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Top Holiday Rentals in Owings

The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

10.0 out of 10, Exceptional, (44)
"We had a great stay! Thanks."
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

10.0 out of 10, Exceptional, (211)
"Great views and location. Well furnished and very comfortable. We will definitely be staying here again. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

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

10.0 out of 10, Exceptional, (45)
"This was our 2nd time at the house and it was just as relaxing as we hoped. Nice, quiet location and beautiful home!"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (61)
"The property was well- maintained and the kitchen was well-equipped for our needs. Short walk to North Beach for dining and Boardwalk strolls. Nice and toasty for our winter stay - really enjoyed the trip."
The Blue Crab Beach House - Free beach passes

Private Cottage on gated estate

10.0 out of 10, Exceptional, (24)
"Excellent location, Excellent property, Excellent owners!"
Private Cottage on gated estate

Annapolis Condominium in the heart of the historic center

9.8 out of 10, Exceptional, (274)
"The location and amenities are great. The host are very friendly, helpful and easy to make contact with. My family used this location for commission week and could not have asked for more. "
Annapolis Condominium in the heart of the historic center

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

10.0 out of 10, Exceptional, (223)
"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (248)
"Our stay was great and Rob and Clarissa were very welcoming!"
Family and Pet-Friendly, Waterfront with Pier

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (31)
"Great location, close to the beach and restaurant. Cozy and comfortable, with a beautiful view of sunset. "
Chesapeake Houseboat Getaway on Kent Island, Maryland

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (182)
"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (160)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek

Romantic Two Bedroom Condo

10.0 out of 10, Exceptional, (76)
"Very good "
Romantic Two Bedroom Condo

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (36)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is £239
includes taxes & fees
26 Jun - 27 Jun
Relax on Kent Island in 3 Bedroom Home w/Waterview

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

9.8 out of 10, Exceptional, (9)
"Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!"
The price is £1,258
includes taxes & fees
23 Jul - 24 Jul
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

The Cottage

10.0 out of 10, Exceptional, (6)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is £336
includes taxes & fees
7 Jul - 8 Jul
The Cottage

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

10.0 out of 10, Exceptional, (6)
"Lovely little rustic cottage full of charm.We arrived over Thanksgiving,the off season was wonderful thank s again"
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Edgewater/Mayo Getaway!

9.8 out of 10, Exceptional, (17)
"We had a wonderful experience with our latest stay. They were flexible on arrival time, beds were very comfortable and the house was very comfortable! Will definitely stay again!"
The price is £406
includes taxes & fees
9 Jul - 10 Jul
Edgewater/Mayo Getaway!

Bright and airy waterfront getaway

9.8 out of 10, Exceptional, (13)
"This property was everything we wanted. We hope to return next year."
Bright and airy waterfront getaway

Wright's Cottage- Pet's Welcome & EV Charging

9.0 out of 10, Wonderful, (12)
"This was a wonderful peaceful stay and the host was great. Loved it!!! "
The price is £303
includes taxes & fees
30 Jun - 1 Jul
Wright's Cottage- Pet's Welcome & EV Charging
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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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?

5 minutes from Washington DC 3 bedrooms 2 bath single family home with driveway : This holiday home rental outside of Owings offers a fireplace, a patio and air conditioning 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.

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 Bayside History Museum.

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.