51+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Massachusetts
  3. Worcester
  4. Westborough

Westborough pickleball Stays, Resort Rentals, & Homes

About Westborough Vacation Rentals

Discover over 51 amazing vacation rental options in Westborough 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 Westborough.

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 324.83 ft², with prices averaging US $197 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 Westborough.

Show more
Show less

Top Pickleball-Ready Accommodation Types in Westborough

Type Count
Vacation Homes 29
Holiday Apartments 1

Use these Quick Filters to Find a Vacation Rental in Westborough

★ 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 Westborough with PickleTrip™.

Weather in Westborough, MA

View the weather forecast for Westborough before booking your Westborough 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 Westborough, MA

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


Westborough Country Club
Lake Chauncy Public Beach
Wachusett Mountain Ski Area
DCU Center
Patriot Place
Worcester Polytechnic Institute
Wrentham Village Premium Outlets
Wellesley College
Hall at Patriot Place
Nashoba Valley Ski Area
College of the Holy Cross
Clark University
Union Station
New England Sports Center
Babson College
Auburn Mall
Natick Collection
Brandeis University
Southwick's Zoo
Indian Ranch

Other Places to Stay in Westborough, MA


Lake Chauncy Public Beach 52 Properties
Westborough Country Club 45 Properties

Frequently Asked Questions About Westborough?

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

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

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

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 51 properties listed in Westborough 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 51 Westborough, MA Vacation Rentals

Recently Booked Vacation Rentals in Westborough