Title: Book the Best Hotels with POOL in Deep Hole in 2026 | Expedia.ca [Flights to Chincoteague](https://expedia.ca/Cheap-Flights-To-Chincoteague.d55637.Travel-Guide-Flights)[Things to do in Chincoteague](https://expedia.ca/Things-To-Do-In-Chincoteague.d55637.Travel-Guide-Activities)[Deep Hole Car Rentals](https://expedia.ca/Car-Rentals-In-Deep-Hole.d553248635975848368.Car-Rental-Guide)[Deep Hole Vacations](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) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](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) - ![](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 [Feb 20 - Feb 21](https://www.expedia.ca/Hotel-Search?regionId=553248635975848368&startDate=2026-02-20&endDate=2026-02-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 21 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=553248635975848368&startDate=2026-02-21&endDate=2026-02-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=553248635975848368&startDate=2026-02-20&endDate=2026-02-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=553248635975848368&startDate=2026-02-27&endDate=2026-03-01&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Deep Hole hotels with a pool ![Exterior](https://images.trvl-media.com/lodging/2000000/1170000/1166900/1166858/454df0e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1170000/1166900/1166858/dce9bfe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/2000000/1170000/1166900/1166858/40fa75d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1170000/1166900/1166858/2c5bd168.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spark by Hilton Chincoteague Island [](https://www.expedia.ca/Chincoteague-Hotels-Spark-By-Hilton-Chincoteague-Island.h1166858.Hotel-Information) Piney Island 9.4/10 Exceptional (752 reviews) "The front desk young lady was excellent and gave us great recommendations. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary CA $111 CA $125 total includes taxes & fees Feb 28 - Mar 1 [](https://www.expedia.ca/Chincoteague-Hotels-Spark-By-Hilton-Chincoteague-Island.h1166858.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/22000000/21390000/21381400/21381363/98d3ba4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/22000000/21390000/21381400/21381363/9a7af02b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oyster Cottage](https://images.trvl-media.com/lodging/22000000/21390000/21381400/21381363/78e32203.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oyster Cottage | View from room](https://images.trvl-media.com/lodging/22000000/21390000/21381400/21381363/50c3bcc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Key West Cottages [](https://www.expedia.ca/Chincoteague-Hotels-Key-West-Cottages-On-The-Chincoteague-Bay.h21381363.Hotel-Information) Downtown Chincoteague 9.8/10 Exceptional (511 reviews) "This was a Wonderful place to stay!! So much charm a the staff was wonderful! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) CHRISTIE [](https://www.expedia.ca/Chincoteague-Hotels-Key-West-Cottages-On-The-Chincoteague-Bay.h21381363.Hotel-Information) ![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/50000/40500/40487/3acf3bc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/50000/40500/40487/ec239931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/50000/40500/40487/976261e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/50000/40500/40487/05163863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Refuge Inn [](https://www.expedia.ca/Chincoteague-Hotels-Refuge-Inn.h40487.Hotel-Information) Piney Island 9.8/10 Exceptional (1,001 reviews) "Comfortable room, pleasant staff, great indoor pool, and easy access to Assateague Island bike paths." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $126 CA $142 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Chincoteague-Hotels-Refuge-Inn.h40487.Hotel-Information) ![Indoor pool, outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/300000/295900/295865/17e42883.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fishing](https://images.trvl-media.com/lodging/1000000/300000/295900/295865/0c592b6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/300000/295900/295865/b355d149.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/300000/295900/295865/049f9c77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Suites Chincoteague Island Bayfront Resort [](https://www.expedia.ca/Chincoteague-Hotels-Comfort-Suites-Chincoteague-Island-Bayfront-Resort.h295865.Hotel-Information) Downtown Chincoteague 9.6/10 Exceptional (1,001 reviews) "Over all friendly, clean, great continental breakfast and cheerful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tim CA $135 CA $153 total includes taxes & fees Feb 28 - Mar 1 [](https://www.expedia.ca/Chincoteague-Hotels-Comfort-Suites-Chincoteague-Island-Bayfront-Resort.h295865.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/7000000/6160000/6157400/6157368/440afcca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/7000000/6160000/6157400/6157368/68796c26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boating](https://images.trvl-media.com/lodging/7000000/6160000/6157400/6157368/0959dd25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/7000000/6160000/6157400/6157368/3d0001b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront [](https://www.expedia.ca/Chincoteague-Hotels-Fairfield-Inn-Suites-By-Marriott-Chincoteague-Island-Waterfront.h6157368.Hotel-Information) Downtown Chincoteague 9.2/10 Wonderful (588 reviews) "Excellent " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edward CA $146 CA $164 total includes taxes & fees Feb 27 - Feb 28 [](https://www.expedia.ca/Chincoteague-Hotels-Fairfield-Inn-Suites-By-Marriott-Chincoteague-Island-Waterfront.h6157368.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1620000/1615600/1615555/43b08add.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 1 King Bed](https://images.trvl-media.com/lodging/2000000/1620000/1615600/1615555/1284edf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor spa tub](https://images.trvl-media.com/lodging/2000000/1620000/1615600/1615555/08963dd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 1 King Bed | View from room](https://images.trvl-media.com/lodging/2000000/1620000/1615600/1615555/a496f685.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterside Inn [](https://www.expedia.ca/Chincoteague-Hotels-Waterside-Inn.h1615555.Hotel-Information) Downtown Chincoteague 9.0/10 Wonderful (1,001 reviews) "Love this hotel. Have stayed here numerous times. Rooms are clean, great view, great staff, decent breakfast. I highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael [](https://www.expedia.ca/Chincoteague-Hotels-Waterside-Inn.h1615555.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/899200/899134/e2dcc559.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Jetted Tub (Waterfront)](https://images.trvl-media.com/lodging/1000000/900000/899200/899134/ae8e848b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/900000/899200/899134/64014904.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/899200/899134/72fcaffc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Chincoteague Waterfront [](https://www.expedia.ca/Chincoteague-Hotels-Hampton-Inn-Suites-Chincoteague-Waterfront.h899134.Hotel-Information) Downtown Chincoteague 9.8/10 Exceptional (760 reviews) "Clean room, friendly staff, great continental breakfast!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $145 CA $163 total includes taxes & fees Feb 28 - Mar 1 [](https://www.expedia.ca/Chincoteague-Hotels-Hampton-Inn-Suites-Chincoteague-Waterfront.h899134.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/77000000/76570000/76568400/76568355/14c145df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76570000/76568400/76568355/0fec7ff0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/77000000/76570000/76568400/76568355/f4d02134.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/77000000/76570000/76568400/76568355/4b07d519.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunset Villa [](https://www.expedia.ca/Chincoteague-Hotels-2-Bedroom-Bath-12-Villa-Just-Minutes-To-The-Beaches-8.h76568355.Hotel-Information) Piney Island 10/10 Exceptional (6 reviews) "This place was perfect for myself, two adult daughters, and 5 year old grandson. We enjoyed the quiet location that was still close to everything. The indoor pool was a great way to end our busy days. Communication and check in was winderful. Will stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie B. CA $135 CA $266 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Chincoteague-Hotels-2-Bedroom-Bath-12-Villa-Just-Minutes-To-The-Beaches-8.h76568355.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/93000000/92200000/92196900/92196891/b93f4f72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/93000000/92200000/92196900/92196891/92bc7b6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92200000/92196900/92196891/c64e4d1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92200000/92196900/92196891/3dcf8717.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Assateague Inn 104 by Seaside Vacations & Sales [](https://www.expedia.ca/Chincoteague-Hotels-Only-5-Min-To-Assateague-National-Seashore.h92196891.Hotel-Information) Chincoteague Island 9.6/10 Exceptional (22 reviews) "Convenient location with everything we needed" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John S. CA $138 CA $260 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Chincoteague-Hotels-Only-5-Min-To-Assateague-National-Seashore.h92196891.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/10000000/9380000/9378400/9378334/07175244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/10000000/9380000/9378400/9378334/020f56b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/10000000/9380000/9378400/9378334/38580758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fountain](https://images.trvl-media.com/lodging/10000000/9380000/9378400/9378334/8d4e68b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Island Resort [](https://www.expedia.ca/Chincoteague-Hotels-Island-Resort.h9378334.Hotel-Information) Downtown Chincoteague 9.2/10 Wonderful (451 reviews) "Beautiful place, very well kept, great breakfast, great location, super clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anna CA $178 CA $200 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Chincoteague-Hotels-Island-Resort.h9378334.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-03-07&endDate=2026-03-08®ionId=553248635975848368&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Deep Hole Breakfast included 4 stars Ocean view 5 stars Hot tub ## Top Deep Hole Hotel Reviews ![Waterside Inn](https://images.trvl-media.com/lodging/2000000/1620000/1615600/1615555/43b08add_y.jpg) ### Waterside Inn 10/10 Excellent "Everything was wonderful!... Room was clean, staff was friendly, and view from the room was soothing. Day of checkout we had homemade biscuits and red velvet waffles with strawberries, topped with whipped cream! Perfect ending to our weekend! " [](https://expedia.ca/Chincoteague-Hotels-Waterside-Inn.h1615555.Hotel-Information) ![Spark by Hilton Chincoteague Island](https://images.trvl-media.com/lodging/2000000/1170000/1166900/1166858/8f220cfc_y.jpg) ### Spark by Hilton Chincoteague Island 10/10 Excellent "Nice place and friendly " [](https://expedia.ca/Chincoteague-Hotels-Spark-By-Hilton-Chincoteague-Island.h1166858.Hotel-Information) ![Comfort Suites Chincoteague Island Bayfront Resort](https://images.trvl-media.com/lodging/1000000/300000/295900/295865/e422830e_y.jpg) ### Comfort Suites Chincoteague Island Bayfront Resort 10/10 Excellent "Yes" [](https://expedia.ca/Chincoteague-Hotels-Comfort-Suites-Chincoteague-Island-Bayfront-Resort.h295865.Hotel-Information) ![Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront](https://images.trvl-media.com/lodging/7000000/6160000/6157400/6157368/1ee5649e_y.jpg) ### Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront 10/10 Excellent "Excellent " [](https://expedia.ca/Chincoteague-Hotels-Fairfield-Inn-Suites-By-Marriott-Chincoteague-Island-Waterfront.h6157368.Hotel-Information) ![Marina Bay Hotel & Suites, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/16000000/15040000/15030800/15030757/f262e98b_y.jpg) ### Marina Bay Hotel & Suites, an Ascend Collection Hotel 10/10 Excellent "I had a wonderful stay at this hotel. The room was very clean, the bed was comfortable, and everything smelled fresh. The staff was extremely friendly, especially the front desk team who made check-in fast and easy. The location is perfect, close to restaurants and stores. Breakfast was also really good with plenty of options. I felt safe and relaxed the whole time. I would definitely stay here again and highly recommend it!" [](https://expedia.ca/Chincoteague-Hotels-Marina-Bay-Hotel-Suites.h15030757.Hotel-Information) ![Best Western Plus Pocomoke City](https://images.trvl-media.com/lodging/1000000/480000/477500/477474/89421cb5_y.jpg) ### Best Western Plus Pocomoke City 10/10 Excellent "This hotel was amazing, cleaned, service was amazing. Everyone is really nice. Family friendly. The room we stayed had a kitchen area without a stove. Two microwave, a fridge. Two tv. A sofa which was cleaner. Room service was provided everyday which i was really happy because i have a toddler. Fresh towels everyday. Pool was cleaner. Breakfast was amazing they had different eggs options everyday. They had pork sausage and turkey as a alternative which i thought was very kind of them since we dont eat pork. Milk, yogurt. Lots of fruits and cereal options. Coffee machine was amazing, u can get any coffee in it. They took care of us very nicely. Highly recommend to anyone. Although theres isnt much to do around. It was a very boring city. Went for a work trip so me and my family enjoyed our stay." [](https://expedia.ca/Pocomoke-City-Hotels-Best-Western-Plus-Pocomoke-City.h477474.Hotel-Information) ![Refuge Inn](https://images.trvl-media.com/lodging/1000000/50000/40500/40487/3acf3bc5_y.jpg) ### Refuge Inn 10/10 Excellent "Very nice property with clean and spacious rooms and friendly staff " [](https://expedia.ca/Chincoteague-Hotels-Refuge-Inn.h40487.Hotel-Information) ![Chincoteague Inn](https://images.trvl-media.com/lodging/2000000/1090000/1080600/1080519/4a32c16f_y.jpg) ### Chincoteague Inn 10/10 Excellent "Me and my brother enjoyed our stay " [](https://expedia.ca/Chincoteague-Hotels-Chincoteague-Inn.h1080519.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Deep Hole? ### What is there to see and do in Deep Hole? ### When is the best time to book a hotel with a pool in Deep Hole? ## 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) - 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