
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.

Bayside Oasis of Southern Maryland
1 1/2 blocks from the beautiful Chesapeake Bay. Walk to boardwalk, restaurants and shopping. Beach opens, with some restrictions, May 28, 2021. Free beach pass provided. Quiet friendly town where everyone knows your name. King bed, private bath with shower (no tub). Free WiFi, private off street parking, 45” TCL-Roku TV, Echo Dot, Keurig w/pods for coffee and tea, full kitchen (no dishwasher), beach chairs, beach towels, dishes, flatware, pots pans. Chesapeake Beach is 1-mile south on Rt 262.

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!

Chestertown Private cottage with NFL Sun Ticket
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.

Serene setting great location surrounded by woods
The one-bedroom apartment will sleep 2 adults and 1 child under 18. In a serene setting with woods, a fish pond, and a comfortable patio. Separate code lock entrance. Well-equipped kitchen. Free WiFi, two TVs with Netflix and Amazon Prime. There is also a cedar sauna. Parking is on the property. Apartment situated near shops, restaurants, St. Mary's College and the Patuxent River Naval Air Station. 15 minutes from Chesapeake Bay, 1 hour to DC beltway. French and German also spoken.

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.

Cute and Convenient, 5 mins to Metro
Spacious, private one-bedroom apartment, only 5 minute walk to Metro! Ideal for remote workers, couples, friends, families. Full kitchen comes well-stocked for cooking, plus there are a ton of amazing restaurants & bars just down the block. Right on the Green line means a 15-minute ride to the National Mall, which makes this a great home base for exploring all of DC's free museums, historic monuments, live concerts, and world-class fine dining. Free street parking within half a block.

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.

Adorable Waterfront Apartment Weekend Getaway
Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

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.

Adams Morgan One Bedroom Retreat
This light, airy one-bedroom English basement apartment has its own private entrance. Cable TV, WiFi, washer/dryer and a full kitchen make it easy to make yourself at home. The bedroom features a queen size bed (and the living room is equipped with a pull-out sofa that converts to a standard size bed). We never charge a cleaning fee! The apartment is located below the main house. It is 500 square feet with a ceiling height of 6’ 9”.
Popular amenities for flat rentals near Chesapeake Bay
Weekly apartment rentals

Butchershill- Clean, Fireplace, King Bed, Parking!

Beach Highway Hobby Farm

Luxury escape in DC now with a private Deck!

Spacious and Comfortable Studio Apartment

Small cabin style- 23 min drive to US Capitol!

Stay in a Former Fells Point Bar! - Private Studio

Pelican Place, Cozy Retreat | Pool | Walk to Tides

Terrace Suite - Private Flat in Historic Manor.
Private apartment rentals

The Fish House

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

DC Urban Oasis - Best Value in Town!

Capitol Hill Basement Apartment - Private Parking

Spacious Apartment in Historic Townhouse

Walk to famous Tiki Bar on Solomons Island!

Escape to a Sunny Apartment in a Quiet D.C. Suburb

Luxury apartment in the heart of Georgetown
Apartment rentals with a hot tub

National Harbor 1 Bedroom w/ Balcony

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

Private Serene Suite with Jacuzzi- Non Smoking

Westgate Historic Williamsburg One Bedroom

Fox Haven

Central and Stylish DC Apartment

Waterfront Studio • Pool • Near DE Turf & Beach

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

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

Private, spacious basement suite; great location

NEW Renovated Studio near St. Mary's City

Pixie's Place

Spacious unit in Arts District

Centrally Located Sleek Studio Apartment

Retro Downtown One Bedroom at JoRetro

The Solomons Sunrise Suite
Quick stats about flat rentals near Chesapeake Bay

Total holiday rentals
Explore 1,040 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at £15 per night before taxes and fees

Verified guest reviews
Over 41,850 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 460 rentals that welcome pets

Holiday rentals with a pool
70 properties feature pools

Rentals with dedicated workspaces
580 properties have a dedicated workspace

Wifi availability
1,030 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
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
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- Water Country USA
- First Landing State Park
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- Buckroe Beach
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