Condo rentals near Chesapeake Bay

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Top-rated condo rentals near Chesapeake Bay

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

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Top guest favorite
A vibrant neon sign reading 'Sea Glass Sunrise' is framed by lush green foliage, set against a backdrop of a serene beach at dawn. The soft pastel colors of the sky create a peaceful atmosphere, enhancing the welcoming ambiance of the space.
Condo in Ocean City
4.99 out of 5 average rating, 143 reviews

Gorgeous Beachfront! King Bed, Direct Ocean View!

Stunning beachfront condo with direct view of the ocean! Your vacation home away from home! Everything you need right ON the beach. All linens, supplies and a well-stocked kitchen! New 65" TV w/free 4K Netflix provided! Modern serene decor in the heart of OC! Feel like getting out? Enjoy walking distance to Seacrets, Mackey's, and Fager's Island, Subway, Candy Kitchen or Dumsers' Dairyland! More adventure? Walk to minigolf, pontoon boats and jetski rentals! Only 4 minute drive to the boardwalk!!

Top guest favorite
A stylish living area features hardwood flooring, a cozy gray couch, and a dark coffee table. Wall art and framed photographs adorn the walls, while large windows allow natural light to enter. A kitchen bar with stools is positioned alongside the living space.
Condo in Frederick
4.99 out of 5 average rating, 182 reviews

The Grand Delphey: Downtown Modern Penthouse

Enjoy this stylish condo located in the heart of downtown's Historic District. The condo resides within a beautiful mansion known as the The Grand Delphey with lounge rooms on the first level perfect for photo sessions or gathering. The unit has the ability to rent with 3 other units to SLEEP UP TO 16 PEOPLE! Please let us know if you would like to book the entire mansion for wedding parties or other events. Just steps away from wedding venues, Baker Park, the creek, downtown nightlife & shops!

Top guest favorite
The living area displays a light-filled space with large sliding glass doors that open to an oceanfront balcony. A neutral-colored couch is accompanied by a round wooden dining table. A large mirror and minimalist decor enhance the room's serene atmosphere, with a view of the sea in the background.
Condo in Ocean City
4.92 out of 5 average rating, 904 reviews

Light and Airy Oceanfront Condo with Large Porch

Wake up to the sound of the waves crashing outside your window and finish off your days relaxing on the private balcony as you watch the moon rise over the ocean. Come find your serenity by the sea in our modern oceanfront condo. Located in midtown Ocean City, you can keep your car parked in our dedicated spot and walk to many of the towns best restaurants, bars, and entertainment as well as the Convention Center and Performing Arts Center. Morning beach strolls and evening sips await :)

Guest favorite
The living area features a light grey sofa, two teal armchairs, and a wooden coffee table. A woven basket holds a soft throw. In the background, a kitchenette is visible, along with cabinets and appliances, illuminated by natural light from skylights.
Condo in Williamsburg
4.95 out of 5 average rating, 149 reviews

2 Bedroom Stylish Kingsmill condo

Located in the beautiful Kingsmill resort, this charming two bedrooms, two baths condo with stunning seasonal views over the pond is only a few minutes away from CW, Busch Gardens, water country, William and Maryand other Williamsburg attractions. All Kingsmill amenities are not included as they are strictly for Kingsmill residents Guests have access to the Spa and to the Mill Coffee House which is within walking distance from the condo and serves breakfast and lunch every day..

Guest favorite
A bright studio space features a queen bed with cozy linens and decorative pillows. A sofa provides additional seating, while a desk and chair are positioned near a window. Light wood flooring and neutral walls create an open and welcoming atmosphere.
Condo in Occoquan
4.92 out of 5 average rating, 858 reviews

The Bird's Nest in Historic Occoquan (Mins to DC)

Spacious condo in the heart of walkable historic Town of Occoquan. Second floor loft with full kitchen, bath, a comfortable queen bed, work station, w/d in unit & one free parking spot. The Town of Occoquan offers unique experiences (kayaking, fishing, birdwatching and shopping) all within walking distance. Excellent dining choices from award winning restaurants to casual eateries. Mins to I-95, 123, VRE. D.C. (35min); Quantico (25min); Potomac Mills (10min). Tysons (25min).

Top guest favorite
Condo in Ocean City
4.96 out of 5 average rating, 179 reviews

Ocean Side 1BR / 1.5BA Renovated Modern Condo

Ocean Side! Two minute walk to the beach! Fully renovated. Bright, modern, clean condo. First floor. Located in the heart of Ocean City ( Midtown ) in walking distance from restaurants, bars, shops, and public transportation. Brand new appliances and furniture. Free WiFi, King Size Bed, 65" TV (living room) & 50" TV bedroom. Pullout Queen Sofa, Brand New Full Bathroom + Half Bathroom, Washer and Dryer in the unit. Keurig Coffee, Private balcony. Free Parking Space.

Top guest favorite
The spacious master bedroom features a large bed with decorative pillows and a coordinating gold bedspread. A patterned rug lies beneath, while a stylish lamp and a plant add warmth. An elegant mirror and chair provide additional functionality, and soft lighting enhances the serene ambiance.
Condo in Alexandria
4.98 out of 5 average rating, 136 reviews

Cozy Old Town Apartment

Welcome to our charming condo in the heart of historic Old Town Alexandria! Enjoy a fully equipped kitchen, cozy living room with a 55” smart TV, and a peaceful master bedroom with en-suite bathroom. With two private entrances, dedicated parking, and easy access to King Street’s dining, shopping, and metro, this home offers comfort and convenience. Perfect for relaxing after exploring D.C., or enjoying the charm of Old Town on foot!

Guest favorite
An oversized balcony features comfortable seating with deep blue cushions. A glass-top table sits between the chairs. Below, the water view showcases boat traffic, while string lights add a gentle ambiance. The surrounding area includes other residential units and docks.
Condo in Ocean City
4.88 out of 5 average rating, 271 reviews

Bayside Retreat in the Heart of Ocean City!

Newly renovated condo!! -Water view. Watch the boat traffic. -Oversized balcony with comfortable seating. -Comfy LoveSac couch. -Walk to boardwalk or beach - 15 minutes. -Walk to Jolly Roger amusement park. -Fish off community dock down below unit. -Close to dining and shopping. -Kitchenette for cooking meals. -Fast Wifi and Streaming TVs. -Fully Stocked Home. Clean linens, towels, toilet paper, paper towels & more!

Top guest favorite
A workspace with a wooden desk and a comfortable chair is situated by large windows, offering expansive views of the ocean. Natural light streams in, highlighting the tranquility of the beach outside. The windows are framed by light-colored blinds, with a small plant placed on the desk.
Condo in Norfolk
4.99 out of 5 average rating, 109 reviews

Beachfront Getaway, Pet Friendly, Mermaid Suite

Escape to a serene, semi-private beach with breathtaking views and everything you need for the perfect vacation. Welcome to Big Blue, where unforgettable memories await. Beach access, Fully stocked kitchen, modern upgrades, comfy beds, large open floor plan, bbq pit, outdoor patio, beach gear & many personal touches. Condo not suitable for children under 7. Pet fee $100 for max of 2 with approval.

Top guest favorite
A light-filled living area features a comfortable gray sofa and two modern chairs. A coffee table sits in the center, and a large TV is mounted on the wall, providing entertainment options. A painting of a serene beach scene is displayed above the sofa.
Condo in Lewes
4.96 out of 5 average rating, 343 reviews

Beach Camp Lewes: Bikes, Beach Chairs & Coffee

Start your morning at Beach Camp with a fresh brew from our coffee bar before taking a walk to see a beach sunrise. After a day of exploring the pristine trails and wildlife of Cape Henlopen on our complimentary cruiser bikes, skip the "camp cooking" and walk 2 minutes into town for a five-star meal. We’ve provided the bikes and the beach chairs—all you need to bring is your sense of adventure.

Top guest favorite
The serene coastal view features gentle waves lapping at a sandy beach, with lush green dunes in the foreground. Sailboats are visible on the horizon against a clear blue sky, creating a peaceful seaside atmosphere.
Condo in Virginia Beach
4.98 out of 5 average rating, 252 reviews

Chic's Beach Rental and Fishing

Duplex on Chic's Beach, expansive water view and private beach access right out the back door. Everything needed for the House & Beach included, including Coffee. We also offer Fishing Trips, Fish for Sale, Dolphin Cruises and Seafood & Greek Dinners! Michael Griffith, President/Manager, Chic's Beach Rental and Fishing LLC

Guest favorite
A balcony railing frames a wide view of the ocean, where gentle waves meet a sandy shore under a clear blue sky with scattered clouds. The horizon line is visible, enhancing the sense of openness and tranquility.
Condo in Ocean City
4.9 out of 5 average rating, 129 reviews

One Bedroom Beachfront Apartment Mid-Town

Midtown serves as the intersection between the vibrant inlet and boardwalk and the serene North Ocean City. In addition to stunning views of the beach and impressive hotels and condos, it also provides easy access to a wide range of activities, restaurants, shops, and attractions that cater to individuals of all age groups.

Popular amenities for condo rentals near Chesapeake Bay

Quick stats about condo rentals near Chesapeake Bay

  • Total vacation rentals

    Explore 140 vacation rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay vacation rentals start at ﺩ.ﺇ 37 per night before taxes and fees

  • Verified guest reviews

    Over 5,840 verified reviews to help you choose

  • Family-friendly vacation rentals

    100 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    130 of Chesapeake Bay vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chesapeake Bay rentals

  • 4.8 Average rating

    Chesapeake Bay stays are highly rated by guests—averaging 4.8 out of 5!

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