Skyland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Erica R Hopper

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

    Plan, 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.
Motel 6 Baltimore, MD

Motel 6 Baltimore, MD

2 out of 5
Charles North
Price was CA $1,414, price is now CA $1,010 per person
CA $1,010
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
5/10 (137 reviews)
I never got to stay because my kids booked the room off my phone and I will be thank for my refund 8 never stay there and I will never poche a motel 6 and that dirty as downtown junk ass infested I was trying to get my refund please help me with my refund or we can take it to court im a lawyer so please fixed my problem

Reviewed on Jul 4, 2026

Element by Marriott Arundel Mills BWI Airport

Element by Marriott Arundel Mills BWI Airport

3 out of 5
Arundel Mills
Price was CA $1,525, price is now CA $1,032 per person
CA $1,032
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8/10 Very good! (1,006 reviews)
Didn’t like that room service wasn’t available during my visit. Other than that the location was perfect!

Reviewed on Jul 5, 2026

Lord Baltimore Hotel

Lord Baltimore Hotel

3.5 out of 5
Downtown Baltimore
Price was CA $2,066, price is now CA $1,422 per person
CA $1,422
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8.4/10 Very good! (2,841 reviews)
Everything was everything

Reviewed on Jul 6, 2026

Sheraton Baltimore North Hotel

Sheraton Baltimore North Hotel

3.5 out of 5
Price was CA $1,484, price is now CA $1,042 per person
CA $1,042
per person
Sep 19 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8.4/10 Very good! (1,000 reviews)
The Sheraton is in a great location, we were there for a family wedding and close to everything. Parking was very easy on site (for a fee). There was no breakfast included so we didn’t make it down to the restaurant but there is a very convenient Starbucks in the lobby. The only negative I would say is when you get off the elevator on the floor it felt very humid and hot bc there seemed to always be someone doing laundry. Highly recommend

Reviewed on Jul 2, 2026

Convention Center PH Free indoor parking

Convention Center PH Free indoor parking

4 out of 5
Downtown Baltimore
Price was CA $1,449, price is now CA $1,047 per person
CA $1,047
per person
Sep 19 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
6/10 (1 review)

Ready to book your vacation to Skyland?

 

Choose your dates

Skyland Hotel Deals

Skyland

Skyland

2 out of 5
Skyline Dr Mile 41.7 & 42.5 Luray VA
The price is CA $243 per night from Jul 27 to Jul 28
CA $243
CA $290 total
Jul 27 - Jul 28
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"Location awesome. Staff friendly. Food good. Rooms ok — clean enough but nothing special. Perfect if you want to stay inside the national park."

Reviewed on Jul 5, 2026

Skyland
Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America

3 out of 5
401 W Main St Luray VA
The price is CA $149 per night from Jul 9 to Jul 10
CA $149
CA $183 total
Jul 9 - Jul 10
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"What was very nice stay with good food, fancy atmosphere and nice evening in a hot tub 👍"

Reviewed on Jul 5, 2026

Mimslyn Inn Historic Hotels Of America
Big Meadows Lodge

Big Meadows Lodge

3 out of 5
Mile 51.2 Skyline Drive Luray VA
The price is CA $196 per night from Jul 27 to Jul 28
CA $196
CA $228 total
Jul 27 - Jul 28
includes taxes & fees
7.8/10 Good! (864 reviews)
"Power outage due to storms. Main lodge has generators but not the other buildings"

Reviewed on Jul 5, 2026

Big Meadows Lodge
See all 907 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

What to do in Skyland

Great Smoky & Shenandoah National Park Driving Audio Tour

Great Smoky & Shenandoah National Park Driving Audio Tour

CA $37
per traveller
Great Smoky & Shenandoah National Park Driving Audio Tour
Shenandoah National Park Self-Guided Driving Audio Tour

Shenandoah National Park Self-Guided Driving Audio Tour

CA $24
per traveller
100% of travellers recommend
Shenandoah National Park Self-Guided Driving Audio Tour
Discover US East Coast Self Guided Audio Tour

Discover US East Coast Self Guided Audio Tour

CA $201
per traveller
Discover US East Coast Self Guided Audio Tour
See all activities in Skyland

Frequently asked questions

How much does a Skyland vacation package cost?
You'll find cheap prices from CA $1,010 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?

  1. Choose your dates: What you plan to do in Skyland and your preferred season will help you decide when to get away.
  2. 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.
  3. 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.
  4. 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

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.