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Owings Vacation Rentals

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Our top choices for Owings vacation rentals

1. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (24 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is CA $136
CA $487 total
includes taxes & fees
Oct 4 - Oct 5
Beachside Oasis with Beach Passes & King Suite by A Haven Away

2. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (37 reviews)
"We enjoyed our stay in North Beach at this lovely residence. It was spacious, clean, nicely furnished and only a few minutes walk to the bay. The beds were so comfortable too!!"
United States
Penny N.
The price is CA $260
CA $737 total
includes taxes & fees
Oct 12 - Oct 13
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

3. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
"Great place to stay! Location was nice and close to water views. House was charming and CLEAN. Owners went above and beyond to make the stay welcoming and convenient. Price was reasonable until additional Vrbo fees were added."
United States
Sharon t.
The price is CA $318
CA $611 total
includes taxes & fees
Oct 4 - Oct 5
Rose Haven Coastal Cottage

4. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is CA $385
CA $653 total
includes taxes & fees
Oct 1 - Oct 2
Plum Point Cottage #17

5. 3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views
Deale
The price is CA $302
CA $705 total
includes taxes & fees
Oct 27 - Oct 28
3-bedroom house in Deale located on Bay many amenities and great views

6. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is CA $185
CA $465 total
includes taxes & fees
Oct 8 - Oct 9
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

7. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is CA $438
CA $822 total
includes taxes & fees
Oct 6 - Oct 7
Sunset Cottage - West River Access and Views!

8. Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is CA $204
CA $643 total
includes taxes & fees
Oct 27 - Oct 28
Family Beach House: Spacious Deck, Grill & Views

9. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
9.0 out of 10, Wonderful, (2 reviews)
"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"
United States
David S.
The price is CA $246
CA $543 total
includes taxes & fees
Oct 26 - Oct 27
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

10. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.2 out of 10, Wonderful, (15 reviews)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
United States
ed r.
The price is CA $217
CA $377 total
includes taxes & fees
Sep 30 - Oct 1
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

11. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
"Almost everything that you might need is provided, but if not there is shopping close by. Hot tub was nice. Very clean home."
United States
Sharon Z.
The price is CA $293
CA $696 total
includes taxes & fees
Oct 5 - Oct 6
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

12. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is CA $151
CA $441 total
includes taxes & fees
Oct 6 - Oct 7
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

13. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (24 reviews)
"Amazing host and home, great view with the water right there, and short drive to any shopping needs. It was the serene getaway I needed to recharge from city life and corporate burnout."
United States
George
The price is CA $293
CA $505 total
includes taxes & fees
Sep 30 - Oct 1
Bright and airy waterfront getaway

14. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (13 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is CA $321
CA $859 total
includes taxes & fees
Oct 20 - Oct 21
Renovated Bungalow | Walk to Beach | Dog-Friendly

15. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (78 reviews)
"Our family had a wonderful stay at your beautiful home! The views are to die for! House was very clean with all equipment and kitchen appliances all available! Very happy with our stay! "
United States
Whitney M.
The price is CA $503
CA $1,005 total
includes taxes & fees
Sep 30 - Oct 1
Charming Annapolis WaterVIEW Home

16. Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (5 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is CA $407
CA $1,069 total
includes taxes & fees
Oct 5 - Oct 6
Family Home on Mayo Peninsula | Deck | Sleeps 10

17. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (94 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
The price is CA $278
CA $440 total
includes taxes & fees
Oct 5 - Oct 6
Your Annapolis Waterfront retreat for a weekend or any-day getaway!

18. Londontowne Home | Beach | 3BR

Londontowne Home | Beach | 3BR
Edgewater
9.4 out of 10, Exceptional, (3 reviews)
"The property was beautiful with plenty of space to have a getaway with friends. The host was super communicative when we had issues with check in. Would highly recommend staying here!"
United States
Sam A.
Londontowne Home | Beach | 3BR

19. Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is CA $349
CA $907 total
includes taxes & fees
Oct 5 - Oct 6
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

20. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is CA $271
CA $723 total
includes taxes & fees
Oct 12 - Oct 13
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
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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Top Owings Hotel Reviews

Find out more about Owings

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Owings. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Owings?

Yes, you can find vacation rentals near top sights in Owings, or you can go with a more remote option if you're looking for relaxation.

What's the top vacation rental in Owings?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This vacation home rental outside of Owings is located near the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 larger area, you’ll find Fridays Creek Winery and Bayside History Museum.

What’s a vacation rental in Owings like?

A vacation rental is a private property you can stay in for several days or longer in Owings. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a small group gathering.