Skyland Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Skyland Vacation
There's no better way to head off on a break than with one of our vacation packages to Skyland. The outdoorsy activities and spectacular views are just two of the countless reasons to stay in this fascinating city. If taking in sights is on the to-do list during your trip to Skyland, stop by well-known attractions like Yogi Bears Jellystone Park, Thorton Gap Entrance Shenandoah and Rose River Falls. Your dream Skyland vacation is just clicks away. Search flights, hotels and more on Expedia for a trip that's tailored just for you.
Top Skyland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Sofitel Washington DC Lafayette Square
Downtown Washington D.C.
CA $1,189
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
9/10 Wonderful! (1,260 reviews)
We had a lovely stay and a special thank you to Pablo on the front desk. He was amazing.
Reviewed on Oct 4, 2026
Crowne Plaza Crystal City-Washington, D.C. by IHG
Crystal City
CA $837
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
8.2/10 Very good! (1,002 reviews)
Chris who was on duty when we arrived was amazing! Very friendly and kind! The breakfast staff were amazing along with the bar staff- hotel is a little dated however we were looked after.
Reviewed on Oct 4, 2026
Riggs Washington DC
Downtown Washington D.C.
CA $1,030
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
9.4/10 Exceptional! (1,415 reviews)
Overall good stay. Location is good, service good and room was comfortable. My only complaint would be that they didn’t make up our room. I would expect that from this level of hotel. But would definitely stay here again.
Reviewed on Oct 3, 2026
Ready to book your vacation to Skyland?
Skyland Hotel Deals
Skyland
Skyline Dr Mile 41.7 & 42.5 Luray VA
CA $290
CA $334 total
Nov 3 - Nov 4
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
"Check in was a breeze. Our room was clean and ready before check in time. The view from our room was wonderful."
Reviewed on Oct 4, 2026
Mimslyn Inn Historic Hotels Of America
401 W Main St Luray VA
CA $167
CA $206 total
Oct 6 - Oct 7
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"Great food in both of the restaurants! Bed was comfy and great service overall."
Reviewed on Oct 4, 2026
Big Meadows Lodge
Mile 51.2 Skyline Drive Luray VA
CA $200
CA $232 total
Oct 5 - Oct 6
includes taxes & fees
7.8/10 Good! (943 reviews)
"One we had no electricity, no hot water. Manager would only discount by 30% The room was very dated and the bed low to the floor and rustic( not in a good way)"
Reviewed on Oct 4, 2026
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.
What to do in Skyland
Shenandoah National Park Self-Guided Driving Audio Tour
CA $24
per traveller
100% of travellers recommend
Discover US East Coast Self Guided Audio Tour
CA $203
per traveller
Learning Lunch of Wine and Food Pairing with Winemaker Donna
CA $84
per adult
Frequently asked questions
How much does a Skyland vacation package cost?
You'll find cheap prices from CA $805 on Expedia for your Skyland getaway. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Skyland costs.
What are the cheapest months to go to Skyland?
The off-season is the best time to travel to Skyland if you're trying to keep costs down. Another tip for finding cheap Skyland vacation packages? Avoid visiting during public holidays and any major festivals or events.
How many days is enough for Skyland?
With a well-organized itinerary, you can easily visit the top Skyland sights in a few days. But if you prefer to discover hidden gems or go on day trips, consider booking your Skyland vacation for longer.
How to find the best Skyland package deals?
Finding a cheap Skyland package deal is easy with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget range, add a few filters and see what's available. You can customize your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Skyland package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Skyland vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually snag a better deal than booking each component separately. And you'll still have the flexibility to create a customized Skyland vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Skyland?
Secure incredible discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment Skyland adventure.
How to plan a trip to Skyland?
- Choose your dates: What you plan to do in Skyland and your preferred season will help you decide when to get away.
- Set your budget: Factor in expenses like flights, food and transportation when calculating how much to put aside for your trip to Skyland. Then, pick a property that suits your budget, whether that's an economical option or a more luxurious getaway.
- Decide how long to go away for: Now that you know more about Skyland, you can work out the right length of your break. Pull together a rough itinerary and allocate enough time to cover everything you want to see.
- Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a customized Skyland vacation package.
Explore a world of travel with Expedia
- Luray Hotels
- A quiet
- Condo Rentals in Skyland
- River Oasis Water Front
- Motel 6 Hotels in Woodstock
- Lafayette Inn
- Magical
- Spa Hotels in New Market
- Resorts in Syria
- Life IS BETTER AT THE SHENANDOAH RIVER AT OUR COZY RIVERFRONT COTTAGE!!
- Hillside
- Hotels near Swift Run Gap Entrance Shenandoah
- Farmstay in Woodville
- Lush Countryside & Shenandoah Mountain Views at Quiet Hills Retreat
- "Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray
- The Estate at Meander
- Washington Hotels
- Private Mountaintop Cabin w/ Views! (Pet Friendly)
- Apartments in Skyland
- Luna`S_landing
- Hotels near Luray Caverns
- Haywood Haven
- Graves Mountain Farm & Lodges
- Independent Hotels in Willow Grove
- Hotels near Yogi Bear's Jellystone Park
- Ultimate Adults
- B&B in Pratts
- Chalets in Syria
- Dreamy Couples Cabin With Hot Tub And Fire Pit
- Stanley Hotels
- Golf Hotels in Luray
- B&B in Shenandoah
- Hotels near Shenandoah National Park
- Vacation Homes in Luray
- Woodstock Hotels
- 3 Star Hotels in Syria
- Tucked Away | 1 Bed, 1 Bath
- Gorgeous Cabin Overlooking The Shenandoah River
- Cabin Rentals in New Market
- Sperryville Hotels
- Riverfront Cabin! Farm
- Direct Slopeside
- Hotels with Free Breakfast in Boston
- Walk to Old Rag
- Blue Ridge Mini Lux Retreat 1 with Hot Tub & Sauna
- Condo Rentals in Syria
- Cottages in Forestville
- Rv Parks in Syria
- Mountain cabin by Shenandoah National Park
- Shenandoah Lodge
- Peaceful 3
- Lgbt Friendly Hotels in Sperryville
- Syria Hotels
- Ski/Mtb/Golf Condo (#126)
- Motel 6 Mount Jackson
- Falling Leaf Cabin Rustic Charm With Modern Decor! Newly Renovated Kitchen!
- Hotels near New Market Battlefield
- Luxury Retreat in the Shenandoah Valley w/ Hot Tub & 6 Passenger ATV
- Banco Hotels
- Hotels near Narmada Winery
- Honeymoon Resorts and in Syria
- Hampton Inn & Suites Woodstock
- Comfort Inn Woodstock Shenandoah
- Lookout Cabin in the mountains
- Sleepy Hollow 5BR Cabin
- Flights to Boston
- Flights from Toronto (YYZ) to Charlottesville (CHO)
- Flights to Banco
- Flights from Washington Dulles Intl.
- Flights from Montreal (YUL) to Washington (IAD)
- Flights to Luray
- Flights to Skyland
- Flights to Syria
- Flights from Toronto (YYZ) to Washington (IAD)
- Flights from Vancouver (YVR) to Washington (IAD)
- Natural Chimneys
- Fbi Academy
- Masanutten Ski Resort
- Splash Down Water Park
- Syria Vacations
- Steven F. Udvar-Hazy Center
- Orange Vacations
- Fredericksburg and Spotsylvania National Military Park
- Visit Luray
- Charlottesville Vacations
- Visit Syria
- Broadway Vacations
- Luray Caverns
- Wisteria Farm and Vineyard
- Swoope Vacations
- Scottsville Vacations
- Mary's Rock Summit Trailhead
- Round Hill Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
