Chestnut Springs Vacation Packages
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Top Holiday Package Deals in Chestnut Springs
Price found within the past 48 hours. Click for updated prices.
Shenandoah Wilderness Traveler
CA $660
per person
Dec 19 - Dec 21
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Charlottesville (CHO)
8.8/10 Excellent! (121 reviews)
The property was much larger than expected and included a lake. Our cabin was tucked in the woods off of a one lane paved road, with good parking spaces. We had a few mosquitoes in our cabin, and also a spider that stayed in its upper corner of the bathroom. The beds and pillows in our two bedroom cabin were very comfortable. Most of the channels on the TV were a little out of focus and we were unable to mirror our phones on the TV, even through we had property internet connected. The breakfast in the main lodge was good and reasonably priced. Prices in the General Store were very reasonable compared to typical resorts. Looking forward to another stay at a future date.
Reviewed on Sep 30, 2026
Little Mod Hotel at the University
Venable
CA $1,314
per person
Nov 18 - Nov 20
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Charlottesville (CHO)
9.2/10 Wonderful! (389 reviews)
The room was clean and modernised. However, our room 9 was next to the reception and was very noisy with customers in and out and while ear plugs and eye masks were provided the noise from the reception and party noise from the street did disturb us. We are not kill joys and stayed up past 11pm but the noise didn’t stop until the early hours. Apart from that we did enjoy our stay, but wouldn’t stay again. I am sure the rooms further away were quieter and so perhaps our bad luck.
Reviewed on Oct 17, 2026
Chestnut Springs Hotel Deals
Theater Room, Fooseball, Firepit, Mountains!
Wintergreen VA
New Build! Log Cabin with Hot Tub in Wintergreen
Wintergreen Resort VA
10/10 Exceptional! (26 reviews)
"Loved this for a Girls' weekend in the Fall. Only reason I didn't give it 5 stars is we did have an issue with the hot tub. We booked it for that reason and checked prior to arriving that it was working and would be ready. We were told it was and it was....not. Whomever checked didn't look closely ..."
Reviewed on Sep 28, 2026
WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS
Wintergreen Resort VA
10/10 Exceptional! (94 reviews)
"Comfy, cozy fall getaway in the mountains, complete with woodburning fireplace and amazing views. One morning, we were above the clouds, looking down into a cloud filled valley with mountain peaks, poking through.We’ve traveled a lot, and this was one of the nicest condos we have stayed in and one ..."
Reviewed on Oct 16, 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 $660. 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.