
Holiday rentals with a patio near Chesapeake Bay
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Top-rated rentals with a patio near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness and more.

Hideaway on the Bay: Waterfront Vintage A Frame
The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

Waterfront Cottage w Private Beach, Sauna, Hot Tub
Come relax in our delightful waterfront home decorated with classic cottage décor. Sit out on one of the two big screened-in porches, go for a swim in the shallow brackish (mostly fresh) water, relax in our hot tub, sweat in the sauna, or throw one of our crab pots in the water and enjoy the spoils of the waters off the Potomac River. Our house is situated off the Potomac on Hull Creek, which means the water is nice and shallow for little ones to play, and there are plenty of crabs to be caught!

Waterfront with sweeping bay view & private beach
Year-round private beach oasis on Chesapeake Bay! Perfect Fall & Winter Escape. An hour from DC beltway & world away. Recharge & relax to the sound of waves & sailboats. Spacious & fully renovated, with modern features, ample outdoor terraces. Enjoy long walks, nature spotting (bald eagles, rays, dolphins), shark tooth collecting. Kayaks provided! Short drive to Solomons Island, and local amenities: restaurants, bars, store, national parks & vineyards. No parties or events. Only relaxing.

Soul Oasis - home on the Chesapeake Bay
Listen to the waves of the Chesapeake Bay from the trex deck. There are 2 private community beaches in the neighborhood where you can find fossils and sharks teeth. A great place to relax and unwind. You will hear the sounds of all kinds of birds, see lots of very tiny frogs in spring and summer and maybe some deer around the house! You can also expect to see/hear aircraft from Pax River Base fly overhead! Book your stay today and let the magic of the woods and water wash away your cares.

Pretty Byrd Cottage, a Victorian Bayfront Getaway!
Imagine getting away from it all by crossing a footbridge to a private island with a Victorian cottage on your own private 3-acre lake! This property is a unique oasis that combines today's modern conveniences with the charm of elegant decor. Enter the front door and be taken in by the surrounding water views, and enjoy charming verandas and a balcony that overlook the lake and gardens surrounding the cottage. Guests can also enjoy the use of a private beach, fishing, kayaks and a paddleboat!

The Little House on Back Creek
Get away and relax at this peaceful, very private and centrally-located home in the heart of Solomons Island on Back Creek with beautiful water views overlooking Solomons Harbour. The property is shared with Jacqueline Morgan Day Spa and The Blue Shell Gifts and Décor. Just a quick walk to a enjoy a massage, facial, mani/pedi, salon services and shopping! Enjoy fishing, kayaking, bicycling, walk to so many great restaurants nearby and bring your boat! Docking is available during your stay.

Bay Breeze Home on private waterfront
On Virginia's beautiful Eastern Shore, the Bay Breeze Home on Occohannock Creek is the ultimate getaway for two or a large family desiring outside adventures. This 1970's spacious home has plenty of room. Experience the water with our three kayaks or family canoe and watch the abundant wildlife. Right outside your door, you may see Ospreys, Great Blue Herons, Eagles, wild ducks, porpoises, deer, geese, otters, & more. Be our guest and forget your worries in this spacious and serene spot.

Private Country Beach Retreat
Welcome to Mason Jar Retreats Beach Home. Our home is a private beachfront property with the best of both country and beach living. Located on 6 acres on a private road with only a few steps to take to your private oasis on the Chesapeake Bay. Enjoy sunsets from the beautiful porches while taking in the natural surroundings. Our home is only three miles from a vineyard and winery and 20 minutes to Cape Charles with lots of shopping and dining in a quaint beach town. *LGBTQ+Friendly Home

Water's Edge Cottage | Luxury Retreat
We are thrilled to host guests at the newly renovated Water's Edge Cottage -- a serene oasis offering what may be the best views on the Potomac. The rural charm of St. Mary’s County is among Maryland’s best kept secrets -- 90 minutes but a world away from Washington DC (with no Bay Bridge traffic!). We are near historic Leonardtown, boasting one of Maryland’s few remaining town squares (we affectionately call it “Mayberry”). And be sure to visit our sister property, White Point Cottage!

Waterfront Log Cabin with Hot Tub
Situated on the water's edge of Muddy Creek, this newly renovated log cabin offers a unique, luxury getaway for those seeking a stay immersed in all that nature has to offer. While relaxing on the spacious outdoor deck, you will be treated with a panoramic view of Muddy Creek complete with an occasional sighting of the neighborhood eagle. Perfectly set up for a romantic getaway for two, The Log Cabin on Muddy Creek was created to provide a space for couples to rest and reconnect.

Long Beach Cottage, Hot Tub,Wood Burning Fireplace
The cottage is waterfront and is a PERFECT spot for a WINTRY romantic couple's getaway! honeymoon/celebrations Designed with that in mind,a kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity,a large soaking tub,a tile shower with a soothing 3 function rain shower is complete with luxury linens, cozy robes & soft towels

"Dragonfly" Waterfront Cottage on Chesapeake Bay
Bayfront beach vacation? Kayak out to dolphins? Breathtaking sunrises & sunsets? Yes, please! Relaxation and fun await at 'Dragonfly', a gorgeous cottage right on the Chesapeake Bay with spectacular views from every room. Nestled on acres and acres of waterfront, this magical property has its own cove for all the swimming, kayaking, SUP boarding and fishing you can manage. If you love nature, bring your water shoes and sense of adventure and we will take care of the rest!
Popular amenities for rentals with a patio near Chesapeake Bay
Flat rentals with a patio

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

Luminous Architectural Gem

2nd floor studio apartment

Small town getaway- Bel Air

Blue Crab Lodge

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

Historic Annapolis Rental Minutes from Downtown

Luxury 2BR Apartment in Vibrant Logan Circle, DC!
House rentals with a patio

3N+ PROMO-Waterfront w/Gamerm, Firepit, Dog+EV OK

Waterfront Charm w/ Dock & Kayaks. Pet Friendly

Anne's Beachfront Shangri-La

Annapolis Area Waterside Retreat

Waterfront 4-BR home w/ hot tub & charging station

1891 Coastal Charmer: fully renovated farmhouse

Gunpowder Retreat

River Refresh - Waterfront with Spa on Placid Bay
Apartment rentals with a patio

Cozy beach side condo

Bethany Bay. Sleeps 4. AC, Pool, Ground Floor

☀️ Ocean block | Midtown OCMD

Stylish Apartment Steps From the Beach

Gorgeous New Beachfront! King Bed, Direct Sea View

1st Floor Condo in Annapolis

Sunrise Studio - Ocean Front, on Boardwalk, Pool!

Luxury Oceanfront Escape!
Other holiday rentals with a patio

Cozy Cottage, Hot Tub, BlockToBeach, 1hr to DC

Mid-Century Modern: Direct Private Beach Access

Rivah Getaway!

The Crab House - a Private, Waterfront Guest House

Waterfront home-225' pier kayak firepit pool beach

Madison Bay Club House

Waterfront Cottage in Mt. Vernon

Quiet Coastal Cottage Escape with Water Views
Quick stats about holiday rentals with a patio near Chesapeake Bay

Total holiday rentals
Explore 4,380 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at £7 per night before taxes and fees

Verified guest reviews
Over 217,830 verified reviews to help you choose

Family-friendly holiday rentals
3,280 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 1,830 rentals that welcome pets

Holiday rentals with a pool
570 properties feature pools

Rentals with dedicated workspaces
2,700 properties have a dedicated workspace

Wifi availability
4,310 of Chesapeake Bay holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chesapeake Bay rentals

4.9 Average rating
Chesapeake Bay stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
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- Rentals with a patio United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Water Country USA
- First Landing State Park
- Buckroe Beach
- Jamestown Settlement
- Cape Charles Beachfront
- Outlook Beach
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Virginia Zoological Park
- Colonial Williamsburg's Merchants Square
- Nauticus
- Town Point Park
- Old Dominion University
- First Landing Beach
- Virginia Living History Museum
- Chrysler Hall
- USS Wisconsin (BB-64)
- Hampton University
- The NorVa
- Neptune's Park




