Wescliff Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Your Wescliff Vacation

When a city adventure is calling your name, answer it with a Wescliff vacation package. With all your travel plans in order before you go, all you need to do here is focus on making unforgettable memories. If your trip to Wescliff includes a little sightseeing, visit well-known attractions like Richard Childress Vineyards, Weathervane Winery and The Candy Factory. Check out Expedia's wide range of travel options and begin planning your dream vacation to Wescliff today.

Top Wescliff Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Julian Price House

Julian Price House

3 out of 5
Fisher Park
per person
Aug 29 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Greensboro (GSO)
10/10 Exceptional! (94 reviews)
This place is absolutely beautiful, everything was perfect

Reviewed on Jul. 26, 2025

Proximity Hotel

Proximity Hotel

4 out of 5
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Greensboro (GSO)
9.6/10 Exceptional! (816 reviews)
Beautiful hotel and dining

Reviewed on Jul. 29, 2025

O.Henry Hotel

O.Henry Hotel

4 out of 5
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Greensboro (GSO)
9.8/10 Exceptional! (674 reviews)
The design of the hotel and the special events like Jazz night and Tea in the afternoon were a delight.

Reviewed on Jul. 21, 2025

Hotel Denim

Hotel Denim

3.5 out of 5
per person
Oct 9 - Oct 13
found 21 hours ago
Roundtrip flight included
Victoria (YYJ) to Greensboro (GSO)
9/10 Wonderful! (957 reviews)
I had a truly wonderful stay at this establishment, and I must commend the staff for their exceptional service. The room was immaculate, comfortable (except the pillows), and provided a serene environment, which was exactly what I was hoping for.

Reviewed on Jul. 29, 2025

Dailey Renewal Retreat Bed & Breakfast

Dailey Renewal Retreat Bed & Breakfast

3 out of 5
Lindley Park
per person
Oct 9 - Oct 13
found 21 hours ago
Roundtrip flight included
Victoria (YYJ) to Greensboro (GSO)
9/10 Wonderful! (203 reviews)
Delightful and great! Vibrant atmosphere and lively breakfast array of delicious gluten free vegan food

Reviewed on May 15, 2025

Ready to book your vacation to Wescliff?

 

Choose your dates

Wescliff Hotel Deals

Hawthorne Inn and Conference Center

Hawthorne Inn and Conference Center

3 out of 5
420 High St, Winston-Salem, NC
Fully refundableReserve now, pay when you stay
8/10 Very Good! (1,000 reviews)
Pleasant stay
"Friendly staff, clean room and comfortable bed."

Reviewed on Jul. 28, 2025

Get rates
Hawthorne Inn and Conference Center
The Historic Brookstown Inn, Trademark Collection by Wyndham

The Historic Brookstown Inn, Trademark Collection by Wyndham

3.5 out of 5
200 Brookstown Ave, Winston-Salem, NC
Fully refundableReserve now, pay when you stay
The price is CA $160 per night from Aug 3 to Aug 4
CA $160
CA $181 total
Aug 3 - Aug 4
includes taxes & fees
9.4/10 Exceptional! (1,014 reviews)
"Great place!"

Reviewed on Jul. 27, 2025

The Historic Brookstown Inn, Trademark Collection by Wyndham
Kimpton Cardinal Hotel by IHG

Kimpton Cardinal Hotel by IHG

4.5 out of 5
51 East 4th St, Winston-Salem, NC
Fully refundable
The price is CA $190 per night from Aug 10 to Aug 11
CA $190
CA $215 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
"Everything was fabulous. The room, the restaurant, and the rec facilities in the basement? What??!!?? The best I’ve ever seen in a hotel."

Reviewed on Jul. 15, 2025

Kimpton Cardinal Hotel by IHG
See all 584 properties in Wescliff
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

Discover the most popular places to visit in Wescliff

Boone's Cave Park

Boone's Cave Park

Explore the great outdoors at Boone's Cave Park, a lovely green space in Lexington. While in this family-friendly area, you can savor the wineries and restaurants.

Boone's Cave Park

Richard Childress Vineyards

You can enjoy a tasting or tour at Richard Childress Vineyards during your travels to Lexington. Stroll along this family-friendly area's lakeside, or simply enjoy its wineries.

Richard Childress Vineyards

Frequently asked questions

How much does a Wescliff vacation package cost?
You can pick up a vacation package to this top destination from CA $1,011 on Expedia. However, how much your vacation to Wescliff costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Wescliff?
January, February and March are the best times to look for cheap Wescliff vacation packages. Choosing to travel in quieter months means you can generally find better prices on flights and hotels.
How many days is enough for Wescliff?
When planning your Wescliff vacation, a handful of days will be enough to explore the best spots. Make sure to stop by Weathervane Winery — it's one of the leading sights in this destination. If you're looking for more adventure, think about basing yourself here and venturing off on some tours from Wescliff.
How to find the best Wescliff package deals?
Landing a cheap Wescliff package deal is a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can personalize your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to view the most pocket-friendly Wescliff package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Wescliff vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component individually. And you'll still enjoy the freedom to create a customized Wescliff vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Wescliff?
If you've got your Wescliff travel dates confirmed, book as early as you can to grab some incredible deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for travelling on a whim.
How to plan a trip to Wescliff?

  1. Choose when to travel: Check your schedule and pack your bags. Your favourite season and the type of activities on offer will also help you decide when to vacation in Wescliff.
  2. Work out your budget: Make sure you have enough money to cover everything from transportation and food to flights and activities. Your hotel will probably be the largest expense during your trip to Wescliff.
  3. Decide how many days away: Start by compiling a list of the attractions you want to experience in Wescliff. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a personalized Wescliff vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.