Vacation 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.

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Superhost

Guesthouse in Chincoteague

4.88 out of 5 average rating, 65 reviews

Horseshoe Haven

Please note: There is an attached host apartment that may or may not be occupied . Horseshoe Haven is located in a quiet setting just a few minutes' drive / bicycle ride to historic downtown. Five miles to Assateague Beach. You will have exclusive use majority new 10 plus bicycles,12", 16", 18", 24", 26", 28", 2 kayaks, badminton/volleyball white sand court, swimming pool and gas grill. No dogs in pool . Outdoor shower. Fenced in yard for dogs 45 pounds and under. We look forward to your stay.

Guest favorite

Home in Berlin

4.96 out of 5 average rating, 75 reviews

Private pool, waterfront, kayaks, bikes, firepits!

The Golden Quarter Farm is 150-acre waterfront, nature preserve, centrally located 5 miles from Assateague Island and its wild ponies, small town charm of Berlin, and OC Boardwalk. With a pool, kayaks, SUP, hiking trails, bikes, and birding, there's little reason to leave the property! Max of 8 adults. No parties. No Pets. Renters must sign a Rental Agreement & provide $250 refundable damage deposit. Pool open April-Sept 30th, NOT heated. 5% local room tax will be collected after booking.

Superhost

Bungalow in Horntown

4.8 out of 5 average rating, 150 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.

Top guest favorite

Home in Berlin

5 out of 5 average rating, 107 reviews

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!

Top guest favorite

Home in Accomac

4.98 out of 5 average rating, 270 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.

Top guest favorite

Farm stay in Westover

5 out of 5 average rating, 59 reviews

The Homestead at Sugar Water Manor Farm Stay

The Homestead at Sugar Water Manor sits on nearly 70 acres of farm and woods on the Manokin River. Guests have full access to the property including kayaks, the pool and can make arrangements to enjoy the farm crew, collect eggs & harvest for your meals. A breakfast treat will be delivered for your breakfast. It has the best sunset views from it’s screened in porch. With views of the river, garden and farm you will not know where to look first. No WiFi/TV or smoking on property

Guest favorite

Home in Chincoteague

4.93 out of 5 average rating, 15 reviews

Sunset Bay Villa #202-Pool, Waterfront, Sunsets!

Fully updated condo located directly on Chincoteague Bay & the heart of Downtown Chincoteague! Enjoy watching wildlife, boats, and stunning sunsets from your private bay front balcony. Crab/ fish from the private community dock area. Walk to downtown restaurants, shops, downtown park & fishing pier. Lounge by the Bayfront pool (seasonal & unheated) or keep up with your workout routine in the newly updated fitness room! 2rd Floor Unit (accessible by elevator or stairs).

Guest favorite

Farm stay in Princess Anne

4.94 out of 5 average rating, 102 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).

Guest favorite

Cottage in Cambridge

4.96 out of 5 average rating, 154 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. 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!

Superhost

Villa in Chincoteague

4.63 out of 5 average rating, 8 reviews

Sol Villa

The Sol Villa @ The Reef Features two bedrooms upstairs and 1/2 bath. Each bedroom has a Queen Bed Downstairs has a fully equipped kitchen, bathroom with a shower and a sleeper sofa in the living room The Reef Vacation Villas has an indoor pool, bikes, stand up paddle boards, corn hole, and Two passes to MAUI JACKS WATERPARK just a short walk away Stay with us and beat the traffic to the beach since we are located just over a half mile from the beach

Superhost

Tiny home in Millsboro

4.81 out of 5 average rating, 135 reviews

Farm Cottage - POOL - 30 Min to BEACH

Enjoy this beautiful cottage/studio apartment. Perfect little getaway space for 2 (or 3). Our little cottage is surrounded by fields and the quiet sound of country sunrise. You'll wake up to chickens anxious to get out of their coop or Lucy, the turkey, peeking in your window. In the evenings, light the firepit or enjoy and a quiet nighttime swim with our duck. And our very friendly dog, Tanka (Cane Corso) will welcome you to our family.

Guest favorite

Condo in Ocean City

4.93 out of 5 average rating, 117 reviews

Oceanfront 2 Bedroom-Sleeps 6-Indoor/Outdoor Pool

Kick back and relax in this beautiful and modern newly remodeled condo in Golden Sands! This rare 2 bedroom, 1.5 bathroom unit has an amazing Master Suite with full-length windows providing panoramic views down the coastline, and direct access to the private patio. Renowned building amenities include outdoor pool, top floor indoor pool, gym, tiki bar, sun deck & more. Linens & towels included!