Chestnut Springs Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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Top Holiday Package Deals in Chestnut Springs

Price found within the past 48 hours. Click for updated prices.
Staybridge Suites Charlottesville Airport by IHG

Staybridge Suites Charlottesville Airport by IHG

3 out of 5
Hollymead
Price was CA $1,293, price is now CA $1,240 per person
CA $1,240
per person
Apr 3 - Apr 7
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Charlottesville (CHO)
9/10 Wonderful! (891 reviews)
Great staff, nice size room with great amenities.

Reviewed on Feb 9, 2026

Mayhurst Inn

Mayhurst Inn

3.5 out of 5
Price was CA $1,432, price is now CA $1,306 per person
CA $1,306
per person
Apr 3 - Apr 7
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Charlottesville (CHO)
9.2/10 Wonderful! (288 reviews)
A perfect spot with the delicious breakfast. Highly recommend staying here.

Reviewed on Sep 4, 2025

Home2 Suites by Hilton Charlottesville Downtown

Home2 Suites by Hilton Charlottesville Downtown

3 out of 5
North Downtown
Price was CA $1,384, price is now CA $1,348 per person
CA $1,348
per person
Apr 3 - Apr 7
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Charlottesville (CHO)
8.8/10 Excellent! (720 reviews)
The receptionist, Veronica, was extremely friendly and professional. She assisted us promptly and always with a smile. She epitomizes "Hilton". This stay would have been excellent, except for the abysmal morning breakfast. Faux bacon, sausage, eggs, which were all cold and tasteless.

Reviewed on Feb 17, 2026

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! (9 reviews)
Troy was the best!

Reviewed on Feb 8, 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 CA $277 per night from Mar 5 to Mar 6
CA $277
CA $825 total
Mar 5 - Mar 6
includes taxes & fees
9.6/10 Exceptional! (29 reviews)
Beautiful place. Exactly as depicted in the listing. Very responsive host with questions prior to my stay.

Reviewed on Jan 1, 2026

4 BR cabin mins to trails & breweries pets welcome
WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS

WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS

Wintergreen Resort VA
10/10 Exceptional! (84 reviews)
Wonderful property. In great condition, solid furniture, amazing views, full equipped kitchen. Fantastic view. We used the shuttle to go back and forth to the slopes and dinner which worked well and added fun to the days.

Reviewed on Feb 18, 2026

Get rates
WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS
See all 1,272 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $1,240. 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 Bundle

Blue Ridge Parkway Self-Guided Audio Tour Bundle

CA $33
per traveller
Blue Ridge Parkway Self-Guided Audio Tour Bundle
Shenandoah National Park Self-Guided Driving Audio Tour

Shenandoah National Park Self-Guided Driving Audio Tour

CA $23
per traveller
100% of travellers recommend
Shenandoah National Park Self-Guided Driving Audio Tour
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.