Winton Vacations from $682

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The Latest Winton vacation packages

Price found within the past 48 hours. Click for updated prices.
John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Price was $914, price is now $682 per person
$682
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
9.2/10 Wonderful! (1,955 reviews)

The Historic Cavalier Hotel and Beach Club, Autograph Collection

The Historic Cavalier Hotel and Beach Club, Autograph Collection

4 out of 5
Northeast Virginia Beach
Price was $1,987, price is now $1,567 per person
$1,567
per person
Dec 28 - Jan 2
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
9.4/10 Exceptional! (410 reviews)

The Inn at Four Eleven York

The Inn at Four Eleven York

4 out of 5
West Freemason
Price was $1,453, price is now $1,158 per person
$1,158
per person
Dec 28 - Jan 2
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
10/10 Exceptional! (114 reviews)
We stayed for our honeymoon before embarking on our cruise to Bermuda out of Norfolk. The port was very close to the Inn. The Inn is beautiful and so romantic. The area around the Inn had several options for dining. The walkable area was so romantic with its old architecture and cobblestone streets. I would love to come and stay longer and experience their restaurants and the city of Norfolk. I would highly recommend the Inn to anyone wanting a place that is not a big box type hotel. If you want charm and romance this place is for you!!!!

Reviewed on Oct 20, 2026

Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Price was $887, price is now $707 per person
$707
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.4/10 Very Good! (1,005 reviews)

Ocean Pines Resort

Ocean Pines Resort

3.5 out of 5
Price was $1,024, price is now $818 per person
$818
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.2/10 Very Good! (162 reviews)
Perfect location and enjoyable stay

Reviewed on Oct 11, 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
$79 nightly
The price is $89 total per night from Nov 8 to Nov 9
$89 total
Nov 8 - Nov 9
Total with taxes and fees
7.2/10 Good! (265 reviews)
"Liked that there was housekeeping daily. Furniture and counters , floors updated but shower and walls need gutted. Room smelled musty and the ppl that had rooms there are up all over the complex yelling and smoking and drinking all night. Really needs quiet time enforced"

Reviewed on Oct 3, 2026

Quality Inn & Suites 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
$62 nightly
The price is $68 total per night from Nov 27 to Nov 28
$68 total
Nov 27 - Nov 28
Total with taxes and fees
6.6/10 (141 reviews)
"It was a horrible place and they are charging way to much. I have photos."

Reviewed on Oct 26, 2026

Southern Star Inn
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
$69 nightly
The price is $79 total per night from Oct 29 to Oct 30
$79 total
Oct 29 - Oct 30
Total with taxes and fees
Super 8 by Wyndham Franklin
See all 22 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 $682 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.