
Places to stay near Chesapeake Bay
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Top-rated vacation rentals near Chesapeake Bay
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Unique style, Waterfront Dock,Yard,Kayaks,SUP,King
Nestled on Little Oyster Creek in the charming small town of White Stone, is Beacon Bay Getaway. This lighthouse style home is situated on 3 private acres and has 3 water views: the Creek, the Chesapeake Bay and the Rappahannock River all which can be viewed from the wrap @ deck and top observation lookout. Enjoy the large yard with fire pit. Launch a kayak/SUP from our dock or bring your fishing rods to catch Croaker. Have fun catching blue crabs with our crab traps. Follow @beaconbaygetaway

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.

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!

Beach Please! River cottage w/private beach & dock
Come unwind at "Beach, Please!" Our renovated cottage on the river with a private beach and dock is waiting for you! What's there to do? There's boating, fishing, crabbing, bird watching, tanning, and hammock-napping. Need more? Ok, antique shops, breweries, wineries, live music, crab boils and oyster fests. Still need more? Cornhole, can jam, horseshoes, hiking, and swimming and tennis at the community pool. That's not all, so just trust us - you will LOVE your time in Montross, Virginia!

The Laughing King Retreat Honeymoon Island Cottage
Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.

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...

Ultimate Cabin Farm Stay Cape Charles
Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

Waterfront-View of Bay from your Bed-Steamy Sauna
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.

Historic Rousby Hall, Waterfront, Pool, Beach
Rousby Hall is a stunning waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee is additional).

Waterfront Cottage ❤️ Private Beach, Dock & Kayaks
Welcome to Sunset View Cottage. A spacious and bright two-level waterfront home with a private dock and beach access in Leonardtown, MD. Enjoy swimming off the dock and beach in the Potomac River. Full western views across the widest part of the river make for unbelievable sunsets. Your ideal family vacation, couples getaway, or work-from-home retreat just 90 minutes outside DC. Visit us on IG @sunsetviewcottage
Popular amenities for vacation rentals near Chesapeake Bay
Condo rentals with wifi

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

Ocean block condo

Beach Baby Ocean Block Studio-Mid Town-All U Need

Gorgeous New Beachfront! King Bed, Direct Sea View

Bayside Retreat in the Heart of Ocean City!

1st Floor Condo in Annapolis

Cozy Old Town Apartment

Funky Uptown Apt meets Downtown - Hist District
Family-friendly house rentals

Osprey's roost: Spring and summer 2026

Peace Point - Waterfront, Secluded, Home w/hot tub

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

Waterfront with sweeping bay view & private beach

Private Country Beach Retreat

Blue Heron WaterSide

Upper Chesapeake Getaway

Waterfront Chesapeake Bay Sunrises & Fishing Pier!
Apartment rentals with air conditioning

Luminous Architectural Gem

Our Little Piece of Heaven

Secluded and romantic getaway in Chestertown

Serenity Suite on Chesapeake Bay

Luxury escape in DC now with a private Deck!

A unique place on sue creek

Private Annapolis Inlaw Apartment

Romantic Wtrfnt Flat w Hot Tub@Chesapeake Paradise
Other great vacation rentals near Chesapeake Bay

Chesapeake Bay Cottage

Relaxing Water Views - Mill Creek Cottage

Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces

“Cabana by the Bay”-tiny home on a pier!

Bay cottage 🏖on the beach. Stunning views🏝

Hideaway on the Bay: Waterfront Vintage A Frame

Waterfront Cottage on the Potomac River

Coastal Waterfront 1 Bedroom Cottage
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
- Resort rentals Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farmstay rentals Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Bungalow rentals Chesapeake Bay
- Guesthouse rentals Chesapeake Bay
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- Hotel rooms Chesapeake Bay
- Private suite rentals Chesapeake Bay
- Beach house rentals Chesapeake Bay
- Cabin rentals Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- Rentals with a firepit Chesapeake Bay
- Rentals with a washer and dryer Chesapeake Bay
- Waterfront rentals Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Vacation home rentals Chesapeake Bay
- Rentals with outdoor seating Chesapeake Bay
- Campsite rentals Chesapeake Bay
- Rentals with an accessible height toilet Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Beach condo rentals Chesapeake Bay
- Rentals with pools Chesapeake Bay
- Condo rentals Chesapeake Bay
- Rentals with an accessible height bed Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Rentals with a fireplace Chesapeake Bay
- Boat rentals Chesapeake Bay
- Loft rentals Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Villa rentals Chesapeake Bay
- Rentals with a patio Chesapeake Bay
- Cottage rentals Chesapeake Bay
- Fitness-friendly rentals Chesapeake Bay
- Smoking-friendly rentals Chesapeake Bay
- Boutique hotels Chesapeake Bay
- Rentals with an EV charger Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Bed and breakfasts Chesapeake Bay
- Rentals with a home theater Chesapeake Bay
- House rentals Chesapeake Bay
- RV rentals Chesapeake Bay
- Busch Gardens Williamsburg
- Virginia Beach Oceanfront
- Chincoteague Island
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Cape Charles Beachfront
- Jamestown Settlement
- Norfolk Botanical Garden
- Outlook Beach
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Nauticus
- First Landing Beach
- Virginia Zoological Park
- Colonial Williamsburg's Merchants Square
- Hampton University
- Town Point Park
- Old Dominion University
- Virginia Living History Museum
- Chrysler Hall
- Neptune's Park
- USS Wisconsin (BB-64)
- Harbor Park




