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Top Holiday Rentals in Owings

Cozy place close to the city dock
10.0 out of 10, Exceptional, (55)
"We enjoyed our 2 nights at Cozy Place Close to the docks. Easy access and personalized connection with Nathalie were appreciated! We enjoyed the French and sail boating themes in the apartment, aligned the Annapolis maritime history! The docks are a short drive and old Town Annapolis was pleasant and historical! We recommend Cozy Place to others!"
Cozy place close to the city dock
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, (21)
"Everyone really loved the house and the location. The pool was great"
Pool and Bay Views on wrap around deck in Kent Island
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (181)
"Prime location!"
Directly Across from Gate One & Steps from the Waterfront
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (187)
"The cottage is fully stocked, clean, and cozy. We thoroughly enjoyed sitting on the deck and watching all the wildlife."
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, (4)
"We extremely enjoyed our stay. The house was beautiful, kitchen was well equipped and the view was spectacular, especially with the Eagles that have nested on the 32 acre property. However was disappointed in the fact that the fire places were not in working conditions and rooms should have been number. We enjoy kayaking up and down the bay and taking it all in. I would definitely stay again."
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, (44)
"This house was perfect for a group of friends celebrating a 50th birthday! The house was so clean and well cared for! The front porch and outdoor backyard space provided even more room for us to gather together. We will be back!"
Recently Renovated Annapolis Home - Conveniently Located
Chesapeake Houseboat Getaway on Kent Island, Maryland
10.0 out of 10, Exceptional, (7)
"My husband and I and our dog had a lovely getaway on "Julia's Arc". This was our first time on a Houseboat and it was a wonderful experience. So much light! And the movement of the boat was just enough to be comforting. The home was very clean and beautifully adorned with great attention to detail. Julia, the host, was very responsive and very generous in doing all she could to make our trip as comfortable and pleasurable as possible. The views over the water were gorgeous and we really...
Chesapeake Houseboat Getaway on Kent Island, Maryland
Waterfront Cottage on the Eastern Shore
9.4 out of 10, Exceptional, (3)
"Very much as pictured in ad. Convenient to we did venue we were attending"
The price is £909
per night
17 Jun - 18 Jun
Waterfront Cottage on the Eastern Shore
Clean&Cozy English Basement
9.6 out of 10, Exceptional, (18)
"I thoroughly enjoyed my stay. The property was clean and even smelled nice! NJay was a great host and easy to communicate with. I stayed for a little over 2 weeks by myself and felt safe. The parking seems a bit obscure but it was very convenient. The neighbourhood is quiet and private and not far from most key spots in the DMV."
Clean&Cozy English Basement
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (43)
"Beautiful house and views. Amenities and grounds were great. Loved the playground and beach. Peace and quiet at its finest in nature."
The price is £666
per night
27 Jun - 28 Jun
Charming Annapolis WaterVIEW Home
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (19)
"We have nothing but great things to say about Adam and his beautiful home! He was so accommodating and the home was comfortable and spacious for our family of 5! Couldn’t have had a better experience :)"
The price is £196
per night
17 Jun - 18 Jun
Relax on Kent Island in 3 Bedroom Home w/Waterview
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (106)
"This is our third visit. You can’t have a better location! We love St. Michael’s and this historical cottage."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
10.0 out of 10, Exceptional, (25)
"I chose to stay at this property for the duration of my wedding weekend. It was really great to be able to spend that extra time with family all together! Getting ready at the house, rather than a hotel was also really nice because we had much more room to space out. The make up artist and hair stylist also complimented the ample natural light and space to work. The pool and hot tub were beautiful! The only downside was a lack of curtains in the master bedroom. The sunrise is beautiful but...
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Maryland Vacation Rental w/ Private Pool & Dock
10.0 out of 10, Exceptional, (4)
"Had a great time fishing from the dock while we got out of the city for a weekend."
Maryland Vacation Rental w/ Private Pool & Dock
Gorgeous dog-friendly retreat w/ fireplace, patio, & firepit - centrally located
10.0 out of 10, Exceptional, (6)
"This location was extremely clean and perfect for a weekend get away. It’s located not even 2 miles from downtown Annapolis. 10/10 would recommend"
Gorgeous dog-friendly retreat w/ fireplace, patio, & firepit - centrally located
Indulge or be still near Naval Academy/ Annapolis
9.2 out of 10, Wonderful, (9)
"Great place, super neighborhood!"
Indulge or be still near Naval Academy/ Annapolis
Entire 3-Bedroom Retreat Free Parking & Amenities
Entire 3-Bedroom Retreat Free Parking & Amenities
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (39)
"It was clean and had everything we needed. We had a very comfortable stay. There are one or two steps between many of the rooms so keep that in mind."
The Blue Crab Beach House - Free beach passes
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (18)
"We enjoyed our trip, the house was fully equipped and had all the comforts you could need. The water view, watching the birds, the kayak, the dock at sunrise, were our favorite things. We look forward to coming back sometime soon."
The price is £406
per night
18 Jun - 19 Jun
Beautiful Waterfront Retreat in Cambridge!
Bay View Studio Apartment
10.0 out of 10, Exceptional, (26)
"Chespeake Bay waterfront with beautiful views. Very close to Annapolis Sailing School, as well as Annapolis itself."
Bay View Studio Apartment
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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.

Owings Holiday Rental Travel Info

Other types of properties in Owings you may be interested in

Harborside Hotel
3.0 star property
8.8 out of 10, Excellent, (1004)
"Staff was nice, very keen on customer service, the area around it and the people who hang out in the area near the hotel are sketchy and you would wish you had armed security with you. "
The price is £128
per night
2 Jul - 3 Jul
Harborside Hotel
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1623)
"It was our first stay in Annapolis. We were very impressed with the condition of the hotel. "
The price is £140
per night
30 Jun - 1 Jul
Historic Inns of Annapolis
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
2.5 star property
6.6 out of 10, (1280)
"Good "
The price is £96
per night
16 Jun - 17 Jun
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
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.

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, apart-hotels, 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 favorite 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 depends 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 £196 per night. Entering your travel dates in the search wizard you might find 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?

Pool and Bay Views on wrap around deck in Kent Island: This holiday home rental outside of Owings offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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.

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