Greenville Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Top Greenville Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Massanutten Resort by Tripforth

Massanutten Resort by Tripforth

3 out of 5
Price was CA $995, price is now CA $947 per person
CA $947
per person
Sep 9 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Weyers Cave (SHD)
7.8/10 Good! (163 reviews)
Over all average but we have to change room one time as there was very bad smell in our room so they change the room.it was nice experience hope next visit will get good welcome....

Reviewed on Jul 16, 2026

The Blackburn Inn and Conference Center

The Blackburn Inn and Conference Center

3.5 out of 5
Price was CA $1,520, price is now CA $1,405 per person
CA $1,405
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Weyers Cave (SHD)
9.2/10 Wonderful! (1,005 reviews)

Frederick House

Frederick House

3.5 out of 5
Price was CA $1,515, price is now CA $1,434 per person
CA $1,434
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Weyers Cave (SHD)
9.4/10 Exceptional! (459 reviews)
Room was clean and comfortable. Staff was very helpful and breakfast was delicious!!

Reviewed on Jul 4, 2026

Holiday Inn Staunton Conference Center by IHG

Holiday Inn Staunton Conference Center by IHG

3 out of 5
Price was CA $1,180, price is now CA $1,136 per person
CA $1,136
per person
Oct 9 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Weyers Cave (SHD)
8.2/10 Very good! (1,004 reviews)
I like that it is right off the highway but hidden from the road,beds are comfortable,lots of tv channels to watch there is a dining room near the lobby that has food and drinks. I was tired so did not get a chance too have something in dining area As far as food places around probably a 12 minute drive Which has A Krogers, and gas station there but there is also a Walmart 15 minute drive . I did not like having to go downstairs for something to drink and snack the candy was 3 dollars and teas three fifty I only bought it there because I forgot to pick it up while at grocery store. There is. Fridge and microwave which I Loved.

Reviewed on Jul 14, 2026

Massanutten's Regal Vistas by Tripforth

Massanutten's Regal Vistas by Tripforth

3.5 out of 5
Price was CA $1,186, price is now CA $1,143 per person
CA $1,143
per person
Sep 9 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Weyers Cave (SHD)
8.8/10 Excellent! (68 reviews)
Massanutten is a nice getaway.

Reviewed on Jun 8, 2026

Ready to book your vacation to Greenville?

 

Choose your dates

Greenville Hotel Deals

Hotel 24 South

Hotel 24 South

3 out of 5
24 South Market Street Staunton VA
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from Jul 30 to Jul 31
CA $169
CA $190 total
Jul 30 - Jul 31
includes taxes & fees
Hotel 24 South
Sleep Inn Staunton

Sleep Inn Staunton

2.5 out of 5
222 Jefferson Hwy Staunton VA
Fully refundable
The price is CA $139 per night from Jul 19 to Jul 20
CA $139
CA $155 total
Jul 19 - Jul 20
includes taxes & fees
9.2/10 Wonderful! (1,435 reviews)
"Nice and helpful staff"

Reviewed on Jul 10, 2026

Sleep Inn Staunton
Howard Johnson by Wyndham Lexington

Howard Johnson by Wyndham Lexington

2 out of 5
2836 North Lee Highway Lexington VA
Fully refundableReserve now, pay when you stay
The price is CA $84 per night from Jul 21 to Jul 22
CA $84
CA $96 total
Jul 21 - Jul 22
includes taxes & fees
8.2/10 Very good! (1,371 reviews)
"Aging hotel that is being modernized gradually. With that in mind, everything this hotel is doing is fantastic. Situated with great vistas of blue mountains, pet friendly (noticed many guests this way). Fantastic swim area and play park area."

Reviewed on Jul 15, 2026

Howard Johnson by Wyndham Lexington
See all 1,424 properties in Greenville
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

Frequently asked questions

How much does a Greenville vacation package cost?
Offering great value package deals from CA $947 on Expedia, you'll be thrilled with how little a vacation to Greenville costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Greenville?
January, February and November are great times to look for cheap Greenville vacation packages. Travelling in less busy months means you'll typically find better prices on accommodations and flights.
How many days is enough for Greenville?
The ideal length for your Greenville vacation depends on what you'd like to see. Generally, a handful of days to a week will give you time to visit all the top sights and discover some hidden gems along the way.
How to find the best Greenville package deals?
Landing a cheap Greenville package deal is easy with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply some filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Greenville package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Greenville vacation as a package?
You can enjoy significant savings on your Greenville escape by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to browse some great airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Greenville?
If you're considering an impromptu Greenville trip, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to Greenville?

  1. Choose when to get away: Check your schedule and get your bags packed. Your preferred season and the type of activities on offer will also help you decide when to vacation in Greenville.
  2. Set your budget: Consider costs such as flights, food and transportation when working out how much to save for your trip to Greenville. Then, choose a property that matches your budget, whether that's an affordable option or a more upscale getaway.
  3. Determine how many days away: Start by listing all the attractions and activities you want to experience in Greenville. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to pick a Greenville vacation package that brings all your bookings together.

Explore a world of travel with Expedia

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