Windsor Hills Vacations from $427

Book a Hotel + Flight or Car together to unlock savings

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!

The Latest Windsor Hills vacation packages

Price found within the past 48 hours. Click for updated prices.
Home2 Suites by Hilton Blacksburg - University

Home2 Suites by Hilton Blacksburg - University

3 out of 5
Airport Acres
Price was $515, price is now $427 per person
$427
per person
Dec 4 - Dec 7
found 14 hours ago
Roundtrip flight included
Chicago (CHI) to Roanoke (ROA)
9.2/10 Wonderful! (472 reviews)
Very pleasant stay and reasonably priced.

Reviewed on Sep 1, 2025

The Liberty Trust

The Liberty Trust

4 out of 5
Downtown Roanoke
Price was $681, price is now $526 per person
$526
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Roanoke (ROA)
9.2/10 Wonderful! (1,226 reviews)
The property itself is great even if the parking garage is a little inconveniently placed. It’s not a far walk, but can be tedious with traffic. Rooms and property maintain the historic elements of the previous bank usage now with modern amenities. The biggest downside is the homeless outreach center across the street, which isn’t the hotel’s fault, but there are some extremely aggressive individuals that can make you feel unsafe.

Reviewed on Sep 4, 2025

Best Western Plus Inn at Hunt Ridge

Best Western Plus Inn at Hunt Ridge

2.5 out of 5
Price was $667, price is now $535 per person
$535
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Roanoke (ROA)
8.4/10 Very Good! (1,005 reviews)
We had a great stay. Loved our balcony room. Also loved that the hotel was off the main road/highway.

Reviewed on Aug 22, 2025

Mountain Lake Lodge

Mountain Lake Lodge

3.5 out of 5
Price was $759, price is now $613 per person
$613
per person
Dec 4 - Dec 7
found 14 hours ago
Roundtrip flight included
Chicago (CHI) to Roanoke (ROA)
8.8/10 Excellent! (487 reviews)
Everyone and everything at the Lodge was great. The vibe at Harvest could use an upgrade as could the menus, but the service was great. Maybe go for brighter, farm-to-table Appalachian vibe.

Reviewed on Aug 22, 2025

Affordable Corporate Suites of Overland Drive

Affordable Corporate Suites of Overland Drive

2.5 out of 5
Price was $527, price is now $439 per person
$439
per person
Dec 4 - Dec 7
found 14 hours ago
Roundtrip flight included
Chicago (CHI) to Roanoke (ROA)
9.4/10 Exceptional! (303 reviews)
Was very clean and quiet. Staff was extremely helpful. Not a new place but everything worked and there was no road noise.

Reviewed on Mar 7, 2025

Don't see what you're looking for?
See all available trips from Columbus to Windsor Hills
View all trips

Discover the most popular places to visit in Windsor Hills

Downtown Roanoke is an awesome hangout with some great bars and restaurants

Center in the Square

Find out about the history of Roanoke when you spend time at Center in the Square. Discover the area's mountain views and shops.

Center in the Square
Mill Mountain Star which includes outdoor art

Mill Mountain Star

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
One of the many trains on display. It's not the best museum by any means but for $8, you can't complain.

Virginia Museum of Transportation

You can spend time studying the exhibits at Virginia Museum of Transportation in Roanoke. Attend a sporting event or discover the area's mountain views.

Virginia Museum of Transportation

What to do in Windsor Hills

Blue Ridge Parkway Bundle

Blue Ridge Parkway Self-Guided Audio Tour Bundle

$24
per traveler
Blue Ridge Parkway Self-Guided Audio Tour Bundle
Sharp Top Mountain

Blue Ridge Parkway Virginia Self-Guided Audio Tour

$13
per traveler
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

$109
per adult
3-Hour E-Bike Sightseeing and Breweries Tour in Roanoke
See all activities in Windsor Hills

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
$98 nightly
The price is $110 total per night from Sep 28 to Sep 29
$110 total
Sep 28 - Sep 29
Total with taxes and fees
Country Inn & Suites by Radisson, Roanoke, VA
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
$195 nightly
The price is $221 total per night from Sep 21 to Sep 22
$221 total
Sep 21 - Sep 22
Total with taxes and fees
The Liberty Trust
Baymont by Wyndham Salem Roanoke Area

Baymont by Wyndham Salem Roanoke Area

2.5 out of 5
179 Sheraton Drive, I-81 Exit 141, Salem, VA
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $76 total per night from Sep 14 to Sep 15
$76 total
Sep 14 - Sep 15
Total with taxes and fees
Baymont by Wyndham Salem Roanoke Area
See all 365 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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Windsor Hills vacation package cost?
You can grab a vacation package to this top destination from $427 on Expedia. But how much your vacation 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?
December, January and February are the best times to look for cheap Windsor Hills vacation packages. Choosing to travel in quieter months means you can usually find lower prices on hotels and flights.
How many days is enough for Windsor Hills?
The ideal duration of your Windsor Hills vacation depends on what you'd like to do. Generally, a few days to a week will give you plenty of time to tick off all the major sights and discover some hidden gems along the way.
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 vacation package as early as possible.
Is it cheaper to book a Windsor Hills vacation as a package?
Expedia vacation 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 customized Windsor Hills vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation 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.
Does Expedia offer Book Now, Pay Later Windsor Hills vacation packages?
Your Windsor Hills getaway should be an escape from your daily routine, not a source of money worries. So to allow you that extra flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.