
Vacation rentals with a pool in Chincoteague
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Chincoteague
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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.

Newly renovated cute apartment 🏄 12 street 🌸
Welcome to our sweet, quite, enhanced clean and cozy place! Our apartment is the perfect escape for couples looking to spend some lovely days on the beach! We’ve got 1 bedroom but also a nice sofa where your friend can sleep if decides to join you! With its location being only couple minutes walking distance away from the beach and the Boardwalk, our beach home is the perfect place to stay. You will not have to worry about your car because we’ve got free parking spot for you! See you soon! 🌸

Gone Coastal *Pool* Bayside with view* Top Floor
Welcome to Gone Coastal! Relax in this beautiful 2BR/2BA getaway featuring: 🛏 1 King (Master) | 1 Twin-over-Full Bunk | 1 Sleeper Sofa 🏊♂️ Outdoor Community Pools – Lap & Family Pool (Directly Across!) 🔑 Keyless, Contactless Check-in 🌅 Spacious Deck – Outdoor Dining + Bay & Pool Views 📺 Smart TVs + YouTube TV 🛒 1-Minute to Grocery Store 🍽 Fully Equipped Kitchen 📍 Prime Location – 120th St, Heron Harbor 🚗 Ample Free Onsite Parking A perfect retreat for families & beach lovers! 🌊☀️

Camelot
HIGHEST RATED HOUSE IN OCEAN PINES! CHECK OUT OUR AMAZING GUEST REVIEWS :) Jumpstart your ultimate beach getaway at this impressive 3-bedroom, 2-bathroom retreat house! Complete with amenity-packed living spaces with vaulted ceilings and a serene location, you’ll never hunger for entertainment at this family friendly home. Grill out on the patio, roast marshmallows by the fire pit, tee off at a nearby golf course, or enjoy some retail therapy at Outlets Ocean City! A short drive to the beach!

Updated 3 Bedroom 2 Bathroom Home - Ocean Pines
Beautifully updated and recently renovated, rancher on a great street in Ocean Pines perfect for families and adults looking for a relaxing stay. We offer 3 bedrooms and 2 bathrooms on one level, with new large flat screen TV's, stainless appliances, and everything you'll need for your stay. We have a large driveway and a screened patio. Ocean Pines boasts over a dozen parks and walking trails, a public Yacht Club, 5 pools, 2 marinas, and a championship golf course - 10 min to the beach!

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.

Oceanfront 1 Bedroom, Balcony, Sitting Room, Pool
Opal Osprey: This OVERSIZE one-bedroom condo has been completely remodeled... giant oceanfront balcony PLUS a large patio room on the bayside! Expansive ocean views from every angle, super easy beach access, wonderful atmosphere in the quiet north end of OC. Linens included! Property Amenities - King size bed & queen sleeper - Large outdoor pool - Elevators - Dedicated high-speed WiFi and router w/ ethernet (Xfinity 100Mbps) - 2 Smart TVS with Xfinity, Roku - Keyless check-in 24/7

Bayside community, near OCMD, great rates
Welcome to MERMAID DREAMS where you can have FUN or just RELAX! We are ONLY 5 miles from OC, MD beaches & Assateague National Park/beaches. Our gated, beautiful community, is bayside, has 2 awesome pools, big splash pool, rec center, a fishing/crabbing pier, pond with paddle boats, 2 playgrounds+ more For kiddos of all ages, we are located right next door to Frontier Town, which has awesome water slides , western shows, mini golf, a rope course, ice cream shop.. short term stay

Newly built bright and airy guest suite!!!!
FREE oceanfront parking pass with bookings. 2nd floor private suite with parking, patio/firepit, and self check-in private entry. We are located just minutes from the Ocean City beaches, quaint small town of Berlin, Ocean Downs Casino, Assateague, Windmill Creek Winery, restaurants, and outlets. Enjoy neighborhood amenities such as a waterfront Yacht Club with restaurant and live music (seasonal), golf, farm market, playgrounds, 5 pools/fee, (no pool on property) racquet club.

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).

PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck
Book 2 nights, get 1 night FREE stays thru March 10. inquire before booking This is a Ocbeachfrontrentals .com premier property 24/7 SUPPORT LINEN & TOWELS PROVIDED 8TH FLOOR PENTHOUSE! This stunning top floor 3 b 2.5 ba unit is the ULTIMATE friends & family beach trip, located in a premier building in Ocean City. Enjoy the ocean breeze and stunning views from over 150 square ft of private balcony. Wake up to ocean views from every room!

Water Front Condo w/Pool Short Walk to Beach
FIRST FLOOR UNIT Bayside Condominium Sleeps 4 - 6 max Walking Distance to Northside Park Walk to the Ocean , don't worry about beach parking NON SMOKING 1 Bedroom 1 Bath condo, First floor unit with an outside deck This Air Conditioned, One Bedroom Condo has a fully equipped kitchen, washer/dryer, full refrigerator. There is a Queen bed and a full bed along with 1 Queen Sleep sofa in the living room *MUST BE 21 OR OVER* No Pets!
Popular amenities for Chincoteague rentals with a pool
House rentals with a pool

Snowbird Bay Cottage

Ocean City Escape | Spacious Home | Pool & Golf

Beautiful Cottage W/ shared pool & close 2 beach

Cozy 3 BR Pet Friendly Beach, Bay & Pond nearby.

Coastal Oasis in Ocean Pines

Mosaic Life Escapes -Bayfront Million Dollar Views

Bayside West

Waterfront Wonder | Private Dock, Ocean Pines
Condo rentals with a pool

Oceanfront Oasis: Sunrise Balcony, Pool and Beach!

Oceanfront Family Oasis: Pool, Beach & Parking!

"Aren't You Fancy?!" Prime Coastal Getaway

Updated Mid- Town Condo at Ocean City Beach!

Harrington Towers Oceanfront 2BR 2BA Condo w/POOL

Direct Ocean Front/Gorgeous Views/Indoor Pool

Extraordinary Oceanfront Penthouse - Unit 1209

Oceanside Haven -Steps to Sand-Indoor Pool-Game Rm
Other vacation rentals with a pool

Meet at the Marina

Oceanfront 2BR Condo w/ Balcony & Pool

Seaside Rendezvous Chincoteague

Tranquil Waters, OceanPines, 3 br, Dog Friendly

Assateague Views! Top Floor -Assateague House #505

Big Cozy Loft Overlooking the Farm and River

Direct Oceanfront Newly Renovated W/ Pool 2 Bd

Assateague Inn 100 by Seaside Vacations & Sales
When is the best time to visit Chincoteague?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$31,620 GYD | G$32,876 GYD | G$33,085 GYD | G$40,624 GYD | G$44,603 GYD | G$55,491 GYD | G$75,385 GYD | G$69,940 GYD | G$40,624 GYD | G$38,111 GYD | G$35,389 GYD | G$30,782 GYD |
| Avg. temp | 3°C | 4°C | 8°C | 13°C | 18°C | 23°C | 26°C | 25°C | 22°C | 16°C | 10°C | 6°C |
Quick stats about vacation rentals with a pool in Chincoteague

Total vacation rentals
Explore 130 vacation rentals in Chincoteague

Nightly prices starting at
Chincoteague vacation rentals start at G$8,376 GYD per night before taxes and fees

Verified guest reviews
Over 2,370 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wi-Fi availability
130 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
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- Chesapeake Bay
- Ocean City Beach
- Ocean City Boardwalk
- Assateague Island National Seashore
- Jolly Roger Amusement Park
- Bayside Resort Golf Club
- Northside Park
- Bear Trap Dunes
- Assateague State Park
- Fenwick Island State Park Beach
- Delaware Seashore State Park
- Trimper Rides of Ocean City
- Chincoteague Island
- Old Pro Golf
- Roland E Powell Convention Center
- Ocean City Boardwalk
- Salisbury Zoo
- Bethany Beach Boardwalk




