Chestnut Springs Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Chestnut Springs

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$134 per night from 13 Jul to 14 Jul
S$134
13 Jul - 14 Jul
includes taxes & fees
9.2/10 Wonderful! (1,157 reviews)
"Very nice with comfortable beds."

Reviewed on 10 Jun, 2025

Sleep Inn Staunton
Hotel 24 South
Hotel 24 South
3 out of 5
24 South Market Street, Staunton, VA
Fully refundableReserve now, pay when you stay
The price is S$158 per night from 29 Jun to 30 Jun
S$158
29 Jun - 30 Jun
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
"We highly recommend this hotel. The hotel is in close proximity to a great Indian restaurant down the hill and the American Shakespeare Center's Blackfriar Theater right next door. We were thrilled to experience a great performance of The Winter's Tale. We also appreciated that the hotel was willing ..."

Reviewed on 9 Jun, 2025

Hotel 24 South
Holiday Inn Express And Suites Waynesboro East by IHG
Holiday Inn Express And Suites Waynesboro East by IHG
2.5 out of 5
108 Chicurel Lane, Waynesboro, VA
Fully refundable
The price is S$162 per night from 23 Jun to 24 Jun
S$162
23 Jun - 24 Jun
includes taxes & fees
9/10 Wonderful! (347 reviews)
"Nice location, lots of restaurants nearby, friendly staff."

Reviewed on 11 Jun, 2025

Holiday Inn Express And Suites Waynesboro East by IHG
See all 1,191 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

Shenandoah National Park Self-Guided Driving Audio Tour

Shenandoah National Park Self-Guided Driving Audio Tour

S$22
per traveller
100% of travellers recommend
Shenandoah National Park Self-Guided Driving Audio Tour
Blue Ridge Parkway Bundle

Blue Ridge Parkway Self-Guided Audio Tour Bundle

S$33
per traveller
Blue Ridge Parkway Self-Guided Audio Tour Bundle
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.