Bayside Vacations from $777

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Your Bayside Vacation

Bayside is calling your name! Whatever type of break you have in mind, get ready to discover the best of this neighborhood with a Bayside vacation package. When it's time to explore the sights, you'll find plenty of big-name attractions nearby including Frontier Town Water Park and Golf, Eagles Landing Golf Course and Eagle s Landing. Visit one, two (or even all!) during your trip to Bayside. Expedia will help turn your ideal Bayside vacation into reality, no matter your travel plans or budget.

The Latest Bayside Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

Downtown Ocean City
$777
per person
Dec 25 - Dec 30
found 4 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Salisbury (SBY)
9/10 Wonderful! (3,946 reviews)
We found our room to be surprisingly spacious, very clean, and comfortable; however, the kitchenette/bathroom areas were a bit dated. The property location was excellent and there were restaurants and a pool within the property. The common areas inside the hotel and the outdoor space at the front of the hotel were adequate, but guests were somewhat disrespectful, leaving their trash, not replacing chairs after their use, etc... The staff was pleasant enough when checking-in and helpful when we had a question but were ignoring simple tasks like straightening up the common areas when time allowed. Although this was a little off-putting, we would return if the opportunity presented itself.

Reviewed on Oct 19, 2026

Beach Walk

Beach Walk

Downtown Ocean City
$1,808
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
7.6/10 Good! (126 reviews)
We never slept here. The room was incredibly dirty. Stained sheets, stained carpet, god only knows what on the walls in the bathroom. The table and chairs were a table that folded out from the wall with a stick underneath. The chairs were two rusty folding chairs. The blinds in the window were busted up and only covered half the window. I honestly don’t know how they’ve not been shut down. We quickly found another hotel.

Reviewed on Oct 13, 2026

Plantation Lakes Townhouse

Plantation Lakes Townhouse

Save 100% on your flight
$3,826
per person
Dec 25 - Dec 30
found 4 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Salisbury (SBY)
No reviews
Wingate by Wyndham Salisbury MD Airport North

Wingate by Wyndham Salisbury MD Airport North

$899
per person
Dec 25 - Dec 30
found 4 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Salisbury (SBY)
8.2/10 Very Good! (1,002 reviews)
Great job and great work from the crew

Reviewed on Oct 16, 2026

Dagsboro Retreat

Dagsboro Retreat

$1,081
per person
Dec 25 - Dec 30
found 4 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Salisbury (SBY)
10/10 Exceptional! (1 review)
I loved it

Reviewed on Jul 17, 2026

Where to stay in Bayside

Find the best Bayside areas and neighborhoods for the activities you enjoy most. Learn more about Bayside
A beach with a clear sky and calm sea.

Ocean Pines

3 out of top 10 points of interest in this area

Boasting the largest concentration of retirees on the Eastern Shore, this community offers the Ocean Pines Golf Club, designed by Robert Trent Jones, and 13 parks, including White Horse Park. Enjoy golfing, park visits, and a peaceful atmosphere.

A sunset over a marshy landscape with a calm water body reflecting the sky.

Assateague Pointe

While Assateague Pointe isn't home to many top sights, Frontier Town Water Park and Golf and Ocean City Beach are some notable places to visit nearby.

A wetland landscape with numerous small ponds surrounded by dense green vegetation.

Glen Riddle

While visiting Glen Riddle, you might make a stop by sights like Isle of Wight Bay and GlenRiddle Golf Club.

A sunset over a calm lake with reflections of trees and the sky.

Downtown Berlin

Downtown Berlin might not have many top sights, but Casino at Ocean Downs and Frontier Town Water Park and Golf are two attractions nearby that you can check out.

Bayside Hotel Deals

Castle in the Sand

Castle in the Sand

3701 Atlantic Avenue Ocean City MD
$84 nightly
$94 total
Oct 22 - Oct 23
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
"Great front office staff. Made me feel welcome from the get-go. Nice overall set-up with a restaurant on the premises and an outdoor bar with live music."

Reviewed on Oct 20, 2026

Castle in the Sand
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

2100 N Baltimore Ave Ocean City MD
Fully refundableReserve now, pay when you stay
$64 nightly
$72 total
Nov 1 - Nov 2
Total with taxes and fees
9/10 Wonderful! (3,964 reviews)
"We found our room to be surprisingly spacious, very clean, and comfortable; however, the kitchenette/bathroom areas were a bit dated. The property location was excellent and there were restaurants and a pool within the property. The common areas inside the hotel and the outdoor space at the front ..."

Reviewed on Oct 19, 2026

Grand Hotel Ocean City Oceanfront
Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG

1701 Atlantic Avenue Ocean City MD
Fully refundable
$90 nightly
$101 total
Nov 19 - Nov 20
Total with taxes and fees
Holiday Inn & Suites Ocean City by IHG
See all 9,318 properties in Bayside
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.

Things to do

Boat Tours of Chincoteague & Assateague - Wild Ponies

Boat Tours of Chincoteague & Assateague - Wild Ponies

$78
per adult
Boat Tours of Chincoteague & Assateague - Wild Ponies
Ocean City: Ripley's Believe It or Not! + Mirror Maze

Ocean City: Ripley's Believe It or Not! + Mirror Maze

$28
per adult
Ocean City: Ripley's Believe It or Not! + Mirror Maze
Chincoteague and Assateague Island Boat Tour with Capt. John

Chincoteague and Assateague Island Boat Tour with Capt. John

$95
per adult
Chincoteague and Assateague Island Boat Tour with Capt. John
See all activities in Berlin
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.