Chestnut Springs Holidays

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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
The price is AU$2,005 per night from 16 Oct to 17 Oct
AU$2,005
16 Oct - 17 Oct
includes taxes & fees
10/10 Exceptional! (1 review)
"House was beautiful and spacious! Plenty of rooms and main lifting room was gorgeous. The bedrooms did not have any king size beds which might have been a problem but since there were so many rooms we just spread out more. We stayed in the late summer and there were countless beautiful hikes nearby ..."

Reviewed on 27 Sept 2025

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
The price is AU$956 per night from 15 Oct to 16 Oct
AU$956
15 Oct - 16 Oct
includes taxes & fees
9.6/10 Exceptional! (28 reviews)
"Nice place and very clean"

Reviewed on 22 Aug 2025

4 BR cabin mins to trails & breweries pets welcome
Luxury 5Bd 4Ba Sleeps 16+ Hot-tub/Dog Friendly

Luxury 5Bd 4Ba Sleeps 16+ Hot-tub/Dog Friendly

Wintergreen Resort
10/10 Exceptional! (14 reviews)
Good Stay
"Nice place with great amenities."

Reviewed on 4 July 2025

Get rates
Luxury 5Bd 4Ba Sleeps 16+ Hot-tub/Dog Friendly
See all 1,223 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.

Activities

Blue Ridge Parkway Bundle

Blue Ridge Parkway Self-Guided Audio Tour Bundle

AU$37
per traveller
Blue Ridge Parkway Self-Guided Audio Tour Bundle
See all activities in Roseland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.