Preston Vacations

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Preston Hotel Deals

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd, Cambridge, MD
Fully refundableReserve now, pay when you stay
$185 nightly
The price is $210 total per night from Nov 23 to Nov 24
$210 total
Nov 23 - Nov 24
Total with taxes and fees
8.6/10 Excellent! (1,014 reviews)
The room was spotless. The staff were courteous and helpful. Fantastic hotel!

Reviewed on Oct 28, 2025

Hyatt Regency Chesapeake Bay
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundable
$107 nightly
The price is $118 total per night from Dec 7 to Dec 8
$118 total
Dec 7 - Dec 8
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
Basic room, clean and comfortable. Only complaint, it took 15 minutes to get hot water in the shower -- wasted a lot of water waiting. Good TV selection, too.

Reviewed on Oct 17, 2025

St Michaels Inn
Quality Inn & Suites Harrington - Milford

Quality Inn & Suites Harrington - Milford

2.5 out of 5
1259 Corn Crib Road, Harrington, DE
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $89 total per night from Nov 30 to Dec 1
$89 total
Nov 30 - Dec 1
Total with taxes and fees
7.6/10 Good! (1,017 reviews)
staff wasvery helpful

Reviewed on Oct 25, 2025

Quality Inn & Suites Harrington - Milford
See all 421 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 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.