Beach house vacation rentals in Wildwood Beach

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Popular amenities for Wildwood Beach beach house rentals

Beachfront house rentals

Top guest favorite
A group of seated individuals enjoys a view of the Chester River, surrounded by lush green grass. Comfortable lounge chairs are arranged in a line, facing the water. The scene is framed by trees, with a cloudy sky overhead, creating a peaceful atmosphere.
Home in Chestertown
5 out of 5 average rating, 24 reviews

Chestertown Watson Family Farm

AmyRating, 5 stars1 day ago
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 favorite
An open living space is visible, featuring a comfortable sofa and a wooden coffee table. A dining area with black chairs is situated near a well-equipped kitchen, which includes stainless steel appliances. A large window allows natural light to fill the room.
Home in Middle River
4.95 out of 5 average rating, 22 reviews

The Shore House

CeceRating, 5 stars1 day ago
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 favorite
Home in Annapolis
5 out of 5 average rating, 42 reviews

Peaceful Waterfront Home in Annapolis 3BR 2BA.

AndrewRating, 5 stars2 days 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 favorite
A waterfront home is depicted with a screened-in porch and a gabled roof. A wooden pier extends from the shore, leading to the water. Lush greenery surrounds the property, and stone embankments partially border the shoreline.
Home in Shady Side
4.96 out of 5 average rating, 107 reviews

Waterfront w/ Private Pier, 35 Mins to Annapolis

LeilaRating, 5 stars3 days ago
We had a wonderful time, great location and loved reading about the house history.
Guest favorite
A serene view from the balcony showcases the expansive Gunpowder River, framed by leafless trees along the shore. The water reflects a cloudy sky, offering a peaceful atmosphere that blends nature with the home's outdoor living spaces.
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 favorite
A wooden dock extends over the water, featuring two white Adirondack chairs positioned for relaxed seating. The serene water stretches toward the horizon, while the sky is dotted with fluffy clouds, creating a calming outdoor retreat.
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 favorite
A serene sunset is captured over calm waters, with vibrant oranges and yellows reflecting on the surface. The horizon blends into deep blues and subtle cloud formations, while the shoreline features a natural landscape leading to the water's edge.
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 favorite
The spacious exterior of a waterfront home is set against a lush green lawn. Large windows reflect natural light, and a patio area is furnished with a dining table and seating. The property features a barbecue grill and is surrounded by mature trees.
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

Guest favorite
An aerial view showcases a spacious waterfront property, featuring multiple sections connected by pathways. Lush greenery surrounds the home, with the serene water visible in the background. The layout is complemented by a large circular driveway and manicured landscaping.
Home in Sherwood
4.95 out of 5 average rating, 21 reviews

Time Stands Still, While Memories Are Made.

KirstenRating, 5 stars2 days ago
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.
Superhost
A spacious exterior of a two-story home is presented, showcasing a brick facade and a covered balcony above the entrance. The driveway is paved, leading to a gravel area, with a fenced yard visible in the background, offering ample outdoor space.
Home in Pasadena
4.87 out of 5 average rating, 61 reviews

Beautiful Home Near Beach and Patapsco River

KristinaRating, 5 stars3 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
A refreshing saltwater pool is framed by comfortable lounge chairs in vibrant red and blue. A large grassy area is visible beyond the pool, leading to serene waterfront views under a clear blue sky, complemented by a tree providing shade.
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 favorite
The backyard features a well-maintained lawn with colorful blooming flowers, surrounded by lush greenery. A hot tub is positioned nearby, and outdoor seating includes a set of chairs arranged around a fire pit. The house is visible in the background, with a spacious screened porch.
Home in Edgewater
5 out of 5 average rating, 15 reviews

StayAhoy! | Swim spa | Fishing

AlvaroRating, 5 stars2 months ago
Perfect place to explore DC while also being close to the water (and with an amazing hot tub to relax in)
Top guest favorite
A clear swimming pool reflects the overcast sky and surrounding buildings. Multiple white lounge chairs are arranged around the pool, accompanied by blue umbrellas offering shade. The pool area is enclosed by a low fence, creating a serene atmosphere for relaxation.
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 favorite
Home in Edgewater
4.98 out of 5 average rating, 60 reviews

Entire Beach House with Pool and Hot Tub

LisaRating, 5 stars5 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 favorite
A charming neoclassical farmhouse is observed, set among leafy trees. A wide gravel driveway leads to the welcoming front porch, which features white columns. Lush greenery surrounds the home, enhancing the tranquil setting of the property.
Home in Chester
4.95 out of 5 average rating, 96 reviews

Waterfront Farmhouse Meets Modern Luxury

EricaRating, 5 stars4 days ago
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!
Guest favorite
A cozy living area features a large wall-mounted television displaying a scenic view. Comfortable seating is provided by two blue sofas, positioned around a rectangular coffee table. Natural light filters through large windows adorned with blinds, with a glimpse of the waterfront visible outside. A fireplace adds warmth to the space.
Home in Tilghman
5 out of 5 average rating, 10 reviews

Waterfront Bliss: Ultimate Tilghman Retreat

TyraRating, 5 stars1 week ago
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

Top guest favorite
A charming gray house is situated beside a manicured lawn, featuring a well-maintained driveway and an adjacent garage. Green shrubs and small trees are positioned around the property, creating a welcoming environment. A clear blue sky with fluffy clouds is visible overhead.
Home in Stevensville
4.92 out of 5 average rating, 83 reviews

Cheerful & Spacious Shore Life Beauty!

RebeccaRating, 5 stars1 week ago
Extremely comfortable accommodations. Loved all the cozy touches in the apartment. Access was simple. Privately located. Host was very friendly and very responsive.
Top guest favorite
The living area is arranged with various seating options, including a bright orange couch and green chairs. A large area rug anchors the space, complemented by a coffee table and side tables. Windows offer expansive views of the bay, filling the room with natural light.
Home in Stevensville
5 out of 5 average rating, 21 reviews

Chessie Cottage - Chesapeake Bay

CarolineRating, 5 stars1 month ago
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!
Guest favorite
A cozy living area features warm wood paneling and a rustic ceiling. A spacious sectional sofa is arranged around a wooden coffee table on top of an area rug. A dining table for four is positioned nearby, with natural light coming through the windows.
Home in Chestertown
4.93 out of 5 average rating, 30 reviews

River Cottage, Chestertown

FranklinRating, 5 stars8 months ago
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.
Top guest favorite
Two beach chairs are positioned on the sandy shore, facing the calm waters of the Chesapeake Bay. The scene captures a clear sky filled with fluffy clouds, reflecting the tranquil atmosphere of the private beach.
Home in Perryville
5 out of 5 average rating, 25 reviews

Stay Anchored Chesapeake Bay, 5 bedrooms, 3 bath

Mrs. BrownRating, 5 stars2 months ago
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.
Superhost
The spacious living area features a warm wood ceiling and large windows overlooking the greenery outside. A comfortable sectional sofa and an accent chair are positioned around a rectangular coffee table, creating an inviting space. A modern fireplace stands elegantly against the wall, complemented by tasteful decor.
Home in Grasonville
4.83 out of 5 average rating, 6 reviews

Relax - Eastern Shore Creek Home - 3 Br, 3.5 Ba

GinnyRating, 5 stars4 days ago
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
Top guest favorite
A charming home is showcased with light blue siding and autumn foliage framing the entrance. A large tree with bright yellow leaves dominates the front yard, complemented by well-maintained landscaping and decorative elements on the front porch.
Home in Havre de Grace
5 out of 5 average rating, 46 reviews

Quaint home in charming town

IngerRating, 5 stars1 day ago
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!
Guest favorite
A spacious living room features a large, L-shaped sectional sofa adorned with decorative pillows. A coffee table sits centered on a patterned area rug. Natural light enters through windows, and a potted plant adds a touch of greenery. Ceiling fans provide ventilation while maintaining a relaxed atmosphere.
Home in Shady Side
5 out of 5 average rating, 11 reviews

The Wise Quack 2 - A Taste of the Chesapeake Bay!

ToddRating, 5 stars2 weeks ago
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.
Superhost
A spacious waterfront house is shown surrounded by lush trees, with multiple balconies and large windows. A sandy area extends toward the water's edge, and smooth stones form a barrier along the shore, reflecting the natural beauty of the Chesapeake Bay.
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