Beachfront holiday rentals in Wildwood Beach

Find and book unique beachfront homes on Airbnb

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Popular amenities for beachfront rentals in Wildwood Beach

Pet-friendly beachfront home rentals

Superhost
Home in Middle River
4.95 out of 5 average rating, 21 reviews

The Shore House

BalaRating, 5 stars1 month ago
Lauren is an excellent host. The property was wonderful, clean and suit our needs. The perfect top it off was… there were adequate chips, and fritters - just after we drove in the house.👌 I was a bit hungry, and gave me some time to get my essentials for the stay - which, btw…wasn’t too far. It had a nice walk to the small beach, and we thoroughly enjoyed it. Lastly, Lauren was exceptional with our request for a late check out. Thank you. Definitely a 5 star! Will definitely stay at this same place, again. Regards Bala
Superhost
Houseboat in Stevensville
4.94 out of 5 average rating, 53 reviews

Chesapeake Houseboat Getaway

RomaRating, 5 stars1 month ago
I loved Julia’s Arc. First time I Airbnb’d in a houseboat; won’t be my last. I loved this experience! Julia’s was inviting, comfortable, well appointed. I enjoyed sitting on the upper deck but even sitting inside with the blinds up and the windows open afforded the sounds of the water while enjoying the view of the marina and boats. I wish I had more time here to explore more. This was exactly what I needed for some time alone.
Superhost
Home in Perryville
4.93 out of 5 average rating, 218 reviews

Top of the Chesapeake - Private Waterfront Home

DebRating, 5 stars1 month ago
We had a wonderful stay. We enjoyed being outdoors on the deck and walking the shoreline. The interior accommodations were very comfortable and met all our needs and expectations. The weather was perfect, too! Would definitely like to return again. 👍🏻👍🏻👍🏻
Superhost
Guest house in Annapolis
4.86 out of 5 average rating, 101 reviews

Chesapeake Bay Escape | Cozy Retreat

JacquelineRating, 5 stars1 month ago
We loved our weekend stay at Melanie’s place!! It was clean, easy to access and a lovely location!! She was super helpful with our questions about the areas and places she recommended. Definitely recommend!!
Superhost
Home in Tilghman Island
5 out of 5 average rating, 18 reviews

Panoramic water views

MeganRating, 5 stars1 month ago
This was one of the loveliest Air BnBs I’ve had the pleasure of staying at. The photos don’t do it justice. A warm, welcoming and cozy home, filled with sunlight and stunning water views from every window. You literally feel like you’re on a boat! Comfortable furnishings and beds, a super well-stocked kitchen with lovely dishes and decor, bikes, kayaks, gas grill… everything you could want. The Tilghman Island General Store was just a short walk through a lovely neighborhood with the friendliest people. Breakfast at Two if by Sea was amazing! And crab cakes at Gina’s on the Bridge were delish. My dog loved the stay too! Tilghman Island is a peaceful treasure in today’s crazy world.
Superhost
Cottage in North Beach
4.94 out of 5 average rating, 50 reviews

Cozy Waterfront Cottage - Pet Friendly

LisaRating, 5 stars6 days ago
This was a fantastic vacation rental- the kids’ favorite yet! You can’t beat the views and the proximity to the beach and shops. There is also a playground, library, ice cream shop, and pizza just a block away. The host had snacks, water, and milk available for us and the kids when we arrived, which was very welcome after a long car ride! And having beach chairs and beach umbrellas for use made our beach days so much better! We brought our paddle board and launched it off the local beach which was quite fun. Annapolis and DC are both far drive and, when we weren’t enjoying the local amenities, we found plenty to do just an hour drive or less away. I highly recommend this rental. Thank you for allowing us to rent your lovely home and we will definitely be back
Superhost
Home in Annapolis
5 out of 5 average rating, 42 reviews

Bay Home in Annapolis with Private Dock

ToddRating, 5 stars2 weeks ago
Beautiful place, beautiful location. Joel thought of anything you could want.
Superhost
Flat in Annapolis
4.92 out of 5 average rating, 101 reviews

Dazzling day/night water views,1st class amemities

ThomasRating, 5 stars8 months ago
Wonderful host—I felt right at home. Had conversation prior to arrival and felt like I knew her very well before arriving. The view was spectacular I could have just sat on the patio and watched the woods and water all day. Was there for a school reunion so I had other activities that I had scheduled. This was by far, the best Air B&B experience I have had. Fantastic host, comfortable, and stunning scenery. I am going to try and revisit soon.

Beachfront home rentals with a pool

Top guest favourite
Home in Chestertown
5 out of 5 average rating, 23 reviews

Chestertown Watson Family Farm

LukeRating, 5 stars4 days ago
We had a great time. The view is one of the best we have stayed at. The hosts have thought of almost everything you could need or want to do. Our kids wanted to come back just to do more of the activities. The interior is obviously dated but it is thoughtful, functional, and clean. We felt cozy and at home! We will be back!
Home in Stevensville
4.9 out of 5 average rating, 10 reviews

Waterfront Escape with Pool Nature Lover Paradise

AnnetteRating, 5 stars2 days ago
The house and surroundings are beautiful. Unfortunately, we had rain during most of our trip. There was plenty of room and board games inside the house. We were able to get outside and try crabbing and fishing one of our days. All of the supplies needed for cooking were in the immaculate kitchen. We would love to come back in the fall.
Top guest favourite
Place to stay in Annapolis
4.94 out of 5 average rating, 121 reviews

Chesapeake Bay View 3BR/2BA Duplex*Hot Tub*

PaulRating, 5 stars1 month ago
We found Paul’s home very comfortable and accommodating. Paul was accessible when we reached out to him and he communicated well with us. It was a very nice location with a fantastic view of the bay, as we hoped for.
Guest favourite
Home in Worton
4.97 out of 5 average rating, 30 reviews

Chesapeake Bay Estate; 2 Houses, Beach&Heated Pool

LauraRating, 5 stars9 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!
Guest favourite
Cottage in Neavitt
4.88 out of 5 average rating, 24 reviews

Grandview - Cottage 1B, Queen Bed, Pool, Bay, WIFI

HeatherRating, 5 stars1 month ago
A cozy and quiet cottage right along the water. The kitchen is very well stocked. You can find any pot or utensil you may need. The best part of the cottage is the sun room, it was a great place to enjoy a glass of wine in the evening or enjoy a cup of coffee in the morning and soak in the sparkling water and peaceful surroundings. A peaceful spot away from everything, but a short 15 minute drive into St. Michaels. The road to the cottage is a bit rough, a small car has to navigate it with some care.
Superhost
Home in Saint Michaels
4.58 out of 5 average rating, 12 reviews

10 Minutes to St. Michaels with a Private Pool

SarahRating, 5 stars4 days ago
This home gave us something we hadn’t experienced before: a vacation with two small children that actually felt like a vacation! From the moment we arrived, we were blown away by how perfectly suited the home is for families with young kids. The pool has a shallow platform area that our toddlers could safely enjoy, and the expansive, beautifully maintained yard gave them plenty of space to run and play freely along with a swing and hammock. Inside, the house is just as exceptional. The layout is thoughtfully designed, with a separate bedroom wing that allowed us to put the kids to bed and then relax in the evenings without worrying about noise. Every detail felt intentional and welcoming, and the water views were absolutely stunning. The home is just a short drive from the charming town of St. Michael’s, which we loved exploring. This trip was such a joy for our entire family, and we’re already talking about when we can come back. Highly, highly recommend!
Superhost
Apartment in Betterton
4.92 out of 5 average rating, 38 reviews

3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!

SihamRating, 5 stars1 week ago
My family & I booked for three nights. Thought it was a beautiful and private little area, and just a couple steps away from the beach and a pool. Very quiet and away from noise which was a plus. The house itself was lovely and mostly clean. There were board games available and my kids had a fun time playing with them. We enjoyed barbecuing using the grill provided on the balcony which was nice as well. A plenty of towels and anything you need in the kitchen! Other than a full trash bag left over in the kitchen, finding some clothing items from other guests (I’m assuming) in drawers, and the keurig having what looked like mold inside. Pretty small things when looking at the big picture though. Will most likely come again & we enjoyed our stay!
Top guest favourite
Home in Kent Narrows
5 out of 5 average rating, 301 reviews

Chester Riverfront At Kent Narrows

CassandraRating, 5 stars2 weeks ago
A great place to enjoy a long weekend at the Eastern shore in Maryland.

Private beachfront home rentals

Top guest favourite
Home in Edgewater
5 out of 5 average rating, 56 reviews

Waterfront South River Edgewater Sunrises & Beach!

KatRating, 5 stars8 months ago
We had a lovely stay at Heather’s place. The house was clean, comfortable, and we felt taken care of. The porch with the view of the water and sunrises was so relaxing. Visiting during the off-season was peaceful, but there was still plenty to do in the area. We couldn’t have asked for a better getaway weekend.
Guest favourite
Cottage in Earleville
4.95 out of 5 average rating, 84 reviews

The Bohemia Charmer

FrankRating, 5 stars1 day ago
An unforgettable stay! The photos simply don’t do this place justice. From the moment we arrived, we were blown away — but nothing compared to the breathtaking view of the Bohemia River right outside the window. It felt like our own private slice of tranquility. Marla was a fantastic host — thoughtful, responsive, and clearly passionate about creating a welcoming space. Every detail of the home was spot on, and the atmosphere was even better than expected. Honestly, the whole experience exceeded our expectations. We’re already looking forward to coming back — would definitely book this property again without hesitation.
Top guest favourite
Home in Charlestown
5 out of 5 average rating, 64 reviews

The Cooper House in Charlestown, MD

HeatherRating, 5 stars4 days ago
This house was AMAZING! So much space. The rooms were so large, high ceilings and windows, it was just gorgeous! Trey was very responsive to any questions that we had. Lots of parking, just be sure to leave the far left space open for the host to park, since he lives on site at the back of the home (I missed this piece in the description). We had alot of friends visit that were down for the one day and everyone was blown away by the house, and many want to book in the future. The park next door was great for the kids to spread out..and Saturday was a BONUS, when they had live music playing, a food truck and beer tent..we had our own front row seat all afternoon....can't beat live music, by the campfire, by the water. A few notes for future renters: take your own toiletries (soap/shampoo not provided), the "no access" closet to the right of the stove, is actually where the brooms/trash bags and cleaning supplies are housed and you do have access to it. Thank you Trey!
Guest favourite
Cottage in Annapolis
5 out of 5 average rating, 9 reviews

Wonderful Cottage Nestled On Chesapeake Bay

EdmondRating, 5 stars2 weeks ago
The cottage looks just like the photos. Very quiet and peaceful location. They provided a binder that catalogs anything you may need during your stay. EXCELLENT communication. Easiest Check out EVER. Would certainly book again if we return to the area.
Guest favourite
Bungalow in North Beach
4.88 out of 5 average rating, 96 reviews

Bayside Bungalow: Cozy North Beach Getaway

AmandaRating, 5 stars4 days ago
We had a wonderful visit to North Beach staying at William's bayside bungalow! The location is absolutely perfect. The bungalow is steps away from the boardwalk and conveniently located to the beach and all the fun shops in town. The bungalow was comfortable and perfect for our trip. We especially loved sitting on the front porch and enjoying the view of the bay. William was a gracious and communicative host. We'd be excited to stay here again in the future!
Guest favourite
Home in Deale
4.9 out of 5 average rating, 20 reviews

Quiet Getaway in Waterfront Community

PinkyRating, 5 stars1 month ago
My husband and I stayed here for a month while we had work done on our boat at a local marina. The location is perfect for access to the local marina as well as all the restaurants in Deale. Yen was super responsive as was John. They responded to all our questions in a timely manner, and were always very kind. The home is well laid out, and worked perfectly to use as a homebase. Good wifi, comfy couch, comfy bed with good pillows. The master suite is gorgeous and well lit. Kitchen is well appointed and had all the appliances/utensils we needed. Had several work spaces that were great for zoom calls and other "office" type work. The tap water didn't have any odors. Enjoyed having coffee on the front porch with a lovely view of the Chesapeake and the screened in porch in the back was great as the evening bugs came out. Highly recommend this home!
Top guest favourite
Home in Edgewater
5 out of 5 average rating, 14 reviews

Waterfront home on the Bay

Steven JayRating, 5 stars2 weeks ago
This is one of the best Airbnb experiences we have ever had. Teresa’s house was 10 out of 10. Everything was absolutely fantastic. Very clean with everything we needed. The view was spectacular!!!! We absolutely loved everything especially the bald eagle that flew by on our last morning. I highly highly recommend staying here and next time we make the trip up there from Texas it will be scheduled based on the availability of Teresa’s house. Thank you for being a great host!!
Guest favourite
Home in Stevensville
4.95 out of 5 average rating, 20 reviews

Bayou on the Bay

AaronRating, 5 stars3 days ago
Very nice stay!! We enjoyed the place and thought it was super nice. Would highly recommend

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