
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.
4.93 out of 5 average rating, 255 reviews
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!
4.85 out of 5 average rating, 117 reviews
Beach Highway Hobby Farm
We are a hobby farm with pygmy goats and free-range hens located along Beach Highway near Greenwood, Delaware, in the heart of the Mennonite Community (not to be confused with the Amish). We are centrally located in southern Delaware with many attractions within easy driving distance: Rehoboth Beach (35 minutes) Delaware State Fairgrounds (10 minutes) Dover Downs/Firefly (30 minutes) Ocean City, MD (50 minutes) Cape May/Lewes Ferry Terminal (30 minutes) DE Turf Sports Complex (20 minutes)
4.97 out of 5 average rating, 701 reviews
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.
4.97 out of 5 average rating, 626 reviews
Stunning Sunsets on Breton Bay, Seaside apartment
Charming efficiency apartment decorated with a coastal theme overlooks Breton Bay. Use of pier for hanging out... or crabbing and fishing. Apartment is in the second floor of detached garage on the premises of a private home. Beautiful serene surroundings 5 min. from downtown Leonardtown with shopping, restaurants and events. Area offers historical sites, wonderful parks, a large Mennonite and Amish community, great restaurants and friendly people! 25 minutes from Solomons Island.
4.98 out of 5 average rating, 151 reviews
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.
4.98 out of 5 average rating, 162 reviews
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.
4.96 out of 5 average rating, 253 reviews
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.
4.91 out of 5 average rating, 625 reviews
Carriage House Studio -Secluded "Treehouse" Escape
Escape to a hidden sanctuary in Chestertown. Perched on the 2nd floor of a historic building, this private 800 sq ft carriage house feels like a luxury treehouse with canopy views, fully screened from the outside world. Perfect for a romantic getaway or solo retreat, it blends total privacy with town-center access. Enjoy a fireplace, premium linens, off-street parking, and full access to over an acre of breathtaking private gardens.
4.97 out of 5 average rating, 304 reviews
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.
4.97 out of 5 average rating, 320 reviews
Charming, Chic Downtown Annapolis Apartment #1
In the heart of Downtown Annapolis. One block from Main Street/West Street/Church Circle. Close proximity to USNA, Ego Alley, Eastport, State House, shops, galleries, restaurants/bars and all other DTA amenities. This private apartment has an open floor plan and is elegantly decorated (with a modern twist). One Full Bathroom with tiled shower. One Bedroom with walk-in closet (with W/D).
4.9 out of 5 average rating, 125 reviews
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.
5.0 out of 5 average rating, 137 reviewsPopular amenities for flat rentals near Chesapeake Bay
Weekly apartment rentals

The Fish House
4.92 out of 5 average rating, 145 reviews
Walk to famous Tiki Bar on Solomons Island!
4.99 out of 5 average rating, 352 reviews
Boutique by the Bay
4.97 out of 5 average rating, 316 reviews
Hygge Haven: A cozy apartment in a canal-side town
4.95 out of 5 average rating, 129 reviews
Sail Away To - Beachfront Views & Private Balcony
4.94 out of 5 average rating, 101 reviews
Charming Studio in the heart of St. Michael's, MD.
4.92 out of 5 average rating, 234 reviews
Nature's Rest in Church Creek
4.97 out of 5 average rating, 451 reviews
Cozy Waterfront Apartment Chester, MD
4.96 out of 5 average rating, 304 reviewsPrivate apartment rentals

The Nook
4.83 out of 5 average rating, 520 reviews
Cozy Rehoboth Beach Condo w/ 2 bedrooms
4.99 out of 5 average rating, 181 reviews
Salty Sisters on the Bay. Enclosed yard on the Bay
4.95 out of 5 average rating, 324 reviews
Little Slice of Cambridge. 2 bedroom, pet friendly
4.91 out of 5 average rating, 158 reviews
Private Annapolis Inlaw Apartment
4.89 out of 5 average rating, 373 reviews
Centrally Located Sleek Studio Apartment
4.98 out of 5 average rating, 256 reviews
Modern 1BR heart/Dupont Circle
4.96 out of 5 average rating, 109 reviews
Union Market Penthouse Apartment
4.75 out of 5 average rating, 1201 reviewsApartment rentals with a hot tub

Safe, quiet neighborhood close to downtown!
4.97 out of 5 average rating, 114 reviews
Private Serene Hideaway Suite with Jacuzzi
4.98 out of 5 average rating, 164 reviews
Westgate Historic Williamsburg One Bedroom
4.85 out of 5 average rating, 237 reviews
Celebrate Summer In Your Private Pool & Hot Tub
4.96 out of 5 average rating, 196 reviews
Comfortable Space at a Great Location
4.89 out of 5 average rating, 103 reviews
HUGE bright 5BR, steps from the beach & downtown!
4.9 out of 5 average rating, 146 reviews
Waterfront Studio • Pool • Near DE Turf & Beach
4.83 out of 5 average rating, 288 reviews
Historic Church Hill Gem | Walk to Chimborazo Park
4.96 out of 5 average rating, 161 reviewsFamily-friendly apartment rentals

Sunshine By The Sea near Bethany Beach
4.98 out of 5 average rating, 153 reviews
Bright and Airy Oceanside Condo
4.9 out of 5 average rating, 143 reviews
Retreat at Fenwick
4.96 out of 5 average rating, 113 reviews
Spacious Apartment, Centrally Located Dwntn
4.88 out of 5 average rating, 253 reviews
Oceanside Condo Steps From Beach
4.96 out of 5 average rating, 123 reviews
Artist Windmill Pt Condo Sunset Pool Relaxation
4.86 out of 5 average rating, 28 reviews
Heron Roost
5.0 out of 5 average rating, 96 reviews
Waterfront on the North Beach Boardwalk
4.93 out of 5 average rating, 28 reviewsQuick stats about flat rentals near Chesapeake Bay

Total holiday rentals
Explore 950 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at $26 SGD per night before taxes and fees

Verified guest reviews
Over 40,530 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 400 rentals that welcome pets

Holiday rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
540 properties have a dedicated workspace

Wifi availability
950 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
Destinations to explore
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