Beachfront holiday rental in Dares Beach

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Popular amenities for Dares Beach beachfront rentals

Pet-friendly beachfront home rentals

Top Guest favourite
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 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
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.
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 !
Superhost
Home in Dunnsville
4.75 out of 5 average rating, 144 reviews

Cozy & Content River Retreat Beach Hot Tub & Games

ChristineRating, 5 stars1 month ago
We had a great time at Nicholas and Dana's place! It was both fun and relaxing. We really enjoyed the little beach, the dock and the kayaks. We caught some catfish and one tiny crab in the crab trap (and threw everything back in). It was nice to have the firepit and hot tub to use too. And, the kids really liked being downstairs in their own space. The only issues were that the key pad wasn't working to get in to the front door which was frustrating after a long drive and the grill was very slow to heat up and probably needs to be replaced. Overall, this home was a really good choice for us and we would stay again when visiting family in the area.
Top Guest favourite
Cottage in North Beach
4.94 out of 5 average rating, 50 reviews

Cozy Waterfront Cottage - Pet Friendly

LisaRating, 5 stars1 day 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
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 favourite
Home in Chestertown
5 out of 5 average rating, 22 reviews

Chestertown Watson Family Farm

TaraRating, 5 stars8 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.
Top Guest favourite
Home in Montross
4.98 out of 5 average rating, 44 reviews

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

JenniferRating, 5 stars3 weeks ago
Easthaven is a gem! We thoroughly enjoyed our time there. Something to do for everyone, indoors and outdoors. Really nice to have the SUP and kayaks available, as well as the crab pots. So many thoughtful touches, probably the most well stocked home we’ve stayed in. Definitely hope to return in the future!
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 stars5 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.
Guest favourite
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 stars2 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!

Private beachfront home rentals

Guest favourite
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 favourite
Cottage in Lottsburg
4.98 out of 5 average rating, 87 reviews

Enchanting Edge of the World Cottage

JuliaRating, 5 stars1 month ago
Perfect Lake Side Vacation Spot!!! My friends and I spent the weekend and we absolutely loved it! The home is beautiful and the surroundings are so serine. Perfect place to get away and spend pleasurably days participating in outdoor activities like fishing, grilling and watching the sunset. We loved our stay so much we are already planning our next trip to the wonderful spot! Tim is an amazing host! Check in and check out were a breeze, he kindly checked in on us and was always prepared to help facilitate an enjoyable stay. I couldn’t recommend this listing any higher :)
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 stars3 weeks ago
We had a beautiful stay. It was exactly what we needed.
Top Guest favourite
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 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
4.96 out of 5 average rating, 55 reviews

Bahia Breeze - Beachfront Cottage

KellyRating, 5 stars2 weeks ago
This was a cute little home to stay at over the weekend. Only downside was having to pay for beach access. But the house itself was very nice and had all the kitchen items we needed. Would stay again.
Top Guest favourite
Campsite in Benedict
4.97 out of 5 average rating, 61 reviews

Beachfront camping under the stars

SarahRating, 5 stars3 weeks ago
Super fun place really peaceful The house was super nice. I loved waking up in the morning and seeing the sunrise.😁🫶🏻
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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