
Beach house vacation rentals in Wildwood Beach
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Top-rated beach house rentals in Wildwood Beach
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Popular amenities for Wildwood Beach beach house rentals
Beachfront house rentals

Chestertown Watson Family Farm
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.

The Shore House
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.

Peaceful Waterfront Home in Annapolis 3BR 2BA.
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.

Waterfront w/ Private Pier, 35 Mins to Annapolis
We had a wonderful time, great location and loved reading about the house history.

Mac's Waterfront Wonder
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.

*Waterfront Sunset Bayview* sleeps 6
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)

Panoramic water views
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.

Bay Home in Annapolis with Private Dock
Beautiful place, beautiful location. Joel thought of anything you could want.
Beach house rentals with a pool

Time Stands Still, While Memories Are Made.
We had such a wonderful stay and Jason the groundskeeper was super awesome and responsive to any questions we had about the property. The Farm at Bald Eagle Point is expansive with so many things to do - we fished at the pond, the dock, swam in the pool. I wish we had the time to kayak and hang out at the private beach. If we were proactive we should have brought some beach chairs (the property does not come with beach chairs that we could find). We had 2 small children with us - the house came with 1 highchair that was pretty difficult to figure out and the fabric on the highchair was kinda yucky and 2 booster seats (note, that the boosters buckled to the chairs but there were no buckles to keep the child in the booster seat). There were also no baby gates which we knew about ahead of time (2 sets of stairs). Other than that the drive to St. Michaels is short and there are plenty of shops and restaurants to peruse. Our stay was overall awesome and I highly recommend it.

Beautiful Home Near Beach and Patapsco River
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.

Bay Breeze Retreat
Fabulous views of Chesapeake Bay, pool was great, deer everywhere, house was spacious with three living areas. Would definitely stay there again.

StayAhoy! | Swim spa | Fishing
Perfect place to explore DC while also being close to the water (and with an amazing hot tub to relax in)

The Mariner's House
Wonderful property with lots of amenities!

Entire Beach House with Pool and Hot Tub
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!

Waterfront Farmhouse Meets Modern Luxury
Beautiful house! Clean, well maintained, and exactly as described. The host was easy to communicate with and very responsive throughout our stay. The space felt comfortable and welcoming, and everything we needed was thoughtfully provided. We had a great experience and would definitely love to come back!

Waterfront Bliss: Ultimate Tilghman Retreat
My stay was absolutely incredible truly beyond anything I expected! One piece of advice: definitely have transportation, as the property is on an island and things are a bit spread out. That said, I enjoyed a lovely walk into town where I dined at some charming local spots and even did a little boutique shopping. Be aware that Uber and Lyft aren’t readily available in the area, and when they are, they’re pretty pricey. But honestly, the property itself feels like something straight out of a Lifetime movie peaceful, picturesque, and exactly the kind of escape I didn’t know I needed. I can’t say enough good things about this stay… so I’ll just say: BOOK IT!
Private beach house rentals

Cheerful & Spacious Shore Life Beauty!
Extremely comfortable accommodations. Loved all the cozy touches in the apartment. Access was simple. Privately located. Host was very friendly and very responsive.

Chessie Cottage - Chesapeake Bay
We had the BEST time staying at this beautiful home this past weekend while we were in town for a wedding. The location is absolutely perfect for a peaceful weekend on the water and this house is a DREAM. Thank you so much for letting us stay at your incredible home!

River Cottage, Chestertown
Beautiful location and the bikes, kayaks and fire pit all added fun and relaxation to our stay! Close enough to Chestertown to enjoy the farmers’ market and shopping and far enough out to be a peaceful retreat.

Stay Anchored Chesapeake Bay, 5 bedrooms, 3 bath
We had a great time. There was plenty of space to move around so that everyone was not in each other's space. The place was very clean and well-stocked with some everyday items you would normally have in your house to cook, shower and clean with. Jen was very responsive with any questions we had. Even the small children loved the house, especially the bunk beds. It was easy to get to places we needed to go to. All 11 of us enjoyed our stay and everyone said they wouldn't mind returning for another family staycation.

Relax - Eastern Shore Creek Home - 3 Br, 3.5 Ba
Holly and Nash's home was clean, beautiful, and very spacious for 3 couples. Complete renovation and all new furnishings inside. As listed, all 3 bedrooms are downstairs, along with 2 1/2 bathrooms. The beds (3 queens) were comfortable. The kitchen is gorgeous for meal prep. Kuerig and coffee pods, Nespresso and pods, salt, pepper, dish soap and some spices were provided. Bring anything else you need. Beautiful new grill on deck. Upstairs (using a tight, spiral staircase) housed more seating another TV, pool table, wet bar and another full bath--basically, an adult entertainment area. Beautiful neighborhood. Bridges Restaurant in Kent Narrows (12 min drive) had very good food and service. We visited the cute town of St. Michaels (49 min drive). Communication with Holly was excellent. She was super responsive and helpful, provided suggestions and went the extra mile. Great stay

Quaint home in charming town
What a warm and welcoming place to stay in Havre de Grace! We felt right at home and had everything we needed for our stay. We spent quite a bit of time on the lovely deck, enjoying the flowers and birds. So much to do within a short walking distance. We’ll be back!

The Wise Quack 2 - A Taste of the Chesapeake Bay!
The Wise Quack 2 is a cozy, clean Airbnb steps from the Chesapeake Bay, perfect for a relaxing getaway. Sidco’s warm hospitality, comfy beds, and thoughtful touches like the deep tub and hammock make it a gem. The quiet Shady Side location and quick host responses ensure a delightful stay.

Cattail Landing- Photographer's Waterfront Retreat
We had a wonderful time during our visit. The peaceful environment on the water was just what our group needed. Thank you!
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- Nationals Park
- The White House
- Betterton Beach
- National Mall
- Georgetown University
- Oriole Park at Camden Yards
- National Museum of African American History and Culture
- Hampden
- District Wharf
- Smithsonian National Museum of Natural History
- M&T Bank Stadium
- Sandy Point State Park
- Arlington National Cemetery
- Washington Monument
- Georgetown Waterfront Park
- Patterson Park
- National Air and Space Museum
- Great Falls Park
- National Harbor
- Smithsonian American Art Museum
- Lincoln Park
- Meridian Hill Park
- Congressional Country Club
- Quiet Waters Park