Beach house holiday rentals in Wildwood Beach

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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, 24 reviews

Chestertown Watson Family Farm

AmyRating, 5 starstoday
Words can’t describe how incredible this home/property is! You have the option to just sit by the water or in the hammock watching the birds play and fish jump, or you can do one of the MANY activities Molly has provided for you. Kayaks, canoes, paddle boards, pickleball, yards games, pool activities, etc are all provided. The family room is all windows so it not only provides the most incredible breeze- it is great for enjoying all the sights even if you’re not outside in it. Inside there are tons of toys for kids- you do not have to bring a thing if you have kids. They have inside toys, outside toys, kids life jackets, goggles, water balloons, rafts, floaties, pack and play…. Molly and her family have thought of it ALL. We are already talking about coming back. Molly was the best host- responsive, helpful and inviting.
Guest favourite
Home in Middle River
4.95 out of 5 average rating, 21 reviews

The Shore House

CeceRating, 5 starstoday
My friends and I stayed here for a wedding weekend, Lauren was responsive and the house is very nice, and impeccably clean. Lauren mentioned that she lives here part time and it shows, this is a home. You have everything you need in the kitchen/bathrooms. She was kind enough to leave emergency items that we may have forgotten and welcome snacks. This place was the perfect weekend getaway and I honestly wish we were able to spend more time and use the house and the surrounding areas to a fuller extent. It’s peaceful and a short walk to a small waterfront.
Top guest favourite
Home in Annapolis
5 out of 5 average rating, 42 reviews

Peaceful Waterfront Home in Annapolis 3BR 2BA.

AndrewRating, 5 stars1 day ago
I would definitely come back here. If you want to unwind, decompress, or just slow-living for a couple of days, you won’t find a better place. The sounds of small waves all day and the birds chirping in the morning were almost as good as the break-taking ocean view. Better than advertised. I could sit in the cabana and read all day.
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 stars2 days ago
We had a wonderful time, great location and loved reading about the house history.
Top guest favourite
Home in North East
4.96 out of 5 average rating, 54 reviews

Boho River Cottage

PeggyRating, 5 stars1 week ago
Cece had everything ready for us and our pup. The home was very clean and well stocked. She even had kindling and dry wood ready for the chimania. Instructions were clear and a binder with local attractions and restaurants was ready for us.
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 Annapolis
5 out of 5 average rating, 42 reviews

Bay Home in Annapolis with Private Dock

ToddRating, 5 stars3 weeks ago
Beautiful place, beautiful location. Joel thought of anything you could want.

Beach house rentals with a pool

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 stars4 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, 60 reviews

Entire Beach House with Pool and Hot Tub

LisaRating, 5 stars4 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 stars3 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 stars1 week 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 stars4 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
Guest favourite
Home in Edgewater
4.99 out of 5 average rating, 68 reviews

Waterfront | Pool | Hot tub | Beach Access

TaraRating, 5 stars1 month ago
Great stay for our group. Comfortable beds, and well stocked home. Easy communication. Thanks! We’ll definitely rent with you again next time!

Private beach house rentals

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

Bay Beach Oasis

CarolineRating, 5 stars3 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 Havre de Grace
5 out of 5 average rating, 45 reviews

Quaint home in charming town

PaigeRating, 5 stars2 weeks 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!
Top guest favourite
Home in Pasadena
5 out of 5 average rating, 28 reviews

Kayak Cove

KellyRating, 5 stars1 week 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 Betterton
5 out of 5 average rating, 44 reviews

Ruby's Sea Glass Cottage near Betterton Beach

NaomiRating, 5 stars1 week ago
This was such a peaceful and beautiful getaway. The house was so charming and immaculate. That goes for interior and the exterior. We celebrated Father’s Day weekend here and our husbands had a blast fishing the pier and our littles walking to the beach. The rain head shower head and the heated bathroom floor was to die for, and enjoying a book on all the wonderful porches and beautifully kept backyard! We hope to visit again soon! Thank you so much.
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 stars3 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!
Top guest favourite
Home in Annapolis
4.95 out of 5 average rating, 81 reviews

Serene Riverfront Home

Alexandra GraceRating, 5 stars2 weeks ago
This house was beautiful and included so many amenities for guests to use! Scott was very responsive and even gave us recommendations of local markets and activities happening in the neighborhood. Check in and check out were very easy. We loved sitting on the back deck in the mornings watching the boats go by!

Destinations to explore