Chestnut Springs Holidays

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to NZ$616 when you book a flight and hotel together*

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    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! (2 reviews)
Overall great experience. We did take down one smoke detector in down stairs bedroom due to beeping and I did not know where any batteries were. Other than that, everything was great!

Reviewed on 17 Oct 2025

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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 NZ$1,031 per night from 16 Nov to 17 Nov
NZ$1,031
16 Nov - 17 Nov
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
Fully Loaded 8BR in Wintergreen! Sleeps 23

Fully Loaded 8BR in Wintergreen! Sleeps 23

2 out of 5
Wintergreen Resort, VA
Our family had an excellent experience staying at this home during the fall. The host was extremely responsive, promptly addressing all of our questions and making sure we felt welcome. The house was exceptionally comfortable, spacious, and thoughtfully stocked with all the necessary utensils and ...

Reviewed on 13 Nov 2025

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Fully Loaded 8BR in Wintergreen! Sleeps 23
See all 1,234 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.

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.

Discover the most popular places to visit in Chestnut Springs

Woodson's Mill

You can spend an afternoon studying the exhibits at Woodson's Mill during your travels in Lowesville. Take in the museums while you're in the area.

Woodson's Mill

Activities

Blue Ridge Parkway Bundle

Blue Ridge Parkway Self-Guided Audio Tour Bundle

NZ$42
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.