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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

Compare 657 Vacation Homes in Owings with updated reviews, rates, and availability.

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (209)
"Perfect Location - Easy Process - Comfortable Home!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Property grounds

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

9.8 out of 10, Exceptional, (70)
"Great for the price. The motel of VRBOs would be my best description. Plenty of space for what we needed though and no issues during our stay. "
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
The Blue Crab Beach House - Free beach passes
Miscellaneous

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (51)
"The Blue Crab Beach House was perfect for my wife and I and our dog. Very comfortable with a great backyard space for our dog. We loved the location - it’s just a short walk to restaurants and the bay. Very enjoyable stay and we hope to return."
The Blue Crab Beach House - Free beach passes
Modern Waterfront House with Amazing views!
Fridge, microwave, oven, stovetop

Modern Waterfront House with Amazing views!

Modern Waterfront House with Amazing views!
Historic Annapolis Home 1.5 blocks from center of town.
Interior

Historic Annapolis Home 1.5 blocks from center of town.

10.0 out of 10, Exceptional, (34)
"Great wx and weekend visit to the Naval Academy. Walking distance to everything and neighborhood was a nice getaway from main street "
Historic Annapolis Home 1.5 blocks from center of town.
Luxurious, ideal for large groups, and two families + free parking
Fridge, microwave, oven, stovetop

Luxurious, ideal for large groups, and two families + free parking

9.8 out of 10, Exceptional, (37)
"Me and my family (9 total) came to visit our family up in DC! The stay was great! Everything you needed was already in the home. There is plenty of space for everyone! The home was clean as well. The host is easy to get in contact with as well. It was also easy to get uber to come to the house to get us when we wanted to go out too! It’s about a 15 minute drive from downtown DC. We will be staying here again. "
Luxurious, ideal for large groups, and two families + free parking
Sweet Bamboo Beach Cottage
Fridge, microwave, oven, stovetop

Sweet Bamboo Beach Cottage

9.8 out of 10, Exceptional, (70)
"Couldn’t be happier with our stay. The house was exactly as pictured. Neighborhood was quiet with a small town feel. Most of the major appliances appeared relatively new, the beds were comfortable and the house was staffed with an abundance of linens and towels. Front and back yards are completely fenced in which is perfect for those with small dogs. North Beach is only a short drive from College Park, Baltimore and Annapolis. Check in was a breeze. Would definitely consider staying there...
Sweet Bamboo Beach Cottage
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
View from property

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

9.8 out of 10, Exceptional, (87)
"This lovely home sets in a beautful location. The hosts are available and accommodating. They are definitely available if needed. The house itself is very comfy. All amenities you need are there. "
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (34)
"Great location with two parking spots and a small yard. Great for family vacation. "
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
On the beach

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

10.0 out of 10, Exceptional, (113)
"This place was a wonderful spot for our family to have a long weekend getaway. It's on a bluff right next to the ocean with a glorious view and a stairway access to the beach. The beds are comfortable, the house has lots of great spaces to relax or play games, and the beach is a wonderful space to explore, find seashells and possibly a fossil sharks tooth (we had no luck there, but we did find a whale vertebrae, so that's something!). But in any event, we highly recommend! "
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Your Annapolis Adventure Starts Here!!
Fridge, microwave, oven, stovetop

Your Annapolis Adventure Starts Here!!

10.0 out of 10, Exceptional, (138)
"We enjoyed our stay as much as the 1st time. Great spot for an Annapolis getaway! House is comfortable and location is ideal. Gracious and responsive host."
Your Annapolis Adventure Starts Here!!
Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
Interior

Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

2.0 star property
Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
Steps to USNA Gate 3 at historic Gatehouse, on-site parking
Fridge, microwave, oven, stovetop

Steps to USNA Gate 3 at historic Gatehouse, on-site parking

2.5 star property
10.0 out of 10, Exceptional, (5)
"A great location and plenty of room for visiting groups to be in and out. Clean and well provisioned. Parking was a great feature as well."
Steps to USNA Gate 3 at historic Gatehouse, on-site parking
PERFECT LOCATION in the heart of history
Exterior

PERFECT LOCATION in the heart of history

10.0 out of 10, Exceptional, (194)
"Lovely home steps from the naval academy. More than enough room for our family of 4. There was a storm the night before we arrived that resulted in a partial power outage. Once we notified them, both the owner and property manager responded promptly and were very accommodating. The rest of our stay was comfortable and enjoyable. Highly recommend for the historic Annapolis experience!"
PERFECT LOCATION in the heart of history
The Lazy Crab Beach House - Free beach passes
Property grounds

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (44)
"Great location, well-maintained and comfortable place. Kitchen is well-stocked, rooms are comfortable, and the yard is a real plus!"
The Lazy Crab Beach House - Free beach passes
Relax on Kent Island in 3 Bedroom Home w/Waterview
Marina

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (34)
"Clean, Spacious, and exactly as advertised! "
The price is AED 343
AED 999 total
includes taxes & fees
30 Mar - 31 Mar
Relax on Kent Island in 3 Bedroom Home w/Waterview
The Cottage
Exterior

The Cottage

10.0 out of 10, Exceptional, (3)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is AED 845
AED 1,574 total
includes taxes & fees
1 Apr - 2 Apr
The Cottage
7 mins away from Downtown Annapolis
Outdoor dining

7 mins away from Downtown Annapolis

9.8 out of 10, Exceptional, (16)
"Loved the house, we were glad to be able to book it on short notice for a large group! Beds were insanely comfortable, and the house had everything we needed. It was clean, comfortable, and a fantastic location. Only downside is that the common areas (living room/kitchen/dining area) are a bit small if you have a larger group (8). Overall a great stay and would stay again!!"
7 mins away from Downtown Annapolis
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Fridge, microwave, oven, stovetop

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

9.6 out of 10, Exceptional, (14)
"The house was very clean and super comfortable. We didn’t cook anything during our stay but the kitchen looked well stocked. Beds were comfortable. The location was awesome. Very short walk to downtown and just steps to the Naval Academy visitors entrance. We very much enjoyed our stayed!"
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Walk to Everything House
Fridge, microwave, oven, stovetop

Walk to Everything House

10.0 out of 10, Exceptional, (78)
"Great location. Loved being near town and the Blue Crab. "
Walk to Everything House
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

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (209)
"Perfect Location - Easy Process - Comfortable Home!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Property grounds

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

9.8 out of 10, Exceptional, (70)
"Great for the price. The motel of VRBOs would be my best description. Plenty of space for what we needed though and no issues during our stay. "
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
The Blue Crab Beach House - Free beach passes
Miscellaneous

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (51)
"The Blue Crab Beach House was perfect for my wife and I and our dog. Very comfortable with a great backyard space for our dog. We loved the location - it’s just a short walk to restaurants and the bay. Very enjoyable stay and we hope to return."
The Blue Crab Beach House - Free beach passes
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.