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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, 159 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, 106 reviews
Top guest favorite
A coastal retreat is presented in a light-colored two-story home elevated on stilts. A set of steps leads to a covered porch with a railing. A small seating area with yellow chairs is visible beneath the porch. Lush green trees surround the property.
Home in Chincoteague

Pearl in the Pines: bikes, kayaks, EV charger

Nestled in the shade of tall pine trees in the private community of Oyster Bay, "Pearl in the Pines" is a charming coastal retreat equipped to meet any need. This bright and beachy 3-bedroom, 2-bathroom home accommodates up to 6 guests and is pet-friendly, making 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.

4.98 out of 5 average rating, 121 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, 175 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, 131 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, 105 reviews
Top guest favorite
Home in Shady Side

Iconic Chesapeake. Unparalleled Luxury.

Summer at The Cottage at Silver Water is effortless and indulgent. A sweeping waterfront lawn leads to a private shoreline for swimming, kayaking, and long days in the sun. Evenings bring golden skies, spectacular sunsets, and fires by the water’s edge. Inside, the cottage is beautifully designed with luxurious bedding, curated art, and thoughtful amenities that make every stay relaxed, refined, and unforgettable. See why all our guests only have a 5-Star experience.

5.0 out of 5 average rating, 214 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 cozy living area presents a light brown couch adorned with colorful cushions and a decorative throw. Two accent chairs sit across from the couch, positioned on a patterned area rug. Natural light filters through sheer curtains covering a large window, illuminating the space.
Home in Ocean Pines

Sweet Retreat

Sweet Retreat is conveniently located in Ocean Pines, Maryland. The premiere residential and resort community of Ocean Pines is located eight miles inland from the ocean resort town of Ocean City. Ocean Pines has over 9 miles of waterfront property and 3,000 acres of wooded areas. Community amenities include beaches, a yacht club, golf course, community center, a Beach Club Pool and other community pools. Passes are available at ocean Pines Association.

4.97 out of 5 average rating, 115 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, 125 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, 139 reviews
Top guest favorite
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 private 16-acre property is bordered by a conservation area and a 300-foot private beach. 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).

4.99 out of 5 average rating, 175 reviews

Popular amenities for Chincoteague Bay house rentals

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

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, 307 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, 235 reviews
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, 235 reviews
Top guest favorite
A charming beach house is set on stilts, featuring a pink exterior with white shutters. The front porch offers a welcoming entry, surrounded by a landscaped yard with trees. Gravel driveway and a white picket fence enhance the appealing exterior in a tranquil neighborhood.
Home in Frankford

The Big Chill at Bethany Beach

4.98 out of 5 average rating, 101 reviews
Top guest favorite
The exterior of a single-story house is visible, featuring a spacious front porch with white railings. Large windows allow natural light to enter, while a driveway provides parking for two vehicles. A wooded area surrounds the property, enhancing its peaceful setting.
Home in Ocean Pines

Camelot

4.97 out of 5 average rating, 152 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 ~ Pool ~ ONLY 3 mi to BEACH

4.96 out of 5 average rating, 456 reviews
Top guest favorite
A private hot tub is set on a paved patio beneath a shaded gazebo. Wooden decking surrounds the area, enhancing the serene outdoor setting. Lush greenery provides privacy, while outdoor lighting can be seen strung above, creating a welcoming space for relaxation.
Home in Rehoboth Beach

Perfect Rehoboth Beach Getaway with Hot Tub

4.94 out of 5 average rating, 106 reviews
Guest favorite
A back deck features a seating area composed of a sofa and ottoman with soft cushions, facing a calm canal. A wooden table is positioned nearby. A red umbrella is closed and stands beside the seating, while a sunset casts gentle hues across the water.
Home in Ocean City

3 BR Waterfront Home, Minutes to the Beach

4.93 out of 5 average rating, 150 reviews

Weekly house rentals

Top guest favorite
Four black Adirondack chairs are positioned in a grassy area facing a tranquil body of water. Lush green reeds frame the water's edge, with a blue sky and scattered clouds above. A small dock is visible in the distance, adding to the serene setting.
Home in Belle Haven

Bay Breeze Home on private waterfront

4.97 out of 5 average rating, 159 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

4.96 out of 5 average rating, 103 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

4.99 out of 5 average rating, 224 reviews
Top guest favorite
A light-filled living room is presented with soft beige seating arranged around a round, patterned coffee table. A landscape artwork adorns the wall above the couch. Natural light streams through a nearby window, highlighting a plant tucked in the corner.
Home in Chincoteague

Adorable Beach Cottage Just Steps From Town & Bay

4.94 out of 5 average rating, 207 reviews
Top guest favorite
A modern kitchen and dining area feature light-colored cabinetry and stainless steel appliances. A large wooden dining table accommodates eight, surrounded by aqua-colored chairs. Natural light filters through the window, enlivening the space, while a decorative pendant light adds character above the table.
Home in Chincoteague Island

Rest A'Shored charming Chincoteague getaway

4.92 out of 5 average rating, 218 reviews
Top guest favorite
A spacious great room features large windows that offer sweeping views of the water. Comfortable seating arrangements with soft furnishings are complemented by a working fireplace. A staircase is visible in the background, leading to additional living spaces.
Home in Shady Side

Waterfront Sanctuary only 50 Min. From DC/Balt.

4.97 out of 5 average rating, 110 reviews
Top guest favorite
A barn-style exterior of the condo is showcased, featuring a metal roof and three large garage doors at ground level. The second floor includes a deck with an entrance door. Expansive green space surrounds the property, with trees visible in the background under a clear blue sky.
Home in Berlin

SpaciousCondo nearOcean City|Winery|Golf on 5Acres

4.96 out of 5 average rating, 120 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

4.83 out of 5 average rating, 23 reviews

Private house rentals

Guest favorite
Home in Chincoteague

Captain's Loft

5.0 out of 5 average rating, 14 reviews
Top guest favorite
White Adirondack chairs are positioned around a black outdoor fire pit, surrounded by trees that provide shade. A tranquil view of the river is visible in the background, reflecting the clear blue sky and scattered clouds.
Home in Snow Hill

Riverfront Retreat-Kayaking/Fishing/Nearby Beaches

4.99 out of 5 average rating, 97 reviews
Guest favorite
Home in Chincoteague

Sialang - Waterfront, Pier, Hot Tub & Kayaks

5.0 out of 5 average rating, 13 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
Top guest favorite
The ranch-style house is situated on a spacious green lawn, surrounded by trees. Soft outdoor lighting highlights the front of the home as dusk approaches. A secondary building is visible to the right, with a clear area for parking and landscaping enhancing the natural setting.
Home in Snow Hill

The Puskar’s Landing

5.0 out of 5 average rating, 43 reviews
Top guest favorite
A coastal house is positioned on stilts along a serene beach. The sky displays hues of pink and purple at sunset, reflecting the peaceful atmosphere. Sand stretches along the shore, meeting the calm waters, while neighboring homes create a sense of community.
Home in Milford

Peaceful off the beaten path on the Delaware Bay

5.0 out of 5 average rating, 61 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
Guest favorite
Home in Berlin

Sleeps26 Mins to Beach w. GameRoom-Pool-BBallCourt

4.92 out of 5 average rating, 36 reviews