Windsor Hills Vacations from $388

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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!

The Latest Windsor Hills vacation packages

Price found within the past 48 hours. Click for updated prices.
Budget Inn By OYO Natural Bridge I-81

Budget Inn By OYO Natural Bridge I-81

2 out of 5
Price was $472, price is now $388 per person
$388
per person
Nov 18 - Nov 23
found 12 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Roanoke (ROA)
6.4/10 (329 reviews)
Los baños están en malas condiciones, les falta más limpieza

Reviewed on Aug 31, 2025

The Liberty Trust

The Liberty Trust

4 out of 5
Downtown Roanoke
Price was $1,160, price is now $839 per person
$839
per person
Oct 22 - Oct 26
found 15 hours ago
Roundtrip non-stop flight included
New York (NYC) 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

The West End Flats

The West End Flats

4.5 out of 5
Price was $778, price is now $613 per person
$613
per person
Oct 22 - Oct 26
found 15 hours ago
Roundtrip non-stop flight included
New York (NYC) to Roanoke (ROA)
9.8/10 Exceptional! (49 reviews)
Nice clean and spacious

Reviewed on Sep 6, 2025

Wingate by Wyndham Dublin Near Claytor Lake State Park

Wingate by Wyndham Dublin Near Claytor Lake State Park

2.5 out of 5
Price was $983, price is now $777 per person
$777
per person
Oct 22 - Oct 26
found 15 hours ago
Roundtrip non-stop flight included
New York (NYC) to Roanoke (ROA)
8/10 Very Good! (158 reviews)
No problems. Friendly staff

Reviewed on Aug 19, 2025

The Oaks Victorian Inn

The Oaks Victorian Inn

3 out of 5
Price was $1,312, price is now $1,084 per person
$1,084
per person
Oct 22 - Oct 26
found 15 hours ago
Roundtrip non-stop flight included
New York (NYC) to Roanoke (ROA)
10/10 Exceptional! (80 reviews)
The staff was personable whether through text or in person. I was in the Anna room which was absolutely charming and clean and lovely. Bathroom clean and well stocked. Breakfast served by Kim Gomer was a delightful experience. Even able to eat out on the veranda. I definitely will return!

Reviewed on Aug 5, 2025

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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

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 10 to Sep 11
$76 total
Sep 10 - Sep 11
Total with taxes and fees
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
$196 nightly
The price is $222 total per night from Sep 14 to Sep 15
$222 total
Sep 14 - Sep 15
Total with taxes and fees
The Liberty Trust
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
$97 nightly
The price is $108 total per night from Sep 28 to Sep 29
$108 total
Sep 28 - Sep 29
Total with taxes and fees
Country Inn & Suites by Radisson, Roanoke, VA
See all 366 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.

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Frequently asked questions

How much does a Windsor Hills vacation package cost?
You can grab a vacation package to this top destination from $388 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.