
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

The Rosé Retreat: Pool-Screened Porch-RELAX
Escape to The Rosé Retreat for peace and relaxation. Enjoy a romantic getaway sipping wine on the screened porch, unwind by the refreshing pool, navigate the waterways by kayak, and stroll to great restaurants/shopping. Savor local oysters and explore nearby wineries. Bring the family for a memorable NNK adventure. The Rosé Retreat is a place to get away from it all. Enjoy a bottle (or more, we're not judging) of Rosé while you're here. Follow on IG:roseretreatva Irvington Occupancy Tax #500

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.

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

Magical wooded cottage pool +priv hottub walk2town
Set among the trees on 2 peaceful wooded acres, this cottage delights with gothic architecture, sun-filled rooms, and a bathroom for every bedroom. Relax in the hot tub under the stars, sip local wines, eat oysters. Take a sunset boat cruise or learn oystering and crabbing from a local waterman. Farm stands, markets, and sea-to-table local fare. Live life in an historic working water town with lots of personality. Close to Tides Inn, Kilmarnock, White Stone, Compass Entertainment.

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.

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.

Cedar Gables - Waterfront, Pool, Hot Tub, Dock
Just a few miles from Chincoteague National Wildlife Refuge & Assateague Island Beach, Cedar Gables has everything you are looking for in a Chincoteague Island home! Enjoy the ease and convenience of a central waterfront location. Each bedroom has a seasonal fireplace & private bath w/ deep tub. Lounge outside by the private pool (seasonal), hot tub (year-round) & tiki-bar in screened atrium. Private, deep water pier & boat dock is perfect for crabbing & fishing.

4bed/4.5bath Lux Farmhouse/Pool/Gym/5 min from SU
BEFORE BOOKING: Pool will be open 4/05/26 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
Popular amenities for Chincoteague rentals with a pool
House rentals with a pool

2 BR Ocean Front Condo w/Pool, Expansive Views

Cozy beach home away from home!

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

Dog friendly| community pool | gym| kayak| bayside

Bayside Family Oasis - Perfect for Large Families

Blue Heron WaterSide

Ocean Palms II - Renovated, Ocean Block, Midtown

A Bethany Beach Gem 1.5 miles to Ocean Pickle Ball
Condo rentals with a pool

Gorgeous oceanfront Capri Beach and Bay Views!!!!

Boutique Moments OC • Pool • Walk to Boardwalk

Steps to Beach, Pool, Family Friendly with Linens

Cozy oceanfront condo with stunning ocean views

Oceanview Oasis with 2 private balconies

Oceanfront Bldg.| 2 pools | Tennis | Game Room

Love Above the Waves-OceanView/Rooftop Heated Pool

Gone Coastal *Pool* Bayside with view* Top Floor
Other holiday rentals with a pool

Modern Chesapeake Waterfront - Heated Pool - Dock

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

Waterfront Getaway w/ Pool, Firepit, Kayaks, Dock

Farm Cottage - POOL - 30 Min to BEACH

Luxe Bay Hideaway

Coastal-Chic · Pool, Bay View & Balcony·Walk2Beach

Fenwick Island Sunset Retreat

Oceanfront 2 bedroom, 2 bathroom End Unit Condo
When is the best time to visit Chincoteague?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $193 AUD | $195 AUD | $216 AUD | $272 AUD | $299 AUD | $371 AUD | $505 AUD | $468 AUD | $272 AUD | $240 AUD | $213 AUD | $219 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 $56 AUD per night before taxes and fees

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

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

Pet-friendly accommodation
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wi-Fi availability
130 of Chincoteague holiday 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
Destinations to explore
- Norfolk Holiday rentals
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Rentals with a washing machine and dryer Chincoteague
- Condo rentals Chincoteague
- Beach house rentals Chincoteague
- Family-friendly rentals Chincoteague
- Waterfront rentals Chincoteague
- Rentals with outdoor seating Chincoteague
- Rentals with a fire pit Chincoteague
- Rentals with a fireplace Chincoteague
- Cottage rentals Chincoteague
- House rentals Chincoteague
- Fitness-friendly rentals Chincoteague
- Cabin rentals Chincoteague
- Rentals with a patio Chincoteague
- Rentals with a kayak Chincoteague
- Beach condo rentals Chincoteague
- Beachfront rentals Chincoteague
- Apartment rentals Chincoteague
- Pet-friendly rentals Chincoteague
- Rentals with beach access Chincoteague
- Townhouse rentals Chincoteague
- Rentals with pools Accomack County
- Rentals with pools Virginia
- Rentals with pools United States
- Chesapeake Bay
- Ocean City Beach
- Ocean City Boardwalk
- Ocean City Boardwalk
- Chincoteague Island
- Assateague Island National Seashore
- Northside Park
- Assateague State Park
- Jolly Roger Amusement Park
- Delaware Seashore State Park
- Fenwick Island State Park Beach
- Bethany Beach Boardwalk
- Ocean Pines Golf Club
- Roland E Powell Convention Center
- Trimper Rides of Ocean City
- Old Pro Golf
- Salisbury Zoo
- Bear Trap Dunes
- Layton's Chance Vineyard and Winery
- NASA’s Wallops Flight Facility Visitor Center
- Baja Amusements
- Holts Landing State Park





