
Home rentals with a pool near Chincoteague Island
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Top-rated rentals with a pool near Chincoteague Island
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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!

Beautiful waterview 2B condo w/Dock&Close to Beach
Welcome to the Canal Bungalow! A stylish 1000 sq. foot retreat to enjoy all the fun & relaxation of the coastal lifestyle in North Oc. Bring your boat with you and dock alongside your back porch, enjoy pool access in a private gated community, or bring your sports gear for Northside Park. We are tucked away on the quiet bayside of OC & only a few minutes walk to the beach. Unwind on our beautiful balcony while watching the boats go by & finally understand the true meaning of a coastal lifestyle!

SeaGate Serenity | Oceanfront Condo with Balcony
Wake up to the sound of the waves crashing outside your window and finish your days relaxing on the private balcony as you watch the pastel skies over the ocean at sunset. Come find your serenity by the sea in our newly renovated oceanfront condo. Located in midtown, you can keep your car parked in our reserved spot and walk to many of the towns best restaurants, bars, and entertainment as well as the World Famous Ocean City Boardwalk. Morning beach strolls, pool days, and evening sips await :)

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.

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.

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.

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).

Sunset Bay Villas 219 waterfront condo
Amazing views- Welcome Bird Watchers, Nature and Beach Lovers! Designer condo with direct views of the Intracoastal Waterway Chincoteague Channel and Wallops Long term rental from October-May with government per diem per person and special offers for long term occupancy. Max. occupancy per Chincoteague town fire code is 8. This includes adults, children (2 and older) and infants (children under two). Government ID issued required to be shown on or before check in date.

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!

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

Oceanfront Family Oasis: Pool, Beach & Parking!
Escape to your dream family vacation in this amazing 2-bedroom condo on the 8th floor! Enjoy incredible ocean views, direct beach access, and proximity to Ocean City's top attractions like the vibrant OC Boardwalk and thrilling amusement parks. This condo offers modern amenities, a refreshing seasonal outdoor pool, and the convenience of free parking. Perfect for families seeking fun and relaxation near the ocean.

Oceanfront 2 Bedroom-Sleeps 6-Indoor/Outdoor Pool
Kick back and relax in this beautiful and modern newly remodeled condo in Golden Sands! This rare 2 bedroom, 1.5 bathroom unit has an amazing Master Suite with full-length windows providing panoramic views down the coastline, and direct access to the private patio. Renowned building amenities include outdoor pool, top floor indoor pool, gym, tiki bar, sun deck & more. Linens & towels included!
Popular amenities for rentals with a pool near Chincoteague Island
House rentals with a pool

Ocean City Waterfront Home with Skyline Views!

Upscale Family Home in OC, Community Pool, Grill

The Puskar’s Landing

Cozy beach home away from home!

Harbor Master

Private pool, waterfront, kayaks, bikes, firepits!

Mi Casa at Bay Knolls

Bury Oasis: Pool, Hottub, Movie Theatre, Game Room
Condo rentals with a pool

Completely Renovated Luxury Bay Front Condo

21st Floor Carousel - 2 BR Oceanfront & Bay View

Oceanfront Condo w/ Resort Amenities 3BDR &3pools

Oceanfront Bldg.| 2 pools | Tennis | Game Room

Love Above the Waves-OceanView/Rooftop Heated Pool

Beautiful 2BR 2BA oceanfront condo at the Atlantis

Designer Oceanfront Condo | Pool, Hot Tub & Deck

Caramar Couples Retreat
Other vacation rentals with a pool

Pool/HotTub/RecRoom/Pvt. Dock YearRoundPlayground

Luxury Historic Estate w/ Pool • 7 BR • Sleeps 14

Serene Bayfront Bliss 3 Bedroom Condo

Floating Bungalow - Marina View

Luxury 3BR/4BA Condo: Indoor Pool, Walk to Beach

Seaside Rendezvous Chincoteague

Sunset Bay Villa 212 | Waterfront + Pet Friendly

Big Cozy Loft Overlooking the Farm and River
Quick stats about rentals with a pool near Chincoteague Island

Total vacation rentals
Explore 20 vacation rentals in Chincoteague Island

Nightly prices starting at
Chincoteague Island vacation rentals start at ﺩ.ﺇ 588 per night before taxes and fees

Verified guest reviews
Over 1,590 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
20 of Chincoteague Island vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chincoteague Island rentals

4.6 Average rating
Chincoteague Island stays receive an average rating of 4.6 out of 5 from guests
Destinations to explore
- House rentals Chincoteague Island
- Pet-friendly rentals Chincoteague Island
- Waterfront rentals Chincoteague Island
- Family-friendly rentals Chincoteague Island
- Rentals with beach access Chincoteague Island
- Rentals with pools Chincoteague
- Rentals with pools Accomack County
- Rentals with pools Virginia
- Rentals with pools United States
- Chesapeake Bay
- Assateague Island National Seashore
- Ocean City Beach
- Ocean City Boardwalk
- Bethany Beach Boardwalk
- Assateague State Park
- Northside Park
- Ocean City Boardwalk
- Delaware Seashore State Park
- Jolly Roger Amusement Park
- Fenwick Island State Park Beach
- Roland E Powell Convention Center
- Ocean Pines Golf Club
- Bear Trap Dunes
- Old Pro Golf
- Salisbury Zoo
- Trimper Rides of Ocean City
- Holts Landing State Park
- NASA’s Wallops Flight Facility Visitor Center
- Jolly Roger at the Pier
- Splash Mountain Water Park
- Layton's Chance Vineyard and Winery





