Deals on vacations and trips to Chestnut Springs

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Chestnut Springs flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
The Meadows
Price was $1,091, price is now $916 per person
$916
per person
Nov 4 - Nov 11
found 9 hours ago
Roundtrip non-stop flight included
San Jose (SJC) to Charlottesville (CHO)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Venable
Save 100% on your flight
Price was $1,857, price is now $1,392 per person
$1,392
per person
Nov 4 - Nov 11
found 9 hours ago
Roundtrip non-stop flight included
San Jose (SJC) to Charlottesville (CHO)
This hotel features a restaurant, free WiFi in public areas, and a picnic area. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Express check-in and express check-out are also provided.
Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Save 100% on your flight
Price was $1,801, price is now $1,393 per person
$1,393
per person
Nov 4 - Nov 11
found 9 hours ago
Roundtrip non-stop flight included
San Jose (SJC) to Charlottesville (CHO)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Enjoy the sauna and conveniences like a 24-hour front desk and concierge services.
Virginia Guesthouse Hotel

Virginia Guesthouse Hotel

3 out of 5
Lewis Mountain
Price was $1,600, price is now $1,271 per person
$1,271
per person
Nov 4 - Nov 11
found 9 hours ago
Roundtrip non-stop flight included
San Jose (SJC) to Charlottesville (CHO)
This hotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. A 24-hour business center, a coffee shop, and a snack bar/deli are also on offer.
Country Inn & Suites by Radisson, Charlottesville-UVA, VA

Country Inn & Suites by Radisson, Charlottesville-UVA, VA

3 out of 5
The Meadows
Price was $1,149, price is now $1,020 per person
$1,020
per person
Nov 4 - Nov 11
found 9 hours ago
Roundtrip non-stop flight included
San Jose (SJC) to Charlottesville (CHO)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Top Chestnut Springs hotels deals

New Build! Log Cabin with Hot Tub in Wintergreen

New Build! Log Cabin with Hot Tub in Wintergreen

Wintergreen Resort VA
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A hot tub is featured at this cabin, along with laundry facilities and barbecue grills.
Theater Room, Fooseball, Firepit, Mountains!

Theater Room, Fooseball, Firepit, Mountains!

Wintergreen VA
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This vacation home features laundry facilities.
WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS

WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS

Wintergreen Resort VA
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This condo features laundry facilities.
Wintergreen cabin, hot tub, sauna, walk to trails

Wintergreen cabin, hot tub, sauna, walk to trails

Wintergreen Resort VA
$635 nightly
The price is $645 total per night
$645 total
Oct 14 - Oct 15
Total with taxes and fees
This vacation home features a hot tub and a sauna. Laundry facilities and barbecue grills are also provided.
Fully Loaded 8BR in Wintergreen! Sleeps 23

Fully Loaded 8BR in Wintergreen! Sleeps 23

Wintergreen Resort VA
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This chalet features a gym and a hot tub. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. A sauna and laundry facilities are also provided.
Motel 6 Staunton, VA

Motel 6 Staunton, VA

2 out of 5
96 Baker Lane Staunton VA
Free Cancellation
Reserve now, pay when you stay
$63 nightly
The price is $70 total per night
$70 total
Oct 17 - Oct 18
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A snack bar/deli, express check-out, and dry cleaning are also on offer.
Pet friendly
Parking included
Don't see what you're looking for?
See all available properties in Chestnut Springs
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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 are vacation packages to Chestnut Springs?
Splash out on a one-of-a-kind experience in Chestnut Springs with a vacation package starting from as low as $916. Reserving your flights and hotels with Travelocity is simple. And even better, our great deals will leave you with more savings for loads of fun times.
Where can I get the best vacation package deals for Chestnut Springs?
Travelocity is the only place you need to go to score an awesome Chestnut Springs package deal. Choose from as many as 400 air carriers and 1,000,000 hotels worldwide and create a vacation package that fits your style. With this amount of choice, now's the time to book your next big adventure.
Why should I purchase my Chestnut Springs vacation bundle via Travelocity?
We make traveling the world easy. Whether you're looking for an amazing new place to roam around or want to ensure you get the best price on offer, we've got you covered. Our 24/7 customer support, quality service and Price Match Guarantee mean you can book with confidence.
Can I save on my Chestnut Springs car rental if I combine it with a hotel or flight?
Booking a Chestnut Springs vacation package with Travelocity is a simple way to save your time and money. You can pick a car, flight and hotel, or any combination of them, and land awesome discounts. You could also throw in tours and experiences. After you've picked up the keys to your rental car, venture out of the neighborhood and see what the surrounding area has to offer. Roughly 120 mi from Chestnut Springs, White House is well worth a road trip.

Photos of local treasures

Browse Chestnut Springs vacation photos for more inspiration

A waterfall in a forest with autumn leaves.