Winton Vacations from $642

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The Latest Winton vacation packages

Price found within the past 48 hours. Click for updated prices.
The Ocean Key Virginia Beach Resort

The Ocean Key Virginia Beach Resort

3 out of 5
Northeast Virginia Beach
Price was $800, price is now $642 per person
$642
per person
Aug 28 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
7.6/10 Good! (1,580 reviews)

Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Price was $845, price is now $643 per person
$643
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip flight included
New York (JFK) to Norfolk (ORF)
8.6/10 Excellent! (1,001 reviews)

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

4 out of 5
Northeast Virginia Beach
Price was $1,020, price is now $806 per person
$806
per person
Sep 4 - Sep 8
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.2/10 Very Good! (1,337 reviews)
Muy amables y me dieron la habitación temprano

Reviewed on Jul 24, 2026

Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
Price was $888, price is now $702 per person
$702
per person
Sep 26 - Oct 3
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.8/10 Excellent! (1,007 reviews)

John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Price was $1,024, price is now $820 per person
$820
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip flight included
New York (JFK) to Norfolk (ORF)
9.2/10 Wonderful! (1,938 reviews)
First time staying here. Everything was great. Room very clean. Great access to the beach. Will definitely stay here again.

Reviewed on Jul 24, 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
$80 nightly
The price is $91 total per night from Aug 2 to Aug 3
$91 total
Aug 2 - Aug 3
Total with taxes and fees
7.2/10 Good! (250 reviews)
"Great stay I would definitely stay there again."

Reviewed on Jul 19, 2026

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
$78 nightly
The price is $89 total per night from Aug 23 to Aug 24
$89 total
Aug 23 - Aug 24
Total with taxes and fees
7/10 Good! (476 reviews)
"The towels have stains on them. The pillows on the bed are very small so bring your own. The breakfast option are low but do able."

Reviewed on Jul 19, 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
$70 nightly
The price is $77 total per night from Aug 9 to Aug 10
$77 total
Aug 9 - Aug 10
Total with taxes and fees
6.8/10 (135 reviews)
"Nice quiet property."

Reviewed on Jul 19, 2026

Southern Star Inn
See all 21 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 $642 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.