Chestnut Springs Holidays

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  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

Top hotels in Chestnut Springs

New Build! Log Cabin with Hot Tub in Wintergreen

New Build! Log Cabin with Hot Tub in Wintergreen

Wintergreen Resort VA
10/10 Exceptional! (11 reviews)
Beautiful house! Gorgeous location. Easy access to hiking trails. The host is super helpful and responsive. Highly recommend!!

Reviewed on 9 Apr 2026

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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 £425 per night from 21 May to 22 May
£425
21 May - 22 May
includes taxes & fees
9.6/10 Exceptional! (34 reviews)
Nice weekend with old friends and was exactly as stated .

Reviewed on 19 Apr 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! (86 reviews)
Della was amazing and allowed for an early check in once the condo was cleaned and ready for us, which was much appreciated after traveling with a toddler. She was very responsive and helpful throughout our stay. Place has everything you need and gorgeous views. The deer even came up to our window ...

Reviewed on 6 Apr 2026

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WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS
See all 1,289 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Chestnut Springs travel package cost?
Explore the best of Chestnut Springs from as low as . Choose from a wonderful selection of flights, hotels and rental cars to suit every style and budget. Land even more discounts when you add a few tours or experiences to your travel package.
If I'm not able to travel, can I cancel my Chestnut Springs travel package?
Yes you can, and we'll help you every step of the way. You may be able to cancel or change your Chestnut Springs travel package at no cost if you booked in the last 24 hours. But you may incur a fee from your hotel, airline or car rental company if your booking is older than that. If life throws you a curveball, browse our Customer Service Portal for more information.
How do I get a cheap travel package to Chestnut Springs?
Browse and lock in everything all in one place with our Chestnut Springs travel packages. You'll discover deals on hotels, flights and more that'll keep your bank account happy and your spirit of adventure alive. And, with more than 550 partner airlines and 1,000,000 properties around the globe to pick from, you'll have the flexibility to mix and match as you like.
Does Expedia offer Book Now, Pay Later Chestnut Springs holidays?
Your bank balance shouldn't prevent you from going on holiday, so Expedia has come up with a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book a terrific getaway without draining your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your escape. Consider one of these flexible payment options:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's easy monthly instalment plans. If paying small amounts each month works for you, choose this option during the checkout process.
  • Pay in instalments holidays: If you want to pay off your getaway in multiple transactions, holidays paid in instalments might be the best option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: Hitting the "book now" button is much easier with this option. Simply put down a small deposit on your escape and then start packing your bags.

Where should I stay in Chestnut Springs?
There's loads to explore in Chestnut Springs, so stay close to its best attractions and treat yourself to more time sightseeing. Wintergreen Resort is one spot that should be on your itinerary.
What are the top hotels in Chestnut Springs?
The Mark Addy Bed And Breakfast and 2br/2ba: Million Dollar View From Luxury Condo On The Ridge are two of the most well-known properties in Chestnut Springs. Why not take a look at the rates and facilities at each and then make a decision?
How far in advance should I book my Chestnut Springs holiday?
It's tricky picking the best time for airfares, but we usually say the earlier, the better. Plenty of international flights on Expedia become available up to a year in advance. If you're booking last minute, don't stress. Low prices appear from time to time within a few weeks of departure dates.
What does an Expedia Chestnut Springs travel package include?
It all boils down to what type of getaway you're contemplating. Chestnut Springs holiday deals can include car rentals, hotels and flights. You can mix and match to create the travel package that suits you. You can also add on experiences and activities after you've booked to get even bigger discounts.
What should I know before booking a Chestnut Springs travel package?
When you book your flights, hotels and car rentals together, you'll enjoy amazing discounts. Whether you're organising a wilderness getaway in a cabin or would rather stay in a fancy hotel in the city, Expedia will help make it happen.
Can I choose my airline with a Chestnut Springs Expedia travel package?
You can, and with more than 550 airlines to choose from all over the world, you have plenty of choice. Browse the available options and find out which airline best fits your needs and budget.

Things to do

Blue Ridge Parkway Bundle

Blue Ridge Parkway Self-Guided Audio Tour Bundle

£18
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. Flight-inclusive packages are ATOL protected.