Owings Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Owings

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
The price is 2.370.577 ₫ per night from 7 Jul to 8 Jul
2.370.577 ₫
3.601.644 ₫ total
7 Jul - 8 Jul
includes taxes & fees
9/10 Wonderful! (1,877 reviews)
"I loved the building. It’s in a lovely spot a block from the bay so shops and restaurants are right out the front door. The building I stayed in was terrific. The only bummer, was my room was quite small, so I would advise not staying in room 1408. It was the smallest room I’ve ever stayed in. I ..."

Reviewed on 29 Jun 2026

Historic Inns of Annapolis
Harborside Hotel

Harborside Hotel

3 out of 5
6400 Oxon Hill Road Oxon Hill MD
Fully refundableReserve now, pay when you stay
The price is 3.999.013 ₫ per night from 26 Jul to 27 Jul
3.999.013 ₫
4.519.069 ₫ total
26 Jul - 27 Jul
includes taxes & fees
8.8/10 Excellent! (1,780 reviews)
"Easy parking"

Reviewed on 30 Jun 2026

Harborside Hotel
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is 2.502.998 ₫ per night from 5 Jul to 6 Jul
2.502.998 ₫
2.853.418 ₫ total
5 Jul - 6 Jul
includes taxes & fees
8.6/10 Excellent! (1,020 reviews)
"The room is as very musty smelling. The beds were way too soft. The ice makers didn’t work (one worked on one floor). When I asked to stay an extra night their price was even higher than expedias price. Just not impressed."

Reviewed on 30 Jun 2026

DoubleTree by Hilton Hotel Annapolis
See all 1,307 properties in Owings
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.

Stay near popular Owings attractions

Fridays Creek Winery

This 1920s tobacco barn turned winery showcases Calvert County's agricultural heritage through local wines. Sample vintages on the patio while enjoying art displays and occasional live music.
See properties

Frequently asked questions

How much does an Owings holiday package cost?
You can snap up a holiday package to this top destination on Expedia. But how much your holiday to Owings costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Owings?
Travel in the off-peak season and you're likely to score cheap Owings holiday packages. Keep in mind that school holiday periods and local festivals and events can impact prices, so do your research before you go.
How many days is enough for Owings?
With a well-organised travel plan, you can easily tick off the main Owings sights in a few days. But if you want to discover hidden spots or go on day trips, think about booking your Owings holiday for longer.
How to find the best Owings package deals?
Begin your search for an Owings package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal Owings package deal straight away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Owings escape underway.
Is it cheaper to book an Owings holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component separately. And you'll still enjoy the freedom to create a customised Owings holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday package to Owings?
Enjoy amazing discounts by reserving your flights early with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for an impromptu Owings holiday.
How to plan a trip to Owings?

  1. Choose your dates: What you'd like to do in Owings and your preferred season will help you decide when to travel.
  2. Calculate your budget: Make sure you have enough money to pay for everything from meals and transportation to experiences and flights. Your accommodation will probably be the biggest expense during your trip to Owings.
  3. Set the duration of your trip: Start by compiling a list of the activities and attractions you want to experience in Owings. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a customised Owings holiday package.

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