
Apartment rentals near Chesapeake Bay
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Top-rated apartment rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness and more.

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!!

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!

Luxury Oceanfront Escape!
This unique place has a style of its own. Wake up, pour your cup of coffee, and watch the sunrise from your direct oceanfront balcony. The beach is a few short steps away. Walking distance to many restaurants and shops! This recently renovated one bedroom condo features an outdoor shower, an elevator, fully equipped kitchen, a library of books, 1.5 bathrooms, Wi-Fi, large screen smart tv, bedroom tv, parking spot, washer/dryer and so much more! Fresh linens, towels, and toiletries included.

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 :)

Anchors Away
Eastport: Spacious studio boasts high ceilings & lots of natural light with his and hers walk-in closets. Fully remodeled with fresh paint, new floors, bath & kitchen. Tempur-pedic Murphy bed & cozy electric fireplace below a 58” 4K television. Basement houses additional storage & full-size W/D. Grill area. Free off-on street parking. Walking distance to Eastport's finest restaurants, or take the water taxi across Spa Creek into down-town Annapolis or the Naval Academy.

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.

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.

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!

Gem in the Heart of the Fan #3!
My newest listing is ready to go (June 2020). And with a beautiful hand painted mural to boot. Same great building close to everything in the fan. Just steps from Monument Avenue, VCU, and tons of great restaurants too! Walking distance to Scotts Addition, Carytown, and all the other ‘Fan’ fun Richmond has to offer! Longer walk or quick uber or GRTC to Broadberry, Altria or the National.

Comfy 1BR w pond view Kingsmill
Be close to everything when you stay at Kingsmill’s centrally-located gated community. Minutes from Busch Gardens, Colonial Williamsburg, Jamestown, Yorktown and College of William & Mary. At end of busy day, relax on your private balcony overlooking pond. If you are looking for comfort, convenience, cleanliness and security, this is your place! Sorry, no pets.

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...

Jamaica Couples Getaway
Newly renovated downtown studio unit perfect for a couple (or single traveler). Located right next to jolly rogers water park and within walking distance to several bars and restaurants. Condo is an efficiency so a smaller space than a one bedroom condo but very cute and cozy. Wi-fi and streaming.
Popular amenities for apartment rentals near Chesapeake Bay
Weekly apartment rentals

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

Newly Renovated & Modern 1BR Condo - Unit 3

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

Beach Sunrise: Walk to Downtown & Lewes Beach

2 Bedroom Stylish Kingsmill condo

Chic's Beach Rental and Fishing

1st Floor Condo in Annapolis

The Loft 2B/2BA minutes to Rehoboth & Lewes Beach
Pet-friendly apartment rentals

One Bedroom Beachfront Apartment Mid-Town

Bright, large zen studio on historic Logan Circle

Beachfront Getaway, Pet Friendly, Mermaid Suite

Renovated Apt In Historic Dist w/2 Parking Spots

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

Quiet Stay + Huge Apt + Hot Tub + Dogs, Walkable

Sweet getaway - beach block, steps from the beach!

Hill East BnB - Modern Style and Comfort 3BR/3BA
Apartment rentals with a pool

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE

Right on Silver Lake walk to the beach and town!

OceanfrontJewel|DirectOceanView•NewlyRenovatedPool

Modern & Cozy Retreat | Pool | Close to Beaches

Clean and Comfy, Close to Beach and Shopping

Renovated Condo Near Outlets, 3.5 Miles to Beach

Comfy and Convenient 2 bedroom/2 bath condo

Water view at Ocean Pines Yacht Club Condo
Private apartment rentals

Modern 1BR Downtown | Sofa Bed| Free Park| FIFA WC

The Port - Large condo on Mason Avenue!

The Drinking Gourd: Stunning Cambridge Penthouse

La Pescadora - Cozy. Coastal. Completely Yours.

Annapolis @Gate 1 steps to the Harbor Free parking

A cozy getaway 2 blocks from the beach

The Solomons Sunrise Suite

3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!
Quick stats about apartment rentals near Chesapeake Bay

Total holiday rentals
Explore 140 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at £7 per night before taxes and fees

Verified guest reviews
Over 5,840 verified reviews to help you choose

Family-friendly holiday rentals
100 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
130 of Chesapeake Bay holiday rentals include wifi 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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