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

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.

Nature's Rest in Church Creek
Nature's Rest is located just minutes from Blackwater Wildlife Refuge, The Harriet Tubman Museum, Blackwater Adventures! Boat ramps are close by for easy access to the Chesapeake Bay and its tributaries for enjoying Maryland's Eastern Shore. We have plenty of parking, so bring your boat, bikes, and binoculars. Just mins from downtown Cambridge for dining & shopping. Discover the many quaint towns the area has to offer, come for a night, or stay as long as you'd like, look forward to meeting you.

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.

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!

Secluded and romantic getaway in Chestertown
Escape to a secluded studio hideaway in the middle of Chestertown. Private parking, and over 1 acre of private gardens. Relax in front of the fire with views of gardens in the windows. Kitchenette has large toaster oven, hot plate, microwave, fridge, and Keurig/drip coffee makers. We have an under counter filtration system for pure delicious drinking water. King bed with deluxe linens and mattress, washer dryer. We also host ‘Wren Retweet”, a 5 bedroom house by the carriage house.

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.

A unique place on sue creek
Enjoy your private apartment and deck on the water or come sit down by the waterfront and watch the Ospreys, herons, ducks and the occasional eagle. Fishing off the pier and possible small boat docking available. We are close to Rocky Point golf club, Baltimore yacht club, 20 minutes from Camden Yards and M&T stadium. We are 38 minutes from BWI. You will have private parking in a quiet safe neighborhood. Sorry, no pets allowed.

Pelican Place, Cozy Retreat | Pool | Walk to Tides
Unwind at this stylish apartment with view of Carters Creek and walking distance to the cutest little town and the iconic Tides Inn Resort. Take a refreshing dip in the pool, enjoy the charming outdoor shower, and star gaze under a blanket from the rooftop deck. Several outdoor spaces and large yard with whimsical touches. The perfect hideaway close to all the Northern Neck has to offer.
Popular amenities for flat rentals near Chesapeake Bay
Weekly apartment rentals

Blue House by the Zoo- Mt. Pleasant-AdMo-CoHi

Beachin' Inn Milton

Stunning Sunsets on Breton Bay, Seaside apartment

Historic St. Mary's City, MD

Butchershill- Clean, Fireplace, King Bed, Parking!

Charming Studio in the heart of St. Michael's, MD.

City-chic parkside flat near iconic DC landmarks

Halcyon house. Lovely views on MD eastern shore.
Private apartment rentals

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

South-Facing Studio Overlooking Union Square Park

Union Market Garden Apartment

Luxury Home-DC's Best Walking Neighborhood-Parking

Elegant Green Studio In The Heart of Old Town

Ashland Aerie

Centrally Located Sleek Studio Apartment

Modern and Private Capitol Hill Apartment
Apartment rentals with a hot tub

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

Private Serene Suite with Jacuzzi- Non Smoking

Sea Colony Beach And Tennis Resort

Westgate Historic Williamsburg One Bedroom

Private, Quiet Suite Near Bethesda/DC

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

Peaceful Family-Friendly Retreat Near DC · Pets OK

VB. Oceanfront/ Boardwalk,Beach, Pool, Balcony

Lovely Lodging on Capitol Hill (lower level)

Brick Hill farm guesthouse

The Farmhouse in Historic Occoquan Close to D.C.

Walk to famous Tiki Bar on Solomons Island!

1BR Beachfront w/views near Cape May and WW

Little Slice of Cambridge. 2 bedroom, pet friendly
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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