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

Escape to paradise at our Chesapeake Bay waterfront vacation home in Oliver Beach! Our home is the ideal place to unwind and appreciate the beauty of Chesapeake Bay. You'll love the stunning views, the private beach, the spacious upper deck and the beachside deck surrounded by trees. You'll have so much fun fishing, swimming, kayaking, paddle boarding, or just relaxing by the water! It's the perfect spot for a dreamy retreat, a romantic sojourn, or for shared fun with group of friends or family.

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

A Chesapeake Bay getaway located on the North East River. The renovated cottage sleeps 4 people with secluded backyard gardens. The cottage includes water access, kayaks, bikes, and a SUP board. Explore the town of NE to shop and dine in the region's top restaurants. Minutes from Elk Neck State Park which offers hiking, fishing, bird watching, and mountain biking. Visit the lighthouse, Havre de Grace, Hollywood Casino, or relax & catch a sunset with a cool breeze coming off the North East River.

4.92 out of 5 average rating, 191 reviews

A modern kitchen featuring sleek black and white cabinetry, stainless steel appliances, and a minimalist design. The space includes a gas stove, a microwave, and a refrigerator. Natural light comes in through a window, illuminating the wood-like flooring and nearby staircase.

Home in Timonium

* Lovely Gem w/ Perfect Combo of Flair & Class *

This is our 5th Airbnb in the Towson / Lutherville area. We know how important it is to feel comfortable & relaxed when you arrive back from a long day of work, sightseeing, visiting with family members, playing sports, etc. This inspiration is seen throughout this entire house and you'll find the house to be a place to recharge, relax and enjoy high end amenities to include HDTVs in living and bed rooms, fully stocked kitchen, plush bedding, luxury shower fixtures, and more. You have to see it!

4.98 out of 5 average rating, 102 reviews

The cottage showcases a dark blue exterior with white shutters, set against a lush green yard. A patio area is visible, featuring assorted seating options, including red and black chairs. Tall trees provide natural shade, enhancing the outdoor space.

Cottage in Charlestown

Blue on the Bay

2 bedroom cottage in historic Charlestown with screened porch, large yard & sitting area located in walking distance to the river and beach area. Walk to 3 local restaurants. Community playground, tennis courts, basketball court, pickle ball court, skate park & baseball field all in walking distance. Bring your boat, kayak & fishing poles. Boat launch available . Kayak, sup & pontoon rentals available. 15 minute drive to Great Wolfe Lodge. Monthly discount available, ask for details

4.92 out of 5 average rating, 323 reviews

Home in Frederica

Bowers Beach - pets ok - low cleaning fee

Welcome to Bowers Beach! This house is walking distance to the beach, Bay View Bar/Restaurant/Live Music, JP's Wharf (waterfront restaurant), and The Captains Lady charter boat. Driving distance to DE Turf Sports Complex (12min), Dover (20min), Harrington (23min), and Tanger Outlets/Rehoboth Beach (41min). We welcome couples, solo adventurers, business travelers, families, tournament teams, big groups, and Dogs welcome (NO CATS). However quiet or lively your stay, our location has it all.

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!

Delightful cottage at the confluence of Rock Creek, Patapsco River (Baltimore Inner Harbor) and the Chesapeake Bay. Adjoins Ft. Smallwood Park with its private coves and beaches. Secluded setting features water on 3 sides with beautiful relaxing views. Teeming with wildlife: ducks, geese, egrets, osprey, eagles, deer, foxes and other. Convenient to Annapolis, BWI Airport, Baltimore & Washington, D.C. Walk to the park. Cast a line, catch what you may! Total renovation 2018-2019.

4.88 out of 5 average rating, 124 reviews

A wooden dock extends over calm waters, featuring four Adirondack chairs arranged facing the serene view. A light casts a soft glow on the water's edge, and the distant shoreline is lined with trees and structures, hinting at nearby activity.

Cottage in Pasadena

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Our tastefully appointed cottages sit on almost an acre of waterfront property. Peaceful and tranquil, yet close to shops and restaurants, this property is perfect for serene getaways and family gatherings. With 2 separate cottages on one property, everyone will enjoy a unique and private space to relax. From peaceful mornings to magical sunsets on the 60-foot pier, this setting will quickly become a family favorite. This area is great for fishing, kayaking and paddle boarding!

4.9 out of 5 average rating, 136 reviews

The outdoor deck is lined with string lights, providing a warm ambiance against a stunning sunset backdrop. A hot tub is located to the left, with comfortable seating available for relaxation. Views of rolling fields and a serene landscape can be seen in the distance.

Home in Gap

Dream View

Welcome to our beautiful 3 bedroom,2 bath home with an attached 1 bedroom,1 bath apartment that’s perfect for families or groups who value privacy and convenience. Enjoy breathtaking views of the picturesque surroundings right from the comfort of your home or bask in the serene atmosphere of the big backyard where you will possibly see wildlife. The hot tub is an added bonus,perfect for a relaxing evening under the stars.

4.88 out of 5 average rating, 16 reviews

A clean, modern bathroom is presented with a glass shower enclosure and a white marble countertop. Black and white tiled flooring creates a classic look. Natural light enters through a window, enhancing the space's brightness.

Guesthouse in Arnold

Adorable 1 BR guest house with water views, deck

Immaculately designed separate guest suite/apartment in separate building with private entrance, private bath, Queen bed and gorgeous water views from every window. Guests have their own refrigerator, coffee maker and microwave and convection oven and air fryer, Xfinity tv 43" and high speed 5G internet for guests. Up to 2 guests can dine in the apartment or enjoy outdoor deck dining overlooking Lake Placid.

5 out of 5 average rating, 16 reviews

Condo in Betterton

Beach Haven Hideout

We are a small enclave of condos, perched high on a bluff, overlooking the Chesapeake Bay. From the deck you have wonderful views of the beach and the best Bay sunsets! We are no more than 100 steps to the beach, where you have a picnic pavilion, beach volleyball, and BBQ area with communal grills and picnic tables. This is the perfect getaway for small families or couples.

5 out of 5 average rating, 18 reviews

A covered porch is framed by wooden beams, featuring two rocking chairs on a snow-covered surface. A Maryland flag hangs from a bracket, complemented by a wreath on the door, while a light dusting of snow blankets the surrounding shrubs.

Home in North East

Heron Creek- Historic home on Main Street

Beautiful home located in the heart of downtown. This 3 full bath/3 bedroom was recently renovated. Original hardwood floors throughout. This is an older home with narrow steps. It offers off street parking & is walkable to shops, restaurants, water sports & bike rentals. Close to Turkey Point Lighthouse, the park, fishing, boating & hiking.

4.81 out of 5 average rating, 78 reviews

A wooden pier extends into calm waters, accommodating a boat. Cozy seating areas, including lounge chairs and a shaded table, are positioned on the sandy beach. Lush trees line the waterfront, providing a scenic backdrop.

Home in Essex

Sunset Haven on Sue Creek

Unparalleled Sunsets on the Water! This unique simple renovated cottage, offers an amazing waterfront experience with a private sandy beach, amazing nightly sunsets and a 60 foot pier which can hold most vessels up to 45 feet. Owners are very friendly live next door and are happy to help make your relaxation complete.

Vacation rentals for every style

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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 & Marina23 locals recommend

Schaefer's Canal House16 locals recommend

Prime 2258 locals recommend

The Bayard House Restaurant13 locals recommend

Cafe on the Bay9 locals recommend

Tap Room Inc4 locals recommend

Other great vacation rentals in Chesapeake City

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

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

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

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

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

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

Vacation home in Lancaster

A shared pool area is highlighted, featuring a large blue pool surrounded by a fenced deck. A dining table with black chairs is visible, along with a sun lounger. A shaded area is provided by an umbrella, and red storage units are seen in the background.

4.99 out of 5 average rating, 137 reviews

Sweet Retreat