
Apartment rentals near Chesapeake Bay
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Top-rated apartment rentals near Chesapeake Bay
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Sail Away To - Beachfront Views & Private Balcony
Sail Away To, CoBe Condo’s brand new, waterfront condo w/ stunning views is now available! Reach out to accommodate a group by booking our sister condo, Sail Away! → Private patio w/ 180° views, perfect for a morning coffee or wine at sunset → Access to pool (owners and guests only) → 1,025 ft² of stylish, cozy space, steps from the water and restaurants → Master suite which looks upon the water → Fully equipped kitchen and living room, smart TVs → Reserved parking space → ❤️ of Colonial Beach
4.94 out of 5 average rating, 101 reviews
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, 254 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 place unique 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
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 apartment rentals near Chesapeake Bay
Weekly apartment rentals

Charming, Chic Downtown Annapolis Apartment #1
4.9 out of 5 average rating, 125 reviews
Boutique by the Bay
4.97 out of 5 average rating, 316 reviews
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
Hygge Haven: A cozy apartment in a canal-side town
4.95 out of 5 average rating, 129 reviews
Cozy Waterfront Apartment Chester, MD
4.96 out of 5 average rating, 304 reviews
Nature's Rest in Church Creek
4.97 out of 5 average rating, 452 reviews
Luxury escape in DC now with a private Deck!
4.98 out of 5 average rating, 301 reviewsPrivate apartment rentals

Beachin' Inn Milton
4.97 out of 5 average rating, 232 reviews
Salty Sisters on the Bay. Enclosed yard on the Bay
4.95 out of 5 average rating, 324 reviews
Cozy condo / 3,5 miles from the beach.
4.97 out of 5 average rating, 675 reviews
Union Market Garden Apartment
4.88 out of 5 average rating, 798 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
Gorgeous 1-Bdrm in the Fan near Carytown & VMFA
4.87 out of 5 average rating, 1122 reviews
Studio apartment at Sugarloaf Log House
4.83 out of 5 average rating, 177 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
Waterfront Studio • Pool • Near DE Turf & Beach
4.83 out of 5 average rating, 288 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
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, 124 reviews
Beachfront 1BR (1st floor) *FREE Kayaks, Bikes*
4.89 out of 5 average rating, 112 reviews
3brd /2bth Roof Top Deck & Condo
4.94 out of 5 average rating, 139 reviews
Artist Windmill Pt Condo Sunset Pool Relaxation
4.86 out of 5 average rating, 28 reviewsQuick stats about apartment rentals near Chesapeake Bay

Total vacation rentals
Explore 950 vacation rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay vacation rentals start at G$4,183 GYD per night before taxes and fees

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

Family-friendly vacation rentals
410 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 400 rentals that welcome pets

Vacation rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
540 properties have a dedicated workspace

Wi-Fi availability
950 of Chesapeake Bay vacation rentals include wi-fi 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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