
Flat rentals near Chesapeake Bay
Find and book unique apartments on Airbnb
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!

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)

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.

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.

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.

Salty Sisters on the Bay. Enclosed yard on the Bay
The studio apartment(above main house) is a short walk to the beach (which is on the property.) Studio is fully furnished including linens, towels, hairdryer, pots, pans, etc. Coffee shops and restaurants within a mile, marinas are less than a mile to launch your boat. Fabulous views of the Bay, full kitchen, spacious bath and your own private back yard. There is a dock to fish from or sit and watch the sunrise and set. There is also a small beach. Dog friendly , sorry no cats.

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!
Popular amenities for flat rentals near Chesapeake Bay
Weekly apartment rentals

2nd floor studio apartment

Union Market Garden Apartment

The Farmhouse in Historic Occoquan Close to D.C.

Morning Light Apartment

Cozy Waterfront Apartment Chester, MD

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

Charming Eastport

Romantic Wtrfnt Flat w Hot Tub@Chesapeake Paradise
Private apartment rentals

South-Facing Studio Overlooking Union Square Park

Luxury Home-DC's Best Walking Neighborhood-Parking

Walk to famous Tiki Bar on Solomons Island!

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

Yorktown on the Waterfront

Ashland Aerie

Butchershill- Clean, Fireplace, King Bed, Parking!

Centrally Located Sleek Studio Apartment
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

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

VB. Oceanfront/ Boardwalk,Beach, Pool, Balcony

The Fisherman's Lodge at the 1858 Monkton Hotel

Brick Hill farm guesthouse

1BR Beachfront w/views near Cape May and WW

Creek Suite

Barn Apt on Tranquil Historic Farm--Amazing Views

Sandy Blessings

Stunning 3 Beds/2BA, Ocean Beachfront Condo
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
Destinations to explore
- Holiday home rentals Chesapeake Bay
- Cabin rentals Chesapeake Bay
- Cottage rentals Chesapeake Bay
- Fitness-friendly rentals Chesapeake Bay
- Smoking-friendly rentals Chesapeake Bay
- Hotel rooms Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farm stay rentals Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- Boutique hotels Chesapeake Bay
- Rentals with a cinema Chesapeake Bay
- Rentals with a firepit Chesapeake Bay
- Rentals with a washing machine and dryer Chesapeake Bay
- Rentals with outdoor seating Chesapeake Bay
- Rentals with an accessible-height toilet Chesapeake Bay
- Beach house rentals Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- Rentals with a patio Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Campsite rentals Chesapeake Bay
- Boat rentals Chesapeake Bay
- Loft rentals Chesapeake Bay
- Private suite rentals Chesapeake Bay
- Bed and breakfasts Chesapeake Bay
- House rentals Chesapeake Bay
- Motorhome rentals Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Resort rentals Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Bungalow rentals Chesapeake Bay
- Guest house rentals Chesapeake Bay
- Beach apartment rentals Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Rentals with pools Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Villa rentals Chesapeake Bay
- Waterfront rentals Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Rentals with an accessible-height bed Chesapeake Bay
- Rentals with an EV charger Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Rentals with a fireplace Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- Flat rentals United States
- Busch Gardens Williamsburg
- Virginia Beach Oceanfront
- Chincoteague Island
- Buckroe Beach
- Water Country USA
- Cape Charles Beachfront
- First Landing State Park
- Jamestown Settlement
- Norfolk Botanical Garden
- Outlook Beach
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Nauticus
- Hampton University
- First Landing Beach
- Virginia Zoological Park
- Colonial Williamsburg's Merchants Square
- Town Point Park
- Old Dominion University
- Virginia Living History Museum
- Chrysler Hall
- Neptune's Park
- USS Wisconsin (BB-64)
- Harbor Park





