Ward Two pickleball Stays, Resort Rentals, & Homes

Frequently Asked Questions About Ward Two?

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

• Boston Yacht Haven Inn & Marina
• Best of Boston Houseboat Heat/AC in Boston Harbor Suite1 in Historic Navy Yard
• Historic Home At Freedom Trail
• Historic Townhouse Condo in the center of Boston, across from the Public Garden
• "Travelers Choice Award" Spacious 2BD/2Bath Heat/AC 45 ft yacht Freedom Trail
• Charming House In Downtown Boston, Nearby Attractions, Parking & Free WiFi
• Chic South End Studio With Patio
• Stunning South End/Back Bay Penthouse!
• Great South End/Back Bay location, 1 bed condo near T station
• 3 BR/3 BATH in Historic Home Mins from Kendall Sq , MIT, Harvard, Boston.

How many pickleball-ready properties have private pools in Ward Two?

Discover 39 accommodations with private or nearby pickleball courts in Ward Two. Some of the best destinations to stay and play pickleball are:

• Large 2 Bed/2Bath By MGH, Washer/Dryer in Suite
• Kendall Square 1BR w Concierge Gym nr MIT BOS-715
• Stunning Rooftop Apartment & Garden Deck
• Well-located Kendall Sq 1BR w courtyard BOS-388

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

Looking for a fun and active getaway with pickleball courts in Ward Two? 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.

• Cozy 2-Bed Apt Near MIT/Harvard + Parking
• Beautiful 3BR 3BA Duplex parking Best Location Boston
• Morrison House

How many PickleTrip vacation rentals or resorts are available in Ward Two?

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 3766 properties listed in Ward Two 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.

Nearby Neighborhood (11)