Oyster Vacations from $411

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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.
Pamlico Station Edgecamp

Pamlico Station Edgecamp

2 out of 5
Save 100% on your flight
Price was $776, price is now $411 per person
$411
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
9.4/10 Exceptional! (18 reviews)
The hotel was perfect and spacious. The only thing was when it rained 🌧 🙃 we got wet to the entrance to our room because of the location...maybe adding a overhang to help with not getting wet.

Reviewed on Oct 12, 2025

Sanderling Resort Residences

Sanderling Resort Residences

4 out of 5
Save 100% on your flight
Price was $2,130, price is now $1,330 per person
$1,330
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
No reviews
Ocean 27

Ocean 27

2.5 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $2,440, price is now $1,603 per person
$1,603
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
6.4/10 (1,116 reviews)
Close to beach. Ground level beach access rooms. Grounds need to be picked-up a bit. Centrally located along boardwalk.

Reviewed on Oct 13, 2025

The Sanderling

The Sanderling

4 out of 5
Save 100% on your flight
Price was $778, price is now $545 per person
$545
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.8/10 Excellent! (519 reviews)
It was a nice stay though the room was not what you would expect at the price point. Two of the walls were in need of repairs, windows needed some cleaning, coffee in room was a kettle with tea like bags of coffee that tasted awful, and bathroom had pretty much nothing in it.

Reviewed on Oct 25, 2025

The Atrium Resort, Virginia Beach by Vacatia

The Atrium Resort, Virginia Beach by Vacatia

3.5 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $806, price is now $565 per person
$565
per person
Jan 23 - Jan 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)
8.2/10 Very Good! (1,476 reviews)
We love the homey feeling of the room. The whole apartment aka hotel room was the best. Can't wait to cone back during the warmer season. Thanks for making my birthday

Reviewed on Oct 12, 2025

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Discover the most popular places to visit in Oyster

Cape Charles Beach

Cape Charles Beach

4.5/5(31 reviews)

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

4.5/5(14 reviews)

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

4/5(27 reviews)

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

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
$87 nightly
The price is $97 total per night from Dec 13 to Dec 14
$97 total
Dec 13 - Dec 14
Total with taxes and fees
8.2/10 Very Good! (774 reviews)
Professionalism, cleanliness and overall level of service

Reviewed on Nov 6, 2025

Holiday Inn Express & Suites Exmore - Eastern Shore by IHG
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
$83 nightly
The price is $93 total per night from Dec 12 to Dec 13
$93 total
Dec 12 - Dec 13
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
We were in need of a hotel that took dogs, we were extremely pleased with how pet friendly this hotel was. The free breakfast, especially the fresh waffle baker was a very pleasant surprise.

Reviewed on Nov 10, 2025

Hampton Inn & Suites Exmore - Eastern Shore
Shore Stay Suites

Shore Stay Suites

2 out of 5
26406 Lankford Hwy, Cape Charles, VA
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $129 total per night from Nov 15 to Nov 16
$129 total
Nov 15 - Nov 16
Total with taxes and fees
8.2/10 Very Good! (640 reviews)
The room was clean and the staff was very nice

Reviewed on Nov 3, 2025

Shore Stay Suites
See all 386 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.

Find the Best Oyster Vacation Packages

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Frequently asked questions

How much does an Oyster vacation package cost?
Offering excellent value package deals from $411 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.