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.

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Guest favourite

Home in Ocean City

4.94 out of 5 average rating, 219 reviews

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

After relaxing at the beach (just a 7 min walk away), unwind on our deck "watchin' the tide rollin' away!" Get the best of the bay & the beach with this dog-friendly hidden gem! Imagine evenings enjoying the bay breeze as you crack crabs on the deck! Relax inside our open-concept great room that allows everyone to be together. Fish on our private dock or use it for your own boat or jet-ski to dock there. Witness spectacular sunsets with our Kayaks. Enjoy a well lit, private work space to virtual work w/ high speed internet! A new wood CRIB now in master suite for restful sleep! The pools and tennis/pickleball courts are only a few blocks away for your enjoyment! Plus, a truly unique OUTDOOR MOVIE EXPERIENCE for all our guests to make for the best Vacay EVER!

22–29 Jan

€ 130 per night

Guest favourite

Cottage in Cambridge

4.98 out of 5 average rating, 108 reviews

Church Creek - waterfront cottage & pool - private

Close to Blackwater NWR and the Harriet Tubman Center, enjoy peaceful days at our secluded waterfront cottage on Church Creek. Two miles from a main road, and our closest neighbor is across a cove, our estate offers 50 acres of privacy and one of the best waterfront views on the Chesapeake. Enjoy a view from every window and nature all around you. Excellent walking, swimming (in-ground pool-May 3-Oct 1), great birding and bicycling. Launch your kayak from the backyard. Perfect private getaway!

22–29 Mar

€ 262 per night

Guest favourite

Home in Rehoboth Beach

4.99 out of 5 average rating, 119 reviews

Secluded beach beauty with private, heated pool

The LV home by architect Rocio Romero is a modern classic, we love it… The heated, salt water pool is open mid-May to mid-October. You can cook in the fully equipped kitchen and eat indoors or on the large deck out back, play in the pool or fenced yard, lie in the hammocks, play games, do puzzles... We are right by the Junction and Breakwater bike trail; it's about 2 miles to the Rehoboth Boardwalk, 6 miles to Lewes. There's high speed WiFi, a Sonos audio system, and a Roku smart tv (no cable).

20–27 Sep

€ 687 per night

Guest favourite

Apartment in Ocean City

4.91 out of 5 average rating, 258 reviews

Ocean Front 802 Midtown Oasis Pool & Parking

Wake up to the ocean sunrise in this modern 2 bedroom, completely renovated, condo. Prime location on 29th street, 2 blocks north of the famous OC Boardwalk, 2 blocks east of OC's premier amusement and water park along with two famous crab house and other restaurants within walking distance. One hassle free off street parking spot, free WIFI, full size washer & dryer, and a beautiful outdoor pool steps from the beach. Enjoy the bay sun set view out the front door and fall asleep to the waves.

29 Jan – 5 Feb

€ 197 per night

Guest favourite

Apartment in Ocean Pines

4.96 out of 5 average rating, 109 reviews

Waterview Retreat

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

26 Nov – 3 Dec

€ 143 per night

Guest favourite

Apartment in Rehoboth Beach

4.89 out of 5 average rating, 121 reviews

Right on Silver Lake walk to the beach and town!

Completely renovated, right on Silver Lake! On the most secluded part of Rehoboth Beach watch the sun rise and wildlife sitting at your patio! Park your car and walk or bike everywhere. Steps from the pool and three blocks across Turtle Bridge to get to the less crowded part of the beach. Five blocks from Rehoboth Avenue, where most restaurants and shops are. Full kitchen, Central heat/air, Smart TV, Cable and High speed internet. Pickleball, Tennis, Basketball and Tennis courts next door

18–25 Dec

€ 157 per night

Superhost

Bungalow in Horntown

4.8 out of 5 average rating, 128 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 15 min 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.

7–14 Sep

€ 150 per night

Guest favourite

Cottage in Irvington

4.99 out of 5 average rating, 150 reviews

Peaceful Haven

Do you want to get away from it all, change your surroundings and recharge yourself mentally and physically? Welcome to Peaceful Haven. Shops and restaurants of the lovely historic Village of Irvington are only a couple of minutes away. Hike just outside your door or in nearby parks, ride bikes around the meadows or to town, hang outside and listen to the birds, or just sink into the comfy couch to enjoy a movie on our large TV screen. **Take advantage of our limited time SPECIAL PRICES**

29 Aug – 5 Sep

€ 355 per night

Guest favourite

Home in Accomac

4.98 out of 5 average rating, 219 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.

25 Sep – 2 Oct

€ 175 per night

Guest favourite

Farm stay in Cardinal

4.95 out of 5 average rating, 111 reviews

Wtrfrnt aptmnt w/pool/dock on private farm

Come enjoy all the outdoors has on offer at this secluded, waterfront estate. The spacious studio apartment is fully equipped for comfort. 12 acres of waterfront grounds to enjoy including great outdoor seating, fabulous bayside salt water pool. Fish, canoe and kayak right off the farms private dock. Grill and fire pit. Just 10 mins from the charming villages of Mathews and Gloucesters farm to table amenities. Great local food, music, history and shopping right on the bay!

11–18 Jul

€ 184 per night

Guest favourite

Tiny home in Cape Charles

4.98 out of 5 average rating, 275 reviews

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.

21–28 Jan

€ 275 per night

Guest favourite

Home in Cobbs Creek

4.9 out of 5 average rating, 117 reviews

Millionaire $ Views No Xtra Charge! Hot Tub! POOL!

"Now this is the life!" "A little piece of paradise!" "Livin the Dream!" "It doesn't get any better than this!" Just a few thoughts that may cross your mind when you come for a stay at The Cottage at Misti Cove. While the name may be simple, don't let that fool you, for so are the best things in life! Getting a taste of the simple life doesn't mean you have to sacrifice amenities. Here, you'll enjoy resort-like amenities without resort crowds.

11–18 Oct

€ 250 per night