
Places to stay near Chesapeake Bay
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Top-rated holiday rentals near Chesapeake Bay
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Relaxing Water Views - Mill Creek Cottage
Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

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 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.

Private Waterfront Home W/ Hot Tub, Dock & Kayaks
Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away.

Waterfront Guesthouse II on the Rappahannock
The “Beach House” is a guest cottage at Snug Harbor, a 2 acre private property overlooking the Rappahannock River and Chesapeake Bay. Perfect for a couple’s getaway, this well-appointed cottage has beautiful water views and includes access to our private beach & dock (with guest slip) with use of our paddle boards and kayaks. The cottage’s 1st floor features an open liv/din/kit area, full bath with large shower and a covered patio. The 2nd floor features a large loft bedroom with a queen bed.

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!

Beach Front and 'Perfectly Placed'
Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

*Solitude At Sunset*
YOUR WATERFRONT OASIS AWAITS! If you are looking for a true getaway, look no further. Tucked away on a small, peaceful island, this hidden gem is uniquely surrounded by 3 bodies of water: The Potomac River, the Wicomico River, and Neale Sound. This quiet island oasis offers the perfect place to step away from the busy world! This cottage is incredibly special to us. For four generations, it has been a sanctuary for our family-filled with love, laughter, and countless memories.

Long Beach Cottage, Hot Tub,Wood Burning Fireplace
The cottage is waterfront and is a PERFECT spot for a 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...

Waterfront-View of Bay from your Bed
Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Good Vibe Villa, Tiny houseboat
This tiny houseboat sits permanently on a boat lift, so you will have the unique experience of being over water without the risk of sea sickness! Located in the heart of quaint Solomons Island, this is a great stay if you love being near the water. Unparalleled views from your private porch. Please note, due to extensive pet damage we have changed this property to strictly no animals. You will be asked to leave if you arrive with a pet.

Waterfront Cottage on the Potomac River
Escape to our serene waterfront cottage on the Potomac River, just 2 hours from Washington D. C. and the Richmond area. This retreat comfortably sleeps 5 and features a private pier for fishing, a sandy beach for relaxing, cozy sun room for reading, and breathtaking water views. Enjoy a fully stocked kitchen, fast WiFi, and a spacious deck. The perfect spot for a romantic weekend, a special celebration or a simple peaceful retreat.
Popular amenities for holiday rentals near Chesapeake Bay
Apartment rentals with wifi

One Bedroom Beachfront Apartment Mid-Town

The Bird's Nest in Historic Occoquan (Mins to DC)

Beachfront Getaway, Pet Friendly, Mermaid Suite

Stylish Apartment Steps From the Beach

Gorgeous Beachfront! King Bed, Direct Ocean View!

Bayside Retreat in the Heart of Ocean City!

Ocean Side 1BR / 1.5BA Renovated Modern Condo

1st Floor Condo in Annapolis
Family-friendly house rentals

Waterfront, 3 Beaches, Dock + Kayaks, Potomac

Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces

Private Country Beach Retreat

Sunset Breezes - quiet waterfront retreat

Kent Island Waterfront Home with Amazing Sunsets

Riverfront Home w/Dock · Fire Pit · Kids Play Area

Waterfront home, private dock

Gorgeous Views! 150 ft private beach/Dock
Apartment rentals with air conditioning

Our Little Piece of Heaven

Blue Crab Lodge

Stunning Sunsets on Breton Bay, Seaside apartment

Carriage House Studio -Secluded "Treehouse" Escape

Historic St. Mary's City, MD

Serenity Suite on Chesapeake Bay

A unique place on sue creek

Beach Front Apartment on the Chesapeake
Other great holiday rentals near Chesapeake Bay

Private romantic pet friendly waterfront cottage

The Waverly Treehouse

The Laughing King Retreat Honeymoon Island Cottage

Living on Island Time

Coastal Waterfront 1 Bedroom Cottage

Cottage on the Creek

Stylish Creekside Cabin w/ HotTub, Parklike views.

Rumbley Cottage on the Tangier Sound-Private Beach
Frequently Asked Questions
Where is Chesapeake Bay located?
Chesapeake Bay lies along the east coast of the United States, stretching between Maryland and Virginia. The bay connects surrounding rural landscapes, waterfront communities, and historic towns to the Atlantic Ocean.
When is the best time to visit Chesapeake Bay?
Late spring and early fall are often recommended for fewer crowds and comfortable temperatures around Chesapeake Bay. These periods typically bring mild weather, colorful scenery, and chances to enjoy outdoor activities or local festivals.
What are some things to do near Chesapeake Bay?
Around Chesapeake Bay, you can explore historic towns, nature trails, and maritime museums, or join boating, fishing, and kayaking excursions. Local seafood spots, waterfront parks, and seasonal farmers' markets are frequently suggested for those wanting to connect with the region’s character.
How is the weather near Chesapeake Bay?
Chesapeake Bay experiences chilly winters around 32–47°F (0–8°C) and warm, humid summers near 71–85°F (22–30°C), with rainfall spread throughout the year. Spring and fall usually bring mild temperatures and breezy days, making outdoor activities enjoyable in those seasons.
Destinations to explore
- Beach house rentals Chesapeake Bay
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- Rentals with lake access Chesapeake Bay
- Hotel rooms Chesapeake Bay
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- Chincoteague Island
- Virginia Beach Oceanfront
- Cape Charles Beachfront
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Outlook Beach
- Old Dominion University
- Norfolk Botanical Garden
- First Landing Beach
- Neptune's Park
- Colonial Williamsburg's Merchants Square
- The Mariners' Museum
- Town Point Park
- Chrysler Museum of Art
- Nauticus
- Hampton University
- Virginia Living History Museum
- Cape Henry Light House
- Mount Trashmore Park
- USS Wisconsin (BB-64)
- Sandy Bottom Nature Park
- Chrysler Hall





