Chestnut Springs Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Holiday Package Deals in Chestnut Springs
Price found within the past 48 hours. Click for updated prices.
Little Mod Hotel at the University
Venable
CA $1,066
per person
Oct 6 - Oct 7
found 12 hours ago
Roundtrip flight included
Calgary (YYC) to Charlottesville (CHO)
9.2/10 Wonderful! (360 reviews)
Nice redo of an old structure! Decor is cool. Check in was easy . Very close to restaurants and UVA grounds.
Room noise next door was a problem late at night . Front desk did assist with addressing. You can hear through the walls quite easily!
Also the train is so close-it’s super loud !!
Coffee was promised at 6 am, I went to lobby at 8 am and no one was at the desk and no coffee had been brewed.
Reviewed on Aug 19, 2026
Chestnut Springs Hotel Deals
New Build! Log Cabin with Hot Tub in Wintergreen
Wintergreen Resort VA
10/10 Exceptional! (21 reviews)
"Our family had a wonderful time during our stay at Chestnut Springs. The home is beautiful and nestled in the hills. There was plenty of room for six adults and five kids ages eight to sixteen. The hot tub was a big hit as was the comfortable furnishings and the wood burning fireplace. The kitchen ..."
Reviewed on Aug 8, 2026
WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS
Wintergreen Resort VA
10/10 Exceptional! (91 reviews)
"Lovely property and attentive host. VERY clean and relaxing. The mattress was a bit uncomfortable and the living room had no lighting (i’m a knitter so that was noticeable to me). There was nothing that would keep me from visiting again. This review is for information only! Truly a great stay!"
Reviewed on Aug 15, 2026
Fully Loaded 8BR in Wintergreen! Sleeps 23
Wintergreen Resort VA
10/10 Exceptional! (12 reviews)
"Nice house with great views, but several amenities were broken.The house is beautiful, very clean, has great views, a well-supplied kitchen, and an amazing sauna. However, several advertised amenities were unavailable during our stay. The outdoor projector was missing its remote, the arcade game ..."
Reviewed on Aug 8, 2026
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 vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Chestnut Springs from just CA $1,066. And the more you bundle, the more money you save. The vacation 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 vacation 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 favorites among many travelers.
How far in advance should I book my Chestnut Springs vacation?
Smart travelers 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 vacation 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 vacation 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 vacation.
If I'm not able to travel, can I cancel my Chestnut Springs vacation 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 vacation 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.
Things to do
Blue Ridge Parkway Self-Guided Audio Tour Bundle
CA $34
per traveller
Shenandoah National Park Self-Guided Driving Audio Tour
CA $24
per traveller
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.