Winton Vacations from $559

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The Latest Winton 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

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

Sea Scape Beach and Golf Villas

Sea Scape Beach and Golf Villas

3.5 out of 5
Sea Scape
Save 100% on your flight
Price was $1,368, price is now $974 per person
$974
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
9.2/10 Wonderful! (155 reviews)
Our room was clean, and comfortable. We have the basic amenities we needed during our stay. The kitchen is stocked, the mini fridge worked extremely well (very cold), and there is also a microwave. The villa is clean and cared for. Everyone's friendly and there are plenty dining options around. Lots of things to do aside from the beach.

Reviewed on May 25, 2026

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Winton Hotel Deals

Quality Inn & Suites Franklin

Quality Inn & Suites Franklin

2.5 out of 5
1620 Armory Dr Franklin VA
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $86 total per night from Jun 7 to Jun 8
$86 total
Jun 7 - Jun 8
Total with taxes and fees
Quality Inn & Suites Franklin
Super 8 by Wyndham Franklin

Super 8 by Wyndham Franklin

2 out of 5
1599 Armory Dr Franklin VA
Fully refundableReserve now, pay when you stay
$73 nightly
The price is $83 total per night from Jun 28 to Jun 29
$83 total
Jun 28 - Jun 29
Total with taxes and fees
7/10 Good! (465 reviews)
"This was my first time staying at a budget hotel. This was just out of necessity needing to pull over somewhere to sleep on a road trip. Seemed like the people there tried to make it nice and the people themselves were nice but I'd never stay somewhere like that again. The room smelled like musty ..."

Reviewed on May 28, 2026

Super 8 by Wyndham Franklin
Southern Star Inn

Southern Star Inn

2.5 out of 5
504 E Main St Murfreesboro NC
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $79 total per night from Jul 1 to Jul 2
$79 total
Jul 1 - Jul 2
Total with taxes and fees
6.6/10 (130 reviews)
"It's was decent"

Reviewed on May 13, 2026

Southern Star Inn
See all 23 properties in Winton
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 Winton Vacation Packages

Winton Essential Information

Language
English
Currency
U.S dollars
Population
750

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Frequently asked questions

How much does a Winton vacation package cost?
You'll find cheap prices from $559 on Expedia for your Winton escape. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Winton costs.
What are the cheapest months to go to Winton?
February, September and December are the best times to look for cheap Winton vacation packages. Choosing to travel in less busy periods means you can generally find reduced prices on flights and accommodations.
How many days is enough for Winton?
With a well-organized travel plan, you can easily hit the main Winton sights in a handful of days. But if you want to discover hidden gems or go on day tours, think about booking your Winton vacation for longer.
How to find the best Winton package deals?
Use Expedia's filters to find some fabulous Winton package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or look for Winton package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Winton vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging accommodations and flights separately. Better still, you can tailor your Winton escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Winton?
Land amazing discounts by reserving your flights early with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Winton vacation.
Does Expedia offer Book Now, Pay Later Winton vacation packages?
If you're like us, you love traveling the world but don't love the big price tag that can 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 overall cost of your Winton break across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great 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.