Beachfront holiday rental in Wildwood Beach

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Popular amenities for Wildwood Beach beachfront rentals

Pet-friendly beachfront home rentals

Guest favourite
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 favourite
Home in Charlestown
5 out of 5 average rating, 64 reviews

The Cooper House in Charlestown, MD

HeatherRating, 5 stars1 week 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!
Top Guest favourite
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.
Guest favourite
Cottage in Annapolis
5 out of 5 average rating, 10 reviews

Wonderful Cottage Nestled On Chesapeake Bay

TereskaRating, 5 stars2 days ago
This trip was amazing. The house is so adorable. Everything upgraded and spotless. Beds were very comfy. We ended up having a storm that knocked out power and Christine immediately refunded us for the night. I will return to this home anytime we are in Annapolis.
Top Guest favourite
Home in North East
4.96 out of 5 average rating, 55 reviews

Boho River Cottage

SheriRating, 5 stars1 day ago
The Boho Cottage and gardens were lovely. Cece is attentive and provided thorough information for a seemless stay. Cece also takes great care in ensuring guests have everything they may need. We were welcomed with beautiful flowers, prosecco, and goodies. With much appreciation for making our stay truly memorable.
Superhost
Home in Annapolis

Waterfront Dog-Friendly Home with Private Dock

JoanaRating, 5 stars3 months ago
The home was beautiful, clean, and comfortable. We didn’t spend too much time at the house but found it relaxing and enjoyable while there. It was about a 15 min drive from old city center and has some nice restaurants around. My only criticisms are that the house was hard to find in the dark and we almost missed it. Hosts were great and friendly and my family had a great time in Annapolis!
Guest favourite
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. 👍🏻👍🏻👍🏻
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.

Beachfront home rentals with a pool

Top Guest favourite
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.
Home in Stevensville
4.91 out of 5 average rating, 11 reviews

Waterfront Escape with Pool Nature Lover Paradise

AnnetteRating, 5 stars6 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.
Guest favourite
Home in Georgetown
5 out of 5 average rating, 11 reviews

Georgetown Awesome Townhome 3BR 3.5BA

SuzanneRating, 5 stars1 month ago
Fantastic place in every respect! The house is lovely, pristine, perfectly configured, and outfitted with every amenity. The tiered garden out back is beautiful and charming. The location was A+++ (quintessential Georgetown setting with delightful walking everywhere). We enjoyed everything about the house and our time there. Thank you, Charlotte!
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.
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!
Superhost
Condo in Betterton
4.92 out of 5 average rating, 38 reviews

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

SihamRating, 5 stars2 weeks 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!
Guest favourite
Cottage in Neavitt
4.73 out of 5 average rating, 22 reviews

Grandview - Cottage 1A, King Bed, Pool, Bay, WIFI

SophiaRating, 5 stars2 months ago
This is a beautiful little gem right by the waterfront and very close to St. Michael. We loved it! So cosy, relaxing and peaceful. The overall property is amazing. We will be back!
Top Guest favourite
Home in Kent Narrows
5 out of 5 average rating, 301 reviews

Chester Riverfront At Kent Narrows

CassandraRating, 5 stars3 weeks ago
A great place to enjoy a long weekend at the Eastern shore in Maryland.

Private beachfront home rentals

Guest favourite
Guesthouse in Annapolis
4.91 out of 5 average rating, 107 reviews

Private Cottage on gated estate

JhonaRating, 5 stars1 month ago
Donald's place was great! Even better than advertised. We were a party of 5 attending an Annapolis graduation, and we couldn't have been more satisfied. Our hosts Donald and Julie were fantastic! Its a quiet, peaceful neighborhood with free beach. We highly recommend it!
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 stars3 days ago
We had a wonderful time, great location and loved reading about the house history.
Guest favourite
Guesthouse in Arnold
4.88 out of 5 average rating, 17 reviews

Adorable 1 BR guest house with water views, deck

LaurenRating, 5 stars2 days ago
I loved staying at this wonderful Airbnb! It is just perfect for a single or a couple. On the water, in a quiet setting, just outside Annapolis. Clean, beautifully decorated, very comfortable bed and a great shower and bathroom. Arrived right as a storm was coming and the host met me and helped me get into the unit quickly just as the storm hit (very appreciative!). Set up my work laptop- internet was great. Not a work trip but somehow work usually needs a bit of attention. I can't say enough about how perfect this was for me. The water view front and back was lovely. I sat on the back deck with my coffee and just soaked up the sun. It was so comfortable and I hope to be back to visit again. Thank you!
Top Guest favourite
Cottage in Annapolis
4.93 out of 5 average rating, 29 reviews

Bay View Beach Cottage, plan your family vacation

MeganRating, 5 stars1 month ago
Susan’s place was perfect for my parents’ extended stay with beautiful views of the Chesapeake out the windows and access from a lovely beach. My dad felt right at home going for his daily walks and meeting all the dogs in the neighborhood. The location is super convenient to a grocery store and selection of restaurants as well as getting into downtown Annapolis. The kitchen is well equipped and beds are great. Susan was incredibly communicative and very accommodating in extending the stay beyond their original booking.
Superhost
Apartment in Dundalk
4.82 out of 5 average rating, 11 reviews

2 Bedroom on the Water Close to Baltimore and DC

VickiRating, 5 stars23 months ago
Ebony is one of the best hosts I’ve ever had through Airbnb. Very responsive and helpful! You want crab at 10pm? She’ll find it for you! The view from the home was gorgeous. Very nice and quiet which allowed us some relaxation. Pleasantly surprised by the fireflies in the backyard and the huge magnolias on the tree (neither can be found in Montana where we came from). Great place. Would stay again if I ever return to the area!
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)
Guest favourite
Guesthouse in Grasonville
5 out of 5 average rating, 15 reviews

Quaint Waterfront- access, Private Shorehouse-unit

MichaelRating, 5 stars1 day ago
Awesome place and location. Waking up to the sunrise on the water was a special experience. The house is very roomy and well sectioned, which worked perfectly for our young child to have her own space for sleeping. The front porch was amazing in the evenings to relax and have a beer. Great location, close to Kent island restaurants, fishing, boating, and Annapolis. Wish I was able to use the dock more for fishing and crabbing, but saw plenty of fish jumping out of the water!

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