Windsor Hills Holidays

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    Save up to S$134 when you book a flight and hotel together*

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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
Roanoke which includes interior views

Downtown Roanoke

4 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

Top hotels in Windsor Hills

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 S$119 per night from 8 Feb to 9 Feb
S$119
8 Feb - 9 Feb
includes taxes & fees
9/10 Wonderful! (2,067 reviews)
Clean rooms and great breakfast

Reviewed on 12 Jan, 2026

Country Inn & Suites by Radisson, Roanoke, VA
Tru By Hilton Roanoke Hollins

Tru By Hilton Roanoke Hollins

2.5 out of 5
8161 Gander Way Roanoke VA
Fully refundableReserve now, pay when you stay
The price is S$127 per night from 27 Jan to 28 Jan
S$127
27 Jan - 28 Jan
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
Check in was quick and my room was clean. This hotel has an impressive gym and a pool table in the lobby. Complimentary coffee and tea is nice too. Especially after driving all day.

Reviewed on 8 Jan, 2026

Tru By Hilton Roanoke Hollins
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 S$250 per night from 25 Jan to 26 Jan
S$250
25 Jan - 26 Jan
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
Two things that could be improved, 1 a microwave in the room or at least accessible and the hot tub and pool should be enclosed. The hot tub was not even warm, much less hot. It seems they spent a lot of money cattering to conventions while neglecting couples, families and children. We didn't see ...

Reviewed on 9 Jan, 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.

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.

Popular places to visit

Tanglewood Mall

You can enjoy retail therapy at Tanglewood Mall during your visit to Cave Spring. You can attend a sporting event while in the area.

Tanglewood Mall

Things to do

Blue Ridge Parkway Bundle

Blue Ridge Parkway Self-Guided Audio Tour Bundle

S$31
per traveller
Blue Ridge Parkway Self-Guided Audio Tour Bundle
Shenandoah Lake

Blue Ridge Parkway Virginia Self-Guided Audio Tour

S$17
per traveller
Blue Ridge Parkway Virginia Self-Guided Audio Tour
E-Bike Mural Tour of Roanoke

E-Bike Mural Tour of Roanoke

S$113
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.