Treeloft Holidays

  • Plan, book, travel with confidence
    • payments icon
    Better together
    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Where to stay in Treeloft

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

Chestnut Springs

While Chestnut Springs may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Wintergreen Resort and Raven's Roost Overlook.

Find hotels in Chestnut Springs

Top hotels in Treeloft

Motel 6 Staunton, VA
Motel 6 Staunton, VA
2 out of 5
96 Baker Lane, Staunton, VA
Fully refundableReserve now, pay when you stay
The price is S$87 per night from 29 Nov to 30 Nov
S$87
includes taxes & fees
29 Nov - 30 Nov
8/10 Very Good! (1,004 reviews)
"Easy off and on the 81. Quiet location very nice front desk staff member."

Reviewed on 21 Nov,2024

Motel 6 Staunton, VA
Wingate by Wyndham Waynesboro
Wingate by Wyndham Waynesboro
2.5 out of 5
20 Windigrove Dr, Waynesboro, VA
Fully refundableReserve now, pay when you stay
The price is S$120 per night from 3 Dec to 4 Dec
S$120
includes taxes & fees
3 Dec - 4 Dec
8.4/10 Very Good! (714 reviews)
"Clean and reasonable price"

Reviewed on 22 Nov,2024

Wingate by Wyndham Waynesboro
Sleep Inn Staunton
Sleep Inn Staunton
2.5 out of 5
222 Jefferson Hwy, Staunton, VA
Fully refundableReserve now, pay when you stay
The price is S$129 per night from 10 Dec to 11 Dec
S$129
includes taxes & fees
10 Dec - 11 Dec
9.2/10 Wonderful! (1,001 reviews)
Very nice people, comfy bed
"Our stay was great, the bed was comfortable, and the breakfast was great. The shower hot/cold function was backwards, so we needed to turn it to cold to make it hot. The TV choices were very limited and it was difficult to find the guide. But the staff was so friendly helpful. Al in all, a great ..."

Reviewed on 14 Nov,2024

Sleep Inn Staunton
See all 1,160 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.

Frequently asked questions

How much does a Treeloft holiday package cost?
Perhaps less than you imagined — from as low as , actually! By combining hotels, flights and car rentals into your own tailor-made package, your Treeloft escape is just a few clicks away.
How do I get a cheap travel package to Treeloft?
Our Treeloft holiday packages offer plenty of savings for the savvy explorer. For the best deal, simply combine your flights, hotels and extras (including tours) into a budget-friendly package. But low prices are only the start of your next awesome adventure. When you book with Expedia, you’ll have more than 550 air carriers and 1,000,000 hotel options worldwide to select from. Whatever your style, there’s a package here just for you.
Where should I stay in Treeloft?
If you plan to check out Wintergreen Resort, give commuting a miss and find someplace to stay close by. It’s one of the most popular attractions in Treeloft.
What are the top hotels in Treeloft?
Get your escape off to a good start by reserving a room at Custom Builder Just Completely Remodeled This Mountain Chalet. . . With Hot Tub. It’s one of most popular hotels in Treeloft. Another option is Wintergreen Resort Home With 2 Decks + Ski Access.
How far in advance should I book my Treeloft holiday?
While prices do change, we generally recommend booking your seats as early as possible. Many international airfares are found on Expedia up to a year in advance. If circumstances have left you booking last minute, you might still be lucky. Discount prices to Treeloft sometimes emerge only weeks before departure.
What does an Expedia Treeloft travel package include?
Expedia has all you need to plan your Treeloft escape, but how your package is structured is up to you. Select from any combination of hotels, rental cars and flights. Looking for some activities to keep you on the go? Once you’ve made your booking, you can add them on too. Whatever your budget or style, there’s a deal to meet your needs.
What should I know before booking a Treeloft travel package?
We already have low prices. However, you’ll enjoy even more bargains if you book your hotels, flights and car rentals together. With an Expedia travel package, you’ll always get transparent pricing and tons of choice.
Can I choose my airline with a Treeloft Expedia holiday package?
Yes, the choice is all yours. Expedia has access to more than 550 airlines globally, so you can customize your Treeloft holiday according to your travel preferences.
If I'm not able to travel, can I cancel my Treeloft holiday package?
Whether it’s your hotel or flight, you can cancel or alter it. Locked in your Treeloft holiday package in the last 24 hours? You may be able to make changes at no cost. For bookings older than that, you may be charged a fee by your airline, hotel or car rental company. For more details, head to our Customer Service Portal. We’ll help you each step of the way.

Things to do

Wine Taxi by day, Happy Hour-Chuck Wagon by night!

Tesla Wine Tours of Charlottesville & Wintergreen

S$210
Per adult
Tesla Wine Tours of Charlottesville & Wintergreen
Old Rag Mountain

Shenandoah National Park Audio Driving Tour

S$20
Per adult
Shenandoah National Park Audio Driving 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.