67+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Vermont
  3. Brattleboro

Brattleboro pickleball Stays, Resort Rentals, & Homes

About Brattleboro Vacation Rentals

Discover over 67 amazing vacation rental options in Brattleboro 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 Brattleboro.

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 604.74 ft², with prices averaging US $235 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 Brattleboro.

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Top Pickleball-Ready Accommodation Types in Brattleboro

Type Count
Vacation Homes 23
Holiday Apartments 14

Use these Quick Filters to Find a Vacation Rental in Brattleboro

★ 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 Brattleboro with PickleTrip™.

Weather in Brattleboro, VT

View the weather forecast for Brattleboro before booking your Brattleboro 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 Brattleboro, VT

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


Brattleboro Bowl
Brattleboro Outlet Center
Brattleboro Farmers' Market
The Stone Church
Brattleboro Country Club
Brattleboro Common
Creamery Covered Bridge
Marlboro College
Estey Organ Museum
Retreat Cemetery
Marlboro Music Festival
Vermont Jazz Center
Brattleboro Museum & Art Center
Delectable Mountain Cloth
Fort Dummer State Park
Tasha Tudor Museum
Brattleboro Memorial Hospital
Molly Stark State Park

Other Places to Stay in Brattleboro, VT


Dummerston 109 Properties
West Dummerston 101 Properties
Marlboro College 98 Properties
Marlboro Music Festival 97 Properties
Guilford 59 Properties
Brattleboro Bowl 53 Properties
Brattleboro Country Club 48 Properties
Retreat Cemetery 47 Properties
Delectable Mountain Cloth 47 Properties
The Stone Church 47 Properties
Brattleboro Common 47 Properties
West Brattleboro 32 Properties

Frequently Asked Questions About Brattleboro?

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

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

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

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 Brattleboro 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 67 Brattleboro, VT Vacation Rentals

Recently Booked Vacation Rentals in Brattleboro