Owings Holiday Rentals

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Holiday Rentals in Owings

Floating 2 bed 2 bath condo stunning views of the bay

2.0 star property
Stevensville
6.4 out of 10, (7)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
United States
Natalia F.
Floating 2 bed 2 bath condo stunning views of the bay

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Stevensville
10.0 out of 10, Exceptional, (15)
"The property is excellent for entertaining and family gatherings. Everything was clean and tastefully appointed."
United States
Kerrith D.
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Historic District
9.4 out of 10, Exceptional, (19)
"Great place, excellent location!"
United States
Joseph C.
The price is AU$1,815
includes taxes & fees
8 Dec - 9 Dec
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Historic District
10.0 out of 10, Exceptional, (33)
"Our stay was AMAZING! Perfect location, plenty of space! Will definitely book again when we have a larger group like we did for PPW! "
United States
Charolene P.
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Waterfront Getaway, Dock Your Boat & Play!

Edgewater
10.0 out of 10, Exceptional, (3)
"Great place to stay. It is clean, comfortable, and not lacking convenience.Quick communication with the host. We would definitely recommend!"
United States
Daniel K.
Waterfront Getaway, Dock Your Boat & Play!

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Tracys Landing
9.8 out of 10, Exceptional, (50)
"Our week at Jacob's property was excellent. It was the perfect location for a family getaway, and Jacob was helpful and responsive."
United States
Brett F.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Wonderful villa in National in Harbor next to Gaylord Conference - 6 bedrooms

Fort Washington
9.4 out of 10, Exceptional, (3)
"Beautiful home will definitely be returning!"
United States
Yvenson G.
The price is AU$1,093
includes taxes & fees
8 Dec - 9 Dec
Wonderful villa in National in Harbor next to Gaylord Conference - 6 bedrooms

Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More

Mechanicsville
10.0 out of 10, Exceptional, (7)
"My first thought was "gorgeous", when i walked through the door. This was just the weekend I needed. The screened in porch was relaxing. Be ready to take pictures of the sunrise! "
United States
Lisa R.
Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Saint Michaels
9.6 out of 10, Exceptional, (124)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
United States
Meghan K.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Charming garden row home, easy 4 block walk to the heart of Annapolis.

Historic District
10.0 out of 10, Exceptional, (125)
"Great location, very clean house, wonderful stay"
United States
Kathryn O.
Charming garden row home, easy 4 block walk to the heart of Annapolis.

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cambridge
10.0 out of 10, Exceptional, (16)
"Well equipped and super clean; great place!"
United States
Steve S.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Port Republic
10.0 out of 10, Exceptional, (181)
"We thoroughly enjoyed our stay in this kitschy, cool, rustic cabin with a million-dollar view. Communing with the ospreys, hummingbirds and the bald eagle who perched numerous times on a nearby tree was an added bonus. And, the owner may be the most friendly/helpful we’ve ever rented from. We hope to be back some day. Thanks!"
United States
Brennan H.
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

2.5 star property
Murray Hill
10.0 out of 10, Exceptional, (34)
"Absolutely perfect! Will stay again!!"
United States
Brian
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

Edgewater/Mayo Gateaway w/ Hot Tub

Edgewater
9.8 out of 10, Exceptional, (25)
"Very clean, had everything we needed for our stay!"
United States
Jackie R.
The price is AU$1,088
includes taxes & fees
5 Jan - 6 Jan 2026
Edgewater/Mayo Gateaway w/ Hot Tub

Million Dollar View of the Chesapeake Bay

Deale
9.8 out of 10, Exceptional, (130)
"Absolutely beautiful and peaceful location. Everything was appreciated- the games for lazy evenings, the crab pots, the comfortable beds and living spaces. Stunning view!"
United States
Michelle D.
Million Dollar View of the Chesapeake Bay

Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

Stevensville
10.0 out of 10, Exceptional, (57)
"It’s a fantastic property!! Perfect for a getaway weekend. Everything was as described. A great place to stay home and enjoy all the amenities."
United States
Kurt H.
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Port Republic
10.0 out of 10, Exceptional, (124)
"Well, what a great time we had at this house the house is exactly as advertised, tidy, clean, comfortable, everything close. The view was beautiful, our vacation was amazing. Alicia was very responsive to any question that we had. We definitely would rent again!"
United States
Misael A A.
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

St. Michaels
9.8 out of 10, Exceptional, (45)
"Wonderful home in excellent location!!"
United States
Sydney S.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Family and Pet-Friendly, Waterfront with Pier

Cambridge
10.0 out of 10, Exceptional, (265)
"The property, house and amenities were exactly as described. Absolutely gorgeous views second only to the hospitality extended by Rob and Clarissa!"
United States
Tom K.
Family and Pet-Friendly, Waterfront with Pier

Stunning Water Front Home with Private Dock and Beach and Sunsets

Lusby
10.0 out of 10, Exceptional, (27)
"Great place. Would definitely stay here again. "
United States
Joshua M.
Stunning Water Front Home with Private Dock and Beach and Sunsets
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.
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Top Owings Hotel Reviews

Find out more about Owings

Everything you need to know about Owings holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Owings holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Owings holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Owings holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Owings. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Owings holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Owings holiday rentals we have selected for you start as low as AU$1,088 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Owings rentals

At Expedia, we put the best Owings holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Owings rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Owings holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Owings. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Owings?

Yes, there are holiday rentals close to the most popular sights in Owings, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Owings has to offer?

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA: This holiday home rental outside of Owings is located in the city centre, and offers a selection of games, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What’s there to see and do in Owings?

While exploring the area, visit family-friendly sights like Chesapeake Beach Water Park, or get outside and enjoy nature at Patuxent River. In the wider area, you’ll find Fridays Creek Winery and Rod n Reel Charter Fishing.

What’s a holiday rental in Owings like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Owings. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for family trips.