Treeloft Vacations from $392

Book a Hotel + Flight or Car together to unlock savings

Your Treeloft Vacation

Lock in a vacation package to Treeloft and have fun discovering everything this semi-rural neighborhood has to offer. With a reputation for walking, skiing and adventure sports, your next awesome adventure can be found right here. Your trip to Treeloft has to include some sightseeing. Don't miss must-see attractions nearby such as Bold Rock Hard Cider Nellysford Cidery. Stop daydreaming and start doing. When you're ready to lock in your next vacation to Treeloft, Expedia will help get you there.

The Latest Treeloft Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Doyle Hotel

The Doyle Hotel

3.5 out of 5
Starr Hill
Price was $521, price is now $392 per person
$392
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Charlottesville (CHO)
8.6/10 Excellent! (907 reviews)
The hotel was minimal staff and self check in/out on line. For an old baby boomer I prefer a fully human staffed facility. Not sure I would have booked the hotel. Luckily I found a human in the lobby who helped me. When we left, the valet was nowhere to be found. Had to walk to the car. Hotel manager was unhappy and told me he would refund the parking cost. Have yet to see that money

Reviewed on Oct 12, 2025

Dinsmore Boutique Inn

Dinsmore Boutique Inn

4 out of 5
Venable
Price was $615, price is now $452 per person
$452
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Charlottesville (CHO)
9.6/10 Exceptional! (307 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

Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Price was $674, price is now $502 per person
$502
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Charlottesville (CHO)
9.2/10 Wonderful! (485 reviews)
Staff was so kind and the property was gorgeous. I travel for work and this was one of my favorite places I have stayed.

Reviewed on Sep 30, 2025

Omni Charlottesville Hotel

Omni Charlottesville Hotel

4 out of 5
North Downtown
Price was $582, price is now $471 per person
$471
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Charlottesville (CHO)
9.2/10 Wonderful! (1,007 reviews)
Hotel was fine. Area was iffy.

Reviewed on Oct 12, 2025

Oasis Near Charlottesville With Pool Grill

Oasis Near Charlottesville With Pool Grill

2 out of 5
Save 100% on your flight
Price was $2,909, price is now $2,362 per person
$2,362
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Charlottesville (CHO)
No reviews

Where to stay in Treeloft

Find the best Treeloft areas and neighborhoods for the activities you enjoy most. Learn more about Treeloft
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Chestnut Springs

Though Chestnut Springs might not have many top sights, you can venture to the surrounding area to see attractions like Wintergreen Resort and Raven's Roost Overlook.

Find hotels in Chestnut Springs

Treeloft Hotel Deals

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

Wintergreen Resort
$635 nightly
The price is $713 total per night from Oct 14 to Oct 15
$713 total
Oct 14 - Oct 15
Total with taxes and fees
10/10 Exceptional! (62 reviews)
"Beautiful rental “in the tree tops” with many thoughtful and modern accommodations! The host takes extra efforts to provide a detailed list online of how to use the rental and what activities there are nearby. We absolutely loved our stay here."

Reviewed on Sep 26, 2025

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!
The Distinguished Squirrel Chalet walking distance

The Distinguished Squirrel Chalet walking distance

Wintergreen Resort
$385 nightly
The price is $441 total per night from Oct 20 to Oct 21
$441 total
Oct 20 - Oct 21
Total with taxes and fees
9.6/10 Exceptional! (6 reviews)
"we appreciated that it was stocked with basic spices, coffee, necessary cookware, etc. Nice location"

Reviewed on Aug 28, 2025

The Distinguished Squirrel Chalet walking distance
Motel 6 Staunton, VA

Motel 6 Staunton, VA

2 out of 5
96 Baker Lane, Staunton, VA
Fully refundableReserve now, pay when you stay
$63 nightly
The price is $70 total per night from Oct 16 to Oct 17
$70 total
Oct 16 - Oct 17
Total with taxes and fees
8.2/10 Very Good! (1,017 reviews)
"Every is ok"

Reviewed on Oct 12, 2025

Motel 6 Staunton, VA
See all 1,202 properties in Treeloft
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Treeloft

Everything is frozen over at Wintergreen Resort.

Wintergreen Resort

Hit the slopes in Nellysford with a visit to Wintergreen Resort. Discover the mountain views and top-notch restaurants in this vibrant area.

Wintergreen Resort
Day off 🍺

Bold Rock Hard Cider Nellysford Cidery

You can take time to visit Bold Rock Hard Cider Nellysford Cidery during your travels to Nellysford. Discover the mountain views in this family-friendly area.

Bold Rock Hard Cider Nellysford Cidery

Stoney Creek Golf Course

Enjoy a round of golf in Nellysford at Stoney Creek Golf Course. Discover the mountain views and top-notch restaurants in this vibrant area.

Stoney Creek Golf Course

Things to do

Blue Ridge Parkway Bundle

Blue Ridge Parkway Self-Guided Audio Tour Bundle

$24
per traveler
Blue Ridge Parkway Self-Guided Audio Tour Bundle
Old Rag Mountain

Shenandoah National Park Self-Guided Audio Tour

$16
per traveler
Shenandoah National Park Self-Guided Audio Tour
Shenandoah National Park Self-Guided Driving Audio Tour

Shenandoah National Park Self-Guided Driving Audio Tour

$17
per traveler
100% of travellers recommend
Shenandoah National Park Self-Guided Driving Audio Tour
See all activities in Nellysford
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.