
Apartment rentals near Chesapeake Bay
Find and book unique apartments on Airbnb
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 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!

Barnyard Retreat
We are BACK After a 2 year hiatus!! We cannot wait to see all of our wonderful guests again! Beautiful 750 sq. ft. in-law apartment set up in a very efficient setting with open living space and Jack-n-Jill bathroom. Space is very open with cathedral ceilings and sky-lighting. Apartment has it's own separate entrance and dedicated parking space. The apartment has fast, secure wi-fi and is set-up perfectly for traveling professionals. Please see additional info within our house rules section.

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 :)

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.

The Hideaway By The Bay OCMD
Relax and enjoy your stay in this bright and welcoming waterfront, 1 bed, 1 bath condo. Bring your kayaks or paddle boards! This condo is located right off of 28th street, on the bay. It is a 14 minute walk to the beach and the Ocean City boardwalk, and within walking distance to many Ocean City attractions. All guests are provided with an electronic WELCOME BOOK prior to arrival which includes everything we think they will need to know about the condo and the surrounding area.

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..

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.

Steps to the Beach, Ocean View 1BR, Renovated
Steps to the beach! Fully renovated, bright, modern, clean condo with a balcony view of the ocean. Quiet North Ocean City location with walking distance to restaurants, bus, 7-11, Mini golf course, movie theater, parks, etc. Brand new appliances and furniture. Free WiFi, King Size Bed, 60" & 40" TVs. Pull Out Queen Sofa, Brand New Full Bathroom. Washer and Dryer in the unit. Keurig Coffee Station, iPhone Charging station. Private balcony. Free Parking Space.

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.

Ocean block condo
Kick back and relax in this calm, newly remodeled condo only a few steps from the beautiful Ocean City beach. Located uptown , across the street from Starbucks, Juice Bar, Wawa, Justine's Ice Cream, CVS Pharmacy, McDonald's, Candy Kitchen and a lot of restaurants like Crabcake Factory and Tailchasers. Northside Park on 125th St is a quick walk to watch soccer tournaments or July fireworks. Park your car in the lot and take the OC bus for $4 all day.

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.
Popular amenities for apartment rentals near Chesapeake Bay
Weekly apartment rentals

One Bedroom Beachfront Apartment Mid-Town

Ahoy Condo! Great ocean view just steps to beach!

Annapolis @Gate 1 steps to the Harbor Free parking

☀️ Ocean block | Midtown OCMD

Beach Baby Ocean Block Studio-Mid Town-All U Need

Cozy Old Town Apartment

Direct Oceanfront close to Northside Park!

Cozy Beach Front Condo with Modern Amenities.
Pet-friendly apartment rentals

Bright, large zen studio on historic Logan Circle

Lovely Condo Steps 2Beach+Pool Unlimited Parking

Beachfront Getaway, Pet Friendly, Mermaid Suite

Renovated Apt In Historic Dist w/2 Parking Spots

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

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

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

Quiet Stay + Huge Apt + Hot Tub + Dogs, Walkable
Apartment rentals with a pool

Luxe Oceanfront 1BR | Pool, Hot Tub, Sun Deck

Boutique Moments OC • Pool • Walk to Boardwalk

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE

OceanfrontJewel|DirectOceanView•NewlyRenovatedPool

Renovated Condo Near Outlets, 3.5 Miles to Beach

1st Floor Condo in Annapolis

Sunrise Studio - Ocean Front, on Boardwalk, Pool!

Direct Oceanfront with a View and Amenities Galore
Private apartment rentals

Terrace Apartment at the Rest PF

La Pescadora - Cozy. Coastal. Completely Yours.

Oceanfront•Pool•Private Balcony w/Sunrise Views

Top-Floor Retreat • Union Market • H Street• Metro

Downtown Condo, Parking, Walk to Beach & Boardwalk

Newly Renovated & Modern 1BR Condo - Unit 2

The Daisy in Historic Occoquan (Mins to DC)

The Solomons Sunrise Suite
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 €26 per night before taxes and fees

Verified guest reviews
Over 5,600 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

4.9 Average rating
Chesapeake Bay stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
- Rentals with breakfast Chesapeake Bay
- Farm stay rentals Chesapeake Bay
- Rentals with an accessible-height toilet Chesapeake Bay
- Bungalow rentals Chesapeake Bay
- Guest house rentals Chesapeake Bay
- Beach house rentals Chesapeake Bay
- Private suite rentals Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- Rentals with outdoor seating Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- Rentals with a fireplace Chesapeake Bay
- House rentals Chesapeake Bay
- Motorhome rentals Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Rentals with an EV charger Chesapeake Bay
- Rentals with an accessible-height bed Chesapeake Bay
- Flat rentals Chesapeake Bay
- Beach apartment rentals Chesapeake Bay
- Holiday home rentals Chesapeake Bay
- Cottage rentals Chesapeake Bay
- Fitness-friendly rentals Chesapeake Bay
- Smoking-friendly rentals Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Boat rentals Chesapeake Bay
- Loft rentals Chesapeake Bay
- Cabin rentals Chesapeake Bay
- Rentals with a cinema Chesapeake Bay
- Resort rentals Chesapeake Bay
- Campsite rentals Chesapeake Bay
- Boutique hotels Chesapeake Bay
- Rentals with a patio Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- Villa rentals Chesapeake Bay
- Bed and breakfasts Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Rentals with pools Chesapeake Bay
- Waterfront rentals Chesapeake Bay
- Rentals with a firepit Chesapeake Bay
- Rentals with a washing machine and dryer Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Hotel rooms Chesapeake Bay
- Apartment rentals United States
- Chincoteague Island
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Cape Charles Beachfront
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Outlook Beach
- Norfolk Botanical Garden
- Old Dominion University
- Ocean Breeze Waterpark
- First Landing Beach
- Chrysler Museum of Art
- Neptune's Park
- Colonial Williamsburg's Merchants Square
- Nauticus
- The Mariners' Museum
- Town Point Park
- Hampton University
- Virginia Living History Museum
- Cape Henry Light House
- USS Wisconsin (BB-64)
- Mount Trashmore Park





