Beachfront vacation rentals in Wildwood Beach

Find and book unique beachfront homes on Airbnb

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Popular amenities for Wildwood Beach beachfront rentals

Pet-friendly beachfront home rentals

Guest favorite
Home in Easton
5 out of 5 average rating, 8 reviews

Ferry Bridge House

ColleenRating, 5 stars4 months ago
Beautiful property - everything was just as advertised and more. Spacious bedrooms with comfortable beds. Quiet, private location with gorgeous views. The hosts were exceptional - very gracious, thoughtful and accommodating to any possible need. We were delighted to find the house so beautifully decorated for Christmas. It made for a very special stay. Thank you!
Guest favorite
Home in Middle River
4.95 out of 5 average rating, 20 reviews

The Shore House

JessicaRating, 5 stars1 week ago
House was spectacularly designed and smelled so good upon arrival. The ranch level style with everything on one floor was ideal for stay with a toddler (and 3 adults). We only stayed a weekend but wish it was longer. I would definitely stay here again. One thing to note that this area does not have service if you are not in the house. Once you are in the house you have WiFi and good to go. Lauren was super responsive and very nice.
Superhost
Home in Annapolis
5 out of 5 average rating, 14 reviews

Book for CW Water views, parking, porch, dogs ok

MichelleRating, 5 stars2 months ago
The place was perfect and we loved watching the sunrise over the bay every morning. Nice quiet neighborhood and great fenced in backyard for the dogs. The house was as described and looks like the photos. The host was very responsive and helpful! Would definitely recommend this home to anyone looking to come to the Annapolis area.
Top guest favorite
Home in Charlestown
5 out of 5 average rating, 62 reviews

The Cooper House in Charlestown, MD

MiriamRating, 5 stars1 week ago
We really enjoyed our stay and the peaceful surroundings. The house is very charming, and well maintained. It was clean and spacious and matched the pictures. The view is beautiful and you can see the water from the windows and porches. Trey was a great host, very responsive and helpful whenever we reached out with questions. Would definitely recommend and we would love to come back for another visit.
Guest favorite
Cottage in Annapolis
5 out of 5 average rating, 7 reviews

Wonderful Cottage Nestled On Chesapeake Bay

Anthony Rating, 5 stars1 month ago
Christina's place was amazing. A perfect home away from home. Super clean, peaceful, and scenic. The check-in/out process was simple and smooth. 10 out of 10. I'd stay here again in a heartbeat.
Top guest favorite
Home in North East
4.96 out of 5 average rating, 46 reviews

Boho River Cottage

StaceyRating, 5 stars1 week ago
Our stay at Cece's Boho Cottage was excellent. It started with an egg hunt around the yard for my boys along with some sweet treats for all to enjoy. Cece gave amazing restaurant suggestions along with local hikes and shops. If you happen to forget something, Cece thought of it! We loved morning coffee on the back porch with the rising sun, comfy beds, and enough space to spread out. Thank you for sharing your adorable cottage with us! We are already trying to plan a trip back!
Superhost
Home in Annapolis
4.94 out of 5 average rating, 17 reviews

Spring Waterfront: Dock & Walk to Beach!

JenniferRating, 5 stars1 day ago
Sheila’s place was the perfect weekend getaway. She was a responsive host, and her home was even better than depicted. The house was thoughtfully designed and well-appointed. She accounted for every kitchen utensil / appliance you could possibly need, and even had eye masks for sleeping in the bedrooms. The waterfront views were the main appeal of the house and the master bedroom overlooked a gorgeous view that boasted picturesque sunrises and sunsets. Would definitely come back again—preferably with a boat! I only wish we could have stayed longer.
Top guest favorite
Home in Annapolis
5 out of 5 average rating, 38 reviews

Bay Home in Annapolis with Private Dock

SusanRating, 5 stars4 days ago
We had a peaceful and relaxing stay at Joel’s home. The house and the grounds overlooking the waterfront were beautiful: We watched both sunrises and sunsets from the dock overlooking the bay, chatted with friends out on the screened-in porch and enjoyed evening fires by the outdoor fire-pit. The kitchen had more than everything we needed to cook, but there were also great restaurants just a 10-15 minute drive away. Whether we were inside or outside the house, we had sweeping views of the bay; there were so many windows to let the light in! We thoroughly enjoyed our stay, and look forward to visiting again!

Beachfront home rentals with a pool

Top guest favorite
Home in Chestertown
5 out of 5 average rating, 22 reviews

Chestertown Watson Family Farm

TaraRating, 5 stars7 months ago
We loved our stay at Molly's air B &B. there were lots of toys to use on the river. The water views from the house were fantastic. The house was clean and comfortable. We loved taking a dip in the pool. Great communication with the host.
Home in Stevensville
5 out of 5 average rating, 3 reviews

Waterfront Escape with Pool Nature Lover Paradise

KarenRating, 5 stars3 weeks ago
This property has a breathtakingly beautiful view of the water that has a fully fenced in yard…so you don’t have to worry about little ones getting into the water. The master bedroom and master bath was amazing. My extended family and I traveled from 4 different states to stay at this property and all of us were comfortable. The house had plenty of spaces to kit be on top of each other. I highly recommend booking this property. The host is very responsive and helpful. I will keep this property in mind for future stays.
Guest favorite
Home in North East
4.76 out of 5 average rating, 21 reviews

Pool House by the North East River

JeniferRating, 5 stars7 months ago
Once again the River house is a well appointed comfortable stay! The swimming pool is a gem! The house is bright and well located; very clean. There is great and comfortable furniture. The views are beautiful and the location is wonderful. We will be back next year!
Guest favorite
Home in Worton
4.97 out of 5 average rating, 30 reviews

Chesapeake Bay Estate; 2 Houses, Beach&Heated Pool

LauraRating, 5 stars8 months ago
My family loved staying here. We had my 3-month old and my sister brought her 8-month old so we were looking for a place that could keep everyone entertained in one location and this place did just that! We enjoyed bird watching, collecting rocks on the beach, swimming in the heated pool, and watching the sunset from the hot tub in the evenings. This was also the first time I could say that the listing looked better in person than the pictures. Thank you Joni for letting us stay here! We made some amazing memories!
Superhost
Home in Saint Michaels
4.5 out of 5 average rating, 10 reviews

10 Minutes to St. Michaels with a Private Pool

JoyRating, 5 stars4 months ago
We had a great weekend a gain. Enjoying Christmas in St Michaels. Your home is beautiful. We ate at Ava’s, Limoncello, Carpenters and Talbots. Shopped on Sunday. Highly recommend the house tour. She you again soon.🥰

Private beachfront home rentals

Guest favorite
Guesthouse in Arnold
4.88 out of 5 average rating, 16 reviews

Adorable 1 BR guest house with water views, deck

LauraRating, 5 stars6 months ago
Clean and cute and just as described. Perfect for a long weekend away in Annapolis for the boat show!
Top guest favorite
Cottage in Annapolis
4.93 out of 5 average rating, 28 reviews

Bay View Beach Cottage, perfect for long-term

MichaelRating, 5 stars3 months ago
The house was a perfect location on Cape St. Claire. Well furnished and comfortable. Susan is a great host.
Guest favorite
Cottage in Earleville
4.95 out of 5 average rating, 81 reviews

The Bohemia Charmer

ConnieRating, 5 stars3 weeks ago
We absolutely loved this place for our retreat. We plan to come back next year. Marla was available at all times and quick to respond with any questions.
Top guest favorite
Home in Chester
5 out of 5 average rating, 34 reviews

*Waterfront Sunset Bayview* sleeps 6

MaryRating, 5 stars1 month ago
Beautifully designed house highlighted the stunning view of the bay. Cozy and clean, couldn't have asked for more!
Guest favorite
Cottage in Charlestown
4.96 out of 5 average rating, 164 reviews

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

Joseph & TracyRating, 5 stars3 days ago
The property is beautiful, its just like the pictures. The location is peaceful and quite. Its a perfect spot to just to relax and reconnect. Can't say enough good things about the cottage. Clean, Bed was nice, view was amazing, Hot tub, kayaks, plenty of firewood for a beach fire. During our stay we went to main street in North East it was about a 7 minute drive. It was a nice little town to walk. Chesapeake Coffee Co for a breakfast sandwich and a coffee. We had lunch at Woody's crab shack. Ordered in pizza from Bella Pizza, Went to Nauti Goose. I was underwhelmed at all restaurants and by all meals. If we come back again, I'd get groceries to cook, there is a grill to use (we didn't) and stay in, just take in the view and enjoy the peaceful waves. We would defiantly recommend and hopefully be back again soon.
Superhost
Cottage in Grasonville
4.89 out of 5 average rating, 62 reviews

CoastalBeachCottage*BayViews*Close2WeddingVenues

ColinRating, 5 stars2 months ago
We had a great stay at this property and it was perfect for our visits with friends in Grasonville. The property is well represented in the photos. Conveniently location just off the main highway and just a 2 minute walk to the water front. Thanks, Michelle
Top guest favorite
Guest suite in Annapolis
5 out of 5 average rating, 232 reviews

Cape St Claire waterfront getaway "The Apartment"

JoAnnRating, 5 stars2 days ago
Absolutely beautiful spot. Lise was a wonderful host. The space was amazing and everything was immaculate. Backyard was so nice and relaxing after being out and about all day. I would definitely stay again and recommend to other couples.
Guest favorite
Home in Annapolis
4.9 out of 5 average rating, 199 reviews

Country House on the Bay

AnitaRating, 5 stars5 months ago
Steve is a wonderful host. He greeted us warmly and gave us a very thorough tour of the house. He had recommendations for everything local that was of interest to us. He has a beautiful home and a beautiful setting on the water.

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