Chestnut Springs Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Chestnut Springs

Motel 6 Staunton, VA
Motel 6 Staunton, VA
2 out of 5
96 Baker Lane, Staunton, VA
Fully refundableReserve now, pay when you stay
The price is S$83 per night from 28 Dec to 29 Dec
S$83
includes taxes & fees
28 Dec - 29 Dec
8/10 Very Good! (1,001 reviews)
"Ecellent service checking in, room clean and comfortable. Facilities were good, although a little worn down. Not much outside motel although did not check for local dining."

Reviewed on 28 Nov,2024

Motel 6 Staunton, VA
Wingate by Wyndham Waynesboro
Wingate by Wyndham Waynesboro
2.5 out of 5
20 Windigrove Dr, Waynesboro, VA
Fully refundableReserve now, pay when you stay
The price is S$106 per night from 2 Dec to 3 Dec
S$106
includes taxes & fees
2 Dec - 3 Dec
8.4/10 Very Good! (717 reviews)
"Nice room"

Reviewed on 27 Nov,2024

Wingate by Wyndham Waynesboro
Sleep Inn Staunton
Sleep Inn Staunton
2.5 out of 5
222 Jefferson Hwy, Staunton, VA
Fully refundableReserve now, pay when you stay
The price is S$121 per night from 12 Dec to 13 Dec
S$121
includes taxes & fees
12 Dec - 13 Dec
9.2/10 Wonderful! (1,001 reviews)
"Beautiful room comfortable beds great shower. Breakfast was very good. Definitely stay here again. Very convenient to restaurants shopping attractions. Close to National Park"

Reviewed on 27 Nov,2024

Sleep Inn Staunton
See all 1,178 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.

Frequently asked questions

How much does a Chestnut Springs holiday package cost?
Choose from any combination of hotels, flights and car rentals, and you can be holidaying in Chestnut Springs from just . And the more you bundle, the more money you save. The holiday 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 holiday 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 favourites among many travellers.
How far in advance should I book my Chestnut Springs holiday?
Smart travellers 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 holiday 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 holiday 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 holiday.
If I'm not able to travel, can I cancel my Chestnut Springs holiday 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 holiday 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

Wine Taxi by day, Happy Hour-Chuck Wagon by night!

Tesla Wine Tours of Charlottesville & Wintergreen

S$210
Per adult
Tesla Wine Tours of Charlottesville & Wintergreen
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.