39+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Massachusetts
  3. Sheffield

Sheffield pickleball Stays, Resort Rentals, & Homes

About Sheffield Vacation Rentals

Discover over 39 amazing vacation rental options in Sheffield 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 Sheffield.

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 1408.52 ft², with prices averaging US $389 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 Sheffield.

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Top Pickleball-Ready Accommodation Types in Sheffield

Type Count
Vacation Homes 32
Holiday Apartments 3
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Sheffield

★ 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 Sheffield with PickleTrip™.

Weather in Sheffield, MA

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

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


Magnolia Bluffs Casino
Ashley House
Tanglewood Music Center
Ski Butternut
Catamount Ski Area
Mohawk Mountain Ski Area
Norman Rockwell Museum
National Shrine of the Divine Mercy
Kent Falls State Park
Lee Prime Outlets
Bousquet Ski Area
Lime Rock Park
Cranwell Golf Club
Jacob's Pillow
Otis Ridge
October Mountain State Forest
Beartown State Forest
The Mount
Otis Reservoir
Shakespeare and Company

Other Places to Stay in Sheffield, MA


Magnolia Bluffs Casino 43 Properties
Ashley House 33 Properties

Frequently Asked Questions About Sheffield?

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

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

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

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 39 properties listed in Sheffield 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 39 Sheffield, MA Vacation Rentals

Recently Booked Vacation Rentals in Sheffield