Orange County Vacations & Trips from $353

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Your Orange County Vacation

Book a vacation package to Orange County and make planning your getaway a cinch. With all the details arranged before you depart, you can focus on enjoying every second in this amazing destination. Get your trip to Orange County off to an unforgettable start by making Orange the first stop on your itinerary. This city is a favorite with travelers from all over the globe. Whether you're traveling for a couple of days or a couple of weeks, Expedia are here to help you organize your next dream Orange County vacation.

Top destinations in Orange County

An ancient stone archway with intricate carvings and columns, surrounded by trees and a clear blue sky.

Orange

Orange
A sunset over a calm lake with a silhouette of trees and a cloudy sky.

Gordonsville

Gordonsville
A rural landscape with a white fence, green fields, and a few buildings in the distance.

Barboursville

Barboursville
A cannon on a wooden platform in a forested area.

Locust Grove

Locust Grove
A white church with a tall tower and arched windows.

Rapidan

Rapidan

The Latest Orange County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Blackburn Inn and Conference Center

The Blackburn Inn and Conference Center

$353
per person
Oct 23 - Oct 25
found 11 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Weyers Cave (SHD)
9.2/10 Wonderful! (1,012 reviews)
A beautiful place to stay!!!

Reviewed on Sep 20, 2026

Little Mod Hotel at the University

Little Mod Hotel at the University

Venable
$780
per person
Nov 6 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
St. Louis (STL) to Charlottesville (CHO)
9.2/10 Wonderful! (378 reviews)
The staff is exceptional and ensures your stay is comfortable and you feel welcome. I enjoy the thoughtful amenities and luxurious beds and linens. Hot water! It's a great location near downtown shops and restaurants. Absolutely, darling decor.

Reviewed on Sep 20, 2026

 Oakhurst Inn at the University

Oakhurst Inn at the University

Jefferson Park Avenue
$884
per person
Nov 6 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
St. Louis (STL) to Charlottesville (CHO)
9.2/10 Wonderful! (610 reviews)
The Estate at Meander

The Estate at Meander

$1,395
per person
Nov 24 - Nov 30
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottesville (CHO)
9.2/10 Wonderful! (170 reviews)
Pet friendly

Reviewed on Sep 18, 2026

Virginia Guesthouse Hotel

Virginia Guesthouse Hotel

Lewis Mountain
$907
per person
Nov 6 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
St. Louis (STL) to Charlottesville (CHO)
9.8/10 Exceptional! (104 reviews)

Find the Best Orange County Vacation Packages

Orange County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Charlottesville-Albemarle Airport (CHO)

Orange County Hotel Deals

Round Hill Inn

Round Hill Inn

750 Round Hill Dr. Orange VA
Fully refundableReserve now, pay when you stay
$127 nightly
$140 total
Sep 28 - Sep 29
Total with taxes and fees
Round Hill Inn
English Inn of Charlottesville

English Inn of Charlottesville

2000 Morton Drive Charlottesville VA
Fully refundableReserve now, pay when you stay
$79 nightly
$90 total
Oct 21 - Oct 22
Total with taxes and fees
English Inn of Charlottesville
Omni Charlottesville Hotel

Omni Charlottesville Hotel

212 Ridge McIntire Rd Charlottesville VA
Fully refundableReserve now, pay when you stay
$167 nightly
$191 total
Oct 18 - Oct 19
Total with taxes and fees
Omni Charlottesville Hotel
See all 1,769 properties in Orange County
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Orange County attractions

A large brick building with a central portico and a surrounding lawn.
Photo by Jerry Smith

James Madison's Montpelier

9.2/10 (79 reviews)
You can learn about the history of Orange with a visit to James Madison's Montpelier. Stroll along this relaxing area's lakeside, or simply enjoy its bars.
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A building with a green roof, surrounded by a garden with various plants and flowers.
Photo by mary mahling carns

Honah Lee Vineyard

8.8/10 (6 reviews)
You can enjoy a tasting or tour at Honah Lee Vineyard during your travels to Gordonsville. Discover the countryside in this family-friendly area, or seek out the horseback riding.
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James Madison Museum

9.0/10 (8 reviews)
You can spend an afternoon studying the exhibits at James Madison Museum during your travels in Thornhill. Stroll along the lakeside in this family-friendly area, or seek out the horseback riding.
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Barboursville Ruins

9.0/10 (8 reviews)
Learn about the local history of Barboursville when you take a trip to Barboursville Ruins. While in this family-friendly area, you can savor the top-notch restaurants.
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Lake Of The Woods

Commune with nature and explore the great outdoors at Lake Of The Woods during your travels in Lake of the Woods.
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The Arts Center in Orange

9.6/10 (4 reviews)
Take the family on an outing to The Arts Center in Orange during your trip to Thornhill. Stroll along this relaxing area's lakeside, or simply enjoy its wineries.
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Germanna Community College

Enjoy the collegiate vibe at Germanna Community College as part of your travels around Locust Grove.
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Meadows Farms Golf Course

Enjoy a round of golf in Locust Grove at Meadows Farms Golf Course.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.