Windsor Hills Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$703 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 Windsor Hills Holiday

Prepare to experience Windsor Hills your way with a custom Windsor Hills holiday package! Discovering the charms of this city is made simpler with a base in a neighbourhood such as Old Southwest, which is great for history, among other things. Make your trip to Windsor Hills even more fun by including some sightseeing. Mill Mountain Star, Centre in the Square and Virginia Museum of Transportation are some of the top attractions you'll want to explore. Don't delay exploring this city any longer. The ultimate Windsor Hills holiday is just a few clicks away with Expedia.

Our guide on 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

If you're spending some time in Downtown Roanoke, Center in the Square and Virginia Museum of Transportation are top sights worth seeing.

Find hotels in Downtown Roanoke

Our pick of the best Windsor Hills Hotel Deals

Country Inn & Suites by Radisson, Roanoke, VA

Country Inn & Suites by Radisson, Roanoke, VA

3 out of 5
7860 Plantation Rd Roanoke VA
Fully refundable
The price is AU$170 per night from 18 May to 19 May
AU$170
18 May - 19 May
includes taxes & fees
9.2/10 Wonderful! (2,165 reviews)
The room was very spacious; it could easily have fit a second king-sized bed. We enjoyed the waffles for breakfast. I also appreciated that there were EV charging stations available at a reasonable cost per kW.

Reviewed on 17 Apr 2026

Country Inn & Suites by Radisson, Roanoke, VA
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 AU$106 per night from 21 Apr to 22 Apr
AU$106
21 Apr - 22 Apr
includes taxes & fees
7.4/10 Good! (398 reviews)
Need elevator fs

Reviewed on 17 Apr 2026

Baymont by Wyndham Salem Roanoke Area
Hotel Roanoke & Conference Ctr, Curio Collection by Hilton 

Hotel Roanoke & Conference Ctr, Curio Collection by Hilton 

4 out of 5
110 Shenandoah Ave Ne Roanoke VA
Fully refundableReserve now, pay when you stay
The price is AU$322 per night from 2 May to 3 May
AU$322
2 May - 3 May
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
Everything was perfect, surprised by the $20 parking.

Reviewed on 14 Apr 2026

Hotel Roanoke & Conference Ctr, Curio Collection by Hilton 
See all 357 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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Windsor Hills holiday package cost?
You can grab a holiday package to this top destination on Expedia. But how much your holiday to Windsor Hills costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Windsor Hills?
January, February and March are the best times to look for cheap Windsor Hills holiday packages. Travelling in less busy months means you'll typically find reduced prices on hotels and flights.
How many days is enough for Windsor Hills?
With a well-organised schedule, you can easily hit the main Windsor Hills attractions in a few days. But if you'd like to discover lesser-known spots or go on day tours, think about booking your Windsor Hills holiday for longer.
How to find the best Windsor Hills package deals?
Use Expedia's handy filters to find some great Windsor Hills package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Windsor Hills package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your holiday package as early as possible.
Is it cheaper to book a Windsor Hills holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component individually. And you'll still have the flexibility to create a customised Windsor Hills holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday package to Windsor Hills?
If you're planning a spontaneous Windsor Hills getaway, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land awesome deals on your hotels and flights by booking ahead.
How to plan a trip to Windsor Hills?

  1. Choose the best time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to go to Windsor Hills.
  2. Set a budget: Factor in costs such as flights, food and transportation when working out how much to put aside for your trip to Windsor Hills. Then, select a hotel that fits your budget, whether that's an economical stay or a more luxurious retreat.
  3. Decide how long to go for: Now that you're more familiar with Windsor Hills, you can figure out the perfect length of your holiday. Create a draft itinerary and give yourself enough time for all the things you want to do.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose a Windsor Hills holiday package that brings all your bookings together.

Discover the most popular places to visit in Windsor Hills

Hollins University

Enjoy the student vibe when you visit Hollins University during your trip to Hollins. Attend a sporting event or discover the area's mountain views.

Hollins University

Activities

Blue Ridge Parkway Bundle

Blue Ridge Parkway Self-Guided Audio Tour Bundle

AU$34
per traveller
Blue Ridge Parkway Self-Guided Audio Tour Bundle
Shenandoah Lake

Blue Ridge Parkway Virginia Self-Guided Audio Tour

AU$19
per traveller
Blue Ridge Parkway Virginia Self-Guided Audio Tour
3-Hour E-Bike Sightseeing and Breweries Tour in Roanoke

3-Hour E-Bike Sightseeing and Breweries Tour in Roanoke

AU$155
per adult
3-Hour E-Bike Sightseeing and Breweries Tour in 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.