119+ Treehouses, Forest Homes, Cabin Rentals, and Private Nature Retreats in Old Town Winchester |
  1. USA
  2. Virginia
  3. Winchester
  4. Old Town Winchester

Tree House Rentals in Old Town Winchester

About Old Town Winchester Treehouse Rentals

Explore more than 119 treehouses in Old Town Winchester. From luxurious treetop retreats to cozy forest homes, cabins and off-grid properties, each offers premium amenities designed for families, groups, and adventurers. Enjoy exceptional comfort and a one-of-a-kind nature experience with these incredible accommodations. Perfect for tranquil escapes, adventurous retreats, or nature-inspired getaways, these treehouses provide style and comfort in Old Town Winchester.

Looking for last-minute deals or the best offers on treehouses, cozy forest homes, cabins and off-grid properties? Treehouse Rentals makes it easy to compare options in Old Town Winchester. Choose from spacious family-friendly stays, charming woodland escapes, or luxurious treetop getaways tailored for ultimate relaxation and adventure

Find spacious family-friendly accommodations, cozy forest homes, or luxurious treetop stays—all designed for maximum comfort and convenience during your visit.

On average, treehouses in Old Town Winchester offer approximately 700.54 ft² of space, giving you and your group plenty of room to relax and enjoy the stunning natural surroundings.

The average nightly rate for treehouses in Old Town Winchester typically ranges around US $165.

Treehouse Rentals offers a secure and convenient platform to compare and book the best treehouses in Old Town Winchester. Explore a wide range of properties at unbeatable rates, and enjoy a unique stay immersed in nature with us.

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Top Treehouse Accommodation Types in Old Town Winchester

Type Count
Holiday Apartments 32
Vacation Homes 32
Cottages 1
Villas 1

Use these Quick Filters to Find a Vacation Rental in Old Town Winchester

★ Pro Tip: Treehouse Rentals simplifies your search for the best treehouse accommodations from leading vacation rental OTAs like Booking.com and more. Use our Advanced Filter to explore treehouses, cozy cabins, secluded forest homes and off-grid properties. Filter by availability, pricing, cancellation options, and amenities to discover the ideal treehouse getaway in Old Town Winchester.

Weather in Old Town Winchester, VA

View the weather forecast for Old Town Winchester before booking your Old Town Winchester 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 Old Town Winchester, VA

Treehouse Rentals offers a diverse selection of the finest treehouses and nature-inspired retreats around the world. Old Town Winchester . Research things to do on your vacation before you visit Old Town Winchester.


SheNonedoah Valley Discovery Museum
Handley Regional Library
Bright Box Theater
George Washington's Office
Old Court House Civil War Museum
Hollywood Casino at Charles Town Races
SheNonedoah University
Winchester Medical Center
George Washington National Forest
Bluemont Vineyard
Summit Point Raceway
Dinosaur Land
Apple Blossom Mall
Charles Town Library
Mt Hebron Cemetery
Jim Barnett Park
Wilson's Wild Animal Park
Patsy Cline Historic House
Twin Oaks Tavern Winery
Blue Ridge Arts Council and Gallery

Other Places to Stay in Old Town Winchester, VA


Winchester 359 Properties
Bright Box Theater 114 Properties
Old Court House Civil War Museum 114 Properties
Shenandoah Valley Discovery Museum 114 Properties
George Washington's Office 114 Properties
Handley Regional Library 113 Properties

Frequently Asked Questions About Old Town Winchester?

What are the top treehouse rentals in Old Town Winchester?

Looking for a place to stay in Old Town Winchester? Explore these highly-rated treehouses for a one-of-a-kind retreat surrounded by nature:

How many treehouses with private pools are available in Old Town Winchester?

Find exceptional treehouses with private pools near Old Town Winchester on Treehouse Rentals. Relax in serene treetop accommodations with exclusive pool access and picturesque nature views. Whether it's a spacious treehouse or a secluded forest retreat, these properties provide the ideal mix of luxury and adventure.

What are the top-rated treehouses in Old Town Winchester for family stays?

Searching for a family-friendly treehouse in Old Town Winchester? Discover these top-rated options, each loved by families and groups who have stayed in Old Town Winchester:

How many treehouses are available in Old Town Winchester?

Treehouse Rentals, as of 2025, features over 119 unique treehouse, cabins and forest homes in Old Town Winchester. Choose from treetop hideaways, eco-friendly lodges, and off-grid properties, with new options added frequently.

By 2025, Treehouse Rentals has curated over 119 stunning properties in Old Town Winchester, sourced from trusted platforms. Plan your nature-inspired getaway now.

For 2025, Treehouse Rentals provides access to over 119 premier accommodations in Old Town Winchester. Find your ideal escape among the treetops today.


People Also Ask

There are 119 Old Town Winchester, VA Vacation Rentals

Recently Booked Vacation Rentals in Old Town Winchester