
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.

Quiet Coastal Cottage Escape with Water Views
Want to get away? Come relax and escape in our updated bay view cottage. You'll enjoy stunning sunsets, warm surroundings, and all the amenities you could want in our cozy, peaceful cottage home. You'll find plenty of comfortable spots to relax, inside and out. Located on a quiet street, while still close to the small-town charm and offerings of North Beach, Chesapeake Beach, and Herrington Harbor. Walk along the bay, enjoy the local restaurants, and get ready to relax. Stay a week and save!

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 --

Modern Creekside Escape: HotTub-Lux Shower-FirePit
Escape to this beautifully remodeled guest cottage, designed for an unforgettable stay. Nestled in a serene 6.5-acre setting with private creek views, it's just minutes from shopping, breweries, and dining. Wake up to breathtaking scenery, unwind in a peaceful setting, and enjoy modern amenities. Relax by the fire pit or soak in the hot tub. Perfect for a romantic retreat or a fun-filled family getaway in the Historic Triangle. Unmatched comfort, charm, and relaxation—your perfect escape awaits!

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!

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!

3N+ PROMO-Waterfront w/Gamerm, Firepit, Dog+EV OK
*Ask about our 3 NT+ promotion* Relax - Star Gaze - Kayaks/Paddleboard - Hike - Fish - Swim - Beach & more! ☀️ Waterfront 🛶 Kayak/Paddleboard 👨🍳 Gas griddle ⛱️ 3 Community Beaches 🔥 Fire pit 🐶 Dogs OK (Max 2) 🎯 Gameroom ⚡️EV Outlet If you're looking to take a break or connect with nature, the Riverside Retreat in Montross, VA offers a peaceful sanctuary that is perfect for families, small groups, & couples Book your getaway today or ❤️ us for next time!

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.

1891 Coastal Charmer: fully renovated farmhouse
Built in 1891, this farmhouse has been totally renovated by a professional designer. The Cottage is filled with coastal colors and accessories so it feels fun and updated but still retains the feeling of walking into a well loved family beach cottage. We are pet friendly as any beach cottage should be and love seeing our guests and their pets enjoying the cottage. Follow the cottage on social media @ BlueOysterCottage for more pictures, design ideas and local places to visit.

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
Popular amenities for rentals with a patio near Chesapeake Bay
Flat rentals with a patio

1/2 Block From King Street, King Bed Free Parking

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

Luminous Architectural Gem

Cute room, kitchenette & deck! Heart of Del Ray

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

Amazon HQ-Luxurious DMV-WiFi-Cozy Suite-DC Airport

Luxury apartment in the heart of Georgetown

Private Suite - NIH, Metro
House rentals with a patio

Nautical Retreat 6 Guests • 3 BDR • 2 Baths

River House on the Choptank

Mid-Century Modern: Direct Private Beach Access

Cozy 2 bedroom home on wooded private lane

Waterfront with sweeping bay view & private beach

Luxe Winter Retreat- 5 Star

The Little House on Back Creek

Waterfront Cottage in Colonial Beach at Placid Bay
Apartment rentals with a patio

Cozy beach side condo

Attractive one-bedroom unit on Capitol Hill

Steps to Ocean! Uncrowded Beach Location!

Gorgeous New Beachfront! King Bed, Direct Sea View

2b 2b condo! 2 master bedrooms! rehoboth beach

1st Floor Condo in Annapolis

Light-filled Private Oasis / Close to Capitol Bldg

Sixteen West - Modern Apartment in Richmond
Other holiday rentals with a patio

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

Hobbs & Rose | A Peaceful Cottage Escape

Summer Camp Tiny Cottage Walk to the beach & shops

The Crab House - a Private, Waterfront Guest House

Rest & Recharge, A-frame Cabin on Winery Grounds

York River | Chesapeake Bay Bliss: Fishing Retreat

Summer Waterfront • Dock, Pool, & Kayaks

Away at the Bay: New Home on the Chesapeake Bay!
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




