Windsor Hills Vacation Packages

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Your Windsor Hills Vacation

With all the details planned before you go away, our Windsor Hills vacation packages mean you can focus more on letting the good times roll. No matter if you're based in the neighborhood of Old Southwest, which is good for history, or another area, this captivating city promises an array of discoveries. You'll want to take in the sights during your trip to Windsor Hills. Carve out some time for popular attractions like Center in the Square, Mill Mountain Star and Virginia Museum of Transportation. Expedia can help you escape your routine. Tailor your vacation to Windsor Hills to match your travel style, whatever that may be!

Where to stay in Windsor Hills

Find the best Windsor Hills areas and neighborhoods for the activities you enjoy most. Learn more about Windsor Hills
Downtown Roanoke

Downtown Roanoke

3 out of top 10 points of interest in this area

While visiting Downtown Roanoke, you might make a stop by sights like Center in the Square and Virginia Museum of Transportation.

Find hotels in Downtown Roanoke

Windsor Hills Hotel Deals

Baymont by Wyndham Salem Roanoke Area

Baymont by Wyndham Salem Roanoke Area

2.5 out of 5
179 Sheraton Drive Salem VA
Fully refundableReserve now, pay when you stay
The price is CA $95 per night from Jul 6 to Jul 7
CA $95
CA $108 total
Jul 6 - Jul 7
includes taxes & fees
7.2/10 Good! (520 reviews)
"Clean room"

Reviewed on Jun 22, 2026

Baymont by Wyndham Salem Roanoke Area
The Liberty Trust

The Liberty Trust

4 out of 5
101 S Jefferson St, Roanoke VA 24011 Roanoke VA
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from Jun 29 to Jun 30
CA $172
CA $195 total
Jun 29 - Jun 30
includes taxes & fees
9.2/10 Wonderful! (1,303 reviews)
"The hotel was beautiful, the room exceeded expectations and was super clean. Loved everything except the entree that I had - the Brazilian steak- dry, overcooked, and the vegetables were tasteless. The ‘ Ready Aim Fire’ cocktail was, however, delightful."

Reviewed on Jun 22, 2026

The Liberty Trust
avid hotel Salem by IHG

avid hotel Salem by IHG

2.5 out of 5
501 WILDWOOD ROAD Salem VA
Fully refundable
The price is CA $117 per night from Jul 19 to Jul 20
CA $117
CA $133 total
Jul 19 - Jul 20
includes taxes & fees
9.6/10 Exceptional! (1,008 reviews)
"Don't accept a stay in Room #105. The exterior door leading into building at end of hall slams and can be a real bother if traffic is high. There are no directions for use of tv control devices. All controls are not alike."

Reviewed on Jun 20, 2026

avid hotel Salem by IHG
See all 410 properties in Windsor Hills
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

Frequently asked questions

How much does a Windsor Hills vacation package cost?
You can pick up a vacation package to this top destination on Expedia. However, how much your vacation to Windsor Hills costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Windsor Hills?
If you'd like to snag a cheap Windsor Hills vacation package, consider visiting in January, February and March. You'll generally find better prices on flights and accommodations during these months — ideal for a budget-friendly getaway.
How many days is enough for Windsor Hills?
We'd suggest booking a Windsor Hills vacation for at least 2 days. This will allow you enough time to check off top attractions such as Tanglewood Mall and Taubman Museum of Art, and explore neighbourhoods like Cave Spring and Old Southwest. You might even be able to slot in a day trip (or two) beyond Windsor Hills.
How to find the best Windsor Hills package deals?
Bagging a cheap Windsor Hills package deal is a breeze with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, apply some filters and browse what's available. You can customize your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Windsor Hills package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Windsor Hills vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component individually. And you'll still have the freedom to create a tailored Windsor Hills vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Windsor Hills?
Enjoy fantastic discounts by booking your flights in advance with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Windsor Hills getaway.
How to plan a trip to Windsor Hills?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Windsor Hills.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and dining out to activities and flights. Your accommodations will probably be the biggest expense during your trip to Windsor Hills.
  3. Decide how long to go for: Now that you're up to speed on Windsor Hills, you can work out the ideal length of your break. Put together a draft plan and give yourself enough time to cover everything you want to do.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to pick a Windsor Hills vacation package that brings all your bookings together.

Discover the most popular places to visit in Windsor Hills

Mill Mountain Star

Mill Mountain Star

3/5(1 review)

Visit this iconic mountaintop landmark and admire panoramic views over the city of Roanoke. Look up at the symbol from the city at night when it shines bright.

Mill Mountain Star

Berglund Center

4.5/5(3 reviews)

Catch an event at Berglund Center during your trip to Roanoke. Attend a sporting event or discover the area's mountain views.

Berglund Center

Valley View Mall

3.5/5(7 reviews)

During your trip to Roanoke, you can browse for the perfect souvenirs at Valley View Mall. Attend a sporting event or discover the area's mountain views.

Valley View Mall

Things to do

Blue Ridge Parkway Bundle

Blue Ridge Parkway Self-Guided Audio Tour Bundle

CA $33
per traveller
Blue Ridge Parkway Self-Guided Audio Tour Bundle
Shenandoah Lake

Blue Ridge Parkway Virginia Self-Guided Audio Tour

CA $18
per traveller
Blue Ridge Parkway Virginia Self-Guided Audio Tour
E-Bike Mural Tour of Roanoke

E-Bike Mural Tour of Roanoke

CA $122
per adult
E-Bike Mural Tour of Roanoke
See all activities in Roanoke
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.