Dale Enterprise Vacations from $310

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Your Dale Enterprise Vacation

When you book a Dale Enterprise vacation package, you can really enjoy your adventure to the fullest. Delve into the sights and sounds of this unique city knowing that all your travel arrangements have been taken care of in advance. You'll want to sightsee during your trip to Dale Enterprise. Carve out some time for famous attractions like James Madison University, Rockingham Fairgrounds and A Dream Come True Playground. Your ideal Dale Enterprise vacation is a couple of clicks away. Search flights, accommodations and more on Expedia for a getaway that's tailored to suit your travel style.

The Latest Dale Enterprise vacation packages

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Waynesboro

Days Inn by Wyndham Waynesboro

2 out of 5
Price was $351, price is now $310 per person
$310
per person
Jul 22 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Weyers Cave (SHD)
7.2/10 Good! (1,005 reviews)
Furniture had been updated recently as well as the flooring, however the walls had missing drywall and the ceiling tiles in the bathroom were falling in. A dessicated Wendy’s French fry fell out of the “clean” towels hanging in the bathroom. The bed seemed clean and was comfortable. Most likely will try to stay at different hotel in the future. 4/10 experience

Reviewed on May 11, 2026

Stable Craft Brewing & Cidery

Stable Craft Brewing & Cidery

2 out of 5
Price was $446, price is now $366 per person
$366
per person
Jul 22 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Weyers Cave (SHD)
No reviews
The Anderson Cottage Bed & Breakfast

The Anderson Cottage Bed & Breakfast

3 out of 5
Price was $1,395, price is now $1,216 per person
$1,216
per person
Jun 22 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Weyers Cave (SHD)
9.4/10 Exceptional! (26 reviews)
Well kept and great location

Reviewed on Aug 5, 2025

Grey Pine Lodge

Grey Pine Lodge

2 out of 5
Price was $492, price is now $437 per person
$437
per person
Jul 22 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Weyers Cave (SHD)
9.4/10 Exceptional! (123 reviews)
Clean and convenient. Comfortable beds and pillows.

Reviewed on Apr 18, 2026

The Blackburn Inn and Conference Center

The Blackburn Inn and Conference Center

3.5 out of 5
Price was $655, price is now $581 per person
$581
per person
Jun 24 - Jun 27
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Weyers Cave (SHD)
9.2/10 Wonderful! (1,005 reviews)
The breakfast was delish, the fresh fruit cup was a hit, we went back a second time. The room was clean. The staff was friendly. Love the history and charm of the place.

Reviewed on May 12, 2026

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Discover the most popular places to visit in Dale Enterprise

Colorful trees blooming in spring next to a small pond at Edith J. Carrier Arboretum, James Madison University, Virginia, USA

James Madison University

4.5/5(262 reviews)

Explore the campus of James Madison University, during your travels in Harrisonburg. Attend a football game in the area, or seek out the hiking trails.

James Madison University

Rockingham Fairgrounds

4.5/5(26 reviews)

Enjoy an outing to Rockingham Fairgrounds during your stay in Harrisonburg. Make time to visit the area's shops, or simply enjoy its top-notch restaurants.

Rockingham Fairgrounds

Harrisonburg Farmers Market

4.5/5(53 reviews)

You can browse for the perfect souvenirs at Harrisonburg Farmers Market during your stay in Harrisonburg. Make time to visit the area's shops, or simply enjoy its top-notch restaurants.

Harrisonburg Farmers Market

Dale Enterprise Hotel Deals

Massanutten Resort

Massanutten Resort

2.5 out of 5
1822 Resort Dr McGaheysville VA
$121 nightly
The price is $133 total per night from May 17 to May 18
$133 total
May 17 - May 18
Total with taxes and fees
8/10 Very Good! (1,313 reviews)
Amazing

Reviewed on May 15, 2026

Massanutten Resort
Days Inn by Wyndham Harrisonburg

Days Inn by Wyndham Harrisonburg

2 out of 5
1703 E Market St Harrisonburg VA
Fully refundableReserve now, pay when you stay
$65 nightly
The price is $73 total per night from May 17 to May 18
$73 total
May 17 - May 18
Total with taxes and fees
6/10 (952 reviews)
My goodness, every time I sit or move around in my bed was making metallic noises, so I couldn’t sleep and asked them to change at 2am from king to double, then it was ok. Free breakfast was okay.

Reviewed on May 4, 2026

Days Inn by Wyndham Harrisonburg
Hotel Madison & Shenandoah Conference Ctr

Hotel Madison & Shenandoah Conference Ctr

3.5 out of 5
710 S. Main Street Harrisonburg VA
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $143 total per night from May 21 to May 22
$143 total
May 21 - May 22
Total with taxes and fees
9.2/10 Wonderful! (1,111 reviews)
Good

Reviewed on May 13, 2026

Hotel Madison & Shenandoah Conference Ctr
See all 854 properties in Dale Enterprise
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 Dale Enterprise Vacation Packages

Dale Enterprise Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Shenandoah Valley Regional Airport (SHD)
Top Sights
Explore More Discovery Museum, Valley Brethren-Mennonite Heritage Center and James Madison University

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Frequently asked questions

How much does a Dale Enterprise vacation package cost?
Offering excellent value package deals from $310 on Expedia, you'll be surprised at how little a vacation to Dale Enterprise costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Dale Enterprise?
If you're hoping to snag a cheap Dale Enterprise vacation package, consider planning a trip in May, June and October. You'll typically find lower prices on airfares and hotels during these quieter months — ideal for a budget-friendly break.
How many days is enough for Dale Enterprise?
With a well-organized schedule, you can easily tick off the most popular Dale Enterprise sights in a handful of days. But if you want to venture off the beaten track or go on day tours, think about booking your Dale Enterprise vacation for longer.
How to find the best Dale Enterprise package deals?
Start your search for a Dale Enterprise package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select some filters, like "Popular locations" and "Property type," 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 ideal Dale Enterprise package deal straight away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Dale Enterprise adventure underway.
Is it cheaper to book a Dale Enterprise vacation as a package?
You can enjoy significant savings on your Dale Enterprise escape by booking a tailored vacation package. Click on the "Package" heading, then enter your travel dates and destination to view some great flight and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Dale Enterprise?
If you're considering an impromptu Dale Enterprise adventure, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score terrific deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Dale Enterprise vacation packages?
If you're anything like us, you love going away but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the cost of your Dale Enterprise vacation over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.