
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, large, modern 1 BR on Hist. Logan Circle
Gorgeous, bright, open plan nearly 1,000 square foot 1 bedroom condo with space for an entire family in historic Logan Circle neighborhood on a quiet street. Short walk to White House, Mall & museums. Built in 1900, this brownstone was thoughtfully renovated to blend modern (in-ceiling lighting, stainless steel appliances, bamboo flooring) with historic features (original exposed brick & trim). Warm, spacious & comfortable for your stay. Logan is DC's hottest & hippest area with a 96 walk score.

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!

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 :)

North OC|Fully Stocked 2 Bd 2 Bath
Welcome to Your Beach Lover's Paradise! Experience a vacation in a 2-bed, 2-bath condo, steps from Ocean City's shores. Stocked kitchen w/ new appliances, coffee, pots, pans, & dishes for all your meal needs. The condo features a washer/dryer, a cozy living room w/ a smart TV, and a balcony off the master. Sleeps 6 (twin bunk beds, twin, queen, pullout) Walk to the beach in 11 min & nearby attractions like Harpoon Hannah's, Fenwick Island, & Sunsations. Linens/towels provided. Book now!

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

Beautiful Renovated Ocean Front Condo 1b/1.5ba
Beautiful renovated ocean front condo. Get ready to relax in comfort and style! This large 836 sqft one 1b/1.5ba offers breath taking views of the ocean. You will be just steps away from the sand in one of the closest buildings to the beach. Enjoy your coffee or a different sunrise each day from your private balcony off the living room. Updated patio furniture with a cozy bench and high table with 2 chairs that bring a spectacular, completely unobstructed view of the beach and ocean.

The Loft at Lakeside
Welcome to the The loft at Lakeside! The loft is a completely separate space that comes with its own entrance and parking space. The loft consists of a spacious bedroom with a walk-in closet. There is a full bathroom in the bedroom and a half bath near the kitchen. The main space consists of spacious Kitchen that sits right next to the cozy family room, with a large couch. It also has a full laundry room for anyone looking to take home clean clothes after an amazing stay at The Loft.

Oceanfront 1 Bedroom, Balcony, Sitting Room, Pool
Opal Osprey: This OVERSIZE one-bedroom condo has been completely remodeled... giant oceanfront balcony PLUS a large patio room on the bayside! Expansive ocean views from every angle, super easy beach access, wonderful atmosphere in the quiet north end of OC. Linens included! Property Amenities - King size bed & queen sleeper - Large outdoor pool - Elevators - Dedicated high-speed WiFi and router w/ ethernet (Xfinity 100Mbps) - 2 Smart TVS with Xfinity, Roku - Keyless check-in 24/7

Beachfront with a View and Amenities Galore
Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with a breathtaking view of the beach and ocean.

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, 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.

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.

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

Lovely 1BR condo in quiet neighborhood

PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck

Bijou Space in Downtown Bethesda

Newly Renovated & Modern 1BR Condo - Unit 2

Oceanside Retreat | Steps to the Beach

Private Apt-Old Town Alexandria-Self Check In

VB Condo,Boardwalk/Oceanfront,Beach, Pool,Kitchen

Renovated Ocean Front! Wake up to an Ocean View!
Pet-friendly apartment rentals

One Bedroom Beachfront Apartment Mid-Town

New Downtown Annapolis Condo With Free Parking

Best Location EVER! 2BR/2BA, Pet friendly

𝙂𝙪𝙚𝙨𝙩 𝙛𝙖𝙫𝙤𝙧𝙞𝙩𝙚 Lovely 2lvl Condo Steps 2Beach+Pool

Renovated Apt In Historic Dist w/2 Parking Spots

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

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

BRIGHT 1 BD w/ LARGE BALCONY in PRIME BETHESDA LOC
Apartment rentals with a pool

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE

Oceanfront Family Oasis: Pool, Beach & Parking!

Luxury at the Beach.

Ocean Block - Clean, cozy 1 Bedroom. Pool, Wifi

Oceanfront Gem VaB Studio Exceptional Views

Oceanfront Studio: Boardwalk, Beach, & Pool Views

DownByTheBay 4601-Midtown/Oversize Sleep 15 w/Pool

Renovated Condo Near Outlets, 3.5 Miles to Beach
Private apartment rentals

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

Cozy beach side condo

Direct Oceanfront Condo with Expansive Ocean Views

Cozy Capitol Hill Row Home

A bit of Paradise

NWDC Jewelbox Deluxe 1BDR + Free Parking

THE ROYAL: Nostalgic Go-Go Theme Suite w/Fireplace

Sunny Apartment in Historic Capitol Hill
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 $51 SGD per night before taxes and fees

Verified guest reviews
Over 5,680 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!
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