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

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

Beautiful waterfront apartment in Broomes Island

LisaRating, 5 stars3 weeks 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 North Beach
4.93 out of 5 average rating, 67 reviews

A Little Piece of Paradise - Waterfront Home

LisaRating, 5 stars1 week ago
It was a great stay and a perfect location for our quick family back east. It was very comfortable, clean and a the right size for our family of 4. It was nice to have our own place to stay and not to far from our family. We didn’t spend much time in the town but it looked cute with shops, cafes and restaurants. We had great communication with Maria, she was very quick to respond. Thanks for a great and comfortable stay!!
Superhost
Flat in Cambridge
4.9 out of 5 average rating, 130 reviews

Little Slice of Cambridge. 2 bedroom, pet friendly

JoanRating, 5 stars1 week 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, 175 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

EmilyRating, 5 stars3 weeks ago
Keith’s water view cottage is so beautiful and peaceful. My husband and I had a lovely long weekend stay with our little dog. Even with the storms that passed through the bay we felt extremely safe and cozy throughout our stay. Keith was very responsive and flexible with checkin /checkout. Would definitely stay again!! Thanks Keith !
Guest favourite
Guest house in Annapolis
4.86 out of 5 average rating, 101 reviews

Chesapeake Bay Escape | Cozy Retreat

JacquelineRating, 5 stars4 weeks 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 stars4 weeks 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 stars4 days 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, 278 reviews

Gettin to the point. ( Cove Point Beach)

BarbRating, 5 stars3 days ago
Have now stayed here twice and love it so much we just booked our next visit. It's a lovely and comfortable home!

Beachfront home rentals with a pool

Top guest favourite
Home in Chestertown
5 out of 5 average rating, 23 reviews

Chestertown Watson Family Farm

LukeRating, 5 stars2 days ago
We had a great time. The view is one of the best we have stayed at. The hosts have thought of almost everything you could need or want to do. Our kids wanted to come back just to do more of the activities. The interior is obviously dated but it is thoughtful, functional, and clean. We felt cozy and at home! We will be back!
Home in Stevensville
4.88 out of 5 average rating, 8 reviews

Waterfront Escape with Pool Nature Lover Paradise

AnaRating, 5 stars2 weeks ago
Hosted my intimate wedding at Nancy’s home and we had an amazing weekend! My family & closest friends loved the home, location, amenities & the coziness of the house. Perfect for a lil vacation with friends & family and very kid friendly. Absolutely loved my stay. Thanks for letting us stay at your place, view was incredible and so much space for a big group. Will definitely come back and recommend 100%
Top guest favourite
Home in Lusby
5 out of 5 average rating, 16 reviews

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

DeniseRating, 5 stars7 months ago
The area and view are beautiful and the home's decor is welcoming. The home was very comfortable for our family group and had a VERY well-stocked kitchen. The master bed was VERY comfortable as were the rest of the beds. My husband and I slept well. We all felt at home. MJ was very responsive when I had questions and communicated about the property in clear, concise language. The host provided many outdoor recreation opportunities, which included paddleboards, kayaks, and life jackets. There was a nice sized pool but we were visiting out of season so we did not use it. The exercise room downstairs has a lot of equipment. We all enjoyed our time together. Our family is asking to come back again next year. Thanks for a great stay!
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 Royal Oak
4.67 out of 5 average rating, 3 reviews

Waterfront, Pool, Dock, Hot Tub.Stunning Views! A

HeatherRating, 5 stars3 weeks ago
We had a fantastic stay at this Chesapeake Bay home for our annual family trip! The outdoor space is a total standout—beautiful views, a great pool, and everything we needed for kayaking, crabbing, and making memories by the water. We especially loved the roomy layout, the well-stocked kitchen, and the big dining table that made family dinners a highlight each night. The house is full of personality, with tons of unique decor and interesting items throughout—definitely made for a fun and memorable stay, though we did find ourselves having to keep a very close eye on the kids around all the treasures! Overall, it was a wonderful trip and we’d absolutely book again!
Guest favourite
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 stars2 days 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!

Private beachfront home rentals

Guest favourite
Home in Oxford
4.96 out of 5 average rating, 213 reviews

The Oxford House

GregRating, 5 stars1 week ago
This place is nicely furnished and the kitchen/dining area are very well supplied. We always enjoy our time in Oxford and the surrounding area and Suzanne Marie's place made it very comfortable. Walkable to the market, coffee shop, ice cream shop and 2 restaurants.
Guest favourite
Cottage in Annapolis
5 out of 5 average rating, 9 reviews

Wonderful Cottage Nestled On Chesapeake Bay

EdmondRating, 5 stars2 weeks ago
The cottage looks just like the photos. Very quiet and peaceful location. They provided a binder that catalogs anything you may need during your stay. EXCELLENT communication. Easiest Check out EVER. Would certainly book again if we return to the area.
Guest favourite
Home in Leonardtown
4.96 out of 5 average rating, 67 reviews

The River House: A private waterfront oasis…

PeterRating, 5 stars1 month ago
This was our family's second stay at The River House. We had another relaxing and fun week! Kayaking across to the state park is one of our favorite things to do there. We also enjoy shopping and eating in Leonardtown. We had one rainy day, but reading on the day bed with a beautiful view (in spite of the weather) and working on a puzzle were an enjoyable way to spend the day. We hiked out to Calvert Cliffs State Park one day and enjoyed lunch on Solomons Island on the way back. John's pet friendly Airbnb is such an awesome place to vacation with our dogs. One of them loves to fetch her floating stick off the little beach area and play frisbee in the yard (bring a long leash that you can tie to the badminton net poles). Our other dog loves basking in the sun in the yard and on the deck. There are so many great things about this place, but the sunsets alone are worth the stay!
Guest favourite
Home in Benedict
4.9 out of 5 average rating, 30 reviews

Bright airy waterfront getaway

StephanieRating, 5 stars1 month ago
The lake was the perfect serenity we needed and fun sea life to enjoy. The house felt a little crowded for 4 people but it had everything we needed and our host had plenty of “extras” to make our trip complete
Guest favourite
Home in Deale
4.9 out of 5 average rating, 20 reviews

Quiet Getaway in Waterfront Community

PinkyRating, 5 stars1 month ago
My husband and I stayed here for a month while we had work done on our boat at a local marina. The location is perfect for access to the local marina as well as all the restaurants in Deale. Yen was super responsive as was John. They responded to all our questions in a timely manner, and were always very kind. The home is well laid out, and worked perfectly to use as a homebase. Good wifi, comfy couch, comfy bed with good pillows. The master suite is gorgeous and well lit. Kitchen is well appointed and had all the appliances/utensils we needed. Had several work spaces that were great for zoom calls and other "office" type work. The tap water didn't have any odors. Enjoyed having coffee on the front porch with a lovely view of the Chesapeake and the screened in porch in the back was great as the evening bugs came out. Highly recommend this home!
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 stars2 days 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 stars1 week 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 stars2 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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