
Holiday 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.

Millionaire $ Views No Xtra Charge! Hot Tub! POOL!
Welcome to The Cottage at Misti Cove, where you can experience the epitome of relaxation and tranquility. Immerse yourself in the serene ambiance of our cottage, aptly named for its simplicity, which belies the luxurious amenities that await you. At The Cottage at Misti Cove, we understand that the essence of a fulfilling vacation lies in the delicate balance between embracing the simple life and indulging in modern comforts. Here, you will discover a haven that seamlessly blends these elements

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.

Pines Getaway - Berlin Tree Light & Ice Ice 11/28
Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

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?

Stay Salty OC Beach House
Welcome to your ultimate getaway near Assateague State Park & Ocean City! Our spacious retreat sleeps 14 guests and boasts resort-style amenities including pools, a gym, kayaks, and tennis courts. Located just moments from beaches, charming towns, and exciting attractions, you'll have everything you need for an unforgettable vacation. With a fully stocked kitchen, game rooms, cozy reading nooks, puzzles, and a balcony, there's something for everyone. Book now and let the relaxation begin!

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).

Caramar Couples Retreat
This cute little first floor efficiency condo is ocean front for a perfect vacation to the beach. It’s an older building but has been partially renovated and updated. You can get to the beach by a very short walk through a private walkway from the condo building. The view from the private balcony is perfect and relaxing. WiFi provided upon check in- xfinity, Netflix, and internet. Indoor and outdoor dining areas and a full kitchen. Closet and dresser for storage use.

4bed/4.5bath Lux Farmhouse/Pool/Gym/5 min from SU
BEFORE BOOKING: Pool is open as of 04/5/25 Unless PRIOR AUTHORIZATION….. NO PARTIES/NO EVENTS/NO GATHERINGS, only the amount of guests in your party 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

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!

Sunshine By The Sea near Bethany Beach
Enjoy Southern Delaware and everything it has to offer in this stylish, family friendly condo located just 1.5 miles from the beach. Completely remodeled in 2022 and thoughtfully furnished to create modern, relaxing coastal getaway. Pool access 2026 Opens Memorial Day Weekend Closes TBD (through LDW possibly still open first week in September) Hours: 11am-7:45pm
Popular amenities for Chincoteague rentals with a pool
House rentals with a pool

Beach Paradise 2101-Downtown Luxury Condo Bay View

Direct Bay Front Epic Sunsets Rooftop Pool

Bayside community, near OCMD, great rates

Ocean City Escape | Spacious Home | Pool & Golf

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

Mosaic Life Escapes -Bayfront Million Dollar Views

Pristine 4+ acre waterfront in Bethany Beach area

Waterfront Wonder
Condo rentals with a pool

Beautiful Beach-View Condo

Bayfront Condo 46th St *2 POOLS*Free Linens/Towels

OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom

Beautiful Ocean Front Condo 2b/2ba with pool

Extraordinary Oceanfront Penthouse - Unit 1209

🌊Carousel Oceanfront 2 Bedroom Amazing Amenities

Nice 2 BR Oceanfront, Year Round Fun & Amenities!

2BRCapri: Indoor Pool, Game Room, Massage Chair
Other holiday rentals with a pool

Meet at the Marina

Waterfront panoramic point with pool

NEW Beautiful Peaceful Costal Getaway

Luxury Oceanfront Getaway!

Peaceful Waterfront Home with Pool and Pier

Hidden Gem! Relax & Visit Chincoteague Island

North OC- short walk 2 beaches and park

OceanViewBeachClub-minutes from Bethany Beach/Golf
When is the best time to visit Chincoteague?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $231 AUD | $240 AUD | $242 AUD | $297 AUD | $326 AUD | $405 AUD | $551 AUD | $511 AUD | $297 AUD | $278 AUD | $259 AUD | $225 AUD |
| 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 holiday rentals with a pool in Chincoteague

Total holiday rentals
Explore 130 holiday rentals in Chincoteague

Nightly prices starting at
Chincoteague holiday rentals start at $61 AUD per night before taxes and fees

Verified guest reviews
Over 2,430 verified reviews to help you choose

Family-friendly holiday rentals
110 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wi-Fi availability
130 of Chincoteague holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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 Beach
- Assateague Island National Seashore
- Peninsula Golf & Country Club
- Jolly Roger Amusement Park
- Northside Park
- Bear Trap Dunes
- Bayside Resort Golf Club
- Jolly Roger at the Pier
- Assateague State Park
- Plantation Lakes Golf and Country Club
- Delaware Seashore State Park
- Fenwick Island State Park Beach
- Coin Beach
- Splash Mountain Water Park
- Wallops Beach
- Ocean Pines Golf Club
- Cripple Creek Golf and Country Club
- Guard Shore
- Trimper Rides of Ocean City
- Parramore Beach
- Holts Landing State Park




