
Holiday rentals with a pool in Chincoteague
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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.

Rosses Chance Guest House
This lovely guest cottage is located on a historic 16 acre waterfront estate on Hudson Creek that includes a main house, barn, pool, dock and pond. Built in the 18th century tidewater style, the guesthouse is charming and well decorated and completely self efficient. A special place for your romantic getaway at any season of the year. Recently cell phone service has improved and is reliable. However, in the country, WiFi internetl can be slow at times as well as the Wifi TV streaming.

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.

Big Cozy Loft Overlooking the Farm and River
The cozy loft is located above the apiary workshop. It is a spacious, kind suite with a walk-in bath featuring a rainforest shower. Windows overlook the donkey pasture, river, farm, and gardens. Designed for a true retreat, there is no WiFi, TV, or smoking. For breakfast, travel on over to Sugar Water Restaurant to have a free breakfast with coffee, tea, juice, and more. The Loft includes a small refrigerator plus coffee and tea essentials. Please note: children are not permitted.

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.

The Laughing King Retreat Honeymoon Island Cottage
Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.

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).

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

The Red Chalet

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

Golf, Beach & Pool Escape • 6BR • Game Room

Beautiful Beach House in Rehoboth

Bury Oasis: Pool, Hottub, Movie Theatre, Game Room

Blue Heron WaterSide

Waterfront, pier, hot tub, pool, pizza oven
Apartment rentals with a pool

Boutique Moments OC • Pool • Walk to Boardwalk

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE

Beautiful waterview 2B condo w/Dock&Close to Beach

1 Bedroom 1 Bath Condo on Silver Lake

Love Above the Waves-OceanView/Rooftop Heated Pool

Direct Ocean Front/Gorgeous Views/Indoor Pool

Beach condo w/pool! All linens & beach supplies

Caramar Couples Retreat
Other holiday rentals with a pool

Turtle Cottage by the Bay

Quiet country retreat close to Solomons Island

Oceanfront•Sunrise Views•Pool•Private Balcony

Palm Villa

Farm Cottage - POOL - 30 Min to BEACH

Floating Bungalow - Marina View

"Endless Summer" on the Chesapeake!

Assateague Inn 106 by Seaside Vacations & Sales
When is the best time to visit Chincoteague?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $178 SGD | $179 SGD | $198 SGD | $250 SGD | $275 SGD | $342 SGD | $464 SGD | $430 SGD | $250 SGD | $220 SGD | $196 SGD | $201 SGD |
| 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 $52 SGD 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
130 of Chincoteague holiday rentals include wifi 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
- Ocean City Boardwalk
- Chincoteague Island
- Assateague Island National Seashore
- Northside Park
- Assateague State Park
- Jolly Roger Amusement Park
- Delaware Seashore State Park
- Bethany Beach Boardwalk
- Fenwick Island State Park Beach
- Ocean Pines Golf Club
- Roland E Powell Convention Center
- Old Pro Golf
- Salisbury Zoo
- Trimper Rides of Ocean City
- Bear Trap Dunes
- Holts Landing State Park
- NASA’s Wallops Flight Facility Visitor Center
- Baja Amusements
- Layton's Chance Vineyard and Winery





