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.
Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort

Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort

2.5 out of 5
Price was $365, price is now $288 per person
$288
per person
Feb 20 - Feb 23
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottesville (CHO)
2 outdoor pools, a hot tub, and a gym are all featured at this hotel. There's fun for all ages with a children's pool and a playground, and families will appreciate the onsite laundry facilities. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi.
Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Price was $493, price is now $359 per person
$359
per person
Feb 20 - Feb 23
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottesville (CHO)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. Self parking, a coffee shop, and a terrace are also offered.
The Doyle Hotel

The Doyle Hotel

3.5 out of 5
Starr Hill
Price was $480, price is now $353 per person
$353
per person
Feb 20 - Feb 23
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottesville (CHO)
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. A coffee shop, a terrace, and a picnic area are also on offer.
Dinsmore Boutique Inn

Dinsmore Boutique Inn

4 out of 5
Venable
Price was $553, price is now $421 per person
$421
per person
Feb 20 - Feb 23
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottesville (CHO)
This bed & breakfast doesn't skimp on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. A terrace, concierge services, and wedding services are also on offer.
Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Venable
Price was $488, price is now $375 per person
$375
per person
Feb 20 - Feb 23
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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.

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
Get rates
Enjoy free WiFi, laundry facilities, and patios. Popular attractions Wintergreen Resort and Raven's Roost Overlook are located nearby.
Pool
Hot Tub
4 BR cabin mins to trails & breweries pets welcome

4 BR cabin mins to trails & breweries pets welcome

Roseland VA
$616 nightly
The price is $692 total per night
$692 total
Jan 19 - Jan 20
Total with taxes and fees
This vacation home featured laundry facilities and barbecue grills.
Pool
Kitchen
Fully Loaded 8BR in Wintergreen! Sleeps 23

Fully Loaded 8BR in Wintergreen! Sleeps 23

2 out of 5
Wintergreen Resort VA
Get rates
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.
Pool
Hot Tub
Hotel 24 South

Hotel 24 South

3 out of 5
24 South Market Street Staunton VA
Free Cancellation
Reserve now, pay when you stay
$111 nightly
The price is $125 total per night
$125 total
Jan 25 - Jan 26
Total with taxes and fees
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. Self parking, a 24-hour business center, and a lobby fireplace are also offered.
Pool
Pet friendly
Sleep Inn Staunton

Sleep Inn Staunton

2.5 out of 5
222 Jefferson Hwy Staunton VA
Free Cancellation
$74 nightly
The price is $82 total per night
$82 total
Feb 1 - Feb 2
Total with taxes and fees
Free self parking is available and the hotel's front desk is staffed around-the-clock. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Luggage storage and a safe deposit box are also provided.
Breakfast included
Pet friendly
Quality Inn Verona - Staunton North

Quality Inn Verona - Staunton North

2.5 out of 5
70 Lodge Lane Verona VA
Free Cancellation
Reserve now, pay when you stay
$62 nightly
The price is $69 total per night
$69 total
Feb 3 - Feb 4
Total with taxes and fees
This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free full breakfast each morning. Staff at the 24-hour front desk can provide around-the-clock assistance.
Breakfast included
Pet friendly
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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.

Popular places to visit

Reids Gap Trailhead

You can take time to visit Reids Gap Trailhead during your travels to Roseland. Discover the mountain views in this family-friendly area.

Reids Gap Trailhead

Woodson's Mill

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

Woodson's Mill

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 $288. 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