Beachfront holiday rentals in Dares Beach

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Popular amenities for beachfront rentals in Dares Beach

Pet-friendly 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 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++++++++++++++
Superhost
Cottage in Reedville
4.88 out of 5 average rating, 210 reviews

Private point on the Bay🌤hammock, hot tub, kayaks❤️

LorenRating, 5 stars1 week ago
We loved out time at this Bayside home. My boys spent outside upon hours at the little private beach, where the water doesn't really get deep for quite a ways and the waves were never very rough. it was perfect for them. we all enjoyed the hot tub, kayaks, comfortable beds. My personal favorite was the hammock right by the water, listening to nothing but the waves and the calls of the ospreys that made the area their home. Forget the overly built up touristy areas and give this place a try. You will not regret it.
Superhost
Flat in Cambridge
4.91 out of 5 average rating, 129 reviews

Little Slice of Cambridge. Newly listed, 2 bedroom

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.
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.
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
Cottage in North Beach
4.94 out of 5 average rating, 50 reviews

Cozy Waterfront Cottage - Pet Friendly

LisaRating, 5 stars3 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 favourite
Flat 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 favourite
Home in Montross
4.98 out of 5 average rating, 44 reviews

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

AlishaRating, 5 stars1 day ago
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 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.
Top guest favourite
Home in Cambridge
5 out of 5 average rating, 16 reviews

Turtle's Nest - Hist. Cambridge

CoreyRating, 5 stars1 week 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.
Guest favourite
Home in Montross
4.99 out of 5 average rating, 155 reviews

Beach Please! River cottage w/private beach & dock

SarahRating, 5 stars2 weeks 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 favourite
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!
Top guest favourite
Home in Kent Narrows
5 out of 5 average rating, 301 reviews

Chester Riverfront At Kent Narrows

CassandraRating, 5 stars2 weeks ago
A great place to enjoy a long weekend at the Eastern shore in Maryland.

Private beachfront home rentals

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!!
Guest favourite
Bungalow in North Beach
4.88 out of 5 average rating, 96 reviews

Bayside Bungalow: Cozy North Beach Getaway

AmandaRating, 5 stars1 day ago
We had a wonderful visit to North Beach staying at William's bayside bungalow! The location is absolutely perfect. The bungalow is steps away from the boardwalk and conveniently located to the beach and all the fun shops in town. The bungalow was comfortable and perfect for our trip. We especially loved sitting on the front porch and enjoying the view of the bay. William was a gracious and communicative host. We'd be excited to stay here again in the future!
Guest favourite
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 favourite
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.
Guest favourite
Home in Annapolis
4.9 out of 5 average rating, 203 reviews

Country House on the Bay

MayaRating, 5 stars3 weeks ago
A wonderful stay at Stephen's place for our son's USNA commissioning. Although he lives in the 2nd floor, he was very respectful of our space - we hardly knew that he was there. He was very responsive when you needed him and helped us to host a gathering of friends and family to celebrate at his beautiful home on the water. Highly recommend.
Top guest favourite
Guest suite in Pasadena
4.98 out of 5 average rating, 617 reviews

Sea Dreamer

LisaRating, 5 stars1 week ago
Best airbnb stay yet! Beautiful location and views. You can lay in bed and watch the sunrise. This is a beautiful place where birds rule! Carol made us feel right at home and was always responsive and welcoming. There is a mattress firmness for everyone. We felt like Goldilocks trying out all the beds. There were three of us and we each found the bed that was best for us. The shower is amazing and so is the view! This will become my homebase when I visit the area. Many thanks to Carol. I will be seeing you again.
Guest favourite
Home in Chesapeake Beach
4.91 out of 5 average rating, 56 reviews

Bay Bliss - Beach Cottage

CarlaRating, 5 stars1 month ago
We had a wonderful stay! The home was beautiful, clean, and very comfortable. Frances and Enma were fantastic hosts, very responsive and welcoming. The location was perfect, and everything was exactly as described. We would definitely love to stay here again and highly recommend it to anyone looking for a great place to stay.
Top guest favourite
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.

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