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Home rentals with a pool near Chesapeake Bay

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Top-rated rentals with a pool near Chesapeake Bay

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A modern guesthouse features a peaked roof and large windows, set against a vibrant sunset sky. The surrounding landscape includes wild grasses and a paved pathway, suggesting a serene connection to nature.
Cottage in St. Michaels

La Casita on Harris Creek, St. Michaels

La Casita on Harris Creek is an architecturally unique guest house situated on a private 40-acre farm in the heart of the Chesapeake Bay, 5 min by car to Saint Michaels, MD. The guesthouse, adjacent to the owner's main farm house, features an upstairs loft, open plan first floor TV/WiFi, full bath/shower, galley kitchen/ cook top stove, microwave, stainless refrigerator, microwave, stainless refrigerator. An adjacent private pool is available for guests. TALBOT COUNTY LICENSE NUMBER STRN 26-39

4.98 out of 5 average rating, 204 reviews
Top guest favorite
A serene beach area is depicted at sunset, with soft waves lapping against a sandy shore. The water reflects golden hues, and trees line the distant shoreline, creating a peaceful natural setting.
Barn in Cobbs Creek

The Barn at Pond Point - Riverfront Home

The Barn at Pond Point is perfectly situated on the Piankatank River, a salt water arm of the Chesapeake Bay. It shares 19 acres of wooded and waterfront property with the owner's main home. A unique space, Barn was converted from a working horse barn into a residence in the 1980's. With a quarter mile of private, sand beach and a large pool (May-Sept), the Barn is an ideal space for time with family and friends, swimming, hunting for prehistoric shark's teeth, or simply enjoying the view.

4.95 out of 5 average rating, 147 reviews
Guest favorite
Home in Lexington Park

Serenity Bay-PrivPool-HotTub-AskAbout2NightStays!

Now offering 2-night stays!! Send a msg to ask about this! Just added-Hot Tub! Spacious, relaxing, and scenic bay-view house with canoe/kayak access to the Chesapeake Bay. We've just put in a hot tub!!! Photos will be taken when it stops raining. Six bedrooms and 5 full baths. Lots to do with an outdoor pool, an nicely equipped recreation room, and a dock from which to launch your kayak or canoe. Easy access to plenty of activities in the surrounding area makes for a memorable vacation.

4.93 out of 5 average rating, 107 reviews
Top guest favorite
A spacious deck extends towards the waterfront, surrounded by lush trees. Lounge chairs and seating areas are positioned for relaxing views of the calm water. A sunroom is visible to the right, offering additional indoor space. The overall setting invites outdoor leisure and tranquility.
Home in Cobbs Creek

Blue Heron WaterSide

Blue Heron Waterside awaits you...Private Hot Tub and Pool!Waterfront and Pier- Kayaks included! This retreat is set up with you in mind for a special get away.Relax.Enjoy being together plus space to have quiet time. Sunroom, spacious deck, private Pool, Hot tub and Pier create a waterfront living experience. Grab a book, go for a swim or lounge by the pool. Explore the water with a variety of Kayaks plus a Stand Up Paddle Board.Great location to fish and crab from the pier. Are you ready?

4.98 out of 5 average rating, 176 reviews
Guest favorite
Home in Cobbs Creek

Million $ Views! Pool! Private Hot Tub! EV Charger

Welcome to The Cottage at Misti Cove, where the Piankatank River is just steps from your door. Wake to sunrise views from bed, paddle the river by kayak or paddleboard, and unwind in your private waterfront hot tub as evening settles over the water. Enjoy the peaceful setting of a small community along with a seasonal pool, beach, pier and tennis court. It’s a cozy waterfront escape with exceptional views, thoughtful comforts and plenty of ways to slow down and say, “Now this is the life.”

4.91 out of 5 average rating, 183 reviews
Superhost
Home in Irvington

Gothic Cottage, Hot Tub, Walk to Town

Set among the trees on 2 peaceful wooded acres, this cottage delights with gothic architecture, sun-filled rooms, and a bathroom for every bedroom. Relax in the hot tub under the stars, sip local wines, eat oysters. Take a sunset boat cruise or learn oystering and crabbing from a local waterman. Farm stands, markets, and sea-to-table local fare. Live life in an historic working water town with lots of personality. Close to Tides Inn, Kilmarnock, White Stone, Compass Entertainment.

4.95 out of 5 average rating, 182 reviews
Guest favorite
Home in Montross

Waterfront, 3 Beaches, Dock+Kayak, Potomac, Dog OK

Relax - Star Gaze - Kayak/Paddleboard - Hike - Fish - Swim - Beach & more! ☀️ Waterfront w/Dock 👨‍🍳 Gas griddle 🛶 Kayaks/Paddleboard 🔥 Fire pit ⛱️ 3 Community Beaches 🎯 Gameroom 🐶 Dogs OK (Max 2) ⚡️EV Outlet The Riverside Retreat in the Northern Neck of VA is the perfect spot to relax and connect with nature. We offer a peaceful sanctuary that families & small groups love to visit! Book your getaway today or ❤️ us for next time!

4.98 out of 5 average rating, 161 reviews
Guest favorite
An aerial view of the house showcases a spacious deck with comfortable seating, surrounded by a railing. A dock extends into the water, equipped with a covered boat lift. Lush greenery borders the property, providing a serene backdrop.
Home in Montross

Coastal Waterfront Escape Fire Pit, Dock & Kayaks

Escape to the Rivah and experience the perfect waterfront getaway in the Northern Neck! 🦀 Guests love the peaceful setting, private dock, kayaks, paddle boards, and beautiful sunsets. Spend your days crabbing, fishing, boating, relaxing on the beach, or enjoying the community pool. This freshly renovated coastal retreat is perfect for families & groups looking to unwind, reconnect, and enjoy life on the water — all just a short drive from DC, Richmond, and Northern Virginia!

4.96 out of 5 average rating, 107 reviews
Top guest favorite
A charming two-story cottage is set on a lush green lawn, with a clear view of the Chesapeake Bay in the background. The cottage features large windows and a sloped roof, with a small wooden addition on one side, surrounded by well-maintained grass.
Tiny home in Cape Charles

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.

4.98 out of 5 average rating, 362 reviews
Top guest favorite
The image captures a serene evening scene by the pool with a view of the setting sun over the water. Sunlight filters through trees, creating a warm glow. Poolside lounge chairs are visible, along with a clear pool reflecting the colorful sky.
Guesthouse in Stevensville

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.

4.99 out of 5 average rating, 371 reviews
Top guest favorite
An aerial view captures a spacious home set on a wooded parcel adjacent to a serene body of water. The exterior features a large swimming pool surrounded by decking, with a manicured lawn and tall trees creating a natural boundary.
Home in Cambridge

Gorgeous, Waterfront Home Is Perfect for Families!

Looking for a large, beautiful house for a big family get-away? Casey's Porch is the place to go. Come and see for yourself. Bring your extended Family. Bring your friends. Enjoy the pool. Kayaks and paddle boards and bikes await you at this beautiful home on Hudson Creek. Fish from the dock. Pull crabs from the creek. Walk down quiet country lanes. Sit around the fire pit. So many fun, outdoor things to do. Casey's Porch has it all.

4.96 out of 5 average rating, 140 reviews
Top guest favorite
A charming cottage is visible beside a clear pool, surrounded by well-maintained green lawns. Two shaded umbrellas stand over cushioned lounge chairs by the water's edge, creating a comfortable outdoor space for relaxation. The inviting pool reflects the bright sky, enhancing the serene atmosphere.
Cottage in Easton

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

5.0 out of 5 average rating, 126 reviews

Popular amenities for rentals with a pool near Chesapeake Bay

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top guest favorite
The outdoor area features a spacious concrete saltwater pool surrounded by lounge chairs and tables. The house showcases a light-colored façade with multiple entrances, large windows, and umbrellas providing shade, all set against a backdrop of lush greenery.
Home in Stevensville

Beautiful Kent Island Getaway with Pool

4.97 out of 5 average rating, 133 reviews
Guest favorite
A private beach area is depicted with soft, sandy ground, featuring two beach chairs under a blue umbrella. Calm waters extend to the horizon, complemented by a wooden dock and a distant view of the opposite shore under a clear, blue sky.
Home in Montross

The Glebe

4.92 out of 5 average rating, 234 reviews
Top guest favorite
Home in Locust Hill

Rappahannock Waterfront Pool, Kayak, Deck, Firepit

4.97 out of 5 average rating, 178 reviews
Top guest favorite
The outdoor area features a circular pool surrounded by colorful lounge chairs in yellow, blue, and white. Umbrellas in red and blue provide shade over a dining table with red chairs. Towering trees frame the view of the expansive waterfront beyond.
Home in Kent Narrows

Chester Riverfront At Kent Narrows

5.0 out of 5 average rating, 329 reviews
Guest favorite
The living room features a high, wooden ceiling with large windows allowing natural light to fill the space. A comfortable arrangement of sofas and chairs offers ample seating, complemented by a stylish area rug. A modern fireplace adds warmth to the inviting design.
Home in Perry Hall

Gunpowder Retreat

4.98 out of 5 average rating, 152 reviews
Top guest favorite
Home in Irvington

The Rosé Retreat: Pool-Screened Porch-RELAX

4.99 out of 5 average rating, 134 reviews
Top guest favorite
A green pasture is featured, where a group of five horses graze peacefully. The background showcases a wooded area with tall trees, under a clear blue sky. A small shelter is visible in the distance, complementing the tranquil rural setting.
Home in Accomac

Heartsong Farmhouse , a nature lover's retreat.

4.98 out of 5 average rating, 310 reviews
Guest favorite
An aerial view of the property reveals a spacious backyard featuring a swimming pool surrounded by lounge chairs and inflatable pool toys. Lush greenery encircles the area, enhancing the sense of privacy, and the house is seen with its inviting deck and patio area.
Home in Portsmouth

Wooded Wonderland Miniature Golf Hot tub Pool

4.93 out of 5 average rating, 176 reviews

Condo rentals with a pool

Top guest favorite
A living area features a gray couch adorned with decorative pillows against a light wall. A recliner is positioned nearby, and a wall-mounted Smart TV is visible. A dresser with a plant sits below the TV. Natural light streams in through nearby windows.
Condo in Annapolis

1st Floor Condo in Annapolis

4.96 out of 5 average rating, 180 reviews
Top guest favorite
Condo in Rehoboth Beach

Coastal Modern Condo • Balcony, 2 Baths, East Rt 1

4.99 out of 5 average rating, 121 reviews
Top guest favorite
A dining area is showcased with a grey table set for six, surrounded by vibrant yellow chairs and a metal wire-frame chair. A modern light fixture hangs above, and a decorative wreath adorns the wall, complemented by abstract artwork on either side.
Condo in Rehoboth Beach

Renovated Condo Near Outlets, 3.5 Miles to Beach

4.98 out of 5 average rating, 226 reviews
Top guest favorite
A modern open-concept living area is presented, featuring comfortable seating arrangements and large windows that provide ample natural light. The space includes a dining area with barstools and a kitchen counter. Views of the waterfront are visible through the sliding glass doors.
Condo in Lewes

Beautiful Updated Condo Waterfront, Pool, Sunsets

4.91 out of 5 average rating, 101 reviews
Top guest favorite
A serene waterfront scene is captured at sunset, with vibrant colors reflected in the calm water. A charming building with large windows is illuminated, surrounded by lush trees, and boats are docked along the waterfront, creating a peaceful atmosphere.
Condo in Ocean Pines

Water view at Ocean Pines Yacht Club Condo

4.97 out of 5 average rating, 229 reviews
Top guest favorite
Condo in Annapolis

Captains Quarters | Waterfront & Pool

4.98 out of 5 average rating, 124 reviews
Superhost
A private balcony features two turquoise adirondack chairs facing the ocean. The oceanfront view showcases the sandy beach and rolling waves, inviting moments of relaxation and enjoyment. A decorative 'Seaside' sign is displayed on the wall, enhancing the coastal ambiance.
Condo in Ocean City

DirectOceanFront on Boardwalk/Newly Remodeled/Pool

4.78 out of 5 average rating, 244 reviews
Top guest favorite
A spacious living area is presented, featuring a comfortable green sofa and a matching armchair. A large television is positioned on a low cabinet. Natural light streams through sliding glass doors, leading to a screened-in porch, enhancing the atmosphere with a view of greenery.
Condo in Rehoboth Beach

2BR Coastal Escape with Pool Near Rehoboth Beach

4.95 out of 5 average rating, 123 reviews

Other vacation rentals with a pool

Top guest favorite
Guesthouse in Gloucester

Cozy Fall Retreat - Creek Views & Fire Pits

5.0 out of 5 average rating, 206 reviews
Top guest favorite
A cozy living area features a spacious sectional couch adorned with patterned cushions. A wooden coffee table sits centrally, with a decorative rug beneath. A brick fireplace is present, flanked by windows allowing natural light, and a green door leads to the exterior.
Guesthouse in Cambridge

Rosses Chance Guest House

4.99 out of 5 average rating, 146 reviews
Top guest favorite
A clear blue pool is framed by wooden decking and lush greenery. The inviting water reflects the sky, and the pool features a set of steps for easy access. Surrounding the pool are wooden railings, adding to the private feel of the outdoor space.
Apartment in Irvington

Pelican Place, Cozy Retreat | Pool | Walk to Tides

5.0 out of 5 average rating, 137 reviews
Top guest favorite
Farm stay in Huntingtown

Luxury Farmette -Private & Secluded-1hr to DC

4.99 out of 5 average rating, 129 reviews
Top guest favorite
Farm stay in Cockeysville

The Master's Suite · King Suite, Hunt Valley

4.95 out of 5 average rating, 147 reviews
Top guest favorite
An aerial view captures the spacious backyard featuring a rectangular swimming pool surrounded by a concrete deck. Lounge chairs are placed by the poolside, with a well-maintained lawn and shrubs in the background. The two-story cottage is shown with a screened porch and a shaded area nearby.
Cottage in Chesapeake

The Cottage @ Captain Genes - Secluded Waterfront

4.96 out of 5 average rating, 164 reviews
Guest favorite
A serene view of a private beach meets the calm waters of the bay under a clear blue sky. Gentle waves lap at the sandy shore, with a wooden dock extending into the water. Soft grasses frame the beach area, contributing to the tranquil atmosphere.
Villa in Montross

Beach Retreat

4.85 out of 5 average rating, 127 reviews
Guest favorite
Guest suite in Annapolis

Annapolis Garden Suite

4.94 out of 5 average rating, 147 reviews

Quick stats about rentals with a pool near Chesapeake Bay

  • Total vacation rentals

    Explore 860 vacation rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay vacation rentals start at €17 per night before taxes and fees

  • Verified guest reviews

    Over 27,940 verified reviews to help you choose

  • Family-friendly vacation rentals

    570 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 350 rentals that welcome pets

  • Rentals with dedicated workspaces

    500 properties have a dedicated workspace

  • Wi-Fi availability

    840 of Chesapeake Bay vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chesapeake Bay rentals

  • 4.8 Average rating

    Chesapeake Bay stays are highly rated by guests—averaging 4.8 out of 5!

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