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Compare 525 Vacation Homes in Owings with updated reviews, rates, and availability.

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
9.6 out of 10, Exceptional, (53)
"Great location, a beautiful home, very clean. The host communicated well and responded immediately. I would highly recommend it to others! If visiting, we would like to stay there again! Thank you!"
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
10.0 out of 10, Exceptional, (5)
"This property is a gem! Close to everything but without too much hustle or bustle! Great amenities. Kimberley is very easy to work with and graciously accommodated my need for late check out. Parking is private and off street!"
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (26)
"Great house and location. Very family friendly! "
The price is AED 1,010
AED 1,892 total
includes taxes & fees
26 Sep - 27 Sep
Beautiful Waterfront Retreat in Cambridge!
3bd Family-sized house, 5 minutes to National park, 12 minutes to the Capital.
9.8 out of 10, Exceptional, (7)
"We had 6 adult family members ranging in age from 24 to 93. Your property was everything you said it would be and more. The cleanliness and furnishings provided were top notch. The attention to detail with home accents, finishings, appliances, and specialty beds and toilet were all extras that translated to bonuses for us. The kitchen spices, chilled water, and coffees provided were a nice touch. The seating was a bit tight for 6 adults,and the high top table was not as comfortable for a couple...
3bd Family-sized house, 5 minutes to National park, 12 minutes to the Capital.
Walk to Everything House
10.0 out of 10, Exceptional, (69)
"This home was the perfect place for us to stay. Check-in was easy. The home was clean and well-furnished with lots of space for our family. We loved the four-poster beds. There is a lovely table and chairs to sit outside. The location is convenient for walking downtown to many shops and restaurants."
Walk to Everything House
Blocks to the Boardwalk!
9.8 out of 10, Exceptional, (31)
"We had fun"
Blocks to the Boardwalk!
Waterfront Cottage on the Eastern Shore
9.6 out of 10, Exceptional, (7)
"We rented the house for the weekend and to host a surprise birthday party. We had the party right at the beach and the host/concierge were able to help us with everything we needed. They really went out of their way for us, and it made a huge difference in the party’s success! Plus, you can’t beat the view and the Chesapeake Bay sunsets !!"
The price is AED 1,282
AED 3,008 total
includes taxes & fees
4 Oct - 5 Oct
Waterfront Cottage on the Eastern Shore
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (96)
"We took a quick weekend getaway to Annapolis. It was our first time there and we loved it. The location of the house is perfect. We were so close to the bay with tons of restaurants nearby. It was a quiet neighborhood though so we didn’t feel like we were in a party scene. The house was so clean. The pool was huge (bigger than expected), and the host went above and beyond. Liz was an excellent communicator. She had more than enough essentials at the house that made our stay so relaxing. I felt...
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (29)
"Perfect for a 3 day visit! "
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Dollhouse in Central Historic St Michaels
9.6 out of 10, Exceptional, (44)
"This is a lovely historic home that is close to town. It's nicely decorated, has a screened deck out back, and makes for a comfortable stay."
Dollhouse in Central Historic St Michaels
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
9.6 out of 10, Exceptional, (39)
"I was very impressed with this property. It's a cute little house that was comfortable for our group of 6. It was at a great location, too. The owner was quick to respond to my questions. If we visit North Beach again, I will definitely book here again."
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
10.0 out of 10, Exceptional, (89)
"It was nice to get outside DTA and see another part of Annapolis. 15 minutes from DTA it was quiet and beautiful small cottage perfect for our family. The home was clean and designed well. We would stay again. Thank you!!!"
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
Nautical charmer near the City Dock with open layout, W/D, & AC
10.0 out of 10, Exceptional, (5)
Nautical charmer near the City Dock with open layout, W/D, & AC
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
2.5 star property
10.0 out of 10, Exceptional, (4)
"Cannot recommend enough! Lauren was so sweet and accommodating. The home is gorgeous and filled with so much charm. Perfect location. An absolute 10/10! "
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Charming 3-bedroom house in Annapolis ⚓️🛥️⛵️ on the Chesapeake Bay
8.0 out of 10, Very Good, (1)
"The house was quiet, cozy and fit our needs perfectly. The location was convenient for our trips to and from DTA. Our host, Abber was available for any questions we had and made our stay enjoyable. "
Charming 3-bedroom house in Annapolis ⚓️🛥️⛵️ on the Chesapeake Bay
Pet-Friendly Annapolis Home: Walk to Beach!
Pet-Friendly Annapolis Home: Walk to Beach!
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (198)
"While the cottage may have some of the historic/ older quirks, it is a wonderful (and beautiful ) property that we would highly recommend! We loved the walk-ability to downtown Annapolis and the Naval Academy. Despite its close location, it’s quiet at night lending to a good nights sleep 😊. The owner provided us some great insight on the location as well. "
Directly Across from Gate One & Steps from the Waterfront
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (47)
"Great house qoth ocean view"
Charming Annapolis WaterVIEW Home
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, (14)
"Amazing time with friends and family at this property. I just need to remember to buy more bug spray haha. Regardless though- it was worth it"
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
3 Story Stunner in Murray Hill <1 mile from USNA!
10.0 out of 10, Exceptional, (16)
"Beautiful house in great location! It was the perfect house for our annual trip (group of 10 friends) to Annapolis! It was spacious, clean, and well equipped with everything you need in a rental house. Eric and team were super responsive and accommodating! Highly recommended! Will definitely come back next year!"
The price is AED 709
AED 3,166 total
includes taxes & fees
24 Sep - 25 Sep
3 Story Stunner in Murray Hill <1 mile from USNA!
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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.
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Other property types in Owings

Rockhold Creek Cottage, Water Front, Vacation Home, Docks
9.8 out of 10, Exceptional, (83)
"The house was clean and comfortable. Walking distance to a local restaurant. Screened porch was great for watching the sunrise in the morning and the boats coming in and out of harbor "
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Waterfront Cottage on the Eastern Shore
9.6 out of 10, Exceptional, (7)
"We rented the house for the weekend and to host a surprise birthday party. We had the party right at the beach and the host/concierge were able to help us with everything we needed. They really went out of their way for us, and it made a huge difference in the party’s success! Plus, you can’t beat the view and the Chesapeake Bay sunsets !!"
The price is AED 1,282
AED 3,008 total
includes taxes & fees
4 Oct - 5 Oct
Waterfront Cottage on the Eastern Shore
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (47)
"Great house qoth ocean view"
Charming Annapolis WaterVIEW Home
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.