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, 145 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, 183 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, 906 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 :)

Top guest favorite
A spacious living area features a sectional sofa adorned with red accent pillows. A wooden coffee table sits in front, contrasted by a patterned area rug. Natural light streams through large windows, highlighting a piece of wall art depicting a serene landscape.
Condo in Lewes
4.98 out of 5 average rating, 365 reviews

Beach Sunrise: Walk to Downtown & Lewes Beach

Skip the traffic and parking stress — stay where everything is steps away. Experience the best of Lewes (pronounced loo-iss) from this perfectly located, walkable condo. Step outside and you’re minutes from the beach, downtown dining, scenic parks, and bike trails. With ultra-fast 2-Gig Wi-Fi, KING bed, free bikes, coffee bar, easy parking, and thoughtful amenities, this is the ideal home base for couples or small families seeking comfort, convenience, and an authentic local stay.

Superhost
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, 863 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, 180 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.

Guest favorite
A modern living area features a spiral staircase leading to the upper floor. Natural light filters through skylights and large windows. A mix of furnishings, including a green accent chair, a brown couch, and a glass coffee table, adds to the stylish ambiance.
Condo in Richmond
4.91 out of 5 average rating, 332 reviews

Sixteen West - Modern Apartment in Richmond

Welcome to Sixteen West! This stylish, modern apartment is nestled in the heart of historic Jackson Ward. Recently renovated, the space features beautiful hardwood flooring, updated lighting fixtures, and a sleek, fully equipped kitchen. You'll be within walking distance of some of Richmond’s best spots, including Tarrant's Café, Quirk Hotel, The National, and more! Please note: This unit requires climbing 2.5 flights of stairs — THERE IS NO ELEVATOR.

Top guest favorite
A spacious living area features two large sofas, one being a queen sleeper bed. A wooden coffee table sits on a neutral area rug. A dresser and smart TV are positioned along the wall, with a dining area visible through an open layout.
Condo in Rehoboth Beach
5 out of 5 average rating, 114 reviews

The Loft 2B/2BA minutes to Rehoboth & Lewes Beach

Escape to a stylish coastal 2 bedroom 2 bath condo designed for relaxing beach vacations, family trips, and weekend getaways. Conveniently located just minutes from Rehoboth Beach and Lewes, The Loft offers the perfect combination of comfort, convenience, and coastal charm. Whether you're planning a family beach trip, a couples retreat, shopping weekend, or exploring Delaware’s beautiful coastline, you'll have everything you need for a memorable stay.

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, 272 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, 110 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.

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, 130 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.

Guest favorite
The living area features a light wood floor with a cozy sofa, a coffee table, and a television on a stand. A kitchen island with bar stools separates the space, while a door leads to a patio area, allowing natural light to fill the room.
Condo in Ocean City
4.95 out of 5 average rating, 174 reviews

Lovely 1 bedroom condo/only 2 blocks to the beach

Enjoy a wonderful experience at this centrally-located place only two blocks away from the beach and Ocean City boardwalk. Newly remodeled condo in a great location within a walking distance to many amazing restaurants and bars, convenience stores, amusement park, mini-golf, boutiques, playground...

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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