Vacation rentals with a pool in Chincoteague

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Chincoteague

Total vacation rentals
Explore 140 vacation rentals in Chincoteague
Nightly prices starting at
Chincoteague vacation rentals start at €35 per night before taxes and fees
Verified guest reviews
Over 2,730 verified reviews to help you choose
Family-friendly vacation rentals
110 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 40 rentals that welcome pets
Rentals with dedicated workspaces
90 properties have a dedicated workspace
Wi-Fi availability
140 of Chincoteague vacation rentals include wi-fi access
Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chincoteague rentals
4.7 Average rating
Chincoteague stays receive an average rating of 4.7 out of 5 from guests

Top-rated rentals with a pool in Chincoteague

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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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

After relaxing at the beach (just a 7 min walk away), unwind on our deck "watchin' the tide rollin' away!" Get the best of the bay & the beach with this dog-friendly hidden gem! Imagine evenings enjoying the bay breeze as you crack crabs on the deck! Relax inside our open-concept great room that allows everyone to be together. Fish on our private dock or use it for your own boat or jet-ski to dock there. Witness spectacular sunsets with our Kayaks. Enjoy a well lit, private work space to virtual work w/ high speed internet! A new wood CRIB now in master suite for restful sleep! The pools and tennis/pickleball courts are only a few blocks away for your enjoyment! Plus, a truly unique OUTDOOR MOVIE EXPERIENCE for all our guests to make for the best Vacay EVER!

LocationFamilyAmenities

4.93 out of 5 average rating, 290 reviews

Guest favorite

The image captures the exterior of a charming blue house surrounded by vibrant flower beds, primarily featuring red blooms. A yellow sign displaying the house name and address stands prominently in the foreground. Soft evening light enhances the welcoming atmosphere.

Bungalow in Horntown

Nature's retreat @ the Bug-a-Boo. Beaches nearby

We're inside a lovely gated campground community with full amenities @ the Club House: Wi-Fi, pool, fishing n crabbing, boat ramp, laundry, and bath houses. The Bug-a-Boo is a lovely single dwelling home. It is ADA handicap accessible. There's an outdoor fire pit and space for camping. We are 20 miles from Chincoteague National Wildlife Refuge with miles of protected beaches. This is a peaceful place for soul searching & social distancing. We are also 42 mi from Assateague Is. Nat. Seashore.

ValueLocationParks

4.81 out of 5 average rating, 169 reviews

Guest favorite

An aerial view depicts a private above-ground pool surrounded by a spacious wooden deck. Multiple seating areas with umbrellas offer shade, and lush greenery borders the property, adding a natural ambiance. The outdoor kitchen and grill area are visible, enhancing the deck's recreational space.

Cottage in Marion Station

Pool/HotTub/RecRoom/Pvt. Dock YearRoundPlayground

Discounts Offered! Enjoy best of Eastern Shore living in this unique waterfront retreat offering FULL privacy on 8+ acres! Newly renovated 3BR/2.5BA home blends nature, comfort, & resort‑style amenities PERFECT for families & groups in ALL seasons: *Large Swimming Pool & 7-person Hot Tub *Detached Rec Room w/Pool Tbl *Shaded Outdoor Grill/Sink/Fridge *Private Dock for Fishing/Kayak *W/GOLFING, BEACHES, & HUNTING nearby! Escape the city rushes & don't miss out on Insta-worthy pics! BOOK NOW!!

FamilyLocationCondition

4.81 out of 5 average rating, 59 reviews

Top guest favorite

Home in Parsonsburg

Eastside Oasis: Heated Pool + Pond + Patio!

This Modern Farmhouse home features six spacious bedrooms (five KING bedrooms and one with three queens ALL with en suite bathrooms) so nobody has to fight over who gets the nicest room on your vacation! :) There's a fully stocked chef's kitchen, plenty of seating, and sliding glass doors that open to the outdoor space with views of the pool, pond, and fields. You'll see lots of wildlife on the property including deer, turkeys, geese, lots of waterfowl. Come stay for a unforgettable vacation!

FamilyLocationBathroom

4.96 out of 5 average rating, 24 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.

Heartsong Farmhouse was completely renovated in 2019. Beautiful hardwood floors, brand new furniture, in a modern farmhouse style with a Boho vibe. The entire home is filled with beautiful natural light and the brick walls ensure a peaceful nights sleep. The yard is completely surrounded by a 15ft hedgerow of holly, magnolia and camellias, like walking into a secret garden. You will feel welcome from the moment you drive up. The Farmhouse is also beautifully decorated for the holidays.

FamilyValueParking

4.98 out of 5 average rating, 310 reviews

Top guest favorite

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.

Condo in Ocean City

Oceanfront Condo w/ Resort Amenities 3BDR &3pools

Sea Watch Condo's is an ideal family location with tons of amenities. The until is a recently updated 3 bedroom 2 bathroom condo that sleeps 6 people in 2 queen beds, 2 twin beds . The unit is ocean front with a large oceanfront balcony. The amenities Include, basketball court, tennis courts, playground, arcade, movie theater, billiard room, indoor pool and outdoor pool as well as a restaurant. The condo has 24 hour security and plenty of parking. Pools closed in off season

LocationValueCondition

4.88 out of 5 average rating, 147 reviews

Guest favorite

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.

Condo in Ocean City

Direct Oceanfront with a View and Amenities Galore

Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with full 100% view of the beach and ocean.

LocationValueAccuracy

4.94 out of 5 average rating, 339 reviews

Top guest favorite

A bright living area features wooden beams and large windows adorned with plaid curtains. A variety of cushions decorate a sectional sofa and a leather couch. A television offers a view of a sports event, while an area rug adds pattern to the wooden floor.

Farm stay in Princess Anne

Farmhouse located on a horse farm

Farmhouse located just minutes off of Route 13 in Princess Anne, MD. Enjoy a peaceful farm experience while staying in a charming farmhouse with lots of character. You can walk the grounds of the farm, including a trail through the woods, or take a swim in the pool. We do not offer horseback riding lessons but you can interact with the horses. We are minutes to shopping, groceries, restaurants, UMES, and a short ride to Chincoteague (32 miles) and Ocean City (40 miles).

FamilyLocationAmenities

4.95 out of 5 average rating, 124 reviews

Guest favorite

A spacious waterfront property is featured, showcasing expansive outdoor areas including a heated pool, playground, and large lawn. A comfortable deck surrounds the pool, while the house is adjacent to well-maintained landscaping and pathways, highlighting the scenic surroundings and inviting outdoor activities.

Home in Reedville

Bayfront | Pool Open & Heated, Hot Tub, Dock, Pets

Welcome to The Fleeton House – a serene waterfront retreat perfect for families, friends, or groups! This spacious home offers 6 bedrooms, 3.5 baths, a heated pool, hot tub, private pier, and more. Kids and pets are welcome, and there's plenty of space to unwind, dine, and play. Come for the views, stay for the memories. Shell Landing Public Boat Ramp (2 Mins) Downtown Shops & Restaurants (6 Mins) Reedville Attractions (6 Mins) Waterfront Dining (6 Mins or Less)

FamilyLocationBeach

4.87 out of 5 average rating, 38 reviews

Guest favorite

A modern kitchen is presented with white cabinetry and stainless-steel appliances, featuring a refrigerator, microwave, and coffee maker. A dining table is set for four, and a cozy seating area with a blue couch is visible. Natural light enters through a window, enhancing the space.

Cottage in Chincoteague

Key Lime Cottage

Escape to your own bayfront retreat in Chincoteague Island, Virginia. Our Key Lime Cottage at the Key West Cottages resort offers views of the Chincoteague Bay, giving you a front-row seat to the breathtaking sunsets that Chincoteague offers each night. This one-bedroom private cottage includes a master bedroom with two queen beds, a fully equipped kitchen, living and dining space, waterfront deck and access to many amenities!

LocationValueGetting around

4.94 out of 5 average rating, 130 reviews

Guest favorite

A two-story farmhouse features a welcoming porch and elegant landscaping, including trimmed bushes and a stone pathway. The exterior showcases a mix of wood and shingle siding, with large windows reflecting the greenery surrounding the property. A well-maintained lawn is visible in the foreground.

Home in Fruitland

4bed/4.5bath Lux Farmhouse/Pool/Gym/5 min from SU

BEFORE BOOKING: Pool will be open 4/05/26 NO PARTIES/NO EVENTS/NO GATHERINGS, only the amount of guests in your reservation are allowed on the property. Fully restored top to bottom 1920s farm house. Every bedroom has its own full bathroom Full laundry room with extra refrigerator RH furniture All bedding/towels/paper towels/toilet paper/body wash/shampoo/conditioner/spices/laundry detergent included;Total turn key

LocationValueAccess

4.97 out of 5 average rating, 141 reviews

Guest favorite

A serene canal view captures waterfront homes reflecting in calm waters at sunset. Docked boats and lush trees frame the scene, showcasing the tranquil atmosphere of the eastern shore. The clear sky hints at the day's end, lending a peaceful ambiance to the surroundings.

Home in Greenbackville

Bayfront Modern Retreat • Dock, Kayaks, Views

Wake up to shimmering Chincoteague Bay views in this modern waterfront escape on Virginia’s Eastern Shore. Spend mornings on the water, afternoons by the fire pit, and evenings under glowing sunsets. Kayaks, bikes, pools, golf, pickleball, and trails are moments away, with beaches a short drive. Bring the dog, unplug, and settle in. Your coastal reset starts here.

LocationValueCheck-in

4.91 out of 5 average rating, 135 reviews