42+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Vermont
  3. Middlebury - Warren
  4. Middlebury

Middlebury pickleball Stays, Resort Rentals, & Homes

About Middlebury Vacation Rentals

Discover over 42 amazing vacation rental options in Middlebury 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 Middlebury.

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 648.01 ft², with prices averaging US $430 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 Middlebury.

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Top Pickleball-Ready Accommodation Types in Middlebury

Type Count
Vacation Homes 19
Holiday Apartments 10
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Middlebury

★ 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 Middlebury with PickleTrip™.

Weather in Middlebury, VT

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

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


Middlebury College
Town Hall Theater
Vermont Folklife Center
Halpin Covered Bridge
Danforth Pewter
Pulp Mill Covered Bridge
National Museum of the Morgan Horse
Kevin P. Mahaney '84 Center for the Arts
Holy Cow Inc.
Otter Creek Brewing
UVM Morgan Horse Farm
Henry Sheldon Museum of Vermont History
Porter Medical Center
Porter Hospital
UVM Health Network - Porter Medical Center
Sugarbush Ski Resort
Lake Champlain
Fort Ticonderoga
Green Mountain National Forest
Mad River Glen Cooperative

Other Places to Stay in Middlebury, VT


Middlebury - Warren 679 Properties
Addison County 180 Properties
Halpin Covered Bridge 55 Properties
Cornwall 48 Properties
Middlebury College 36 Properties
Kevin P. Mahaney '84 Center for the Arts 36 Properties
Vermont Folklife Center 35 Properties
Porter Medical Center 35 Properties
UVM Health Network - Porter Medical Center 35 Properties
Porter Hospital 35 Properties
Holy Cow Inc. 34 Properties
National Museum of the Morgan Horse 34 Properties

Frequently Asked Questions About Middlebury?

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

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

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

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 42 properties listed in Middlebury 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 42 Middlebury, VT Vacation Rentals

Recently Booked Vacation Rentals in Middlebury