67+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. New York
  3. Poughkeepsie
  4. Brewster

Brewster pickleball Stays, Resort Rentals, & Homes

About Brewster Vacation Rentals

Discover over 67 amazing vacation rental options in Brewster 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 Brewster.

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 803.67 ft², with prices averaging US $406 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 Brewster.

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Top Pickleball-Ready Accommodation Types in Brewster

Type Count
Vacation Homes 30
Holiday Apartments 7
Cottages 4
Villas 2

Use these Quick Filters to Find a Vacation Rental in Brewster

★ 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 Brewster with PickleTrip™.

Weather in Brewster, NY

View the weather forecast for Brewster before booking your Brewster 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 Brewster, NY

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


Brewster Public Library
Bear Mountain State Park
United States Military Academy
Ridgefield Playhouse
Dia Beacon
Danbury Fair Mall
SplashDown Beach
Harriman State Park
Thunder Ridge Ski Resort
The Glass House
Stormville Airport Antique Show & Flea Market
Candlewood Lake
Elephant's Trunk Flea Market
Westport Country Playhouse
Van Cortlandt Manor
Lake Waramaug
Highlands Country Club
Stamford Museum and Nature Center
Curtain Call
Garrison Golf Club

Other Places to Stay in Brewster, NY


Peach Lake 79 Properties
Town of Southeast 61 Properties
Brewster Public Library 56 Properties

Frequently Asked Questions About Brewster?

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

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

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

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 67 properties listed in Brewster 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 67 Brewster, NY Vacation Rentals

Recently Booked Vacation Rentals in Brewster