Preston Vacations from $830

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The Latest Preston vacation packages

Price found within the past 48 hours. Click for updated prices.
Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Price was $978, price is now $830 per person
$830
per person
Mar 24 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
7.4/10 Good! (170 reviews)
Got better than what I expected for the price. Front desk ladies were happy & helpfully. Only thing that would be nice would be some type of dimmer lights for night, outlets near beds & softer beds. Will definately be staying here again! Full kitchen with full size fridge saved us $ not having to eat out. It's like a hotel sized condo.

Reviewed on Oct 1, 2025

Miramar Condominiums

Miramar Condominiums

2 out of 5
Downtown Ocean City
Price was $1,862, price is now $1,604 per person
$1,604
per person
Mar 24 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
9.4/10 Exceptional! (15 reviews)
Stayed in unit 505 and it was beautiful! We loved it!

Reviewed on Aug 23, 2025

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $963, price is now $842 per person
$842
per person
Mar 24 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
9/10 Wonderful! (3,316 reviews)
The only place we stay when we go to Ocean City. Great location, plenty of parking, friendly staff, good food, 2 arcade areas! On the boardwalk, far enough from the inlet crowds, but a nice walk. Great beach location & views.

Reviewed on Feb 1, 2026

Aloft Ocean City

Aloft Ocean City

3 out of 5
Midtown Ocean City
Price was $1,365, price is now $1,209 per person
$1,209
per person
Mar 24 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
9/10 Wonderful! (1,002 reviews)
Our room had a full kitchen which worked out great for enjoying a take-out dinner. It was very comfortable although looked a bit dated.

Reviewed on Jan 31, 2026

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
North Ocean City
Price was $955, price is now $876 per person
$876
per person
Mar 24 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
8.6/10 Excellent! (2,269 reviews)
Staff was friendly and helpful room was spacious

Reviewed on Feb 3, 2026

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Preston Hotel Deals

Stylish Home on the Choptank River (with Tidal Beach)

Stylish Home on the Choptank River (with Tidal Beach)

Preston MD
10/10 Exceptional! (45 reviews)
Everything was fabulous!

Reviewed on Jan 1, 2026

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Stylish Home on the Choptank River (with Tidal Beach)
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
Fully refundableReserve now, pay when you stay
$211 nightly
The price is $240 total per night from Feb 11 to Feb 12
$240 total
Feb 11 - Feb 12
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
Nice stay, but a little too crowded.

Reviewed on Jan 30, 2026

Hyatt Regency Chesapeake Bay
The Tidewater Inn

The Tidewater Inn

3 out of 5
101 E Dover St Easton MD
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $197 total per night from Feb 8 to Feb 9
$197 total
Feb 8 - Feb 9
Total with taxes and fees
8.8/10 Excellent! (846 reviews)
Beautiful historic but with nice mix-in of modern hotel. Friendly, professional staff. Great location. My wife and I had a fantastic stay.

Reviewed on Jan 13, 2026

The Tidewater Inn
See all 419 properties in Preston
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 Preston Vacation Packages

Preston Essential Information

Language
English
Currency
U.S dollars
Population
700

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Frequently asked questions

How much does a Preston vacation package cost?
Offering excellent value package deals from $830 on Expedia, you'll be thrilled with how little a vacation to Preston costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Preston?
You can typically find lower rates and greater availability in January, June and November. Check out our cheap Preston vacation packages and you could get some great off-season deals.
How many days is enough for Preston?
The ideal length of your Preston vacation depends on what you'd like to do. Typically, a few days to a week will give you plenty of time to visit all the major attractions and discover some hidden treasures along the way.
How to find the best Preston package deals?
Use Expedia's filters to help you find some tempting Preston package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for Preston package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Preston vacation as a package?
You can enjoy significant savings on your Preston break by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to view some great hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Preston?
If you're considering a spur-of-the-moment Preston vacation, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score amazing deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Preston vacation packages?
Jet off on your dream trip to Preston with our Book Now, Pay Later vacations. There's no need to save up or wait for your next payday — we've teamed up with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans allow you to spread the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to budget for your trip and snap up cheap deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.