
Flat rentals near Chesapeake Bay
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Top-rated flat rentals near Chesapeake Bay
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Our Little Piece of Heaven
Our cozy studio apartment sets on the Patuxent River. With the perfect views of Myrtle Beach, Point Patient and Thomas Johnson Bridge. Relax watching the boats and birds or take a walk along the water for a lovely neighborhood to stroll for 2.5 miles. Your favorite moments may be when you wake to see the sun rise and again to see the orange sky set. Just over the bridge from the popular Solomon's Island which is full of fabulous restaurants, boat rentals, charter fishing and summer concerts.

Charming Studio in the heart of St. Michael's, MD.
Welcome to Lucky Ducks Studio! Enjoy a fully renovated furnished studio in the heart of St. Michael's, MD. Located on Talbot Street in the historic 1850’s McMillian House, the 2nd floor studio offers couples a cozy "British" style experience that sleeps 4 (queen size bed & sofa that transitions to queen), a full bath with a claw tub and a gorgeous industrial style kitchen. Your steps away from the Miles River, shopping, museums, restaurants, breweries and wineries. Free WIFI and YouTube TV.

Halcyon house. Lovely views on MD eastern shore.
This charming apartment is located on the Chester river on Maryland's Eastern Shore. The wildlife is abundant and generally very active. The sun rise and sunsets can be spectacular. The property is 20 minutes from Annapolis and 50 minutes from DC. The newly renovated apartment has all new appliances and a well stocked kitchen with many herbs and spices, condiments, coffee, tea, cream and sugar etc. The 8 mile long Cross Island Trail starts a block from the house and leads to several restaurant

Boutique by the Bay
Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Spacious Beach House Top Floors - Walk Everywhere!
This booking is for the entire SECOND story & loft of a DUPLEX-style beach house. Entrance, access, & all indoor spaces of the unit are private, however there are often other guests and families on the first floor. There is also a STAIRCASE to the 2nd floor unit and a STAIRCASE to the loft. Please ensure this home suits your needs. The space has an open floor design with 14' cathedral ceilings for a spacious modern feel with beach-house charm. Walk 2 blocks to the beach, boardwalk, and more!

Luminous Architectural Gem
This luxurious space is filled with natural light streaming through the large windows. Exposed beams create a warm atmosphere. The open plan layout maximizes functionality, featuring a sleek modern kitchenette, a comfortable king size bed, and a stylish living area with a plush sofa and smart TV. The bathroom is crisp and contemporary with premium fixtures. Perfect for solo travelers or couples, the bright, beam-accented retreat offers a blend of comfort and character in an intimate setting.

Little Cove Cottage, Couples Retreat/Mathews
Little Cove Cottage: a charming studio in Mathews County with private entrance. Mathews is a rural town with several beautiful beaches close by and many areas to access the water. This apartment offers a small water view of the North River, with a pier and boat ramp just 400 yards away. Bring your Kayaks or use ours. . We are just minutes away from the Mobjack and Chesapeake Bays. Mathews is home to great restaurants with fresh seafood. We also have a wonderful farmer's market. Come enjoy!

Historic St. Mary's City, MD
1,000 square foot two-bedroom, one bath waterfront apartment features separate entrance and a screened-in porch overlooking the St. Mary’s River. Property has a large dock and a small private beach. Jellyfish, crabs, and oysters make swimming challenging, although many swim off the dock in the deeper water. No Diving! Dogs are welcome. We just ask that they be on a leash. The apartment is attached to part of the house where we reside, although it is sealed off and nothing is shared.

Blue Crab Lodge
Welcome to your charming and cozy short-term rental above the heart of St. Michaels' vibrant community! Nestled right above the delightful aroma of freshly brewed coffee, this unique and inviting space offers the perfect blend of comfort and convenience. Stepping outside, you'll find yourself in the heart of St. Michaels' quaint streets. The rental's prime location provides easy access to the town's boutique shops, waterfront promenades, and a diverse array of restaurants.

Luxury escape in DC now with a private Deck!
History and luxury meet in your rental which is a meticulously renovated luxury floor which includes top of the line amenities, private rooftop deck with Pergola, dual sided gas fireplace, luxurious and spacious bathroom including washer dryer, solar powered black-out blinds and leading gourmet coffee machine! We are close to Capital Hill, Brookland, Ivy City, Union Market, & H street corridor and a 10 minute Uber ride from Union Station. Free parking is provided onsite!

Serenity Suite on Chesapeake Bay
Come enjoy our waterfront home on the scenic Calvert Cliffs. Take in beautiful Bay views in Adirondack chairs with stunning vistas. Photograph wildlife. Comfortable ½ mile walk to private community bay shoreline. Have breakfast in the yard while enjoying the sunrise. Stroll the community shoreline and explore fossil hunting, hike at nearby trails. No pets are allowed because I have a severe allergic reaction to pet hair and dander. Thanks for your understanding.

Romantic Wtrfnt Flat w Hot Tub@Chesapeake Paradise
Gift yourself this private, secluded second floor Flat & Solarium Bedroom. Best hideaway to rest, bond, restore, create, or work. A breezy, country-like setting provides space to escape the city hustle! Nearby scenic drives & groceries, or venture to Annapolis or other local walks. Fully relax with pier, kayaks, hot tub, swings, fire pit, starry nights, sun-drenched loungers, cozy up with books/movies & luxuriate in the deep soaking tub or European shower.
Popular amenities for flat rentals near Chesapeake Bay
Weekly apartment rentals

The Fish House

Stunning 1BR Apt. in Historic Row Home w/ Parking

Union Market Garden Apartment

Luxury Home-DC's Best Walking Neighborhood-Parking

Walk to famous Tiki Bar on Solomons Island!

1BR Beachfront w/ water views near Cape May and WW

Centrally Located Sleek Studio Apartment

Butchershill- Clean, Fireplace, King Bed, Parking!
Private apartment rentals

The Rodney House

Cute room, kitchenette & deck! Heart of Del Ray

The Farmhouse in Historic Occoquan Close to D.C.

Beachin' Inn Milton

3rd/2nd Roof Top Deck & Condo

OceanFront-Fireplace-sleeps4-Balcony-King-Disney+

Studio Apartment with Parking

2BR 1BA Fan house/ Private Parking/Fully Fenced
Apartment rentals with a hot tub

Kone Oasis- hot tub, pool, theater/game rm.

Private Serene Hideaway Suite with Jacuzzi

Sea Colony Beach And Tennis Resort

Westgate Historic Williamsburg One Bedroom

Central and Stylish DC Apartment

HUGE bright 5BR, steps from the beach & downtown!

Waterfront Studio • Pool • Near DE Turf & Beach

Historic Church Hill Gem | Walk to Chimborazo Park
Family-friendly apartment rentals

Beachfront 1BR (1st floor) *FREE Kayaks, Bikes*

The Barn at Belgrove

Ashland Aerie

Beach Highway Hobby Farm

Eco-Friendly Waterfront Apt #3

Barn Apt on Tranquil Historic Farm--Amazing Views

Beach Front Apartment on the Chesapeake

The Solomons Sunset Suite
Quick stats about flat rentals near Chesapeake Bay

Total holiday rentals
Explore 940 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at £22 per night before taxes and fees

Verified guest reviews
Over 39,400 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 410 rentals that welcome pets

Holiday rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
550 properties have a dedicated workspace

Wifi availability
940 of Chesapeake Bay holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chesapeake Bay rentals

4.7 Average rating
Chesapeake Bay stays receive an average rating of 4.7 out of 5 from guests
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- Flat rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Grommet Island Park
- Norfolk Botanical Garden
- Outlook Beach
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Old Dominion University
- Neptune's Park
- Kiptopeke Beach
- Colonial Williamsburg's Merchants Square
- First Landing Beach
- Nauticus
- Town Point Park
- Virginia Zoological Park
- Virginia Living History Museum
- The Mariners' Museum
- Cape Henry Light House





