Beachfront holiday rentals in North Beach

Find and book unique beachfront homes on Airbnb

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Popular amenities for beachfront rentals in North Beach

Pet-friendly beachfront home rentals

Superhost
Flat in Cambridge
4.9 out of 5 average rating, 130 reviews

Little Slice of Cambridge. 2 bedroom, pet friendly

JoanRating, 5 stars2 weeks ago
We rented A Little Slice of Cambridge because of the Iron Man competition held that weekend. It was convenient to the venue...and allowed to walk to the competition and nearby restaurants. Pamela was a wonderful host...communicating easily. The rental was well stocked with toiletries, dishes, pots and pans and extras. The house was comfy and the beds comfortable. An enjoyable stay...unfortunately, we weren't able to stay for more sightseeing...although I did walk down to the Lighthouse and beautiful wharf.
Guest favourite
Cottage in Pasadena
4.97 out of 5 average rating, 176 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

TeresaRating, 5 stars1 week ago
We were very impressed with our stay! Came for rest & reflection and found it. Very secluded and private but close to everything. The house and everything in the house were spotless and the amenities were much appreciated. Many places give you the “starter pack” like half a roll of toilet paper, etc. Not knowing what to expect, we packed everything but we really appreciated that there was enough garbage bags, paper towels, etc for our stay! Not to mention no shortage of bath towels or beach towels, kitchen was well stocked. The park being next door was awesome to walk through with the dogs. Highly recommend!
Guest favourite
Guest house in Annapolis
4.86 out of 5 average rating, 101 reviews

Chesapeake Bay Escape | Cozy Retreat

JacquelineRating, 5 stars1 month ago
We loved our weekend stay at Melanie’s place!! It was clean, easy to access and a lovely location!! She was super helpful with our questions about the areas and places she recommended. Definitely recommend!!
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
Cottage in North Beach
4.94 out of 5 average rating, 50 reviews

Cozy Waterfront Cottage - Pet Friendly

LisaRating, 5 stars1 week ago
This was a fantastic vacation rental- the kids’ favorite yet! You can’t beat the views and the proximity to the beach and shops. There is also a playground, library, ice cream shop, and pizza just a block away. The host had snacks, water, and milk available for us and the kids when we arrived, which was very welcome after a long car ride! And having beach chairs and beach umbrellas for use made our beach days so much better! We brought our paddle board and launched it off the local beach which was quite fun. Annapolis and DC are both far drive and, when we weren’t enjoying the local amenities, we found plenty to do just an hour drive or less away. I highly recommend this rental. Thank you for allowing us to rent your lovely home and we will definitely be back
Top guest favourite
Cottage in Lusby
4.98 out of 5 average rating, 279 reviews

Gettin to the point. ( Cove Point Beach)

Barbara JRating, 5 stars5 days ago
House was larger than expected, very clean with a well-stocked kitchen, and had numerous seating/gathering areas both inside and out. Host was very responsive from booking through checkout. I would certainly stay there again.
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.
Guest favourite
Flat in Annapolis
4.92 out of 5 average rating, 101 reviews

Dazzling day/night water views,1st class amemities

ThomasRating, 5 stars8 months ago
Wonderful host—I felt right at home. Had conversation prior to arrival and felt like I knew her very well before arriving. The view was spectacular I could have just sat on the patio and watched the woods and water all day. Was there for a school reunion so I had other activities that I had scheduled. This was by far, the best Air B&B experience I have had. Fantastic host, comfortable, and stunning scenery. I am going to try and revisit soon.

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 stars2 days 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
4.92 out of 5 average rating, 12 reviews

Waterfront Escape with Pool Nature Lover Paradise

JessicaRating, 5 stars5 days ago
Beautiful spot right on the river. It’s a huge house with tons of space for a large group. The fenced in yard makes it ideal for furry family members. This was ideal for a multigenerational get together. Thank you so much!
Top guest favourite
Home in Lusby
5 out of 5 average rating, 19 reviews

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

AlanRating, 5 stars6 days ago
Our family had such a great time staying at MJ's place last year that we came back again this summer. As before, we all loved the view, pool, firepit, grilling on the deck, and walking down to the neighborhood beach. The house was very clean and the kitchen was well-stocked. All the beds were comfortable, and all bedrooms had well-functioning blinds/shades, which is really helpful when putting younger kids to bed. The lower level bathroom had been renovated since our last stay which was a great bonus. We are looking forward to returning next summer!
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.
Cottage in Neavitt
4.88 out of 5 average rating, 24 reviews

Grandview - Cottage 1B, Queen Bed, Pool, Bay, WIFI

HeatherRating, 5 stars1 month ago
A cozy and quiet cottage right along the water. The kitchen is very well stocked. You can find any pot or utensil you may need. The best part of the cottage is the sun room, it was a great place to enjoy a glass of wine in the evening or enjoy a cup of coffee in the morning and soak in the sparkling water and peaceful surroundings. A peaceful spot away from everything, but a short 15 minute drive into St. Michaels. The road to the cottage is a bit rough, a small car has to navigate it with some care.
Superhost
Home in Woolford

"Endless Summer" on the Chesapeake!

JeannineRating, 5 stars1 month ago
great location and very clean!
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!
Home in Tilghman
5 out of 5 average rating, 3 reviews

Clearview | an ESVR property

TomRating, 5 stars36 months ago
fantastic spot on the Island. incredible sunsets. very clean with stunning views of the Bay. everything you need to enjoy the Island is here with walking distance general store.

Private beachfront home rentals

Top guest favourite
Serviced apartment in Broomes Island
5 out of 5 average rating, 42 reviews

Beautiful waterfront apartment in Broomes Island

LisaRating, 5 stars1 month ago
We loved our stay! Len and Shannon are incredible hosts! Every sunset from the deck was perfect! Having the convenience store below was also nice for grabbing a snack. We wish we could have stayed longer! I would highly recommend the stay! A++++++++++++++
Guest favourite
Home in Cambridge
4.98 out of 5 average rating, 129 reviews

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

HaleyRating, 5 stars2 days ago
This is such a pretty little house! It was a perfect size and layout for two families, including a young child and an infant. The house itself is very nice, and it's well-stocked with items you might need. It has a nice view and access to the river, which was great, and it is close to many of the restaurants and other spots in Cambridge we like to visit. I'd definitely stay here again.
Guest favourite
Home in Lusby
4.99 out of 5 average rating, 92 reviews

Waterfront with sweeping bay view & private beach

CorrineRating, 5 stars2 days ago
We had such a wonderful trip to the Bay! What a beautiful spot! Such lovely views of the bay- with sights of sailboats, ships, rays, and even dolphins one day! It felt very private and quiet: exactly what a vacation should feel like! We loved using the kayaks and searching for shells/shark teeth! The home itself was extremely clean and comfortable to be in. Full kitchen was super helpful when feeding a whole family! It was our first solo trip with small kids and was honestly wonderful in every sense! Colin was very easy and pleasant to communicate with. 10/10- would recommend to anyone!
Guest favourite
Home in Leonardtown
4.96 out of 5 average rating, 68 reviews

The River House: A private waterfront oasis…

ChrisRating, 5 stars1 week ago
What can we say? John's property was everything we hoped it would be. The back yard is full of fun yet also serene and peaceful. The water is perfect for floating in a tube, kayaking, or just wading in and cooling off. The house has everything anyone could want. As an added bonus, you'll enjoy watching an Osprey family, Herons, Ducks, Mockingbirds, Blue Jays, Cardinals, and even some Minks and a Groundhog. The firepit is perfectly placed by the water for a morning fire as the mist rises, and especially in the evening for spectacular sunsets over the bay. Even getting there is a joy, as you go down a quiet country road lined with beautiful farms, quaint churches, and plenty of deer and wildlife. If your looking for a tourest trap vacation, then Leonardtown is not for you. But if you want a quiet getaway with all the amenities, then this is your place!
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
Guest suite in Annapolis
5 out of 5 average rating, 236 reviews

Cape St Claire waterfront getaway "The Apartment"

Donald and CherylRating, 5 stars1 week ago
Lise is an amazing host. She personally greeted us upon our arrival and showed us around the apartment. She went the extra mile in helping us with directions to many of our destinations in Annapolis. She was at our "beckon call". Made us feel like family. The apartment was lovely. It was very spacious, yet cozy. Everything was well appointed and easily accessible. And did I mention the view!! Oh the view from the back yard and the dock overlooking the Bay Area. We actually had breakfast and dinner on the dock. Can't wait to go back for a visit. Thank you Lise and Buzz.
Top guest favourite
Home in Cambridge
5 out of 5 average rating, 34 reviews

• Peaceful Point • A relaxing waterfront retreat

KacieRating, 5 stars2 weeks ago
Peaceful point was stunningly beautiful! A perfect place for adults and kids to unwind and enjoy the scenic views and beautiful nature. Joanna was the best host and surprised us with a little welcome package with a kind welcome card and some of our favorite treats from Trader Joe’s! She was so helpful and responsive via text. Can’t thank her enough!
Top guest favourite
Home in Edgewater
5 out of 5 average rating, 14 reviews

Waterfront home on the Bay

Steven JayRating, 5 stars3 weeks ago
This is one of the best Airbnb experiences we have ever had. Teresa’s house was 10 out of 10. Everything was absolutely fantastic. Very clean with everything we needed. The view was spectacular!!!! We absolutely loved everything especially the bald eagle that flew by on our last morning. I highly highly recommend staying here and next time we make the trip up there from Texas it will be scheduled based on the availability of Teresa’s house. Thank you for being a great host!!

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