Beachfront vacation rentals in Breezy Point Beach

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Popular amenities for Breezy Point Beach beachfront rentals

Pet-friendly beachfront home rentals

Guest favourite
Home in Middle River
4.95 out of 5 average rating, 20 reviews

The Shore House

JessicaRating, 5 stars1 week ago
House was spectacularly designed and smelled so good upon arrival. The ranch level style with everything on one floor was ideal for stay with a toddler (and 3 adults). We only stayed a weekend but wish it was longer. I would definitely stay here again. One thing to note that this area does not have service if you are not in the house. Once you are in the house you have WiFi and good to go. Lauren was super responsive and very nice.
Top guest favourite
Home in Chestertown
4.99 out of 5 average rating, 107 reviews

Entire River Front Home - 4 Bedrooms 4.5 Baths

JeanneRating, 5 stars11 months ago
We had a wonderful stay at this beautiful place. Our extended family and dogs thoroughly enjoyed the private and peaceful location. Bobs place was provisioned very well. We appreciated the numerous coffee cups, wine glasses, etc. it felt very much like staying with family. Lovely art throughout too.
Top guest favourite
Houseboat in Stevensville
4.94 out of 5 average rating, 51 reviews

Chesapeake Houseboat Getaway

RichardRating, 5 stars2 months ago
The houseboat was everything and more than the description. If you are looking for a great winter get away this is a perfect place to go to. You can kick back and relax or stay busy shopping and seeing the historical towns in the are. St Michaels and Easton are a short ride away. The restaurants are very good no matter what price range you are looking for. The shopping is great with many interesting small shops. I will certainly be back to the houseboat later this year.
Top guest favourite
Home in Charlestown
5 out of 5 average rating, 62 reviews

The Cooper House in Charlestown, MD

MiriamRating, 5 stars1 week ago
We really enjoyed our stay and the peaceful surroundings. The house is very charming, and well maintained. It was clean and spacious and matched the pictures. The view is beautiful and you can see the water from the windows and porches. Trey was a great host, very responsive and helpful whenever we reached out with questions. Would definitely recommend and we would love to come back for another visit.
Top guest favourite
Home in Rock Hall
5 out of 5 average rating, 29 reviews

Sunset at Rabbit Run

PatRating, 5 stars7 months ago
This was the perfect location to get some rest and relaxation. It was beautiful with big views of the Bay. Bird and boat watching while sipping wine on the patio. The house was lovely with gorgeous plantings. The welcome treats were a nice surprise. Our dogs loved swimming and running in the yard. Great amenities and a very clean house. Fun restaurants in town which had a Key Westesque feel to it. We hope to be back again.
Guest favourite
Cottage in Annapolis
5 out of 5 average rating, 7 reviews

Wonderful Cottage Nestled On Chesapeake Bay

Anthony Rating, 5 stars1 month ago
Christina's place was amazing. A perfect home away from home. Super clean, peaceful, and scenic. The check-in/out process was simple and smooth. 10 out of 10. I'd stay here again in a heartbeat.
Top guest favourite
Home in North East
4.96 out of 5 average rating, 46 reviews

Boho River Cottage

StaceyRating, 5 stars1 week ago
Our stay at Cece's Boho Cottage was excellent. It started with an egg hunt around the yard for my boys along with some sweet treats for all to enjoy. Cece gave amazing restaurant suggestions along with local hikes and shops. If you happen to forget something, Cece thought of it! We loved morning coffee on the back porch with the rising sun, comfy beds, and enough space to spread out. Thank you for sharing your adorable cottage with us! We are already trying to plan a trip back!
Superhost
Home in Annapolis
4.94 out of 5 average rating, 17 reviews

Spring Waterfront: Dock & Walk to Beach!

JenniferRating, 5 stars2 days ago
Sheila’s place was the perfect weekend getaway. She was a responsive host, and her home was even better than depicted. The house was thoughtfully designed and well-appointed. She accounted for every kitchen utensil / appliance you could possibly need, and even had eye masks for sleeping in the bedrooms. The waterfront views were the main appeal of the house and the master bedroom overlooked a gorgeous view that boasted picturesque sunrises and sunsets. Would definitely come back again—preferably with a boat! I only wish we could have stayed longer.

Beachfront home rentals with a pool

Top guest favourite
Home in Chestertown
5 out of 5 average rating, 22 reviews

Chestertown Watson Family Farm

TaraRating, 5 stars7 months ago
We loved our stay at Molly's air B &B. there were lots of toys to use on the river. The water views from the house were fantastic. The house was clean and comfortable. We loved taking a dip in the pool. Great communication with the host.
Home in Stevensville
5 out of 5 average rating, 3 reviews

Waterfront Escape with Pool Nature Lover Paradise

KarenRating, 5 stars3 weeks ago
This property has a breathtakingly beautiful view of the water that has a fully fenced in yard…so you don’t have to worry about little ones getting into the water. The master bedroom and master bath was amazing. My extended family and I traveled from 4 different states to stay at this property and all of us were comfortable. The house had plenty of spaces to kit be on top of each other. I highly recommend booking this property. The host is very responsive and helpful. I will keep this property in mind for future stays.
Home in North East
4.76 out of 5 average rating, 21 reviews

Pool House by the North East River

JeniferRating, 5 stars7 months ago
Once again the River house is a well appointed comfortable stay! The swimming pool is a gem! The house is bright and well located; very clean. There is great and comfortable furniture. The views are beautiful and the location is wonderful. We will be back next year!
Guest favourite
Home in Worton
4.97 out of 5 average rating, 30 reviews

Chesapeake Bay Estate; 2 Houses, Beach&Heated Pool

LauraRating, 5 stars8 months ago
My family loved staying here. We had my 3-month old and my sister brought her 8-month old so we were looking for a place that could keep everyone entertained in one location and this place did just that! We enjoyed bird watching, collecting rocks on the beach, swimming in the heated pool, and watching the sunset from the hot tub in the evenings. This was also the first time I could say that the listing looked better in person than the pictures. Thank you Joni for letting us stay here! We made some amazing memories!
Superhost
Condo in Betterton
4.92 out of 5 average rating, 36 reviews

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

CaitlinRating, 5 stars7 months ago
A great sunset view from the balcony, such a nice quiet river/bay beach, peaceful community to walk around. Would stay in again! Would note there’s 1 flight of stairs up as it’s a 2nd floor condo of sorts; and a big hill/stairs down to the beach. However, also a parking lot if needed to drive to the beach. Beach chairs were nice to have. There was no cooking oil but I think we left some :) I would only ask they replace the dining room chair with the hole in the seat. The pool was closed and that was not expected! Adam was very responsive when we messaged.

Private beachfront home rentals

Top guest favourite
Home in Edgewater
5 out of 5 average rating, 56 reviews

Waterfront South River Edgewater Sunrises & Beach!

KatRating, 5 stars6 months ago
We had a lovely stay at Heather’s place. The house was clean, comfortable, and we felt taken care of. The porch with the view of the water and sunrises was so relaxing. Visiting during the off-season was peaceful, but there was still plenty to do in the area. We couldn’t have asked for a better getaway weekend.
Guest favourite
Guesthouse in Arnold
4.88 out of 5 average rating, 16 reviews

Adorable 1 BR guest house with water views, deck

LauraRating, 5 stars6 months ago
Clean and cute and just as described. Perfect for a long weekend away in Annapolis for the boat show!
Top guest favourite
Cottage in Annapolis
4.93 out of 5 average rating, 28 reviews

Bay View Beach Cottage, perfect for long-term

MichaelRating, 5 stars3 months ago
The house was a perfect location on Cape St. Claire. Well furnished and comfortable. Susan is a great host.
Top guest favourite
Home in Chester
5 out of 5 average rating, 34 reviews

*Waterfront Sunset Bayview* sleeps 6

MaryRating, 5 stars2 months ago
Beautifully designed house highlighted the stunning view of the bay. Cozy and clean, couldn't have asked for more!
Guest favourite
Cottage in Charlestown
4.96 out of 5 average rating, 164 reviews

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

Joseph & TracyRating, 5 stars4 days ago
The property is beautiful, its just like the pictures. The location is peaceful and quite. Its a perfect spot to just to relax and reconnect. Can't say enough good things about the cottage. Clean, Bed was nice, view was amazing, Hot tub, kayaks, plenty of firewood for a beach fire. During our stay we went to main street in North East it was about a 7 minute drive. It was a nice little town to walk. Chesapeake Coffee Co for a breakfast sandwich and a coffee. We had lunch at Woody's crab shack. Ordered in pizza from Bella Pizza, Went to Nauti Goose. I was underwhelmed at all restaurants and by all meals. If we come back again, I'd get groceries to cook, there is a grill to use (we didn't) and stay in, just take in the view and enjoy the peaceful waves. We would defiantly recommend and hopefully be back again soon.
Superhost
Cottage in Grasonville
4.89 out of 5 average rating, 62 reviews

CoastalBeachCottage*BayViews*Close2WeddingVenues

ColinRating, 5 stars2 months ago
We had a great stay at this property and it was perfect for our visits with friends in Grasonville. The property is well represented in the photos. Conveniently location just off the main highway and just a 2 minute walk to the water front. Thanks, Michelle
Top guest favourite
Guest suite in Annapolis
5 out of 5 average rating, 232 reviews

Cape St Claire waterfront getaway "The Apartment"

JoAnnRating, 5 stars3 days ago
Absolutely beautiful spot. Lise was a wonderful host. The space was amazing and everything was immaculate. Backyard was so nice and relaxing after being out and about all day. I would definitely stay again and recommend to other couples.
Top guest favourite
Cottage in Annapolis
4.98 out of 5 average rating, 46 reviews

Charming Waterfront Cottage on Historic Property

LizRating, 5 stars1 week ago
What an absolute treat to stay at the Cottage at Whitehall. We had such a lovely time, we stayed an extra day! Ty & Susie are gracious hosts and we were so excited to get a tour of the mansion and explore the grounds. The private beach at the back of the cottage is phenomenal, please take the canoe out - or even go for a swim. The sand is silky and soft, it was like a giant swimming pool nearly all to yourself. My husband enjoyed the canoe immensely (the waves scare me, so it wasn’t too much for me / but if you canoe out on the Meredith River it’s much calmer). If you fish - bring your fishing gear!! (Check local laws first, of course) Absolutely do not hesitate to book here if you have the chance, highly recommended 😍

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