Vacation rentals in Chesapeake City

4.95 out of 5 average rating, 39 reviews

An outdoor seating area is set on a wooden deck, featuring a large table surrounded by light blue chairs. A fire pit is visible in the foreground, with lush greenery and a sandy beach in the background, along with the home and upper deck partially shown.

Home in Middle River

Waterfront Home with Private Beach, Stunning Views

EvanRating, 5 stars3 days ago

Great place, we had a family get together and we had a very peaceful weekend. There were so many places to hang out between the porches and dock-side area, big living room and huge dining room table. Very tranquil, I was thoroughly pleased with the home!

5 out of 5 average rating, 4 reviews

A serene outdoor fire pit area features four black Adirondack chairs arranged on gravel, inviting gatherings. In the background, a peaceful waterfront scene is visible, complemented by a view of boats and trees lining the shore.

Home in Essex

The Waterside Nest

NoahRating, 5 stars2 weeks ago

Our family enjoyed our first visit to Maryland and staying here made the visit a relaxing one. We enjoyed the views, the local wildlife, and the amenities within to make it feel like home. Tanya was always easy to reach and had a binder full of local recommendations and best use of items throughout the home. We would recommend any family to stay and will consider it for future trips!

4.98 out of 5 average rating, 101 reviews

A tranquil view of a sandy beach along a calm river, framed by green grass and gentle waves lapping at the shore. The scene is dotted with trees and overlooks a distant white house, creating a serene atmosphere.

Cottage in Charlestown

Blue on the Bay

AndrewRating, 5 stars3 days ago

We loved staying here. The location is beautiful and just a few doors down from the beach. The place was perfectly sized and clean. As a plus, Monica surprised us with a birthday bottle of wine and balloons as a gift. I highly recommend staying here!

4.96 out of 5 average rating, 46 reviews

A modern kitchen features light wooden cabinetry and open shelving. The stainless-steel appliances are complemented by a large island with bar seating. Natural light floods in from nearby windows, illuminating the workspace, while decorative plants add a touch of greenery.

Home in North East

Boho River Cottage

StaceyRating, 5 stars4 days ago

Our stay at Cece's Boho Cottage was excellent. It started with an egg hunt around the yard for my boys along with some sweet treats for all to enjoy. Cece gave amazing restaurant suggestions along with local hikes and shops. If you happen to forget something, Cece thought of it! We loved morning coffee on the back porch with the rising sun, comfy beds, and enough space to spread out. Thank you for sharing your adorable cottage with us! We are already trying to plan a trip back!

4.97 out of 5 average rating, 172 reviews

A new wood pier extends over still waters towards a green, tree-lined shore. The pier is flanked by posts, leading to a rocky bank, with a clear view of a nearby cottage among the trees. Sunshine reflects gently off the water.

Cottage in Pasadena

Ft. Smallwood Overlook. Waterfront with Kayaks!

JulieRating, 5 stars4 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 !

5 out of 5 average rating, 29 reviews

The charming cottage features a covered front porch with a white railing and a decorative door, framed by lush greenery and blooming hydrangeas. A flag is displayed proudly, while stairs lead up to the welcoming entrance. Natural light brightens the overall exterior.

Cottage in Betterton

Charming Home w/Great Porch

NicoleRating, 5 stars3 months ago

We had a great stay at the cottage! The space is beautiful and well maintained. Beds are very comfortable and everyone (including our kids) slept surprisingly well for being in a new space! The kitchen has essentials and a very high quality stove and oven. Wendy and Barry were quick to help us troubleshoot a flipped breaker (completely beyond their control) right after we checked in and followed up with us the next morning to make sure all was well. They are great hosts and have a beautiful property. If you’re looking for a private, quiet getaway near the water this is a great option!

5 out of 5 average rating, 17 reviews

The entrance of the home is framed by a covered porch with wooden support beams. A pair of rocking chairs are positioned on the porch, while colorful flower beds with seasonal blooms enhance the inviting atmosphere. The front door is decorated with a welcome sign.

Home in North East

Heron Creek- Historic home on Main Street

Janet Rating, 5 stars3 months ago

Our stay at Heron Creek home was great. The house is nestled beside the small creek in a lovely setting. It was very clean and so comfortable. Rebecca was a great host, permitting us a late check out. (which we didn’t do after all due to the snow forecast)

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What guests are saying

Eastern Neck Water Paradise w/Brick oven & Beach

4.96 out of 5 average rating, 50 reviews4 months ago

Our family had a lovely Thanksgiving stay at Martha’s Airbnb. The house was well-designed, the location was convenient, and we enjoyed the games in the basement and the beautiful views. The pizza oven was a fun touch, and the kitchen had everything we needed to prepare a great Thanksgiving meal. We also appreciated the nearby nature preserve and had fun playing Catan and putting some jigsaw puzzles together. Martha was very accommodating, even letting us extend our stay briefly when we ran into an issue unlocking our car. It was a great experience overall, and we’d definitely recommend her place.

Home in Rock Hall

What guests are saying

A 5-Star Haven: 4BR, Fireplace, Family-friendly

5 out of 5 average rating, 79 reviews3 weeks ago

Although we have stayed in many rentals, this "home away from home" was the best by far. It was the perfect, peaceful get-away for a trip. Everything was explained. And while in many homes someone has to stay in the "not so nice" bedroom, each room was modern, equally beautiful and the beds were comfortable. Each bedroom even had its own sound machine to help you fall asleep if you're not used to the quiet of the countryside. It was magical to wake-up every morning to the horses and chickens on the property. One could even feed the chickens! It was delightful to enjoy a cup of coffee in the morning or play games at night in the sun room while enjoying the nature surrounding us. The kitchen was well-stocked with everything one could imagine. They even had a delightful coffee and tea bar! All of the bathrooms had everything we needed including soaps, shampoo, and conditioner. It was close to all of the tourists sites such as Sight and Sound, buggy tours, etc. We didn't want to leave!

Home in Paradise

What guests are saying

Vintage Waterfront Cottage with Stunning Sunsets

5 out of 5 average rating, 33 reviews4 months ago

This was our second stay at this cozy cottage, and it was just as wonderful as the first! Every detail is thoughtfully considered, from the clean, stylish interiors to the warm ambiance. The indoor fireplace and outdoor fire pit (perfect for s’mores under the stars) were highlights, and the bay views from the viewing platform never disappoint. Sue & Mark are incredibly friendly and communicative, always quick to help with anything we needed. We also appreciated the provided firewood and all the little extras that made the space feel so comfortable and welcoming. Thank you for another amazing stay – we can’t wait to return!

Cottage in North East

What guests are saying

Water Views in Rock Hall

5 out of 5 average rating, 33 reviews1 week ago

Our stay at Loblolly was perfect. The house is beautifully modern, with gorgeous furnishings and incredible light. We were in Maryland to visit our Midshipman, and this was the perfect location to escape from the pressures of school and work and enjoy meaningful family time. We followed directions from Lauren on restaurants and markets and made a delicious crab and steak feast. It was a chilly and rainy spring weekend, but the fire made our stay cozy and fun. We took advantage of some of the games and enjoyed watching the ospreys soaring over the water. Lauren was extremely responsive and kind when needed, and we would absolutely stay here again.

Home in Rock Hall

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Popular amenities for Chesapeake City vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Chesapeake City's top sights

Chesapeake Inn Restaurant & Marina40 locals recommend

Schaefer's Canal House33 locals recommend

Prime 22520 locals recommend

The Bayard House Restaurant16 locals recommend

Cafe on the Bay10 locals recommend

Tap Room Inc8 locals recommend

Other great vacation rentals in Chesapeake City

4.86 out of 5 average rating, 81 reviews

An outdoor deck is positioned under the shade of tall trees, featuring natural stone flooring. A hot tub sits in the corner, while comfortable wooden seating is arranged around a fire pit, ideal for relaxation and gatherings.

Cottage in Annapolis

Waterfront cottage w/hot tub/ gated/ pier/ firepit

MichelleRating, 5 stars2 weeks ago

Isaac was a great host! He responded very quickly any time we had an issue and the location and home was perfect for our stay! Overall 10/10.

4.96 out of 5 average rating, 56 reviews

The kitchen is designed with modern white cabinetry and natural wood accents. New appliances include a refrigerator, stove, and dishwasher. A central island with seating is complemented by large windows, allowing ample natural light to brighten the space.

Home in Quarryville

Charming 3-Bed Single Level Cottage

Maria & DanRating, 5 stars3 weeks ago

Perfect for our family of 4. Spacious but cozy. Had everything we needed. Loved the quiet, relaxing location that was still close to family we were visiting. The fresh, individual carrot cakes on arrival was a wonderfully, delicious touch. Would definitely stay here again when we visit our PA family.

4.91 out of 5 average rating, 11 reviews

A spacious outdoor area features a gazebo with a red umbrella and a table surrounded by chairs. A grill is positioned nearby on a lush green lawn, framed by trees in a serene natural setting.

Home in New Providence

The Cottage at French Country Manor

DenniseRating, 5 stars1 month ago

This was a peaceful and comfortable place to stay. We would definitely like to stay again!

4.86 out of 5 average rating, 58 reviews

A spacious living area features a large sectional sofa positioned around a coffee table, with a geometric area rug beneath. A flat-screen TV is mounted on the wall, and natural light streams in through large windows, enhancing the open layout that flows to the dining area.

Home in Pasadena

Beautiful Home Near Beach and Patapsco River

EvaRating, 5 stars3 weeks ago

This home is really nice! We stayed there because our daughter was getting married at a venue about 5 minutes away from the home. It was perfect! Plenty of space for our family and was great for the bridal party to get ready! Nice open floor plan. The beds a bedrooms were very large with comfortable beds. The home was well equipped. The outdoor area was nice and I’m sure the pool is nice in the summertime. Thank you for sharing your home with us on this very special occasion.

4.97 out of 5 average rating, 31 reviews

A row of charming urban townhouses features a blend of red brick and stone exteriors. A large tree stands in front, providing natural shade. The street is lined with parked vehicles, indicating a vibrant neighborhood. The sky is bright with scattered clouds.

Apartment in Canton

Patterson Park Apt; Walk to Hopkins, Bars, Cafes

RachelRating, 5 stars1 day ago

Jenny’s place was exactly what we needed for our long weekend trip. I loved that it was spacious, clean and had excellent natural light. We spent lots of time walking through the park across the street and appreciated how quiet the street/block was at night. 10/10 would recommend!

4.96 out of 5 average rating, 136 reviews

A rooftop terrace features six brightly colored blue chairs arranged around a small table, with expansive views of the water and cityscape beyond. The deck is made of light wood planks, and the clear sky enhances the vibrant scene.

Townhouse in Fells Point

Artsy, Historic Rowhouse with Striking Harbor Views

AngelaRating, 5 stars3 months ago

The place is exactly as pictured and listed, very cozy for our group of 3 small families. Hosts were extremely responsive and accommodating with all our requests, and there were lots of conveniences such as extra towels and blankets, coffee beans and grinder, toiletries, baking sheets, kid related supplies, and more. Dining and lounge areas will be a tad short on seating for a max group of 8, but we adapted just fine to that. It was below freezing for much of our stay but the house stayed very comfortable for us. We found the area to be quiet, but we aren't sound sensitive so YMMV. There's a large grocery store and quite a few good restaurants within walking distance. DEFINITELY hit up Cafe Dear Leon if you can, it is a bakery in walking distance and all 8 of us raved about every item.

4.92 out of 5 average rating, 12 reviews

A unique a-frame cabin is situated among tall trees, with a pathway leading up from a snow-covered ground. The clear blue sky provides a bright backdrop to the scene, enhancing the rustic charm of the cabin and surrounding landscape.

Cabin in Airville

AFrame Cabin at Mill Creek

KathrynRating, 5 stars8 months ago

We had a fantistic time getting away at Kelly's A-Frame. Beautiful surroundings, and a rustic lot were just what we needed for a retreat. Thanks for a great stay!