54+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Massachusetts
  3. Bellingham
  4. Midlands

Midlands pickleball Stays, Resort Rentals, & Homes

About Midlands Vacation Rentals

Discover over 54 amazing vacation rental options in Midlands 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 Midlands.

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 292.06 ft², with prices averaging US $226 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 Midlands.

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Top Pickleball-Ready Accommodation Types in Midlands

Type Count
Holiday Apartments 10
Vacation Homes 5

Use these Quick Filters to Find a Vacation Rental in Midlands

★ 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 Midlands with PickleTrip™.

Weather in Midlands, MA

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

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


Gillette Stadium
Xfinity Center
Brown University
Twin River Casino
Dunkin' Donuts Center
Patriot Place
Providence Place Mall
Providence Performing Arts Center
Wrentham Village Premium Outlets
Rhode Island Convention Center
Johnson and Wales University
Providence College
Wellesley College
Hall at Patriot Place
College of the Holy Cross
WaterFire Providence
Plainridge Park Casino
Rhode Island School of Design
Bryant University
Babson College

Frequently Asked Questions About Midlands?

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

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

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

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 54 properties listed in Midlands 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.


People Also Ask

There are 54 Midlands, MA Vacation Rentals

Recently Booked Vacation Rentals in Midlands