Title: Book the Best Hotels with POOL in Deep Hole in 2025 | Expedia.ca [Hotels in Deep Hole](https://expedia.ca/Deep-Hole-Hotels.d553248635975848368.Travel-Guide-Hotels)[Vacation Rentals in Deep Hole](https://expedia.ca/Deep-Hole-Vacation-Rentals.d553248635975848368.Travel-Guide-VacationRentals)[Deep Hole Car Rentals](https://expedia.ca/Car-Rentals-In-Deep-Hole.d553248635975848368.Car-Rental-Guide)[Deep Hole Vacation Packages](https://expedia.ca/Deep-Hole.d553248635975848368.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Deep Hole, VA ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Deep Hole Hotels with a Pool Tonight [Sep 25 - Sep 26](https://www.expedia.ca/Hotel-Search?regionId=553248635975848368&startDate=2025-09-25&endDate=2025-09-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 26 - Sep 27](https://www.expedia.ca/Hotel-Search?regionId=553248635975848368&startDate=2025-09-26&endDate=2025-09-27&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=553248635975848368&startDate=2025-09-26&endDate=2025-09-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248635975848368&startDate=2025-10-03&endDate=2025-10-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Deep Hole Hotels with a Pool ## Top Deep Hole Hotel Reviews ![Best Western Plus Pocomoke City](//images.trvl-media.com/lodging/1000000/480000/477500/477474/89421cb5_y.jpg) ### Best Western Plus Pocomoke City 10/10 Excellent "Nice and clean, and exactly what we needed for a weekend wedding. Free coffee and breakfast were awesome too! Thank You! " [](https://expedia.ca/Pocomoke-City-Hotels-Best-Western-Plus-Pocomoke-City.h477474.Hotel-Information) ![Waterside Inn](//images.trvl-media.com/lodging/2000000/1620000/1615600/1615555/43b08add_y.jpg) ### Waterside Inn 10/10 Excellent "Friendly staff !" [](https://expedia.ca/Chincoteague-Hotels-Waterside-Inn.h1615555.Hotel-Information) ![Atlantic Shores Inn and Suites](//images.trvl-media.com/lodging/2000000/1710000/1709300/1709230/25225706_y.jpg) ### Atlantic Shores Inn and Suites 10/10 Excellent "Great staff! Clean and" [](https://expedia.ca/Chincoteague-Hotels-Atlantic-Shores-Inn-And-Suites.h1709230.Hotel-Information) ![Chincoteague Inn](//images.trvl-media.com/lodging/2000000/1090000/1080600/1080519/4a32c16f_y.jpg) ### Chincoteague Inn 10/10 Excellent "Friendly and help staff, the rooms where clean and kept up. " [](https://expedia.ca/Chincoteague-Hotels-Chincoteague-Inn.h1080519.Hotel-Information) ![Refuge Inn](//images.trvl-media.com/lodging/1000000/50000/40500/40487/3acf3bc5_y.jpg) ### Refuge Inn 10/10 Excellent "Room was very clean, the site was beautiful, surrounded by trees, plenty of outdoor seating and tables to eat. I loved having breakfast brought to the door. The pool area is stunning, surrounded by greenery and plenty of seating. Loved our stay. " [](https://expedia.ca/Chincoteague-Hotels-Refuge-Inn.h40487.Hotel-Information) ![Maddox Inn](//images.trvl-media.com/lodging/1000000/670000/663800/663743/e0d89ff2_y.jpg) ### Maddox Inn 10/10 Excellent "I liked that everyone was so accommodating and especially they were dog friendly and I felt welcomed. " [](https://expedia.ca/Chincoteague-Hotels-Americas-Best-Value-Inn-Suites-Chincoteague-Island.h663743.Hotel-Information) ![Anchor Inn](//images.trvl-media.com/lodging/11000000/10030000/10023700/10023684/90b3f693_y.jpg) ### Anchor Inn 10/10 Excellent "Quiet and clean. Easy check in. " [](https://expedia.ca/Chincoteague-Hotels-Anchor-Inn.h10023684.Hotel-Information) ![Comfort Suites Chincoteague Island Bayfront Resort](//images.trvl-media.com/lodging/1000000/300000/295900/295865/e422830e_y.jpg) ### Comfort Suites Chincoteague Island Bayfront Resort 10/10 Excellent "Stay for our 1 year anniversary and this was great!" [](https://expedia.ca/Chincoteague-Hotels-Comfort-Suites-Chincoteague-Island-Bayfront-Resort.h295865.Hotel-Information) ![Marina Bay Hotel & Suites, an Ascend Collection Hotel](//images.trvl-media.com/lodging/16000000/15040000/15030800/15030757/f262e98b_y.jpg) ### Marina Bay Hotel & Suites, an Ascend Collection Hotel 10/10 Excellent "Clean room and staff was great" [](https://expedia.ca/Chincoteague-Hotels-Marina-Bay-Hotel-Suites.h15030757.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Deep Hole? > [Quaint Cottages Near Everything on Beach Road](https://www.expedia.ca/Chincoteague-Hotels-Quaint-Cottages-Near-Everything-On-Beach-Road.h67544638.Hotel-Information): Provides a water park, a pool, and kitchens. [Sunrise Shore - Waterfront; Private pool & hot tub!](https://www.expedia.ca/Chincoteague-Hotels-Sunrise-Shore.h55396796.Hotel-Information): Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. [The Blue Crab - Your Dream Vacation awaits you!](https://www.expedia.ca/Chincoteague-Hotels-The-Blue-Crab-Your-Dream-Vacation-Awaits-You.h105848508.Hotel-Information): Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. [Waterfowl Watch Cottage - Chincoteague Island Quiet area,bikes, fall rates](https://www.expedia.ca/Chincoteague-Hotels-Waterfowl-Watch-New-Listing-Quiet-Area.h104645745.Hotel-Information): Provides daily, a seasonal outdoor pool, and free self parking. [Chincoteague Inn](https://www.expedia.ca/Chincoteague-Hotels-Chincoteague-Inn.h1080519.Hotel-Information): Features a snack bar/deli, a seasonal outdoor pool, and complimentary wired internet access. ### What is there to see and do in Deep Hole? > Spend some time experiencing the great outdoors at Oyster Bay. Discover sights such as Captain Timothy Hill House, Maui Jack's Waterpark, and Museum of Chincoteague during your stay. ### When is the best time to book a hotel with a pool in Deep Hole? > You may want to think about a place to stay with an outdoor swimming pool if you plan to visit Deep Hole in the warmest months of July, August, or June when the average temp is 75°F. Lodging offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or December when the average temperature is 43°F. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [1 Star Hotels in South Point](https://www.expedia.ca/1Star-South-Point-Hotels.s10-0-d553248635975867426.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Accomac](https://www.expedia.ca/Accomac-Hotels-Luxury-Hotel.0-0-d3000354998-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Hotels near Assateague Lighthouse](https://www.expedia.ca/Assateague-Lighthouse-Hotels.0-l6075486-0.Travel-Guide-Filter-Hotels) - [Apartments in Atlantic](https://www.expedia.ca/Atlantic-Apartments.d553248635975876134-aaApartments.Travel-Guide-Accommodation) - [Rv Parks in Atlantic](https://www.expedia.ca/Atlantic-RV-Parks.d553248635975876134-aaRVParks.Travel-Guide-Accommodation) - [Resorts in Atlantic](https://www.expedia.ca/Atlantic-Resort-Hotels.d553248635975876134-aaResortHotels.Travel-Guide-Accommodation) - 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