Skyland Holidays

Photo by Erica R Hopper

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Top hotels in Skyland

Skyland

Skyland

2 out of 5
Skyline Dr Mile 41.7 & 42.5, Luray, VA
The price is S$445 per night from 26 Jul to 27 Jul
S$445
26 Jul - 27 Jul
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
"interesting for a property with many, many vacancies (in summer!), we could not be assigned a room that did not have an obstructed view - one of the reasons to go to the mountains"

Reviewed on 17 Jul, 2025

Skyland
Big Meadows Lodge

Big Meadows Lodge

3 out of 5
Mile 51.2 Skyline Drive, Luray, VA
The price is S$202 per night from 5 Aug to 6 Aug
S$202
5 Aug - 6 Aug
includes taxes & fees
7.6/10 Good! (691 reviews)
"Super friendly staff. Just what we expected it to be. Rustic comfort."

Reviewed on 18 Jul, 2025

Big Meadows Lodge
Days Inn by Wyndham New Market/I-81

Days Inn by Wyndham New Market/I-81

2 out of 5
9360 George Collin Pkwy, New Market, VA
Fully refundableReserve now, pay when you stay
The price is S$71 per night from 4 Aug to 5 Aug
S$71
4 Aug - 5 Aug
includes taxes & fees
6/10 (1,001 reviews)
"It was just a very quiet place no issues the staff was nice"

Reviewed on 15 Jul, 2025

Days Inn by Wyndham New Market/I-81
See all 884 properties in Skyland
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

Shenandoah National Park featuring mountains, forests and tranquil scenes

Mary's Rock Summit Trailhead

Hike along rugged terrain and amid areas of verdant forest to reach one of the tallest peaks of Shenandoah National Park.

Mary's Rock Summit Trailhead

What to do in Skyland

You'll gain a solid knowledge of wine basics, pairing concepts, and tasting techniques, enabling you to explore and savor wines with a newfound expertise. Cheers to a voyage of flavor and discovery!

Wine Bootcamp - Led by our winemaker

S$77
per adult
Wine Bootcamp - Led by our winemaker
Discover the world of wine at Little Washington Winery! A relaxing drive just west of Warrenton. With our Foodie-U Wine School, you'll enjoy fun classes that add to your appreciation of food and wine.

Cheeseology Un-brie-lievable Wine Pairings and Cheesy Wisdom!

S$77
per adult
Cheeseology Un-brie-lievable Wine Pairings and Cheesy Wisdom!
Indulge in Flavor: A delightful lunch plate featuring three scrumptious sliders including, a savory roast beef slider, chicken and salmon sliders, Then! A sweet finish with dessert and tasty truffles!

Learning Lunch of Wine and Food Pairing with Winemaker Donna

S$77
per adult
Learning Lunch of Wine and Food Pairing with Winemaker Donna
See all activities in Skyland

Frequently asked questions

How much does a Skyland holiday package cost?
You'll find cheap prices on Expedia for your Skyland getaway. However, factors like your choice of hotel, the season and length of stay will determine how much your holiday to Skyland costs.
What are the cheapest months to go to Skyland?
To pick up cheap Skyland holiday packages, plan your getaway outside of peak times such as school holidays. You'll typically find better availability and lower prices when it's less busy.
How many days is enough for Skyland?
With a well-planned itinerary, you can easily tick off the main Skyland attractions in a handful of days. But if you want to venture off the beaten track or go on day trips, think about booking your Skyland holiday for longer.
How to find the best Skyland package deals?
Landing a cheap Skyland package deal is a cinch with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget range, add a couple of filters and browse what's available. You can tweak your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to discover the most affordable Skyland package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Skyland holiday as a package?
An Expedia holiday package could land you considerable savings when compared to booking accommodation and flights individually. Better still, you can personalise your Skyland escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Skyland?
If you have your Skyland holiday dates confirmed, book as soon as you can to grab some outstanding deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Skyland?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to visit Skyland.
  2. Work out your budget: Make sure you have enough money to pay for everything from meals and transportation to experiences and flights. Your hotel will likely be the biggest expense during your trip to Skyland.
  3. Work out your trip length: Think about how long you'd like to spend exploring Skyland. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Skyland holiday package that brings all your bookings together.

* 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.