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House vacation rentals in Chincoteague Bay

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Top-rated house rentals in Chincoteague Bay

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Guest favorite
Home in Chincoteague

Dragonfli Bay House on Chincoteague Island

Relax in this calm, stylish space. This home has been lovingly refreshed by its current owners. Every detail has been considered. Inside you will find well appointed rooms designed for function and comfort. Outside, tranquility awaits you. Enjoy morning coffee overlooking the water, kayaking on the bay, end the day relaxing by the fire. Head to Assateague to swim, surf fish or hike to the famed lighthouse. Return with the day's catch to utilize the fish cleaning station and outdoor shower.

4.94 out of 5 average rating, 160 reviews
Top guest favorite
The front exterior of a charming two-story house is shown, featuring a pitched roof and light-colored siding. A bright blue door welcomes visitors. A white picket fence encloses the front yard, which is neatly landscaped with greenery and flowering plants.
Home in Ocean City

Dolores by the Sea- Family Groups ONLY

This recently remodeled 1950's house is walking distance to the beach, boardwalk, & fabulous restaurants. Tucked away from the hustle & bustle in a quiet neighborhood this cozy home is the perfect place to relax after a fun filled day at the beach. This home has 4 bedrooms & up to 7 beds. With a wheelchair ramp & a fenced in yard this house is perfect for family gatherings & making memories. Please note that due to neighborhood restrictions we cannot book to unrelated renters under 27 years old

4.97 out of 5 average rating, 109 reviews
Top guest favorite
The exterior of the home is showcased with a well-maintained lawn, framed by flowering shrubs. A welcoming front porch is visible, featuring two wooden benches. The entrance is highlighted by a maroon door, accompanied by classic shutters on the windows.
Home in Parsonsburg

Charming Home in a Neighborhood

Our home is well loved and is a great place to spend some quality family time. It is close to the Salisbury Airport (SBY), Salisbury University (SU), Perdue Stadium (Delmarva Shorebirds) and short drives to University of Maryland Eastern Shore (UMES), the beaches in Ocean City MD, Asseteauge Island, Md and some Delaware beaches too. Winterplace Equestrian Park is within 4 miles and Pemberton Historical Park is just across town. Price includes parking in the attached oversized 2 car garage.

4.99 out of 5 average rating, 181 reviews
Top guest favorite
A two-story beach house stands amidst lush greenery, featuring a spacious wrap-around porch with multiple seating areas. Large windows allow for ample natural light, while the light-colored exterior complements the serene surroundings. The property is partially surrounded by trees, enhancing privacy.
Home in Machipongo

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

4.99 out of 5 average rating, 135 reviews
Top guest favorite
A two-story waterfront home is visible, elevated on stilts with a spacious deck featuring steps leading down to a private dock. Brightly colored kayaks are stored on the dock, and lush trees surround the property, providing a natural, serene backdrop.
Home in Chincoteague

Jay's Retreat: dock, kayaks, EV charger, bikes

Welcome to Jay’s Retreat, a charming waterfront oasis nestled in scenic Oyster Bay. This beachy 3-bedroom, 2-bathroom home accommodates up to 6 guests and is pet-friendly it an ideal space to vacation with your entire family. The spacious screened porch offers the perfect perch to savor your morning coffee with the sunrise or relax with friends and family while enjoying fresh, locally sourced seafood. End your days by the fire pit, soaking in the peaceful bay views and coastal breeze.

4.97 out of 5 average rating, 101 reviews
Top guest favorite
Home in Shady Side

Iconic Chesapeake. Unparalleled Luxury.

Autumn at The Cottage at Silver Water is peaceful, cozy, and a little magical. Crisp days invite you to kayak, explore the shoreline, or enjoy the changing colors. Evenings bring golden skies, spectacular sunsets, cool breezes, and fires by the water. Inside, the cottage is warm and inviting, with luxurious bedding, curated art, and thoughtful amenities for a relaxed, memorable stay. Come experience autumn at Silver Water—and see why every guest has given their stay five stars.

5.0 out of 5 average rating, 217 reviews
Top guest favorite
A covered deck area features a large black dining table surrounded by striped chairs. A ceiling fan is present above. Scenic views of the water and shoreline are framed by tall trees, creating a serene outdoor dining space.
Home in Cambridge

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.

4.99 out of 5 average rating, 228 reviews
Top guest favorite
The backyard features a well-maintained putting green, with white flags marking the holes. A spacious home with a covered patio and landscaped garden is visible in the background, surrounded by lush greenery and trees.
Home in Berlin

Assateague, Golf, Ocean City, all Within Minutes!

Worcester Co. Lic. #859 PLEASE NOTE: number of allowed guests: No more than 8 golfers. (Min age 25) No more than 10 adults. (Min age 25) Related families up to 12 guests. We do NOT rent to high school senior groups. Please note, we own the white house next to our STR. Occasionally you may see us there, however, we are committed to your comfort & privacy. Located 1.5 miles from Assateague Island beaches. 3 courses within .5 miles. Towels and linens for every guest.

4.98 out of 5 average rating, 107 reviews
Top guest favorite
A large waterfront estate is viewed from a distance, framed by tall trees. The house features a wraparound porch with blue rocking chairs, surrounded by expansive green lawns. The soft glow of sunset casts elongated shadows on the ground, enhancing the serene atmosphere.
Home in Onancock

Chesapeake Bay Retreat | Private Dock + Beach

Wake up to sunrises over the creek as you sip your morning coffee and soak in the stillness that surrounds you. 🌿 Outdoor Features: Private dock with multiple boat slips – ideal for crabbing, fishing or just taking in the view Covered porch with a fireplace, tv and gas grill Outdoor fire pit for s’mores in summer or oyster roasts in winter Private beach area for lounging, shell collecting 🎯 Yard Games for All Ages: Hammock for afternoon naps beneath the trees

4.96 out of 5 average rating, 104 reviews
Top guest favorite
A scenic view of a sunset over the water, with a silhouette of a person kayaking. Adjacent, a cozy seating area is set up around a fire pit, surrounded by trees. In the foreground, a table with wine and glasses is shaded by a red umbrella, beside a hot tub.
Home in Dameron

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.

4.99 out of 5 average rating, 142 reviews
Top guest favorite
A wooden dock extends over calm water, surrounded by tall trees. A pair of Adirondack chairs provide a peaceful spot to enjoy morning sunlight filtering through leaves, creating a serene atmosphere perfect for relaxation.
Home in Newark

Secluded Waterfront - Beach 15mi, Kayaks, Firepit

Casa Blue Heron is a 2,254 ft² (209 m²) custom waterfront home with a private dock, firepit, and water views throughout - nestled on a tidal inlet connected to Chincoteague Bay - and near Assateague, Berlin, Ocean City, Snow Hill, and much more. ★ "A private and tranquil setting where it is impossible not to relax and appreciate nature… Wish I had booked an extra day!" Add us to your wish list by clicking the ❤️ in the upper-right corner.

5.0 out of 5 average rating, 126 reviews
Top guest favorite
A spacious open-concept living area features large windows offering unobstructed views of the water and sunset. A comfortable sectional sofa is positioned near the windows, with a dining table visible in the background. Natural light fills the space, enhancing the tranquil setting.
Home in Leonardtown

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”).

4.99 out of 5 average rating, 141 reviews

Popular amenities for Chincoteague Bay house rentals

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top guest favorite
A round wooden dining table surrounded by eight woven chairs is positioned in a well-lit dining area. Soft natural light enters through large windows adorned with white blinds. A coastal-themed wall art piece enhances the serene ambiance, and a smaller table can be seen in the background.
Home in Rehoboth Beach

Beautiful Beach House in Rehoboth

5.0 out of 5 average rating, 239 reviews
Guest favorite
A light and airy deck features a rectangular dining table surrounded by aqua-colored chairs. A calm water view is visible beyond the railing, with flags gently waving in the breeze. Soft lighting is provided by string lights overhead, enhancing the inviting atmosphere.
Home in Ocean City

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

4.93 out of 5 average rating, 290 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
Top guest favorite
A modern kitchen is showcased with sleek dark cabinets and a white countertop. A pendant light hangs above, illuminating the space. An open layout allows views into the adjoining living area, which features warm wood tones and natural light from large windows.
Home in Chincoteague

Seas the Day Getaway~CLOSE to Bay~3 mi to BEACH

4.95 out of 5 average rating, 461 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

4.98 out of 5 average rating, 176 reviews
Top guest favorite
A spacious living room features a comfortable dark sofa, two brown chairs, and a cozy fireplace. Natural light enters through large windows adorned with light blue drapes. A ceiling fan and recessed lighting contribute to a bright and airy atmosphere, complemented by modern decor.
Home in Ocean Pines

Ocean Pines Retreat with Beach Club

4.99 out of 5 average rating, 140 reviews
Top guest favorite
A wrap-around deck overlooks a tranquil waterfront view, featuring lush greenery and calm waters. A seating arrangement includes four chairs with cushioned backs, positioned for relaxation. The scene is punctuated by nearby trees, contributing to a serene atmosphere.
Home in Lewes

Beautiful Waterfront Home-Private, Clean, Relaxing

4.99 out of 5 average rating, 238 reviews
Top guest favorite
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

4.99 out of 5 average rating, 255 reviews

Weekly house rentals

Top guest favorite
Home in Exmore

Chesapeake Bay Sunset • Private Beach House

4.88 out of 5 average rating, 125 reviews
Top guest favorite
Home in White Stone

1891 Coastal Charmer: fully renovated farmhouse

4.99 out of 5 average rating, 149 reviews
Superhost
A well-appointed bedroom features a wooden bed with soft green linens and decorative pillows. A bedside table with drawers holds a vintage clock and a decorative object. A woven light fixture hangs above, and natural light filters through the window covered by blinds.
Home in Salisbury

Stella

4.9 out of 5 average rating, 145 reviews
Top guest favorite
An outdoor deck is featured with comfortable seating and a fire table, inviting relaxation with a clear view of the bay. A grill is positioned nearby, while an umbrella provides shade over the seating area. The surrounding beach landscape is visible in the background.
Home in Milton

"Sandy Feet" Broadkill Beachfront Home

4.93 out of 5 average rating, 144 reviews
Superhost
Home in Chincoteague

Bay View - Waterfront, Dock, Stunning Sunsets

4.88 out of 5 average rating, 24 reviews
Guest favorite
A serene waterfront view features a sandy beach bordered by green grass and rocks. A wooden structure leads to the water, where a dock extends into the bay under a clear blue sky, illuminated by sunlight. Gentle waves can be seen lapping at the shore.
Home in Snow Hill

Tiny Gorgeous Waterfront Cottage

4.84 out of 5 average rating, 25 reviews
Guest favorite
A hot tub is situated on a wooden deck, bubbles rising gently from the water's surface. The vibrant blue exterior of the house is contrasted by pink trim. Sunlight reflects off the hot tub, creating a bright and inviting ambiance. A screened porch and balcony are visible in the background.
Home in Chincoteague

Hot Tub. Fire pit. Fenced Yard. Games. Downtown.

4.98 out of 5 average rating, 57 reviews
Superhost
A one-story home is depicted, featuring a light-colored exterior with dark shutters on the windows. A small set of steps leads to the front door, surrounded by a well-maintained lawn and young plants. Sunlight casts gentle shadows across the grassy area.
Home in Girdletree

Private Home in Quiet Beach Country setting

4.7 out of 5 average rating, 79 reviews

Private house rentals

Top guest favorite
Home in Bethany Beach

Oceanside in Bethany Dunes, Steps to Private Beach

5.0 out of 5 average rating, 18 reviews
Guest favorite
The open-plan living area features rich wooden beams and elegant flooring. A cozy fireplace with a stone surround stands beside a modern sofa. A dining area is visible, with a large table and chairs, while a staircase leads to the upper level.
Home in Berlin

Shire Retreat - Berlin, Assateague, Ocean City

4.89 out of 5 average rating, 74 reviews
Top guest favorite
A spacious living area features a large sectional couch and a coffee table, surrounded by wooden flooring. A world map adorns the wall, and natural light streams in through the windows. The open layout flows into a dining area visible in the background.
Home in Chincoteague

The Magnolia House ~Linens Included~

5.0 out of 5 average rating, 58 reviews
Top guest favorite
A large wooden deck features several adirondack chairs positioned to face expansive views of the marshland and water. A clear blue sky complements the serene landscape, with gentle clouds casting soft shadows over the scene.
Home in Parksley

Serene Waterfront Metompkin Retreat - Entire Home

5.0 out of 5 average rating, 24 reviews
Top guest favorite
Home in Stevensville

Away at the Bay: New Home on the Chesapeake Bay!

5.0 out of 5 average rating, 70 reviews
Guest favorite
A serene outdoor area features a sparkling pool accompanied by a hot tub. Surrounding the space are several lounge chairs and a shaded patio with a large umbrella. Colorful flowers in planters add to the lush greenery and natural surroundings.
Home in Rehoboth Beach

Gorgeous 5BR, 4.5BA, in town, pool, hot tub, beach

4.96 out of 5 average rating, 57 reviews
Top guest favorite
A serene sunset is captured over the water, with the sun gently descending on the horizon. Silhouette of dock pilings is visible against the shimmering surface of the water. Tall grasses in the foreground reflect warm hues of orange and pink, enhancing the tranquil scene.
Home in Chincoteague

Waterfront-Views from all rooms-CI bay sunset

4.98 out of 5 average rating, 99 reviews
Top guest favorite
Home in Heathsville

Luxury Beach Hs w/ 4 Suites, PrivateBeach & Htub

5.0 out of 5 average rating, 18 reviews