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Compare 524 Vacation Homes in Owings with updated reviews, rates, and availability.

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Living room
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
9.6 out of 10, Exceptional, (53)
"Trent was a great host, communicative and helpful. We stayed for the Maryland Renaissance festival and it was a great location- about 15-20 minutes from the festival. We also went to DC which was about 30 minutes away. House was clean and spacious. Bring your own Keurig pods and shower products. "
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Grill no longer works
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
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Room
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
9.4 out of 10, Exceptional, (6)
"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
3bd Family-sized house, 5 minutes to National park, 12 minutes to the Capital.
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.
Charming Historic Townhouse Steps From USNA
Living area
Charming Historic Townhouse Steps From USNA
10.0 out of 10, Exceptional, (16)
"Very comfortable and light and bright. Close to all the cute shops and restaurants on Main Street and Maryland Ave. "
Charming Historic Townhouse Steps From USNA
Waterfront Cottage on the Eastern Shore
Exterior
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 SAR 1,309
SAR 3,072 total
includes taxes & fees
1 Oct - 2 Oct
Waterfront Cottage on the Eastern Shore
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Living Area
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
Walk to Everything House
Front of House
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
Relax at our 4-acre South River Waterfront with a Saltwater Pool near Annapolis
Pool
Relax at our 4-acre South River Waterfront with a Saltwater Pool near Annapolis
10.0 out of 10, Exceptional, (11)
"It was a beautiful and private setting for a family reunion."
Relax at our 4-acre South River Waterfront with a Saltwater Pool near Annapolis
Charming brick home with patio, WiFi, AC, & W/D - walk to everything
Charming brick home with patio, WiFi, AC, & W/D - walk to everything
8.6 out of 10, Excellent, (17)
"Loved this location as EVERYTHING is walkable - St John's college, USNA, the capitol and Main Street. One skinny parking place was appreciated and reasonable for a standard size vehicle (not super truck or SUV). Enjoyed the older character of the home and modern conveniences as well as small outdoor space that was very nicely landscaped with flowers. "
Charming brick home with patio, WiFi, AC, & W/D - walk to everything
1 block to Capital Bldg, Parking at Townhouse with multiple gathering spaces
Gather around the large dining room overlooking the living room.
1 block to Capital Bldg, Parking at Townhouse with multiple gathering spaces
10.0 out of 10, Exceptional, (22)
"The place was a perfect location to downtown Annapolis, beautifully decorated and very clean. We had a wonderful stay with long time friends. The only reason it is not a five star is that it listed on the property info that there were two parking passes. That was not the case. There was only one and we had 2 cars. We had to park our cars in lots in downtown, rather than the streets because it was parking with a residential pass only, and pay for the parking in the commercial lots. One of...
1 block to Capital Bldg, Parking at Townhouse with multiple gathering spaces
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
Private kitchen
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
Charming Annapolis WaterVIEW Home
3 covered balconies, a ground floor patio, and ceramic and propane grills.
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (47)
"Great house qoth ocean view"
Charming Annapolis WaterVIEW Home
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Exterior
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!
Beautiful Waterfront Retreat in Cambridge!
Exterior
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (26)
"Great house and location. Very family friendly! "
The price is SAR 1,032
SAR 1,920 total
includes taxes & fees
30 Sep - 1 Oct
Beautiful Waterfront Retreat in Cambridge!
Charming Cottage with Hot Tub 1 Block from the Bay
Marina
Charming Cottage with Hot Tub 1 Block from the Bay
10.0 out of 10, Exceptional, (7)
"Great property. Close to USNA but away from the craziness of town. House was adorable and very clean. The hot tub was a big hit. "
The price is SAR 1,032
SAR 2,189 total
includes taxes & fees
30 Sep - 1 Oct
Charming Cottage with Hot Tub 1 Block from the Bay
Dollhouse in Central Historic St Michaels
Front of House
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
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Amazing Location
Charming garden row home, easy 4 block walk to the heart of Annapolis.
10.0 out of 10, Exceptional, (106)
"Home is gorgeous, beautifully maintained and location is perfect near the Academy. We stayed to drop our son off for induction day, then came back for parents weekend and plan to stay once a month to visit. Owner is responsive and professional. We highly recommend this property. "
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Adorable waterside cottage with pool Beach community
Exterior
Adorable waterside cottage with pool Beach community
9.4 out of 10, Exceptional, (39)
"Neighborhood was cute, perfect spot to relax. Pool was awesome. Kitchen was large and had a great veiw. It was just what we needed to get away."
Adorable waterside cottage with pool Beach community
Bennett House (entire):Haven in Historic Annapolis
First floor kitchen
Bennett House (entire):Haven in Historic Annapolis
10.0 out of 10, Exceptional, (9)
"Great option for a larger group of couples! House has Annapolis charm and lots of character! Very comfortable and lots of walkable fun!"
Bennett House (entire):Haven in Historic Annapolis
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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
Grill no longer works
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
Relaxing Waterfront Cottage Near St Michaels, Maryland
Charming Cottage on a quite creek of the Chesapeake Bay with private pool.
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (212)
"As always our stay was amazing from kayaking, bird watching, sunsets. The cove is a special place."
Relaxing Waterfront Cottage Near St Michaels, Maryland
Directly Across from Gate One & Steps from the Waterfront
Private rear courtyard
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
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.