350+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Gloucester pickleball Stays, Resort Rentals, & Homes

About Gloucester Vacation Rentals

Discover over 350 amazing vacation rental options in Gloucester 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 Gloucester.

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 974.41 ft², with prices averaging US $535 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 Gloucester.

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Top Pickleball-Ready Accommodation Types in Gloucester

Type Count
Vacation Homes 230
Holiday Apartments 69
Cottages 22
Villas 3

Use these Quick Filters to Find a Vacation Rental in Gloucester

★ 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 Gloucester with PickleTrip™.

Weather in Gloucester, MA

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

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


Good Harbor Beach
Wingaersheek Beach
Hammond Castle
Maritime Gloucester
Stage Fort Park
Lucky 7 Arcade
Eastern Point Lighthouse
Niles Beach
The Gorton Theatre
Half Moon Beach
Mount Ann Park
Dogtown
Cape Ann Museum
Plum Cove Beach
Ravenswood Park
Sargent House Museum
Capt Bill & Sons Whale Watch
Fishermen's Memorial Monument
Cape Ann Historical Museum
Gloucester Unitarian Universalist Church

Other Places to Stay in Gloucester, MA


Dogtown 473 Properties
Good Harbor Beach 406 Properties
Plum Cove Beach 294 Properties
Annisquam 270 Properties
Northeast Hospital Corporation - Addison Gilbert Campus 262 Properties
Sargent House Museum 244 Properties
Cape Ann Historical Museum 244 Properties
Cape Ann Museum 244 Properties
Gloucester Unitarian Universalist Church 243 Properties
Lucky 7 Arcade 239 Properties
Schooner Adventure 237 Properties
Magnolia 74 Properties

Frequently Asked Questions About Gloucester?

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

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

Discover 2 accommodations with private or nearby pickleball courts in Gloucester. Some of the best destinations to stay and play pickleball are:

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

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

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 350 properties listed in Gloucester 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 (1) 
Neighborhood Property Count
Annisquam Vacation Rentals in Gloucester, Massachusetts 270

People Also Ask

There are 350 Gloucester, MA Vacation Rentals

Recently Booked Vacation Rentals in Gloucester