Wildewood Holiday Rentals

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Our top choices for Wildewood holiday rentals

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (44 reviews)
"House was very nice and tidy and exactly as described. The host had a small binder full of helpful info including local restaurants and attractions. There was so much to do and everything was close bye. "
United States
Mindy V.
The price is NZ$484
includes taxes & fees
21 Apr - 22 Apr
Soul Oasis - home on the Chesapeake Bay

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
9.0 out of 10, Wonderful, (8 reviews)
"The location was perfect. It was quiet and clean with a wonderful view of the water, especially the sunrise through the bedroom window in the morning. The host kept in touch to answer any questions we had, and made sure our stay was great. We will absolutely be back!"
United States
Coulter L.
The price is NZ$452
includes taxes & fees
15 Apr - 16 Apr
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (43 reviews)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
The price is NZ$534
includes taxes & fees
15 Apr - 16 Apr
Cottage Located on the Patuxent River!

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is NZ$744
includes taxes & fees
15 Apr - 16 Apr
Coles Point Marina

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.8 out of 10, Exceptional, (6 reviews)
"Our family had a great stay. Thank you!"
United States
Colleen G.
The price is NZ$717
includes taxes & fees
15 Apr - 16 Apr
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Dock+Boats+Firepit: Game Theme Waterfront Retreat

Dock+Boats+Firepit: Game Theme Waterfront Retreat
Montross
10.0 out of 10, Exceptional, (31 reviews)
"Great spot"
United States
SHAWN W.
The price is NZ$841
includes taxes & fees
15 Apr - 16 Apr
Dock+Boats+Firepit: Game Theme Waterfront Retreat

Luxury Modern Waterfront Retreat

Luxury Modern Waterfront Retreat
Montross
9.6 out of 10, Exceptional, (15 reviews)
"Very nice inside, love all the windows"
United States
Elizabeth S.
The price is NZ$793
includes taxes & fees
16 Apr - 17 Apr
Luxury Modern Waterfront Retreat

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Prince Frederick
10.0 out of 10, Exceptional, (10 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is NZ$840
includes taxes & fees
15 Apr - 16 Apr
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Anne & Fred`s Leonardtown Home W/ Arcade room!

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.4 out of 10, Exceptional, (6 reviews)
"Amazing place to stay. Very Very clean ! Great location. Definitely will book this place again "
United States
Christy C.
The price is NZ$939
includes taxes & fees
15 Apr - 16 Apr
Anne & Fred`s Leonardtown Home W/ Arcade room!

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Lexington Park
10.0 out of 10, Exceptional, (7 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is NZ$662
includes taxes & fees
20 Apr - 21 Apr
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is NZ$1,308
includes taxes & fees
15 Apr - 16 Apr
4-BR Waterfront Turret Home

Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK

Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
Montross
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home, very clean and comfy "
United States
Julie P.
The price is NZ$811
includes taxes & fees
15 Apr - 16 Apr
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
Lusby
The price is NZ$1,186
includes taxes & fees
15 Apr - 16 Apr
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Peaceful Waterfront Retreat for Bird Lovers- Close to DC

Peaceful Waterfront Retreat for Bird Lovers- Close to DC
Leonardtown
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful property in a peaceful neighborhood. Great location! "
United States
R. L.
The price is NZ$738
includes taxes & fees
15 Apr - 16 Apr
Peaceful Waterfront Retreat for Bird Lovers- Close to DC

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay
Point Lookout
10.0 out of 10, Exceptional, (127 reviews)
"Hideaway at Hayes Beach was amazing It was a wonderful place to spend Christmas with our family. We were lucky enough to get snow! My husband and I enjoy walking so it was a prefect place to for it. Would definitely recommend this place"
United States
April T.
Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is NZ$716
includes taxes & fees
15 Apr - 16 Apr
2 Bedroom Cottage at Coles Point Marina

Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (2 reviews)
"Beautifully and tastefully decorated, immaculately clean, completely stocked top to bottom! You can tell by all of the details that these hosts care about curating a perfect stay for their guests. "
United States
Leslie K.
The price is NZ$988
includes taxes & fees
20 Apr - 21 Apr
Charming Waterfront 3-bedroom house in Piney Point

Come relax yourself a while

Come relax yourself a while
Mechanicsville
The price is NZ$991
includes taxes & fees
15 Apr - 16 Apr
Come relax yourself a while

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Lusby
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is NZ$1,683
includes taxes & fees
15 Apr - 16 Apr
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
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 Wildewood Hotel Reviews

Find out more about Wildewood

Everything you need to know about Wildewood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Wildewood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wildewood holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Wildewood holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wildewood. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wildewood holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wildewood holiday rentals we have selected for you start as low as NZ$484 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Wildewood rentals

At Expedia, we put the best Wildewood holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Wildewood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wildewood holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wildewood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Wildewood?

Yes, there are holiday rentals close to the most popular sights in Wildewood, 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 Wildewood has to offer?

Quaint waterfront home with private beach: This holiday home rental outside of Wildewood is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a patio and a selection of games.

What can I see and do in Wildewood?

Explore the area and family-friendly sights such as Michael P. O'Brien Athletics and Recreation Center, or get out into nature at a spot like St. Mary's River State Park. J.C. Lore Oyster House and Drum Point Lighthouse are a couple of places you'll find in the wider area.

What are holiday rentals like in Wildewood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Wildewood. Holiday rentals feature extras such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for small groups.