Oyster Vacations from $123

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Your Oyster Vacation

The exciting city of Oyster is calling your name. Discover its hot spots and hidden treasures with a Oyster vacation package that's custom made for you. If a sightseeing tour is on the cards during your trip to Oyster, stop by leading attractions like Cape Charles Beach, Bay Creek Golf Club and Cape Charles Museum & Welcome Center. Expedia will help you escape your daily routine. Tailor your vacation to Oyster to suit your style of travel, whatever that may be.

The Latest Oyster vacation packages

Price found within the past 48 hours. Click for updated prices.
The Americana Hotel

The Americana Hotel

2.5 out of 5
Downtown Ocean City
Price was $168, price is now $123 per person
$123
per person
Nov 14 - Nov 16
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Salisbury (SBY)
8.8/10 Excellent! (1,036 reviews)
The Americana was the perfect hotel for our weekend at Oceans calling. It was far enough away from the action to be quiet but also very accessible. Parking was great as was the ocean view. Would stay again

Reviewed on Sep 29, 2025

Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Save 100% on your flight
Price was $610, price is now $409 per person
$409
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (1,006 reviews)
Main ice machine is totally inoperable- dead motor. Elevator was broken one day. Toilet seat was broken at the mount screws.

Reviewed on Sep 25, 2025

The Sanderling

The Sanderling

4 out of 5
Save 100% on your flight
Price was $1,190, price is now $803 per person
$803
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip flight included
New York (JFK) to Norfolk (ORF)
8.8/10 Excellent! (512 reviews)
Staff was excellent!! 1st room not good. Needed maintenance and upkeep. Fan needed dusting. After dinner found ants in bed. Staff moved us to a different room which was better maintained but unfortunately it didn’t have the ocean view. Beach was beautiful loved the chairs and umbrellas provided. Neat fire pits area. For the costs per night I expect better rooms. Staff surprised me with bottle of champagne and a heartfelt note for my special birthday. It was a nice surprise.

Reviewed on Sep 28, 2025

John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Save 100% on your flight
Price was $566, price is now $385 per person
$385
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
9/10 Wonderful! (1,744 reviews)
No but i work all week so i walk there after work

Reviewed on Sep 29, 2025

Hilton Norfolk The Main

Hilton Norfolk The Main

4 out of 5
Downtown Norfolk
Save 100% on your flight
Price was $1,549, price is now $1,104 per person
$1,104
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
9/10 Wonderful! (1,002 reviews)
My only criticism is it was a little loud on Friday night

Reviewed on Sep 22, 2025

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Discover the most popular places to visit in Oyster

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Cape Charles Beach

Why not spend a carefree afternoon at Cape Charles Beach during your travels in Cape Charles? Wander the parks or discover the sunsets in this relaxing area.

Cape Charles Beach
Your secret's safe with me #estuary #loveva #wetlands #landschaft #getoutside #fishingboat #float #livefolk #thecreativephotos #treasures_and_nature

Eastern Shore of Virginia National Wildlife Refuge

Explore the great outdoors at Eastern Shore of Virginia National Wildlife Refuge, a lovely green space in Cape Charles. Wander the beautiful beaches in this relaxing area.

Eastern Shore of Virginia National Wildlife Refuge

Kiptopeke State Park

You can take time to visit Kiptopeke State Park during your travels to Cape Charles. Wander the beautiful beaches in this relaxing area.

Kiptopeke State Park

Oyster Hotel Deals

Shore Stay Suites

Shore Stay Suites

2 out of 5
26406 Lankford Hwy, Cape Charles, VA
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $159 total per night from Sep 30 to Oct 1
$159 total
Sep 30 - Oct 1
Total with taxes and fees
8.2/10 Very Good! (627 reviews)
"We were allowed to enter our room a little earlier than check-in. Thank you. We were pressed for time and this surly helped."

Reviewed on Sep 23, 2025

Shore Stay Suites
Hampton Inn & Suites Exmore - Eastern Shore

Hampton Inn & Suites Exmore - Eastern Shore

2.5 out of 5
4129 Lankford Hwy, Exmore, VA
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $103 total per night from Oct 6 to Oct 7
$103 total
Oct 6 - Oct 7
Total with taxes and fees
8.2/10 Very Good! (1,014 reviews)
"Property is conveniently located off the highway and is clean and quiet. The staff here is always wonderful, a shout out to Brenda, who went out of her way to make sure we had a room that met our needs. We love staying here., and will do so every time we’re in the area."

Reviewed on Sep 19, 2025

Hampton Inn & Suites Exmore - Eastern Shore
Holiday Inn Express & Suites Exmore - Eastern Shore by IHG

Holiday Inn Express & Suites Exmore - Eastern Shore by IHG

2.5 out of 5
3446 Lankford Hwy, Exmore, VA
Fully refundable
$91 nightly
The price is $101 total per night from Oct 12 to Oct 13
$101 total
Oct 12 - Oct 13
Total with taxes and fees
8.2/10 Very Good! (757 reviews)
"Staffer at the front desk, was very courteous and friendly"

Reviewed on Sep 23, 2025

Holiday Inn Express & Suites Exmore - Eastern Shore by IHG
See all 384 properties in Oyster
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.

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Frequently asked questions

How much does an Oyster vacation package cost?
Offering excellent value package deals from $123 on Expedia, you'll be thrilled with how little a vacation to Oyster costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Oyster?
December, January and February are great times to look for cheap Oyster vacation packages. Opting to travel in quieter periods means you can usually find reduced prices on hotels and flights.
How many days is enough for Oyster?
Generally, a handful of days is enough to see the top attractions during your Oyster vacation. However, if you prefer to have more time to unwind or go on day tours, think about extending your trip.
How to find the best Oyster package deals?
Use Expedia's filter tool to find some terrific Oyster package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Oyster package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book an Oyster vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll generally land a better deal than booking each component individually. And you'll still get the flexibility to create a customized Oyster vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Oyster?
If you're planning an impromptu Oyster getaway, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can find awesome deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Oyster vacation packages?
Secure your dream trip to Oyster with Expedia's Book Now, Pay Later vacations. No need to save like crazy or wait for payday — we've joined forces with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans let you spread the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's a breeze to stay on budget and snap up bargains before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.