
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.

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.

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.

Cove Point Cottage with Chesapeake Bay views
Welcome to our beach house, just a block from the Cove Point Beach on the Chesapeake Bay. Start your beach day by grabbing the beach wagon from the shed, loading it up with beach chairs, towels, and your cooler. A short stroll takes you to the beach, where you can spend the day searching for shark teeth and shells or swimming in the bay's refreshing waters. After a day in the sun, rinse off in our outdoor shower. Our shady patio provides the perfect spot to relax and enjoy the evening breeze.

The Little House on Back Creek
Get away and relax at this peaceful, very private and centrally-located home in the heart of Solomons Island on Back Creek with beautiful water views overlooking Solomons Harbour. The property is shared with Jacqueline Morgan Day Spa and The Blue Shell Gifts and Décor. Just a quick walk to a enjoy a massage, facial, mani/pedi, salon services and shopping! Enjoy fishing, kayaking, bicycling, walk to so many great restaurants nearby and bring your boat! Docking is available during your stay.

Kent Island Waterfront Home with Amazing Sunsets
Relax with the whole family at this peaceful and beautiful home on Thompson Creek! Enjoy the gorgeous sunsets all year-long. Bring your boat, fishing gear or other watercraft and discover Kent Island! Thompson Creek is accessible to the Chesapeake Bay and a short ride to discover Annapolis, The Kent Narrows or St. Michaels. In the mornings, sip coffee on the screened-in porch and bring a book - you may be there for a while! Our home feels remote but is accessible to convenient shopping.

Waterfront Home on the Chesapeake Bay-Pvt Beach
A commanding view of the Chesapeake Bay. Enjoy walking the beach to Calvert Cliffs, bike to parks, art and cultural events. Enjoy the private beach with plenty of fine sand and gentle waves, great for teaching little one's water skills, playing with your canine companion or fishing/crabbing off the beach. You’ll love this waterfront hideaway because of the location, views, and the ambiance. My place is suburb for couples, solo adventurers, business travelers, families, and canine friends.

Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces
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**

Sunset Breezes - quiet waterfront retreat
Enjoy well equipped waterfront home styled after historic lighthouses. Relax in the hammock by the water under the pines; Enjoy smores by the fire pit. Wood included. Free use of 4 kayaks, 2 paddleboards, and a 3 person canoe. Yard games include corn hole, croquet, & bocce. Dine on the deck while enjoying beautiful sunsets. Bring your cameras for local wildlife. NEW Fun & Fitness Barn: sauna, golf simulator, free weights, game space and more. Ask about access code and hours.

Spacious Gorgeous Waterfront Home with Sunset View
Dreamy weekends on the water, the perfect getaway for the entire family and friends in the southern tip of St Mary’s peninsula. This gorgeous newly remodeled house with 5 Bedroom 3.5 Bath sleeps 10 very comfortably. Wake up with amazing water views and access to the water with your own private pier. Spend your day crabbing, fishing, kayaking, or paddle boarding. Amazing beaches at Point Lookout State Park, just a few minutes away. High speed internet, WiFi, and cable.

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.

Waterfront Sanctuary only 50 Min. From DC/Balt.
New full home renovation with gourmet kitchen, wide open floor plan, multiple guests rooms, and a bunk room that accommodates 12. An inviting space that welcomes any couple or a large extended family. This home sits with only three other homes on a private peninsula and has water access on both sides. It is conveniently located less than an hour from DC and Baltimore on the west coast of the Bay (no need to cross the Bay Bridge).
Popular amenities for house rentals near Chesapeake Bay
House rentals with a pool

Waterfront, Pool + Beach, Dock + Kayaks, Potomac

The Glebe

Coastal Waterfront Escape + Hot Tub & Kayaks

The Mint Cottage in Chesapeake City

Farmhouse w/hot tub, close to Tuckohoe State Park

Blue Heron WaterSide

The Rosé Retreat: Pool-Screened Porch-RELAX

*Brand New | Modern Farmhouse | Lux 4 BR | Near DC
Weekly house rentals

Pet Friendly,Fence, Waterfront 'Rivah Dog Cottage'

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

Chesapeake Bay Retreat W/Breathtaking Views

Private Country Beach Retreat

1891 Coastal Charmer: fully renovated farmhouse

The Haven On The Chesapeake Bay

Harbor View Haven | Waterfront w/ Hot Tub + Dock!

Waterfront home, private dock
Private house rentals

Waterfront on Solomons Bay - Private Beach & Dock

Waterfront Studio | Bikes & Kayaks | Beach Access

Waterfront Home w/ Private Dock, Beach & Fast WiFi

The Perfect View Virginia Tiny Home

Waterfront Escape • Dock, Views, Peace & Kayaks

Summer Breeze waterfront new home-Private Beach

Waterfront Cabin! BigPorch~CrabFish~Paddle~Karaoke

Haiku Harmony on the Rappahannock River
Pet-friendly house rentals

Waterfront. Spacious. HotTub. Kayaks. DogFriendly.

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

Sunset River Cottage

Iconic Chesapeake. Unparalleled Luxury.

Cozy & Content River Retreat Beach Hot Tub & Games

Magical Bayfrnt Home, Pier, Beach, Fossils, trails

8 Acre Waterfront Oasis! Pets are Free! 140ft Pier

Canary Pointe-A popular getaway for 2!
Quick stats about house rentals near Chesapeake Bay

Total vacation rentals
Explore 3,710 vacation rentals in Chesapeake Bay

Verified guest reviews
Over 145,150 verified reviews to help you choose

Family-friendly vacation rentals
2,900 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 1,490 rentals that welcome pets

Vacation rentals with a pool
420 properties feature pools

Rentals with dedicated workspaces
2,320 properties have a dedicated workspace

Wi-Fi availability
3,610 of Chesapeake Bay vacation rentals include wi-fi 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!
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