
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.

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.

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.

Chestertown Private cottage with NFL Sun Ticket
Escape to a secluded, romantic studio hideaway in the middle of Chestertown. Private parking, and over 1 acre of gardens to call your own. Relax in front of the fire with views of gardens in the windows. Kitchenette has extra large toaster oven, two burner hot plate, microwave, fridge, and Keurig/drip coffee makers. King bed with 100% cotton 1000 thread count linens and deluxe mattress, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a house in front of 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.

Walk to famous Tiki Bar on Solomons Island!
Cute studio apartment on charming Solomons Island. Walking distance to restaurants, live music, boat and kayak rentals. The kitchen has a full sized refrigerator, microwave, toaster, two burner hot plate and coffee maker. We provide all bedding and bath towels for two people. Enjoy your coffee ( provided) or wine on the deck in the fenced in side yard. One well-behaved pet is welcome. Please make sure you pay the pet fee. We also have a boat slip across the street that you can rent

The Nook
Enjoy a getaway in this cozy 1 bedroom apartment attached to a classic 1940s Cape Cod home minutes from Colonial Williamsburg and Jamestown. You'll be within biking distance to many local attractions such as Williamsburg Winery, Jamestown Island, Jamestown Settlement, Jamestown Beach, and Billsburg Brewery. Busch Gardens & Water Country are a 15 minute drive. The Nook was completely refinished in 2020. Need more space or traveling with a group? Inquire about our other units.

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

Blue Crab Lodge

Spacious Apartment in Historic Townhouse

One bedroom apartment in Annapolis

Morning Light Apartment

Butchershill- Clean, Fireplace, King Bed, Parking!

Barn Apt on Tranquil Historic Farm--Amazing Views

Cozy Waterfront Apartment Chester, MD

Harry’s River View couples relax, historic town
Private apartment rentals

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

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

Union Market Garden Apartment

Capitol Hill-1BR basement apt-Free parking

A Home for the Holidays- Mt. Pleasant-AdMo-CoHi

Centrally Located Sleek Studio Apartment

A place unique on sue creek

Romantic Wtrfrnt Flat+Solarium@Chesapeake Paradise
Apartment rentals with a hot tub

Private Serene Suite with Jacuzzi- Non Smoking

902C Coastal King Retreat Steps from Beach + Sauna

Westgate Historic Williamsburg One Bedroom

Fox Haven

Central and Stylish DC Apartment

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

Waterfront Studio • Pool • Near DE Turf & Beach

Stylish 1BR Apt | Arlington | Pool, Gym
Family-friendly apartment rentals

The Fish House

Apartment, centrally located Historic DnTwnFXBG!

DC Urban Oasis - Best Value in Town!

Modern Adams Morgan Private Apt

Hundred Acre Wood: basement apartment/pets welcome

Nice view self-contained Apart.

Charming Eastport

Stay in a Former Fells Point Bar! - Private Studio
Quick stats about flat rentals near Chesapeake Bay

Total holiday rentals
Explore 1,010 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at € 9 per night before taxes and fees

Verified guest reviews
Over 40,000 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 430 rentals that welcome pets

Holiday rentals with a pool
70 properties feature pools

Rentals with dedicated workspaces
570 properties have a dedicated workspace

Wifi availability
990 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
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