Chestnut Springs Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$2,500 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

Our pick of the best Chestnut Springs Hotel Deals

New Build! Log Cabin with Hot Tub in Wintergreen

New Build! Log Cabin with Hot Tub in Wintergreen

Wintergreen Resort VA
10/10 Exceptional! (16 reviews)
"It is a lovely house, and Troy is an excellent host, quickly answering any questions. I highly recommend this vacation destination."

Reviewed on 14 June 2026

Get rates
New Build! Log Cabin with Hot Tub in Wintergreen
4 BR cabin mins to trails & breweries pets welcome

4 BR cabin mins to trails & breweries pets welcome

Roseland VA
The price is AU$845 per night from 15 June to 16 June
AU$845
15 June - 16 June
includes taxes & fees
9.6/10 Exceptional! (35 reviews)
"it is really excellent."

Reviewed on 27 May 2026

4 BR cabin mins to trails & breweries pets welcome
Hotel 24 South

Hotel 24 South

3 out of 5
24 South Market Street Staunton VA
The price is AU$169 per night from 5 July to 6 July
AU$169
5 July - 6 July
includes taxes & fees
9.6/10 Exceptional! (1,159 reviews)
"Room was small but bathroom had large vanity with room to spread out toiletries. Glasses in the room and on the breakfast buffet were dirty. Should have skipped the mediocre breakfast and headed to Beverly street where many options in the open air were available. Coffee had no flavor."

Reviewed on 14 June 2026

Hotel 24 South
See all 1,338 properties in Chestnut Springs
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.
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Frequently asked questions

How much does a Chestnut Springs holiday package cost?
Choose from any combination of hotels, flights and car rentals, and you can be holidaying in Chestnut Springs from just . And the more you bundle, the more money you save. The holiday of your dreams has never been more affordable.
How do I get a cheap travel package to Chestnut Springs?
Browse and lock in everything all in one place with our Chestnut Springs holiday packages. You'll discover deals on hotels, flights, tours and more that'll keep your travel budget happy and your adventurous side busy. And, with more than 550 airlines and 1 000 000 hotel options across the globe to choose from, you'll have the flexibility to mix and match your own way.
Where should I stay in Chestnut Springs?
There's so much to explore in Chestnut Springs, so spend your evenings near its top sights and treat yourself to more time sightseeing. Wintergreen Resort is one place to put on your to-do list.
What are the top hotels in Chestnut Springs?
If it's your first time in Chestnut Springs, make a reservation at Tranquil Cabin With Deck In The Wintergreen Resort or View From The Top. Both will make you feel at home and are favourites among many travellers.
How far in advance should I book my Chestnut Springs holiday?
Smart travellers will likely want to reserve their seats early. You can usually look up international fares on Expedia up to a year before your intended flight. If you're booking last minute, there's no need to worry. Discounted prices sometimes become available just weeks before departure dates.
What does an Expedia Chestnut Springs travel package include?
Expedia has all you need to lock in Chestnut Springs trip, but how your package is structured is entirely up to you. Choose from any combination of hotels, rental cars and flights. Searching for some tours or activities to keep you entertained? Once you've made your booking, you can add them too. Whatever your style, there's a package deal to meet your needs.
What should I know before booking a Chestnut Springs travel package?
A package can be cheaper than individually booking everything you need for your trip. For example, combine your flights, hotels and rental cars and score big savings. Whatever type of holiday you have in mind, there's bound to be a package that suits your budget.
Can I choose my airline with a Chestnut Springs Expedia holiday package?
Expedia has access to more than 550 airline partners globally, so you definitely can. Just select your preferred air carrier and put together your ideal Chestnut Springs holiday.
If I'm not able to travel, can I cancel my Chestnut Springs holiday package?
Because we understand life can throw you a few curveballs, the answer is yes. For further details, visit our Customer Service Portal. But generally speaking, if you've booked your Chestnut Springs holiday package in the last 24 hours, you may be able to change or cancel it for no charge. Your hotel, airline or car rental company may charge a fee if you made your booking a while ago.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.