Greenville Vacations from $305

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The Latest Greenville vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Staunton Conference Center by IHG

Holiday Inn Staunton Conference Center by IHG

3 out of 5
Price was $387, price is now $305 per person
$305
per person
Feb 28 - Mar 4
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Weyers Cave (SHD)
8.2/10 Very Good! (1,002 reviews)
A premier place to spend the night in comfort and quiet. Great location beautiful hotel

Reviewed on Jan 4, 2026

Massanutten's Regal Vistas by Tripforth

Massanutten's Regal Vistas by Tripforth

3.5 out of 5
Save 100% on your flight
Price was $707, price is now $536 per person
$536
per person
Feb 28 - Mar 4
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Weyers Cave (SHD)
8.8/10 Excellent! (58 reviews)
Everything was amazing! Very clean

Reviewed on Dec 31, 2025

Mountainside Villas at Massanutten by Tripforth

Mountainside Villas at Massanutten by Tripforth

3.5 out of 5
Price was $497, price is now $388 per person
$388
per person
Feb 28 - Mar 4
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Weyers Cave (SHD)
9/10 Wonderful! (333 reviews)
Pros- Beautiful view, nice amenities such as jacuzzi anbs sauna) and plenty of space for a family to spread out. Cons- Cleaning could be better (laundry machine still had clumps of used detergent, hair on the floor and furniture) and some appliances are old and not working properly (coffee maker was leaking, microwave was glitching) minimal cookware and kitchen equipment.

Reviewed on Jan 2, 2026

Massanutten's Woodstone Meadows by Tripforth

Massanutten's Woodstone Meadows by Tripforth

4 out of 5
Price was $585, price is now $459 per person
$459
per person
Feb 28 - Mar 4
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Weyers Cave (SHD)
9/10 Wonderful! (219 reviews)
The room was spotless and hostesses were excellent .

Reviewed on Nov 6, 2025

Massanuttens Shenandoah Villas by Tripforth

Massanuttens Shenandoah Villas by Tripforth

4 out of 5
Price was $465, price is now $369 per person
$369
per person
Feb 28 - Mar 4
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Weyers Cave (SHD)
7.6/10 Good! (144 reviews)
Condo was clean. Jacuzzi tub needs updating. Everything else was good.

Reviewed on Dec 31, 2025

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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
$107 nightly
The price is $120 total per night from Jan 15 to Jan 16
$120 total
Jan 15 - Jan 16
Total with taxes and fees
9.4/10 Exceptional! (1,071 reviews)
Halfway between our NY to SC trip. Have stayed here for the past three years.

Reviewed on Jan 6, 2026

Hotel 24 South
Sleep Inn Staunton

Sleep Inn Staunton

2.5 out of 5
222 Jefferson Hwy Staunton VA
Fully refundable
$74 nightly
The price is $82 total per night from Feb 8 to Feb 9
$82 total
Feb 8 - Feb 9
Total with taxes and fees
9.2/10 Wonderful! (1,394 reviews)
Very clean

Reviewed on Jan 7, 2026

Sleep Inn Staunton
Wingate by Wyndham Lexington

Wingate by Wyndham Lexington

2.5 out of 5
1100 N Lee Hwy Lexington VA
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $87 total per night from Jan 18 to Jan 19
$87 total
Jan 18 - Jan 19
Total with taxes and fees
8.2/10 Very Good! (1,011 reviews)
Clean room

Reviewed on Jan 5, 2026

Wingate by Wyndham Lexington
See all 1,325 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.

Find the Best Greenville Vacation Packages

Greenville Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Shenandoah Valley Regional Airport (SHD)
Population
830
Top Sights
Crabtree Falls, American Shakespeare Center and Ravens Roost Overlook

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Frequently asked questions

How much does a Greenville vacation package cost?
Offering great value package deals from $305 on Expedia, you'll be thrilled with how little a vacation to Greenville costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Greenville?
If you're hoping to book a cheap Greenville vacation package, consider visiting in November, December and January. You're likely to find better rates on hotels and airfares during these quieter months — ideal for a budget-friendly break.
How many days is enough for Greenville?
With a well-planned itinerary, you can easily visit the most popular Greenville sights in a handful of days. But if you want to discover hidden spots or go on day trips, consider booking your Greenville vacation for longer.
How to find the best Greenville package deals?
Begin your search for a Greenville package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Greenville package deal straight away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Greenville escape off to a flying start.
Is it cheaper to book a Greenville vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and accommodations individually. Better still, you can tailor your Greenville trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Greenville?
If you have your Greenville vacation dates finalized, book as early as you can to bag some awesome deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are perfect for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Greenville vacation packages?
Jet off on your perfect escape to Greenville with help from our Book Now, Pay Later vacations. No need to save up or wait for the next payday — we've partnered with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans mean you can split the cost across 3, 6 or 12 months. With no late payment fees or extra charges, it's easy to stay on budget and snap up bargains while they last.

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