properties
Silver Beach 49 Properties
Sturbridge 49 Properties
Lenox Dale 28 Properties

Frequently Asked Questions About Worcester County?

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

How many pickleball-ready properties have private pools in Worcester County?

Discover 42 accommodations with private or nearby pickleball courts in Worcester County. Some of the best destinations to stay and play pickleball are:

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

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

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 967 properties listed in Worcester County 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 967 Worcester County, MA Vacation Rentals

Recently Booked Vacation Rentals in Worcester County