Skippers Vacations from $442

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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.
Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $616, price is now $442 per person
$442
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.8/10 Excellent! (1,002 reviews)
Second time staying at this hotel and it was wonderful. The 2 bedroom suite was amazing. The lobby area was clean. The pool was great. The guests just need to rinse the sand off before getting into it. The whirlpool was a welcome addition. Parking was plentiful and on site

Reviewed on Jul 13, 2026

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 $1,471, price is now $927 per person
$927
per person
Aug 29 - Sep 5
found 9 hours ago
Roundtrip flight included
New York (JFK) to Norfolk (ORF)
8.2/10 Very Good! (1,323 reviews)
My wife and I enjoyed our stay. Staff was very friendly. It was sentimental for me because this is where I stayed growing up when it was Triton Towers. Look forward to coming back next year

Reviewed on Jul 13, 2026

Delta Hotels by Marriott Virginia Beach Waterfront Suites

Delta Hotels by Marriott Virginia Beach Waterfront Suites

4 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $695, price is now $464 per person
$464
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.4/10 Very Good! (1,486 reviews)
When I arrive on the property at 2 AM a pipe had busted. They said they was putting us up in a hotel which was across town. It was not a waterfront and it said it was free of charge, but they end up charging me anyway didn’t like the conditions at the hotel it wasn’t it didn’t meet up to my expectation.

Reviewed on Jul 16, 2026

Sea Scape Beach and Golf Villas

Sea Scape Beach and Golf Villas

3.5 out of 5
Sea Scape
Price was $783, price is now $531 per person
$531
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
9.4/10 Exceptional! (165 reviews)
Clean room, practical, family friendly, close to everything. Great value!

Reviewed on Jul 12, 2026

Wedmore Place

Wedmore Place

3.5 out of 5
Price was $1,156, price is now $838 per person
$838
per person
Aug 28 - Sep 3
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
9.4/10 Exceptional! (1,000 reviews)

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Stay near popular Skippers attractions

Good Earth Peanut Company

7.0/10 (26 reviews)
This country store showcases Virginia's finest peanuts with free samples of unique flavors like Cajun and chocolate-covered varieties. Browse gift assortments and learn about local peanut farming.
See properties

Skippers Hotel Deals

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
$94 nightly
The price is $107 total per night from Jul 26 to Jul 27
$107 total
Jul 26 - Jul 27
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
"Courteous staff"

Reviewed on Jul 15, 2026

Holiday Inn Express & Suites Roanoke Rapids SE by IHG
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
$106 nightly
The price is $120 total per night from Jul 26 to Jul 27
$120 total
Jul 26 - Jul 27
Total with taxes and fees
Hilton Garden Inn Roanoke Rapids
Holiday Inn Express Hotel & Suites Emporia by IHG

Holiday Inn Express Hotel & Suites Emporia by IHG

2.5 out of 5
1350 W Atlantic St Emporia VA
Fully refundable
$99 nightly
The price is $115 total per night from Jul 19 to Jul 20
$115 total
Jul 19 - Jul 20
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
"This location of this hotel was perfect for the event I was attending in the area. The room was very spacious, looked like it may have been recently remodeled - a great look!!! Staff were polite and helped with a couple things I needed. I enjoyed the delicious breakfast. I'll definitely return here ..."

Reviewed on Jul 13, 2026

Holiday Inn Express Hotel & Suites Emporia by IHG
See all 308 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 $442 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.