Beachfront vacation rentals in Dares Beach

Find and book unique beachfront homes on Airbnb

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Popular amenities for Dares Beach beachfront rentals

Pet-friendly beachfront home rentals

Top guest favorite
Apartment 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 favorite
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
Apartment in Cambridge
4.91 out of 5 average rating, 129 reviews

Little Slice of Cambridge. Newly listed, 2 bedroom

JoanRating, 5 stars6 days 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 favorite
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 !
Superhost
Cottage in Lottsburg
4.9 out of 5 average rating, 102 reviews

Charming Waterfront Home with Expansive Views

MichaelRating, 5 stars6 months ago
We loved the house; cozy, nicely decorated, with many pieces of original art that really added character. The kitchen is well stocked for those who like to cook. The location right on the water was wonderful, and Nancy provided kayaks, which we took advantage of. Our dog was beside himself with so much room to run. Nancy’s daughter and family live next door, and we spent quite a few hours enjoying conversation and local knowledge with them. We would go back again.
Top guest favorite
Home in Tilghman Island
5 out of 5 average rating, 18 reviews

Panoramic water views

MeganRating, 5 stars3 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 favorite
Cottage in North Beach
4.94 out of 5 average rating, 50 reviews

Cozy Waterfront Cottage - Pet Friendly

LisaRating, 5 stars2 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
Guest favorite
Apartment in Annapolis
4.92 out of 5 average rating, 101 reviews

Dazzling day/night water views,1st class amemities

ThomasRating, 5 stars7 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 favorite
Home in Montross
4.98 out of 5 average rating, 44 reviews

Game Themed Water Fun! Boats+Pool+Beach+King Bed

AlishaRating, 5 starstoday
Absolutely beautiful stay! The cabin has the cutest theme and the proximity to the water was great and a gorgeous view. Abby and family was so kind, responsive, and great hosts. Would highly recommend this getaway!
Top guest favorite
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 favorite
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.
Top guest favorite
Home in Cambridge
5 out of 5 average rating, 16 reviews

Turtle's Nest - Hist. Cambridge

CoreyRating, 5 stars6 days ago
David and Wendy’s home was the perfect place for our family participating in and supporting the Cambridge Ironman with an easy walk to the course and to the Main Street. They went above and beyond accommodating our requests, since we were traveling with a two month old and a two year old. We were very comfortable and loved our evenings in the screened in porch and pool. We would love to stay at David and Wendy’s again.
Superhost
Cottage in Trappe
4.87 out of 5 average rating, 30 reviews

Private Waterfront Cottage on Bolingbroke Creek

IsaiahRating, 5 stars10 months ago
Our stay Rick/Kevin’s place was fantastic. The property and setting exceeded our expectations. Everything was extremely well maintained. We loved staying in the lovely guest house which had everything we could possibly want. There were so many wonderful places to relax, from the screened porch to the pool and the amazing outdoor kitchen in the open air beach house. We loved floating in the pool while watching the big screen TV. The best of both worlds! We highly recommend Rick/Kevin’s place.
Guest favorite
Home in Montross
4.99 out of 5 average rating, 155 reviews

Beach Please! River cottage w/private beach & dock

SarahRating, 5 stars1 week ago
My family and I stayed here for a week for our family vacation. We are a group of 8 (6 adults and 2 kids) and there was plenty of room for all of us. We barely left the house because with the beautiful view, dock, beach area, canoe, kayaks, hot tub, game room/ library, corn hole, and fire pit we all had plenty to keep us entertained. Everyone loved Mary & Shelly’s place, and it provided the perfect space for us to enjoy the river and each other’s company!
Superhost
Cottage in Heathsville
4.84 out of 5 average rating, 80 reviews

Riverfront Retreat with PRIVATE POOL and BEACH!!

YVisRating, 5 stars3 weeks ago
Awesome place with my t, we had everything we needed and more. Great location to disconnect and connect with one another. Plenty of space, locals, location and great amenities.
Guest favorite
Villa in Hague
4.98 out of 5 average rating, 55 reviews

Sea Glass Paradise

MichaelRating, 5 stars1 week ago
We have stayed here twice now, both times in June. Will definitely be making a yearly trip of it, as we enjoyed it enough for many return trips. For our purposes, having a remote & very quiet location, with plenty of room for the dogs to run around, it is a perfect fit. Fenced in yard, private beach and again, not many people, if any around. As far as the home itself, it is very roomy, very clean and free of any clutter so getting settled in feels great. If you have kids, dogs or both, this is the perfect family getaway spot. Highly recommended!

Private beachfront home rentals

Guest favorite
Home in Lusby
4.89 out of 5 average rating, 64 reviews

Beachfront Oasis with Amazing Views

NguyetRating, 5 stars4 weeks ago
We had such a wonderful stay! The kitchen was incredibly well stocked—honestly better than my own at home—with 5-6 large pots, an Instant Pot, every spice you could think of,peelers (which saved me!), and both a NutriBullet and a regular blender. It made cooking for the family a breeze. The kid had a blast on the trampoline, and we all loved the easy beach access with calm waters perfect for swimming all day and kayaking. The beach was also perfect for a peaceful morning run, and at night we could see the lighthouse light on the water. The porch quickly became our favorite spot—we gathered there to watch a rainstorm and were treated to a stunning double rainbow. The sky was full of stars at night, creating such a peaceful atmosphere. The grill on the porch made cooking super convenient. We enjoyed being close to a large park where we played pickleball. The beds were large and comfortable—everyone slept really well. Michael was a fantastic host—very attentive and accommodating.
Guest favorite
Home in Colonial Beach
4.96 out of 5 average rating, 117 reviews

Sunrise Waterfront Potomac Beach Haus

FaithRating, 5 stars2 months ago
Less than .5 miles from sand . The kids loved staying at the house versus a hotel ! Was the perfect spot to relax and go on the deck to hear the water . Would definitely go back for another vacation.
Guest favorite
Bungalow in North Beach
4.87 out of 5 average rating, 95 reviews

Bayside Bungalow: Cozy North Beach Getaway

KimberlyRating, 5 stars1 week ago
Perfect getaway spot on North Beach! Location, location, location!! Walkable to boardwalk, pier, great restaurants and shops. Although it is an older home it has been nicely renovated and we especially loved the front porch where we spent our time relaxing in the morning before we headed out for the day. Extremely responsive host! 5 Star Stay! We would not hesitate to book again!
Guest favorite
Home in Benedict
4.9 out of 5 average rating, 30 reviews

Bright airy waterfront getaway

StephanieRating, 5 stars4 weeks 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 favorite
Home in Chesapeake Beach
4.93 out of 5 average rating, 41 reviews

Chesapeake Beach Charm: Cozy Home with Bay views

CatieRating, 5 stars4 weeks ago
We had a beautiful stay. It was exactly what we needed.
Top guest favorite
Home in Cambridge
5 out of 5 average rating, 33 reviews

• Peaceful Point • A relaxing waterfront retreat

KateRating, 5 stars2 weeks ago
Peaceful Point was incredible and should be the standard that all other rentals follow. The home was well-stocked, organized and cozy, and I was blown away by the thought that went into preparations for guests. The furniture is well maintained and comfortable, the linens soft and clean, and the kitchen was filled with a variety of helpful items unlike the typical haphazard collection of damaged pots, pans and dishes--at Peaceful Point everything was of good quality and seemed to be purchased specifically for that home. The surrounding property was the epitome of peace and quiet, though activities like kayaking and paddleboarding kept everyone entertained. The local wildlife was plentiful and had us endlessly fascinated. Last but not least, our host Joanna was so helpful and proactive in her communications. She should teach a class on hospitality as she's clearly an expert! Thank you for such a wonderful stay, our family will cherish these memories always--hope to visit again soon!
Top guest favorite
Home in Leonardtown
4.99 out of 5 average rating, 81 reviews

Water's Edge Cottage | Luxury Retreat

AngelaRating, 5 stars1 week ago
We loved our experience here. The home was thoughtfully appointed and extremely clean. The view was stunning and very peaceful.
Guest favorite
Home in Lusby
4.92 out of 5 average rating, 13 reviews

Chesapeake Bay Waterfront View

LianaRating, 5 stars1 month ago
We had a wonderful time at Katerina’s place. Everything went well from check-in to check-out. Gus and Katerina provided clear instructions and were responsive. The house was nicely decorated. The neighborhood was peaceful and friendly. Private access to local community beach was the cherry on the top.

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