Skippers Vacations from $559

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Your Skippers Vacation

With one of our vacation packages to Skippers, you'll have infinite opportunities for fun and adventure. There's lots to experience, including its rural countryside and spectacular views. If your trip to Skippers includes a little sightseeing, visit major attractions such as Meherrin River Park, Village View Mansion House and Good Earth Peanut Company. Stop dreaming and start adventuring. Check out the range of options on Expedia today and put your Skippers vacation plans into motion!

The Latest Skippers vacation packages

Price found within the past 48 hours. Click for updated prices.
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

4 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $797, price is now $559 per person
$559
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.2/10 Very Good! (1,286 reviews)
Beautiful view in a perfect location. Friendly staff and a super fun on site bar on the beach.

Reviewed on May 27, 2026

Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Save 100% on your flight
Price was $989, price is now $662 per person
$662
per person
Aug 11 - Aug 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (1,004 reviews)
Our stay at the Sea Ranch Resort was fantastic!! We had Oceanfront with two bedrooms , perfect amenities for families everything you need! Have stayed here before with just hubby and I but had 3 grandkids and it was great! Highly recommend and we will be back!

Reviewed on May 29, 2026

Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Save 100% on your flight
Price was $1,210, price is now $847 per person
$847
per person
Jul 18 - Jul 23
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Richmond (RIC)
8.8/10 Excellent! (1,004 reviews)
The property is located in beautiful Williamsburg, on the Chesapeake. We stayed in a 1 bedroom condominium that was very spacious, clean and overall comfortable. There were 2 things that we had a problem with. The bed was uncomfortable, not the worse I have ever slept in but definitely not comfortable and my back hurt in the morning. Also it seems the shower leaked into the place underneath us. Other than those 2 issues it was good. I would recommend it for location and cleanliness. We did not try the restaurants on location so no comment.

Reviewed on May 24, 2026

The Ocean Key Virginia Beach Resort

The Ocean Key Virginia Beach Resort

3 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $801, price is now $561 per person
$561
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
7.6/10 Good! (1,518 reviews)
There was enough space for each women to get ready and get dressed effectively. Thankful for the kitchen section. Wish the other pool was available. Overall, we will be back.

Reviewed on May 29, 2026

Outer Banks Beach Club

Outer Banks Beach Club

2.5 out of 5
Save 100% on your flight
Price was $1,452, price is now $1,026 per person
$1,026
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.8/10 Excellent! (68 reviews)
We loved staying here! The rooms were so clean and well maintained. The kitchen was well stocked with amenities.

Reviewed on May 28, 2026

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Discover the most popular places to visit in Skippers

Good Earth Peanut Company

4/5(8 reviews)

You can enjoy some culture when you stop by Good Earth Peanut Company in Skippers. While in this family-friendly area, you can savor the top-notch restaurants.

Good Earth Peanut Company

Skippers Hotel Deals

Hilton Garden Inn Roanoke Rapids

Hilton Garden Inn Roanoke Rapids

3 out of 5
111 Carolina Crossroads Pkwy Roanoke Rapids NC
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $97 total per night from Jun 7 to Jun 8
$97 total
Jun 7 - Jun 8
Total with taxes and fees
8/10 Very Good! (1,001 reviews)
"Na"

Reviewed on May 30, 2026

Hilton Garden Inn Roanoke Rapids
Holiday Inn Express & Suites Roanoke Rapids SE by IHG

Holiday Inn Express & Suites Roanoke Rapids SE by IHG

2.5 out of 5
74 Premier Blvd Roanoke Rapids NC
Fully refundable
$98 nightly
The price is $111 total per night from Jun 14 to Jun 15
$111 total
Jun 14 - Jun 15
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
"Excellent location and staff"

Reviewed on May 28, 2026

Holiday Inn Express & Suites Roanoke Rapids SE by IHG
Brentwood Inn & Suites

Brentwood Inn & Suites

2 out of 5
101 Old Farm Rd S Roanoke Rapids NC
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $76 total per night from Jun 1 to Jun 2
$76 total
Jun 1 - Jun 2
Total with taxes and fees
7.8/10 Good! (257 reviews)
"I left because I could not stay in a smoking and pet room. They refused to refund. I did not stay there. I made the reservation within 30 minutes upon arrival. I reserved online a non-smoking pet free room. I was shown 2 rooms and both were smoked in and had pets and it had deodorizer to try to cover ..."

Reviewed on May 28, 2026

Brentwood Inn & Suites
See all 299 properties in Skippers
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 Skippers Vacation Packages

Skippers Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
50ºF
Max Temp Summer
90ºF
Top Sights
Village View Mansion House, Meherrin River Park and Good Earth Peanut Company

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Frequently asked questions

How much does a Skippers vacation package cost?
Offering great value package deals from $559 on Expedia, you'll be surprised at how little a vacation to Skippers costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Skippers?
November, December and January are great times to look for cheap Skippers vacation packages. Choosing to travel in less busy months means you can generally find lower prices on flights and accommodations.
How many days is enough for Skippers?
The ideal duration of your Skippers vacation depends on what you'd like to do and see. Typically, a few days to a week will give you time to tick off all the leading sights and explore some hidden spots along the way.
How to find the best Skippers package deals?
Use Expedia's handy filters to find some tempting Skippers package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or browse for Skippers package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Skippers vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and stays separately. Better still, you can customize your Skippers escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Skippers?
If you have your Skippers travel dates locked in, book early to bag some terrific deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for quick escapes.
Does Expedia offer Book Now, Pay Later Skippers vacation packages?
If you're anything like us, you love jet-setting around the world but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Skippers vacation over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap vacation packages with payment plans as soon as you spot them.

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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.