
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.

Berlin Beach House, near Ocean City & Assateague!
Close to everything when you stay at this newly renovated vacation home in historic Berlin. Big yard, lots of parking, & walking distance to downtown Berlins restaurants, breweries, grocery, & more. 10 minutes to the beaches of Ocean City Maryland or Assateague Island wild horses. Arcade games and bikes added for 2025 season. Above ground pool open Mid May - Mid Sept. 2 washer & dryers. Locally owned managed and cleaned for a worry free stay. All linens and bath towels provided.License#2023-3
4.82 out of 5 average rating, 107 reviews
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.
4.81 out of 5 average rating, 167 reviews
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!!
4.81 out of 5 average rating, 58 reviews
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.
4.98 out of 5 average rating, 307 reviews
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
4.88 out of 5 average rating, 142 reviews
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).
4.95 out of 5 average rating, 123 reviews
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.
4.96 out of 5 average rating, 69 reviews
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)
4.86 out of 5 average rating, 36 reviews
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!
4.94 out of 5 average rating, 130 reviews
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
4.97 out of 5 average rating, 137 reviews
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.
4.91 out of 5 average rating, 133 reviews
Kits Cottage on "Just Ducky Acres"
Escape to Kits Cottage, a serene haven nestled on 6 acres of tranquility at Just Ducky Acres. Unplug and unwind in the peaceful atmosphere, surrounded by friendly farm animals. Perfect for romantic getaways, family retreats, or solo escapes. Relax, reflect, and reconnect in this idyllic setting, just a short drive from Ocean City and other area attractions.
4.94 out of 5 average rating, 118 reviewsPopular amenities for Chincoteague rentals with a pool
House rentals with a pool

3 BR Waterfront Home, Minutes to the Beach
4.93 out of 5 average rating, 150 reviews
Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB
4.94 out of 5 average rating, 287 reviews
Camelot
4.97 out of 5 average rating, 152 reviews
Mosaic Life Escapes -Bayfront Million Dollar Views
4.81 out of 5 average rating, 122 reviews
Bayside community great fall rates & amenities
4.82 out of 5 average rating, 234 reviews
Ocean Pines Retreat with Beach Club
4.99 out of 5 average rating, 135 reviews
Private pool, waterfront, kayaks, bikes, firepits!
4.97 out of 5 average rating, 86 reviews
Assateague surf cottage!
4.83 out of 5 average rating, 41 reviewsCondo rentals with a pool

Beachfront with a View and Amenities Galore
4.83 out of 5 average rating, 252 reviews
Ocean Front Condo
4.97 out of 5 average rating, 101 reviews
Luxury Oceanfront Oasis!
4.95 out of 5 average rating, 103 reviews
Caramar Couples Retreat
4.96 out of 5 average rating, 322 reviews
Oceanfront Paradise | Pool | Hot Tub | Beach
4.92 out of 5 average rating, 290 reviews
Water view at Ocean Pines Yacht Club Condo
4.97 out of 5 average rating, 224 reviews
2 BdrmOceanfront-Pool, Xbox, Pickleball, Gym, WiFi
4.87 out of 5 average rating, 182 reviews
DirectOceanFront on Boardwalk/Newly Remodeled/Pool
4.78 out of 5 average rating, 240 reviewsOther vacation rentals with a pool

Harbor Master
5.0 out of 5 average rating, 12 reviews
Coastal rentals Lighthouse Rd
4.51 out of 5 average rating, 59 reviews
‘Dockside Retreat’ -pool, minutes to OC/beaches
5.0 out of 5 average rating, 63 reviews
Anchors Away, Your Dream Getaway in Fenwick Shoals
4.97 out of 5 average rating, 33 reviews
5BR 3.5B Home w/ Great Amenities
5.0 out of 5 average rating, 33 reviews
Bayside Family Oasis - Perfect for Large Families
5.0 out of 5 average rating, 35 reviews
Charming Getaway Golf Simulator
4.92 out of 5 average rating, 48 reviews
Cozy beach home away from home!
4.95 out of 5 average rating, 21 reviewsWhen is the best time to visit Chincoteague?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €119 | €120 | €133 | €135 | €155 | €232 | €311 | €288 | €167 | €148 | €131 | €135 |
| 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 |
Destinations to explore
- New York Vacation rentals
- Philadelphia Vacation rentals
- Washington Vacation rentals
- Ocean City Vacation rentals
- Virginia Beach Vacation rentals
- Raleigh Vacation rentals
- Jersey City Vacation rentals
- Wilmington Vacation rentals
- Newark Vacation rentals
- Baltimore Vacation rentals
- Richmond Vacation rentals
- Atlantic City Vacation rentals
- Townhouse rentals Chincoteague
- Beach condo rentals Chincoteague
- Waterfront rentals Chincoteague
- House rentals Chincoteague
- Beachfront rentals Chincoteague
- Cottage rentals Chincoteague
- Rentals with beach access Chincoteague
- Beach house rentals Chincoteague
- Family-friendly rentals Chincoteague
- Apartment rentals Chincoteague
- Rentals with a kayak Chincoteague
- Pet-friendly rentals Chincoteague
- Condo rentals Chincoteague
- Rentals with pools Accomack County
- Rentals with pools Virginia
- Rentals with pools United States
- Chincoteague Island
- Chesapeake Bay
- Assateague Island National Seashore
- Ocean City Beach
- Bethany Beach Boardwalk
- Assateague State Park
- Northside Park
- Delaware Seashore State Park
- Jolly Roger Amusement Park
- Fenwick Island State Park Beach
- Roland E Powell Convention Center
- Ocean Pines Golf Club
- Ocean City Boardwalk
- Bear Trap Dunes
- Old Pro Golf
- Salisbury Zoo
- Trimper Rides of Ocean City
- Holts Landing State Park
- Ocean City Boardwalk
- NASA’s Wallops Flight Facility Visitor Center
- Layton's Chance Vineyard and Winery
- Splash Mountain Water Park
- Jolly Roger at the Pier





