
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.

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.

"Bee-Z Haven" Waterfront Cottage on the Ware River
Curious about what makes Gloucester so wonderful? Live like a local at this Upscale Waterfront Retreat and find out for yourself why renters say "Enjoy the Breath Taking Views". Super homey and spacious living allows for guests to have memorable family & friend time. Sit around with the windows open, sipping morning coffee. Our area is quiet & very safe with free parking spaces. Shops, restaurants, hiking, lovely beaches & Colonial Williamsburg all within a short driving distance of our home.

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, 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**

Living on Island Time
Relax with the whole family and spend life on Island Time. Full bar set up with ice maker and wine refrigerator. Private pier, paddle boards and firepit. Unwind on St Goerge Island or head out to one of the local eateries for some southern Maryland faire. Inside you have 2 spacious rooms, 2 bathrooms. A massive island for cooking, card playing or just great conversations with endless views. Crabbing, fishing. The Neighbors have 2 Great Danes and a cat that you may see occasionally

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.

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.

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.
Popular amenities for house rentals near Chesapeake Bay
House rentals with a pool

The Glebe

Wizard's Escape | Sleep15+ | 2 Escape Rooms &Pool

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

Magical wooded cottage pool +priv hottub walk2town
Weekly house rentals

Soul Oasis - home on the Chesapeake Bay

Mid-Century Modern: Direct Private Beach Access

Historic Apothecary | 2 Master Suites | Old Town

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

Historic Downtown in-law suite

Sunset Breezes - quiet waterfront retreat

Upper Chesapeake Getaway

Waterfront Cottage in Colonial Beach at Placid Bay
Private house rentals

Waterfront Studio | Bikes & Kayaks | Beach Access

Pet Friendly,Fence, Waterfront 'Rivah Dog Cottage'

Waterfront Annapolis Getaway!

Magical Waterfront Home Dock, Firepit, Family Fun!

4-BR Unique Waterfront House - Your Perfect Escape

Lewes Carriage House: Spa Hot Tub & Winter Luxury

Stunning Chesapeake waterfront home

Sunset Cottage
Pet-friendly house rentals

Waterfront Getaway with Dock

New Private Beachfront panoramic view every window

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

Stella

Spacious Gorgeous Waterfront Home with Sunset View

Chesapeake Waterfront-Fire Pit- Hot Tub-Pier

Hideaway Home - 1st Pet FREE,Private Beach,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
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- Water Country USA
- First Landing State Park
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