
House rentals near Chesapeake Bay
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Top-rated house rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness and more.

Beautiful and spacious 3 bedroom
Beautifully decorated and spacious home in a charming, Alexandria neighborhood near the King Street metro and the shops and restaurants of Old Town. Just a 16 minute drive to downtown Washington DC, with a chef's kitchen and a relaxing great room. The house is also just a 10 minute drive to the new MGM Casino or the Gaylord Resort and Convention Center at National Harbor. The "no parties in house" rule is strictly followed. If you want to have a party or an event, this is not the place for you.

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.

Luxe Modern Chesapeake Waterfront Oasis - 5 Star
The Cottage at Silver Water is a serene 5-star retreat for those who value tranquility over spectacle. Nestled along the Chesapeake, it offers front-row seats to mesmerizing sunsets, where golden light shimmers across the water. Inside, Nordic-inspired design pairs with quiet luxury, featuring award-winning mattresses and sumptuous bedding for deeply restorative sleep. Here, time slows, and luxury isn’t just seen—it’s felt. Discover why so many guests long to return by reading our reviews.

Sunset Breezes - quiet waterfront retreat
Enjoy our waterfront home styled after historic bay lighthouses. Relax by the water in a hammock under the tall pines. Gather with family and friends around the fire pit. Take in the beautiful water sights while paddling in a kayak, canoe, or paddleboard. Laugh with family and friends while playing corn hole, croquet, or bocce ball waterside. Photograph abundant wildlife - bald eagles, blue herons, osprey, deer, turkey and numerous waterfowl. Dine on the deck while enjoying beautiful sunsets.

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, Dog-friendly, Hot Tub, Peleton
A spectacular, spacious 2 bed, 2.5 bath, pet friendly, waterfront home with stunning, unobstructed views located directly on the Chesapeake Bay. Short walk to beach and pier and several bars and restaurants. A large gourmet kitchen provides everything you'lli need. Workout on the in-house Peleton bike & treadmill. Two cruising bikes are yours to explore town or bike to dinner. Enjoy the private hot tub and 2 gas fireplaces. Solo stove on back deck. **Message host for add’l dates**

Upper Chesapeake Getaway
Come relax with expansive views of the Upper Chesapeake with family or friends. Tucked away in Carpenter's point, you'll find peace watching boats pass by and local wildlife. The newly renovated home features newly 3BR, 1.5 Bath with a fully functional kitchen. You'll enjoy the beautiful sunrise views, water access, kayaks and deck. Local amenities include Great Wolf Water Park, Elk Neck State Park, local restaurants, and Perryville Casino. We welcome you to join the relaxing experience!

Cape Charles | Beach Access & Hot Tub
A sanctuary, an oasis, a one of a kind experience communing with nature while lounging in civilized splendor—all are apt descriptions of this New York architect designed beach house on the shores of the Chesapeake Bay. Guests enjoy stunning waterfront views from a finished floor height of 36 feet. The Eastern Shore of Virginia is famous for its flat tidewaters, but this property is perched amongst unusual relic Sandhills, complete with pines, gum trees and vast sea and sunset vistas.

Waterfront Cottage Getaway Views/Kayaks/Fire Pit
A timeless cottage on a quiet property on the Rappahannock River with charming rose garden, relaxing pool, and quintessentially Virginia feel. Find us on IG @rosehilllcottagerappahannock! Explore nearby towns of Urbanna, White Stone, and Irvington, or stay close to home to enjoy sweeping views, waterfront adirondack chairs, and kayaks — perfect for a cocktail or coffee, or take a dip in the river or pool. With open living spaces and thoughtful decor, this is your waterfront retreat.

Peace Point - Waterfront, Secluded, Home w/hot tub
Take a break and unwind at this peaceful oasis. Very quiet, and secluded waterfront getaway is the perfect spot to relax with nature. House is located approximately 150 feet from the creeks edge providing amazing views. Located on a very quiet and unpopulated creek (no other houses) off the Chesapeake Bay, our home offers a scenic deck with hot tub, waterfront fire pit with seating for up to six people, private floating dock with kayaks to explore the scenic creek.

Hutch's Bluff - Waterfront near Williamsburg
Charming riverfront A-Frame home on 2 acres overlooking the Chickahominy River. Completely updated interior, including all furnishings and appliances. Wake in a King bed loft space with a majestic view of the river, or choose one of the two Queen bedrooms below. First floor all tile bathroom with a walk in shower. Stainless appliances and granite countertops. Bring your fishing gear, relax at the end of the pier, or enjoy the views from the large deck and fire pit.

The Llama House
Located half-way between Mathews and Gloucester on the beautiful North River with views of the Mobjack Bay, New Point Comfort Lighthouse and Gloucester Point. The ideal spot for anyone needing to reconnect with someone, nature, or themselves. Enjoy fishing, crabbing, kayaking, playing corn hole, birdwatching, napping in a hammock, sipping wine, grilling out, amazing sunsets, listening to old records, playing the ukulele, and other simple pleasures of days gone by.
Popular amenities for house rentals near Chesapeake Bay
House rentals with a pool

Stoney Spring Overlook

Starboard on McKeil Point, w/heated pool & hot tub

The Glebe

Come for the Holidays to Gorgeous, Waterfront Home

Blue Heron WaterSide

The Rosé Retreat: Fireplace-Screened Porch-RELAX

Gunpowder Retreat

Beach Please! River cottage w/private beach & dock
Weekly house rentals

Private Dock and 200ft Shoreline w Panorama View

Waterfront Annapolis Getaway!

Mid-Century Modern: Direct Private Beach Access

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

1891 Coastal Charmer: fully renovated farmhouse

Historic Downtown in-law suite

Spacious Gorgeous Waterfront Home with Sunset View

Waterfront Chesapeake Bay Sunrises & Fishing Pier!
Private house rentals

Waterfront Home: Osprey Getaway

Pet Friendly,Fence, Waterfront 'Rivah Dog Cottage'

Waterfront Escape • Dock, Views, Peace & Kayaks

Madison Bay Club House

Welcome to Heron House! Annapolis Waterfront Oasis

Lewes Carriage House: Spa Hot Tub & Winter Luxury

Modern Bayfront Escape with Sweeping Water Views

Downs By The River
Pet-friendly house rentals

Waterfront Getaway with Dock

Dockside Bliss: Kayaks, Fire Pit, Pet-Friendly

Cozy 2 bedroom home on wooded private lane

Grace Cottage, Saint Michaels Walk to everything!

Chesapeake Waterfront-Fire Pit- Hot Tub-Pier

Waterfront Cottage in Colonial Beach at Placid Bay

"The Townsend" - Hot Tub!

8 Acre Waterfront Oasis! Pets are Free! 140ft Pier
Quick stats about house rentals near Chesapeake Bay

Total holiday rentals
Explore 3,870 holiday rentals in Chesapeake Bay

Verified guest reviews
Over 141,530 verified reviews to help you choose

Family-friendly holiday rentals
3,150 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 1,470 rentals that welcome pets

Holiday rentals with a pool
420 properties feature pools

Rentals with dedicated workspaces
2,250 properties have a dedicated workspace

Wifi availability
3,800 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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- House rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Assateague Beach
- Haven Beach
- Buckroe Beach and Park
- Jamestown Settlement
- Grandview Beach
- Bethel Beach
- Kiptopeke Beach
- Outlook Beach
- Piney Point Beach
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Golden Horseshoe Golf Club
- Chrysler Museum of Art
- Cape Charles Beachfront
- Wilkins Beach
- James River Country Club
- Little Creek Beach
- Wallops Beach
- Sarah Constant Beach Park




