Beachfront holiday rental in Highland Beach

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Popular amenities for Highland Beach beachfront rentals

Pet-friendly 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!!
Top Guest favourite
Houseboat in Stevensville
4.94 out of 5 average rating, 53 reviews

Chesapeake Houseboat Getaway

RomaRating, 5 stars1 month ago
I loved Julia’s Arc. First time I Airbnb’d in a houseboat; won’t be my last. I loved this experience! Julia’s was inviting, comfortable, well appointed. I enjoyed sitting on the upper deck but even sitting inside with the blinds up and the windows open afforded the sounds of the water while enjoying the view of the marina and boats. I wish I had more time here to explore more. This was exactly what I needed for some time alone.
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.
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 Port Republic
4.79 out of 5 average rating, 185 reviews

Shewell’s Cottage by the Shore

NoraRating, 5 stars2 months ago
What a gem of a place! So cute and cozy. A great location! Loved all the natural light that came in through the big windows. Everything was so clean yet very comfortable. Enjoyed walking the beach. Found sharks teeth and sea glass! Such a great surprise to find such treasures! Lisa was so very kind and accommodating. Appreciated the extras like coffee, bottled water, shampoo etc and she brought some wood for a cozy fire. They really worked hard at making our stay very comfortable. Definitely will be coming back. But plan on a longer stay because there is so much more in the area to check out!
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.
Top Guest favourite
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
Top Guest favourite
Home in Annapolis
5 out of 5 average rating, 42 reviews

Bay Home in Annapolis with Private Dock

ToddRating, 5 stars2 weeks ago
Beautiful place, beautiful location. Joel thought of anything you could want.

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.
Home in Stevensville
5 out of 5 average rating, 7 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 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 favourite
Cottage in Neavitt
4.88 out of 5 average rating, 24 reviews

Grandview - Cottage 1B, Queen Bed, Pool, Bay, WIFI

HeatherRating, 5 stars4 weeks 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
4.55 out of 5 average rating, 11 reviews

10 Minutes to St. Michaels with a Private Pool

TrevorRating, 5 stars1 week ago
This place is really great. The house is as described and very comfortable, but the star is the yards. The back yard goes right up to the water, has a pool and a grill, and is large. The front yard is even bigger and has a lovely kid swing under a tree. Definitely a great place to come if you want to spend a lot of time outside playing or looking out over the water.
Superhost
Condo in Betterton
4.92 out of 5 average rating, 38 reviews

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

SihamRating, 5 stars1 week ago
My family & I booked for three nights. Thought it was a beautiful and private little area, and just a couple steps away from the beach and a pool. Very quiet and away from noise which was a plus. The house itself was lovely and mostly clean. There were board games available and my kids had a fun time playing with them. We enjoyed barbecuing using the grill provided on the balcony which was nice as well. A plenty of towels and anything you need in the kitchen! Other than a full trash bag left over in the kitchen, finding some clothing items from other guests (I’m assuming) in drawers, and the keurig having what looked like mold inside. Pretty small things when looking at the big picture though. Will most likely come again & we enjoyed our stay!

Private beachfront home rentals

Top Guest favourite
Cottage in Annapolis
4.93 out of 5 average rating, 29 reviews

Bay View Beach Cottage, perfect for long-term

MeganRating, 5 stars1 month ago
Susan’s place was perfect for my parents’ extended stay with beautiful views of the Chesapeake out the windows and access from a lovely beach. My dad felt right at home going for his daily walks and meeting all the dogs in the neighborhood. The location is super convenient to a grocery store and selection of restaurants as well as getting into downtown Annapolis. The kitchen is well equipped and beds are great. Susan was incredibly communicative and very accommodating in extending the stay beyond their original booking.
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 stars8 months ago
Clean and cute and just as described. Perfect for a long weekend away in Annapolis for the boat show!
Guest favourite
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!
Superhost
Cottage in Grasonville
4.89 out of 5 average rating, 64 reviews

CoastalBeachCottage*BayViews*Close2WeddingVenues

GretchenRating, 5 stars3 weeks ago
Michelle’s place is super cute! It’s also got more space inside than you may expect from the front view of the home. It’s got a cute upstairs space that does add to the livable area of the home for guests. We enjoyed the closeness to the water and nearby wedding venue as we were guests at a friend’s wedding in Kent Island a mere 10 minutes away. It was the right place for what we needed as a family of mom, dad & 2 of our grown kids.
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
Guesthouse in Grasonville
5 out of 5 average rating, 14 reviews

Quaint Waterfront- access, Private Shorehouse-unit

MaiaRating, 5 stars1 week ago
Lisa and Jim were two of the loveliest hosts we've had through Airbnb. They even made us a breakfast casserole which was delicious. The house is conveniently located and was very comfortable for our family of three. The kitchen was stocked with everything we needed and there were the basics like coffee and sugar. If you like the great outdoors, this area of Maryland is wonderful. Thank you Lisa and Jim!
Guest favourite
Home in Chesapeake Beach
4.96 out of 5 average rating, 55 reviews

Bahia Breeze - Beachfront Cottage

KellyRating, 5 stars3 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.😁🫶🏻

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