Twin Oaks Vacations from $667
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The Latest Twin Oaks Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Dinsmore Boutique Inn
Venable
Price was $812, price is now $667 per person
$667
per person
Oct 21 - Oct 24
found 19 hours ago
Roundtrip non-stop flight included
New York (JFK) to Charlottesville (CHO)
9.6/10 Exceptional! (300 reviews)
Dinsmore Boutique Inn is everything you'd expect from a small inn -- lovely, spacious, well-appointed rooms, and wonderful management. We were made to feel welcome the entire time, from check-in to delicious breakfasts to helpful advice.
Reviewed on Sep 1, 2025
Graduate by Hilton Charlottesville
Venable
Price was $775, price is now $712 per person
$712
per person
Oct 21 - Oct 24
found 19 hours ago
Roundtrip non-stop flight included
New York (JFK) to Charlottesville (CHO)
8.2/10 Very Good! (1,000 reviews)
Very student and student family oriented. Personnel is nice and efficient. Location is walkable for visiting the area if you like to walk.
Reviewed on Aug 31, 2025
The Draftsman, Charlottesville, University, Autograph Collection Hotel
10th and Page
Price was $855, price is now $835 per person
$835
per person
Oct 21 - Oct 24
found 19 hours ago
Roundtrip non-stop flight included
New York (JFK) to Charlottesville (CHO)
9.4/10 Exceptional! (315 reviews)
The staff were pleasant and attentive. Kudos to the Valet attendants as they were always on time and on point during the entire stay. Will definitely be returning!
Reviewed on Jun 24, 2025
Twin Oaks Hotel Deals
Comfort Inn & Suites Orange - Montpelier
334 Caroline St, Orange, VA
$93 nightly
The price is $102 total per night from Sep 7 to Sep 8
$102 total
Sep 7 - Sep 8
Total with taxes and fees
Round Hill Inn
750 Round Hill Dr., Orange, VA
$109 nightly
The price is $120 total per night from Sep 8 to Sep 9
$120 total
Sep 8 - Sep 9
Total with taxes and fees
Boardwalk Hotel on Lake Anna by Kasa
200 Boardwalk Way, Louisa, VA
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.
Discover the most popular places to visit in Twin Oaks
James Madison's Montpelier
4.5/5(53 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.
The Arts Center in Orange
You can spend an afternoon studying the exhibits at The Arts Center in Orange in Thornhill. Stroll along the lakeside in this relaxing area, or seek out the horseback riding.
St. Thomas Episcopal Church
St. Thomas Episcopal Church is just one of the places to see in Thornhill, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's lakeside, or seek out the horseback riding.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.