Beachfront vacation rentals in Chesapeake Beach

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in Chesapeake Beach

Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.

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Top guest favorite

A spacious living area features large windows offering unobstructed views of the water. A comfortable sectional sofa is complemented by decorative cushions. A coffee table is positioned in front, with planters adding greenery. A wall-mounted television is visible, alongside a cozy fireplace.

Home in North Beach

5 out of 5 average rating, 134 reviews

Waterfront, Dog-friendly, Hot Tub, Peleton, Bikes

A spectacular, spacious 2 bed, 2.5 bath, pet friendly, waterfront home with stunning, unobstructed views located directly on the Chesapeake Bay. Short walk to beach and pier and several bars and restaurants. A large gourmet kitchen provides everything you'lli need. Workout on the in-house Peleton bike & treadmill. Two cruising bikes are yours to explore town or bike to dinner. Enjoy the private hot tub and 2 gas fireplaces. Solo stove on back deck. **Message host for add’l winter dates**

Top guest favorite

The living room features white wicker furniture adorned with blue cushions, arranged on a striped area rug. Large windows allow natural light to fill the space, highlighting a gas fireplace and nautical-themed decor on the walls.

Cottage in Lusby

4.98 out of 5 average rating, 272 reviews

Gettin to the point. ( Cove Point Beach)

Our beach house is for you to enjoy Cove Point Beach, which is only 500 ft away. The kitchen is fully stocked, or use the outdoor grill on the side of the house.PLEASE NON SMOKERS ONLY. One dog allowed on a cases by case bases with a one time pet fee of $65.00. No children under 8 years old. Walk to the beach, but only park your vehicle in our driveway, not on beach inlets. A gas fireplace in the living room. A beautiful sun porch area to enjoy. Enjoy walking on this private community beach.

Guest favorite

The image displays a one-room apartment featuring a king bed, kitchen area, and dining table. Soft lighting enhances the modern décor, with decorative rugs and artwork adorning the walls. A window allows natural light to brighten the space, creating a functional and inviting atmosphere.

Apartment in North Beach

4.97 out of 5 average rating, 127 reviews

Bayside Oasis of Southern Maryland

1 1/2 blocks from the beautiful Chesapeake Bay. Walk to boardwalk, restaurants and shopping. Beach opens, with some restrictions, May 28, 2021. Free beach pass provided. Quiet friendly town where everyone knows your name. King bed, private bath with shower (no tub). Free WiFi, private off street parking, 45” TCL-Roku TV, Echo Dot, Keurig w/pods for coffee and tea, full kitchen (no dishwasher), beach chairs, beach towels, dishes, flatware, pots pans. Chesapeake Beach is 1-mile south on Rt 262.

Guest favorite

A serene waterfront view showcases the Chesapeake Bay, stretching towards the horizon under a clear sky. The shoreline features wooden docks and gentle waves, while quaint homes are seen along the sandy beach. Green trees provide shade in the foreground.

Home in Saint Leonard

4.9 out of 5 average rating, 130 reviews

Perfect Bay and Beach Getaway one hour from DC!

Our waterfront home with sweeping views of the Chesapeake Bay is close to beaches, the Flag Harbor Marina, Solomon's Island, Flag Pond Nature Preserve and Calvert Cliffs State Park. You’ll love the spectacular sunrises/sunsets over the Bay, diving ospreys and eagles, and exploring the bay by kayak, canoe, or paddle board. Our house is great for families (with kids), groups, and well-mannered dogs. New in 2023: we will be replaced the upstairs HVAC system, baby proofing, and fall 2023 paint

Guest favorite

A charming cottage sits at the water's edge, surrounded by lush greenery. A wooden staircase leads down from an elevated deck to the sandy beach. Two blue chairs are positioned on the deck, inviting relaxation as the sun sets in the background.

Cottage in Leonardtown

4.96 out of 5 average rating, 182 reviews

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

Guest favorite

A tranquil view from the porch features a colorful hammock, inviting relaxation amidst lush green grass. The landscape stretches to the water in the distance, framed by trees and an open sky, creating a serene atmosphere.

Home in Montross

4.99 out of 5 average rating, 150 reviews

Beach Please! River cottage w/private beach & dock

Come unwind at "Beach, Please!" Our renovated cottage on the river with a private beach and dock is waiting for you! What's there to do? There's boating, fishing, crabbing, bird watching, tanning, and hammock-napping. Need more? Ok, antique shops, breweries, wineries, live music, crab boils and oyster fests. Still need more? Cornhole, can jam, horseshoes, hiking, and swimming and tennis at the community pool. That's not all, so just trust us - you will LOVE your time in Montross, Virginia!

Top guest favorite

Large glass doors open to reveal a spacious deck overlooking the Chesapeake Bay. The deck features a dining table and chairs, with potted plants adding a touch of color, while the calm water glistens in the sunlight.

Home in Lusby

4.95 out of 5 average rating, 170 reviews

Waterfront Home on the Chesapeake Bay-Pvt Beach

A commanding view of the Chesapeake Bay. Enjoy walking the beach to Calvert Cliffs, bike to parks, art and cultural events. Enjoy the private beach with plenty of fine sand and gentle waves, great for teaching little one's water skills, playing with your canine companion or fishing/crabbing off the beach. You’ll love this waterfront hideaway because of the location, views, and the ambiance. My place is suburb for couples, solo adventurers, business travelers, families, and canine friends.

Top guest favorite

A cozy living area is shown with a light brown leather sofa positioned near a glass door leading to outdoor views. A black television is mounted on the wall, and a small table with a tray sits in the foreground. Natural light filters through sheer curtains.

Place to stay in Annapolis

4.94 out of 5 average rating, 119 reviews

Chesapeake Bay View 3BR/2BA Duplex*Hot Tub*

*Hot tub* “Chesapeake Bay View Paradise" (3BR/2BA Penthouse Suite). Private penthouse level of a 2-level duplex, new deck, gorgeous Chesapeake Bay views, steps to sandy beach. 3 car parking. Gourmet kitchen, SS appl, granite counters, bar. Comfy living & dining areas. Entry handrail installed 9/20/24. 2 King BR, 1 Queen BR + Queen sleeper sofa in living area. Sleeps 8. 2 spa inspired baths, 1 jetted 2-person Jacuzzi tub inside. Outdoor Spa with Jets * Best Places To Stay Annapolis

Top guest favorite

Home in Tracys Landing

4.99 out of 5 average rating, 206 reviews

The Little Gypsy BoHome

Welcome to our Little Gypsy BoHome on the bay! The house is situated in Southern Anne Arundel County, MD in the quaint waterfront town of Tracy's Landing. Our home sits directly on The Chesapeake Bay with breathtaking views from every window. We offer a saltwater swimming pool, two corn hole game sets, a basketball hoop, beach access, canoe, 2 Paddle Boards, a gas grill, and a steam shower, an outdoor redwood panoramic barrel sauna and a redwood cold plunge!

Top guest favorite

A wooden pier extends over calm water, leading to a two-story home with large windows and a welcoming deck. Brightly colored chairs sit in the yard, alongside a grassy area and trees. Two kayaks are visible on the pier, ready for use.

Home in Lexington Park

4.96 out of 5 average rating, 162 reviews

Private beach retreat in historic St. Mary's City

Nestled next to historic St Mary's City and a lovely state park, your Lucas Cove Beach home awaits you with your own private sandy beach and pier with vast views of the water, new salt water hot tub steps away from the beach, four beautifully furnished bedrooms with Casper mattresses, an upstairs deck with adirondack chairs to take in the water views and amazing sunrises while sipping a beverage or just relaxing, high speed Wi-Fi. Kayaks avail for rent.

Guest favorite

Home in Cambridge

4.98 out of 5 average rating, 126 reviews

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Escape to our charming & serene waterfront retreat, perfectly situated on the picturesque Choptank River. This 4-bedroom home accommodates 10 guests w/ 7 comfortable beds & offers the ideal blend of relaxation & adventure. Our property comes fully equipped with bikes, kayaks, paddleboards & yard games for endless fun. Unwind and relax on the new pier. The river offers gorgeous sunrises and sunsets. Your perfect waterfront getaway awaits you!

Superhost

A spacious wooden deck overlooks the expansive Chesapeake Bay, framed by tall trees. The calm water stretches towards the horizon under a clear blue sky, with a sandy beach visible in the distance.

Cottage in Reedville

4.88 out of 5 average rating, 203 reviews

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

180 degree million dollar views in the quaint town of Reedville, VA. Away from all the noise, you won't want to leave our cottage once you get here. Upstairs bedroom has a private balcony with breathtaking views. Bay views from almost every window in the house. Perfect getaway for couples or the whole family. 60 inch Smart TV! Come build some memories!

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What guests are saying

Bayview Cottage 2 BR +Off./Priv Beach/Hot Tub/Deck

4.99 out of 5 average rating, 83 reviews4 months ago

We had an incredible stay with our two dogs. Beautiful property and views. The interior is very comfortable, and Chip goes above and beyond with ensuring that little creature comforts are available, like make-up wipes, coffee creamer, and smores supplies. We even found a tiger shark tooth down by the beach! A few notes that didn’t impact our stay, but some may find useful: -There is a partial fence around the home. It serves as a barrier to prevent you from stumbling down a slope, but won’t fully contain dogs or kiddos. This wasn’t an issue for us as the screened in porch was convenient to leash dogs, and the fence served as a visual barrier for them so they didn’t get distracted during quick potty breaks. -The garage is very well stocked with games and toys. There is no interior access and you must enter through the main garage doors, which may impact the needed supervision of kiddos. Overall amazing place, would definitely visit again!!

Home in Huntingtown

What guests are saying

Beachfront Oasis with Amazing Views

4.89 out of 5 average rating, 63 reviews1 week ago

Michael's place was perfect for our spring break getaway. I really liked the laid back beach vibe and how kid friendly the house was. The kids were able to walk to beach themselves and had a great time on the trampoline! We loved seeing who could find the most shark teeth.

Home in Lusby

What guests are saying

Bayside Bungalow: Cozy North Beach Getaway

4.87 out of 5 average rating, 93 reviews6 months ago

William was a wonderful host for our family members in town after we had to get them out abruptly from another stay due to a safety concern. He accommodated an early check in and early check out and was very kind in his communications. He even offered a military discount which we so very much appreciated after being out the money from the first stay. The place was larger than it looks from the outside, right by the water and nicely decorated. Backyard would have been great with pets. Very close to all local restaurants and boardwalk! If we have family in town again we will certainly rebook! Thank you again!

Bungalow in North Beach

What guests are saying

Ft. Smallwood Overlook. Waterfront with Kayaks!

4.97 out of 5 average rating, 172 reviews4 months ago

The place is wonderful. We were down for Thanksgiving with my family and were travelling with our 2 dogs, Wally & Dolly. The location was perfect, close to Riviera Beach where our Family Thanksgiving Dinner was, very private, no noise or distractions for the dogs (that was great). The property was surrounded by water on three sides, great views! It is right next to Ft. Smallwood Park where we took the dogs for walks every day, they loved it. As for the house it was perfect for us, just about the size of our home, so that made it very comfortable for us. All one level, which made it great for us older people. It was furnished with very comfortable furniture. Lots of information about the local surroundings, things to do, and restaurants. Keith was wonderful to work with, very easy to communicate with which made the whole process very easy for us. We even had a conversation over the phone once we were in the house to make sure everything was to our liking, and we were happy !

Cottage in Pasadena

What guests are saying

Farmhouse by the bay! Beach and pier access.

4.94 out of 5 average rating, 31 reviews6 months ago

We had a lovely stay at Patrick’s place! It had everything we needed for a long weekend on the shore. A very comfortable home. Patrick was extremely responsive and helpful, with easy check in and check out. The kitchen was particularly lovely and well appointed! The house number is a little small so keep an eye out. And the mosquitos were fierce - don’t forget bug spray! Thanks, Patrick!

Home in Madison

What guests are saying

Rio Vista along Potomac

5 out of 5 average rating, 23 reviews6 months ago

We had an amazing stay at this riverside house! The views were absolutely breathtaking, especially at sunrise and sunset. The house was clean, cozy, and well-equipped with everything we needed for a comfortable stay. Being so close to the water made it feel like a peaceful retreat. Highly recommend for anyone looking to relax and enjoy nature!

Home in Colonial Beach

What guests are saying

Waterfront Bay Cottage w/ Your Own Private Beach

4.88 out of 5 average rating, 43 reviews3 weeks ago

We booked this beautiful beachfront home for my husband's birthday, and it was perfect. Check-in was seamless, and the breathtaking water view greeted us upon entry. The house was spotless and peaceful, with only the soothing sound of waves. We enjoyed most meals in the sunroom overlooking the water and took advantage of the outdoor seating as the weather warmed. Fawn, a great coffee and breakfast/lunch spot, was just five minutes away. The well-equipped kitchen allowed us to cook fresh seafood from Little River Seafood. Mornings were magical with stunning sunrises, and the nearby beach access was perfect for walks, yoga, and birdwatching. A highlight was Hughlett Point, a hidden nature preserve 30-40 minutes away, leading to a secluded beach with only 11 parking spots. Thank you for sharing your home—it made for a peaceful and unforgettable celebration!

Cottage in Reedville

What guests are saying

Cozy Waterfront Cottage - Pet Friendly

4.93 out of 5 average rating, 41 reviews2 weeks ago

We just had another wonderful stay at the Cozy Cottage in North Beach. The house is just lovely and quite comfortable. Our dog Frankie certainly felt as relaxed as we did. The view from the large front window is just great. The Chesapeake Bay, and all the dog walkers on the boardwalk are just amazing. Jerome and Carrie are always friendly, responsive and accomodating. Last, but not least, we can't wait to go back.

Cottage in North Beach

What guests are saying

Private beach with comfort

4.94 out of 5 average rating, 32 reviews7 months ago

if you need a place with privacy and respite with beautiful sunsets this is the place to go. we took our dogs and it was great for our dogs in that there was an outdoor deck that was fenced in as well as a yard area for the dogs to go to the bathroom in a little spot on the beach to take small walks. I also took my elderly mom and she appreciated the ramp as well as the low shower in the main floor bedroom. this place accommodates elderly, dogs, kids, people who want to do water activities, or people who just want to get away and rock in a rocking chair. there were a lot of games and activities in the house for probably ages 12 and up. host was absolutely fantastic as well

Home in Westover

What guests are saying

Private Beachfront Cottage with 2 Bedrooms + Loft

4.95 out of 5 average rating, 82 reviews2 months ago

I think this'll become an annual retreat. The cottage is lovely, the location gorgeous and quiet, all the amenities we could want in the kitchen. Chelsea is a wonderful host, communicating about all the details of access and amenities. it's a hidden gem, perfect for a romantic weekend, family holiday or solo retreat. The sunrise and sunsets are unparalleled.

Cottage in Deal Island Historic District

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