Beach house holiday rentals in Wildwood Beach

Find and book unique beach houses on Airbnb

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Popular amenities for Wildwood Beach beach house rentals

Beachfront house rentals

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

Chestertown Watson Family Farm

LukeRating, 5 stars5 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!
Guest favourite
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
Top Guest favourite
Home in Annapolis
5 out of 5 average rating, 41 reviews

Peaceful Waterfront Home in Annapolis 3BR 2BA.

OctaviakRating, 5 stars5 days ago
Our Airbnb stay was absolutely fantastic! My family and I really loved all the amenities. The waterfront view was stunning, and we had a great time grilling and just hanging out together with friends and family. It was truly a memorable experience! I would definitely recommend this Airbnb for a family getaway and to have a peaceful time enjoying the water and the beach. I definitely will come back again!
Guest favourite
Home in Shady Side
4.96 out of 5 average rating, 107 reviews

Waterfront w/ Private Pier, 35 Mins to Annapolis

LeilaRating, 5 starstoday
We had a wonderful time, great location and loved reading about the house history.
Guest favourite
Home in Joppatowne
4.95 out of 5 average rating, 40 reviews

Mac's Waterfront Wonder

IsaiahRating, 5 stars3 weeks ago
I’ve been to this location three (3) times now and each time was a pleasure. Communication was great and him allowing a late check out was fantastic (especially with multiple kids, trying to get them ready). I will continue to select this location when we have to come into town for the location, price, communication, and peace of mind knowing exactly what we’ll receive. The only issue with this last stay (and I can only assume it was due to holiday because never happened before) was the trash can being full. I do not suspect this is a regular occurrence as he is very transparent. I’d recommend this place to anyone and again, will be booking multiple times in the future as we will be traveling to MD a lot more.
Top Guest favourite
Home in Chester
5 out of 5 average rating, 39 reviews

*Waterfront Sunset Bayview* sleeps 6

KellyRating, 5 stars2 weeks ago
The perfect mom and teen boy getaway! The house is on the water with gorgeous sunsets and super clean! My boys attempted fishing daily even without any luck. Altho we didn't kayak because of the choppy water, its great location (there's a ladder at the private pier or a public launch a few yards away) We cooked and ate in a few nights and also enjoyed a local spot on the water (The Narrows). The neighborhood was quiet, relaxing and peaceful. We enjoyed a visit to the Chesapeake Environmental center (abt a 12 min drive) which was a hidden treasure. The Chesapeake Outdoors (recommended by our host Jeremiah) was a great find for bait and info from the locals. Morning coffee on the patio and evening sunsets on the pier were some of my favorites, along with the spacious open floor plan (yet privacy with bedrooms). Jeremiah was super responsive and kind! We'll be back to kayak, fish more, enjoy the hot tub coming soon, the serenity and gorgeous sunsets! (maybe we'll even bring dad -LOL)
Top Guest favourite
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.
Top Guest favourite
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.

Beach house rentals with a pool

Top Guest favourite
Home in North Beach
5 out of 5 average rating, 16 reviews

Stunning North Beach Getaway w/ Inground Pool

IsabelRating, 5 stars1 week ago
We had our wedding at the Herrington on the Bay venue Finding Patii’s place was a gem! I had the most wonderful stay—truly one of those rare experiences that stays with you long after you’ve left. It wasn’t just a trip or a few nights in a beautiful place. It was peace. It was comfort. It was healing. From the moment I arrived, I felt something different in the air—something warm, gentle, and full of care. The home was spotless, cozy, and filled with thoughtful details that made me feel instantly at ease. But beyond the beauty of the space, it was the feeling that made it unforgettable. Patti was so communicative and always responsive. She made sure that we will have the best weekend
Superhost
Home in Pasadena
4.87 out of 5 average rating, 61 reviews

Beautiful Home Near Beach and Patapsco River

KristinaRating, 5 stars2 weeks ago
Place was great and large enough to accommodate 2 families (9 total people). We were excited to have a place with a pool but didn’t end up using it because it was a little chilly. Neighborhood was quiet and early morning walks were pleasant. Beds were comfortable too.
Superhost
Home in Queenstown
4.81 out of 5 average rating, 157 reviews

Bay Breeze Retreat

TobyRating, 5 stars3 weeks ago
Fabulous views of Chesapeake Bay, pool was great, deer everywhere, house was spacious with three living areas. Would definitely stay there again.
Top Guest favourite
Home in Rock Hall
5 out of 5 average rating, 15 reviews

The Mariner's House

ErinRating, 5 stars1 month ago
Wonderful property with lots of amenities!
Top Guest favourite
Home in Edgewater
4.98 out of 5 average rating, 59 reviews

Entire Beach House with Pool and Hot Tub

LisaRating, 5 stars3 days ago
Peggy’s house is beautiful! The inside and the outside are just wonderful! The pool, hot tub are just perfect! Wishing only that the house could sleep 6 adults plus a couple of kids. The location is just perfect!
Guest favourite
Home in Chester
4.95 out of 5 average rating, 95 reviews

Waterfront Farmhouse Meets Modern Luxury

TrishRating, 5 stars2 weeks ago
The house is beautiful and worked well for our family. The host was very helpful and responded quickly to any questions we had. The grounds are lovely and very peaceful. Pictures don’t do this property justice.
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 stars5 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!
Top Guest favourite
Home in Stevensville
5 out of 5 average rating, 16 reviews

Bayside Escape

JohnRating, 5 stars2 days ago
Our family of 3 had an amazing vacation on our 4 day stay. It was so peaceful and relaxing. The place was exceptionally clean and organized with everything needed. Amazing views on the water and pool was great. We had some rainy weather but still managed enough dry time to enjoy the pool and outdoors

Private beach house rentals

Top Guest favourite
Home in Rock Hall
5 out of 5 average rating, 15 reviews

Bay Beach Oasis

CarolineRating, 5 stars2 weeks ago
Not only was our stay reasonably priced it was spacious and well equipped. Check out the Bed & Breakfast that is directly behind the house for a good bite to eat! A nice perk was the small community beach was in walking distance.
Guest favourite
Home in Chester
5 out of 5 average rating, 15 reviews

Spacious waterfront home private pier dog-friendly

KarenRating, 5 stars1 week ago
The accommodations did not disappoint! Fabulous view, fun choices to take advantage of on the water, great neighborhood and local seafood restaurants! Our family gathering was memorable as a result of this venue! Will be sure to return!
Top Guest favourite
Home in Saint Michaels
4.99 out of 5 average rating, 171 reviews

Grace Cottage, Saint Michaels Walk to everything!

RhondaRating, 5 stars3 days ago
Beautiful home steps away from all the shops and restaurants in St. Michaels. We walked everywhere and had a fantastic time. I’d love to come back and stay here again!
Top Guest favourite
Home in Havre de Grace
5 out of 5 average rating, 45 reviews

Quaint home in charming town

PaigeRating, 5 stars1 week ago
Had a great stay. Booked to stay at after a friends wedding and so happy we did. Hoping to come back in the future just to visit the area for a weekend. Lindsay was very friendly and responsive!
Superhost
Home in Queenstown
5 out of 5 average rating, 9 reviews

The Perfect Waterfront Escape!

AnnRating, 5 stars6 months ago
As others have said, beautiful and spacious house with stunning views on the water! The house was clean, kitchen filled with all the tools for cooking (even things like wax paper, aluminum foil, all the spices you could think of, etc.), and we loved the ping pong table in the garage. The grounds were super peaceful and fun to walk around. We came in November so the pool was covered, but it was great to go out on the dock and kayak on the water. Not sure if it was the cold or not, but on some of the doors, the deadbolt was a little sticky and difficult to turn, so we just avoided these doors throughout our stay. We would love to come back in the summer time/when the weather is warmer to enjoy the pool! Also very much appreciated that we could bring our dog.
Top Guest favourite
Home in Pasadena
5 out of 5 average rating, 28 reviews

Kayak Cove

KellyRating, 5 stars6 days ago
Great location for our family of 6. Plenty to do. Our kids enjoyed visiting fort Smallwood park. Comfortable and clean!
Top Guest favourite
Home in Stevensville
5 out of 5 average rating, 46 reviews

Away at the Bay: New Home on the Chesapeake Bay!

PaigeRating, 5 stars2 weeks ago
Cannot put into words how wonderful our time was at Away at the Bay! Just left my soon-to-be SILs bachelorette trip and the entire weekend was nothing short of incredible. Thank you so much to Ryan and Eric for creating such a wonderful experience in a place that truly feels like home but BETTER! Memories we will cherish forever.
Superhost
Home in Shady Side
4.88 out of 5 average rating, 181 reviews

Cattail Landing- Photographer's Waterfront Retreat

AshleyRating, 5 stars8 months ago
We had a wonderful time during our visit. The peaceful environment on the water was just what our group needed. Thank you!

Destinations to explore