417+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Massachusetts
  3. Milford

Milford pickleball Stays, Resort Rentals, & Homes

About Milford Vacation Rentals

Discover over 417 amazing vacation rental options in Milford 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 Milford.

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 935.15 ft², with prices averaging US $502 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 Milford.

Show more
Show less

Top Pickleball-Ready Accommodation Types in Milford

Type Count
Vacation Homes 244
Holiday Apartments 39
Cottages 34
Villas 1

Use these Quick Filters to Find a Vacation Rental in Milford

★ 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 Milford with PickleTrip™.

Weather in Milford, MA

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

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


Vietnam Mountain Biking Trail
The Tasting Room - An Italian Wine Shop
Dana-Farber/Brigham and Women's Cancer Center at Milford Regional Medical Center
Gillette Stadium
Xfinity Center
Twin River Casino
DCU Center
Patriot Place
Worcester Polytechnic Institute
Wrentham Village Premium Outlets
Wellesley College
Hall at Patriot Place
College of the Holy Cross
Clark University
Union Station
Plainridge Park Casino
New England Sports Center
Bryant University
Babson College
Auburn Mall

Other Places to Stay in Milford, MA


Massachusetts 18,866 Properties
Berkshire 300 Properties
West Wareham 195 Properties
Readville 112 Properties
Greenbush 112 Properties
Minot 101 Properties
Prides Crossing 72 Properties
Monroe Bridge 63 Properties
Glendale 48 Properties
Silver Beach 45 Properties
Lenox Dale 30 Properties
Ashley Falls 29 Properties

Frequently Asked Questions About Milford?

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

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

Discover 18 accommodations with private or nearby pickleball courts in Milford. Some of the best destinations to stay and play pickleball are:

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

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

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 417 properties listed in Milford 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 417 Milford, MA Vacation Rentals

Recently Booked Vacation Rentals in Milford