
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.

Beach Retreat: Easy Walkable Living, Bikes, Coffee
Your basecamp for the best of the Delaware. From the pristine dunes of Cape Henlopen to the gentle waves of Lewes Beach, adventure starts at your front door. We’ve stocked this single-level retreat with everything you need: a pair of cruiser bikes for the trails, beach chairs for the sand, and a curated local coffee bar to fuel your day. Explore the wildlife of the state park by afternoon and walk to world-class restaurants by evening. It’s more than a stay; it’s your key to living like a local.

The Grand Delphey: Downtown Artist Retreat
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 shared 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!

Coastal Condo Near Rehoboth Beach and Lewes.
Welcome to The Loft, a cozy Rehoboth Beach retreat. Feel right at home in this spacious 2BR, 2BA condo conveniently located East of Rt. 1 between Rehoboth Beach and Lewes Beach. The condo is also just minutes from Junction & Breakwater Trail, Georgetown Lewes Trail and Cape Henlopen State Park... perfect for walks and biking. Love shopping? There are 3 Tanger Outlets and an abundance of other stores. Explore endless dining options in downtown Rehoboth Beach, Lewes and all along Coastal Highway.

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 :)

Annapolis Waterfront Condo - Unit #: A-203
Cozy, comfortable condo. Great views - 2nd flr. Fireplace 1 bed/bath condo, sleeps 4 max, covered, water front deck, reserved parking! .5 mile walk to dwnt Annapolis and the Naval Academy, 1.9mi to the Navy stadium. Book NOW for the Summer! Easy access to Spring/Fall boatshows. 12 stairs, no elevator. Pool Memorial to Labor Day: MWTh 4pm-8 Tues: Closed FSS and Holidays: 12pm-8 The pool is one of the best places to be on a hot summer day. If hours are unacceptable, pls select another

The Daisy in Historic Occoquan (Mins to DC)
Modern & spacious condo in the heart of walkable historic Town of Occoquan. Full kitchen, bath, a comfortable queen bed, work station & free parking. The Town of Occoquan offers unique experiences (kayaking, fishing, birdwatching and shopping) all within walking distance. Excellent dinning choices from award winning restaurants to casual eateries. Mins to I-95, 123, VRE. D.C. (35min); Fort Belvoir (20min); The Pentagon (25min); Quantico (25min); Potomac Mills (10min). Tysons (25min).

Oasis by the Ocean - Direct Oceanfront
Looking for direct Ocean Front stay? The Oasis by the Ocean is perfect for a quick weekend getaway or an extended stay in Ocean City. You can enjoy the Windjammer's private sandy front yard that includes chaise lounges, grills, picnic tables, swing, and children's play area. Oasis by the Ocean is an upscale efficiency that includes a full kitchen with new retro fridge, stove, and microwave. Enjoy a comfortable rest in the Queen Bed or relax in the 2 chair/futon combo.

Funky Uptown Apt meets Downtown - Hist District
Location location location where Uptown meets Downtown in the Historic District. 1/2 block to Dinner Under The ✨ , First Sunday Arts. Tsu, 49 West, Level in the front yard Ramshead, Stan and Joes and Reynold's Tavern in the back. EVERYTHING Annapolis (USNA, Stadium, Statehouse, Ego Alley, Main St, Eastport) is walking distance from this unique 2nd floor unit w elevated deck for morning coffee as Jazz wafts in, full kitchen, w/d, clawfoot shower/tub, MBR with Queen.

1st Floor Condo in Annapolis
This newly renovated, 1st floor studio is perfectly located just across Spa Creek from historic Annapolis in Eastport. Within easy walking distance of restaurants (3 min), Main Street/City Dock (10 min) & USNA's Gate 1 entrance (14 min), our studio includes a full kitchen, high-speed wifi, free onsite parking lot, a secure building entrance, dock and a rooftop patio (with a seasonal pool) that offers beautiful views of downtown Annapolis.

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!

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!

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
Weekly condo rentals

Beachfront Getaway, Pet Friendly, Mermaid Suite

Historic Federal hills urban lifestyle

Capts Qrtrs - Awesome downtown Annapolis location!

On the Bay, Private Beach-Boat Slip

2 Bedroom Stylish Kingsmill condo

Newly Renovated & Modern 1BR Condo - Unit 2

Great Ocean Block 1 BR Condo by Convention Center!

Luxury Riverfront Condo w/ sunrise & sunset views
Pet-friendly condo rentals

Luxury water-view condo with high-end finishes

Bright, large zen studio on historic Logan Circle

Walk to beach lovely 2/2 in "Kingsmill on James"

Where the Locals Live!!

Bethany Bay. Sleeps 4. AC, Pool, Ground Floor

1st Floor 2BR/2BA | Pool | Quiet & Convenient

Elegant Condo with a Spacious Porch

Rehoboth 1st floor, Pool, Beaches, Shopping
Condo rentals with a pool

Cozy Condo on Silver Lake - Walk to the beach!

Right on Silver Lake walk to the beach and town!

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE

Oceanfront Family Oasis: Pool, Beach & Parking!

PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck

Sunset Beach Condo

Renovated Condo Near Outlets, 3.5 Miles to Beach

First Floor Comfort and Convenience
Private condo rentals

Walk to Beach Relaxing Ocean City Apartment

Vista Del Mar Oceanfront | 46th St

Stunning Luxury Bayfront Escape

Harbor Gem

Barnyard Retreat

Oceanside Charm, desirable midtown Ocean City, MD

3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!

Beach Haven Hideaway ~ stunning water views!
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 G$6,276 GYD per night before taxes and fees

Verified guest reviews
Over 5,600 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

4.9 Average rating
Chesapeake Bay stays are highly rated by guests—averaging 4.9 out of 5!
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- Condo rentals United States
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