Home rentals with a pool near Chesapeake Bay

4.95 out of 5 average rating, 148 reviews

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.

FamilyLocationAmenities

4.94 out of 5 average rating, 108 reviews

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.

ValueLocationDecor

4.98 out of 5 average rating, 177 reviews

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?

LocationFamilyHot tub

4.91 out of 5 average rating, 185 reviews

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.”

LocationValueBackyard

4.99 out of 5 average rating, 146 reviews

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

This lovely guest cottage is located on a historic 16 acre waterfront estate on Hudson Creek that includes a main house, barn, pool, dock and pond. Built in the 18th century tidewater style, the guesthouse is charming and well decorated and completely self efficient. A special place for your romantic getaway at any season of the year. Recently cell phone service has improved and is reliable. However, in the country, WiFi internetl can be slow at times as well as the Wifi TV streaming.

ValueFamilyCheck-in

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.

LocationFamilyLaundry

4.95 out of 5 average rating, 183 reviews

4.98 out of 5 average rating, 163 reviews

Home in Montross

Waterfront, Dock+Kayak, Firepit, Gameroom, Potomac

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!

FamilyLocationBathroom

5.0 out of 5 average rating, 209 reviews

Guesthouse in Gloucester

Halloween Hideaway - Waterfront & Firepits

Explore the thrills of Williamsburg's Halloween festivities (45 minutes away), then escape to your peaceful waterfront retreat on 10 wooded acres overlooking Bland Creek. - Creekside fire pits for cozy fall evenings - Screened porch with beautiful fall water views - Dock, kayaks, fishing, and direct water access - Outdoor dining and hammocks beneath the trees - Immaculately clean and thoughtfully stocked for a relaxing stay - Just 45 minutes from Busch Gardens and Williamsburg

FamilyLocationGrill

4.99 out of 5 average rating, 181 reviews

The historic home features a charming exterior with a mix of white clapboard and dark shingles. An inviting porch is framed by green shutters and surrounded by well-maintained landscaping. A gravel driveway leads to the front entrance, enhancing the property’s welcoming appeal.

Home in Lusby

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 very private 16-acre property is bordered by a conservation area and a 300-foot private beach; no shared driveways or houses right next door. 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).

LocationFamilyAmenities

4.96 out of 5 average rating, 107 reviews

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!

LocationFamilyBeach

Tiny homes in Cape Charles

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.

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.

ValueLocationPool

4.98 out of 5 average rating, 363 reviews

Guesthouse in Stevensville

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.

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.

LocationFamilyPets

4.99 out of 5 average rating, 377 reviews

Popular amenities for rentals with a pool near Chesapeake Bay

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 113 reviews

An aerial view of a spacious red farmhouse surrounded by lush greenery and open fields. A saltwater pool is visible in the backyard, complemented by a patio area. The landscape includes manicured lawns and trees, creating a serene rural setting.

Home in Queen Anne

Farmhouse w/hot tub, close to Tuckohoe State Park

LocationFamilySleep quality

4.99 out of 5 average rating, 255 reviews

A spacious living area features two comfortable sofas, one draped with a soft blanket. Natural light streams through large windows, highlighting the wooden flooring. A small wooden table is visible in the background, and a decorative piece hangs above the mantel.

Home in Tracys Landing

The Little Gypsy BoHome

LocationFamilyCheck-in

4.97 out of 5 average rating, 134 reviews

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

LocationFamilyLayout

4.99 out of 5 average rating, 134 reviews

Home in Irvington

The Rosé Retreat: Pool-Screened Porch-RELAX

ValueLocationBiking

4.92 out of 5 average rating, 234 reviews

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

ValueFamilyWifi

4.98 out of 5 average rating, 310 reviews

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.

FamilyValueAir conditioning

4.97 out of 5 average rating, 179 reviews

Home in Locust Hill

Rappahannock Waterfront Pool, Kayak, Deck, Firepit

FamilyValueGrill

5.0 out of 5 average rating, 329 reviews

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

LocationFamilyHeating

Condo rentals with a pool

A panoramic view of the ocean is visible, with gentle waves lapping at the sandy beach. Below, an outdoor pool is surrounded by lounge chairs and clear pathways, providing a peaceful atmosphere. Skies are blue, enhancing the serene coastal setting.

4.89 out of 5 average rating, 148 reviews

Oceanfront Condo w/ Resort Amenities 3BDR &3pools

ValueLocationSleep quality

A serene ocean view is presented from a private balcony, featuring two teal chairs. The sandy beach stretches into the distance, with gentle waves lapping at the shore. A clear sky completes the tranquil coastal scene, creating a peaceful atmosphere.

4.92 out of 5 average rating, 297 reviews

Oceanfront Paradise | Pool | Hot Tub | Beach

FamilyLocationView

The living area features soft blue furnishings and a light wood coffee table. Floor-to-ceiling windows offer direct views of the ocean, while two lamps provide warm lighting. A coastal-themed artwork adorns the wall, enhancing the serene atmosphere of the space.

4.94 out of 5 average rating, 341 reviews

Direct Oceanfront with a View and Amenities Galore

FamilyLocationIndoor spaces

4.95 out of 5 average rating, 182 reviews

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

ValueFamilySleep quality

4.98 out of 5 average rating, 226 reviews

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

LocationValueOutdoor spaces

4.97 out of 5 average rating, 232 reviews

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

FamilyLocationKitchen

A bright living area features a blue sofa, a striped armchair, and a wooden coffee table. Natural light flows through sliding glass doors that lead to a balcony with ocean views. Light curtains frame the view, and a TV is mounted on a light-colored media console.

4.96 out of 5 average rating, 121 reviews

21st Floor Carousel - 2 BR Oceanfront & Bay View

LocationFamilyComfort

A modern kitchen is complemented by a spacious dining area and cozy living room with ocean views. White cabinetry and stainless steel appliances enhance the kitchen, while large windows allow natural light to fill the space, highlighting the wood-paneled ceiling.

4.94 out of 5 average rating, 192 reviews

Oceanfront 1 Bedroom, Balcony, Sitting Room, Pool

LocationFamilyView

Other vacation rentals with a pool

4.85 out of 5 average rating, 127 reviews

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

LocationValueParks

4.98 out of 5 average rating, 204 reviews

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

LocationValuePool

4.96 out of 5 average rating, 164 reviews

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

LocationValueTV

4.99 out of 5 average rating, 131 reviews

Farm stay in Huntingtown

Luxury Farmette -Private & Secluded-1hr to DC

ValueFamilyGetting around

5.0 out of 5 average rating, 138 reviews

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

ValueLocationRiver

Farm stay in Cockeysville

The Master's Suite · King Suite, Hunt Valley

LocationValueCheck-in

4.95 out of 5 average rating, 149 reviews

Apartment in Upper Marlboro

Kone Oasis- hot tub, pool, theater/game rm.

FamilyLocationBeach

4.94 out of 5 average rating, 222 reviews