Title: Book the Best Hotels with POOL in Deep Hole in 2025 | 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) # Find Hotels with a Pool in Deep Hole, VA from CA $99 - ![](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 [Nov 1 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635975848368&startDate=2025-11-01&endDate=2025-11-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 2 - Nov 3](https://www.expedia.ca/Hotel-Search?regionId=553248635975848368&startDate=2025-11-02&endDate=2025-11-03&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635975848368&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635975848368&startDate=2025-11-14&endDate=2025-11-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Deep Hole Hotels with a Pool ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/2000000/1170000/1166900/1166858/81dc4f49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1170000/1166900/1166858/8f220cfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1170000/1166900/1166858/3f5552ae.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 Piney Island 9.4/10 Exceptional (743) "Great staff, clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Diana CA $114 CA $128 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chincoteague-Hotels-Spark-By-Hilton-Chincoteague-Island.h1166858.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40500/40487/a52febea.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) ![Property grounds](https://images.trvl-media.com/lodging/1000000/50000/40500/40487/08d9572e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Refuge Inn Piney Island 9.8/10 Exceptional (1003) "Staff was superb, Clean Room and Comfortable" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian CA $139 CA $157 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Chincoteague-Hotels-Refuge-Inn.h40487.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/899200/899134/72fcaffc.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) ![Restaurant](https://images.trvl-media.com/lodging/1000000/900000/899200/899134/f2f953b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Chincoteague Waterfront Downtown Chincoteague 9.8/10 Exceptional (728) "Hotel was great for a quick weekend getaway with out kids" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Saby CA $125 CA $141 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Chincoteague-Hotels-Hampton-Inn-Suites-Chincoteague-Waterfront.h899134.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) ![Palm Cottage](https://images.trvl-media.com/lodging/22000000/21390000/21381400/21381363/2b19b712.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) ![Fishing](https://images.trvl-media.com/lodging/22000000/21390000/21381400/21381363/1cd80aeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Key West Cottages Downtown Chincoteague 9.8/10 Exceptional (475) "Amazing place for vacation " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) carla CA $314 CA $353 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Chincoteague-Hotels-Key-West-Cottages-On-The-Chincoteague-Bay.h21381363.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/7000000/6160000/6157400/6157368/1ee5649e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6160000/6157400/6157368/4a904801.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pillowtop beds, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/7000000/6160000/6157400/6157368/b31f08dc.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) ### Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront Downtown Chincoteague 9.2/10 Wonderful (568) "We absolutely loved this hotel!! Great location and super clean!! Staff was super friendly with answering all of our questions! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashley CA $163 CA $183 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Chincoteague-Hotels-Fairfield-Inn-Suites-By-Marriott-Chincoteague-Island-Waterfront.h6157368.Hotel-Information) ![Indoor pool, outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/300000/295900/295865/e422830e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Direct Bay Front Double Queen Suite - Bayfront | View from room](https://images.trvl-media.com/lodging/1000000/300000/295900/295865/e9bbde17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/300000/295900/295865/86f5de21.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) ### Comfort Suites Chincoteague Island Bayfront Resort Downtown Chincoteague 9.6/10 Exceptional (1010) "Very clean & right on the water! Would definitely stay again if in the area! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bryce CA $142 CA $161 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Chincoteague-Hotels-Comfort-Suites-Chincoteague-Island-Bayfront-Resort.h295865.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) ![Indoor spa tub](https://images.trvl-media.com/lodging/2000000/1620000/1615600/1615555/39d08bcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1620000/1615600/1615555/3ab005a8.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 Downtown Chincoteague 9.0/10 Wonderful (1003) "Stayed here many times and love it! Great breakfast in the morning and proximity to all attractions a huge plus." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Catherine [](https://www.expedia.ca/Chincoteague-Hotels-Waterside-Inn.h1615555.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas](https://images.trvl-media.com/lodging/16000000/15040000/15030800/15030757/e51297d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/16000000/15040000/15030800/15030757/f64c1fad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fishing](https://images.trvl-media.com/lodging/16000000/15040000/15030800/15030757/0ce74b19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/16000000/15040000/15030800/15030757/217311fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marina Bay Hotel & Suites, an Ascend Collection Hotel Downtown Chincoteague 9.0/10 Wonderful (995) "Staff was very friendly and helpful! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joel CA $118 CA $153 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chincoteague-Hotels-Marina-Bay-Hotel-Suites.h15030757.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/65000000/64620000/64616700/64616626/b50f64cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/65000000/64620000/64616700/64616626/54989b5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/65000000/64620000/64616700/64616626/9280f4d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, free WiFi, bed sheets](https://images.trvl-media.com/lodging/65000000/64620000/64616700/64616626/7408cc30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Birchwood Inn Downtown Chincoteague 7.0/10 Good (387) "Its a very nice area/hotel. We only stayed one night so it was nice for that. Felt safe and the room was clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katie CA $82 CA $99 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chincoteague-Hotels-Birchwood-Inn.h64616626.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/10000000/9380000/9378400/9378334/be49ca02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/10000000/9380000/9378400/9378334/2b542aae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/10000000/9380000/9378400/9378334/f35d7902.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dock](https://images.trvl-media.com/lodging/10000000/9380000/9378400/9378334/68ecb6c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Island Resort Downtown Chincoteague 9.2/10 Wonderful (451) "Very tranquil and quiet. Service all around was exceptional! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer CA $182 CA $205 total includes taxes & fees Nov 2 - Nov 3 [](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=2025-11-15&endDate=2025-11-16®ionId=553248635975848368&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Deep Hole Hotel Reviews ![Hampton Inn & Suites Chincoteague Waterfront](//images.trvl-media.com/lodging/1000000/900000/899200/899134/72fcaffc_y.jpg) ### Hampton Inn & Suites Chincoteague Waterfront 10/10 Excellent "Beautiful view from the balcony. Breakfast was good! The room was clean. " [](https://expedia.ca/Chincoteague-Hotels-Hampton-Inn-Suites-Chincoteague-Waterfront.h899134.Hotel-Information) ![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 "Our visit overall was excellent. Only thing we wish is that hotels would put more hooks in the bathrooms to hang wet towels and cloths on." [](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 "There were good quality items to select from for the breakfast menu. What I really liked was that the coffee was Starbucks and not that cheap Cisco brand stuff that most hotels stick you with. They even had Starbucks coffee in the room with the coffee maker. The view from our balcony was excellent. The staff mentioned to me that every room has a view of the water. The hotel room was very clean efficient The only thing I would mention is to have backup towels. When we use the song the hot tub there were no towels located there so we did have to take the ones from our room. Therefore allowing us to ask for more towels.. another thing we learned after taking a tour of the island that the hotel is excellently located for the pony pinning time frame every year however you need to book your room in January at the absolute earliestif you're interested in being there during the pony pinning. Overall we had a great time even though it was off season We were able to go to one other end of the island for shopping the thrift store was a great place to go and get many deals and then we went to another place sensations where everything in the store was pretty much reduced 50% and 25%. We left with some great deals. We arrived at our stay on October 19th and we went there for our mini honeymoon. Overall our stay was great We went to Zach's seafood house for the first restaurant visit the second restaurant visit was Prime Bill's Steakhouse.. " [](https://expedia.ca/Chincoteague-Hotels-Waterside-Inn.h1615555.Hotel-Information) ![Refuge Inn](//images.trvl-media.com/lodging/1000000/50000/40500/40487/3acf3bc5_y.jpg) ### Refuge Inn 10/10 Excellent "Very clean and fresh room. Nice staff. Good location. " [](https://expedia.ca/Chincoteague-Hotels-Refuge-Inn.h40487.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 "Breakfast was great, Room spotless and roomy!! Staff friendly and helpful! " [](https://expedia.ca/Chincoteague-Hotels-Comfort-Suites-Chincoteague-Island-Bayfront-Resort.h295865.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 "The staff is very kind and helpful. " [](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 "Me and my brother enjoyed our stay " [](https://expedia.ca/Chincoteague-Hotels-Chincoteague-Inn.h1080519.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 "Two night stay, very comfortable and clean" [](https://expedia.ca/Chincoteague-Hotels-Marina-Bay-Hotel-Suites.h15030757.Hotel-Information) ![Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront](//images.trvl-media.com/lodging/7000000/6160000/6157400/6157368/1ee5649e_y.jpg) ### Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront 10/10 Excellent "The whole facility was clean. The outdoor space was attract and the pool heated. Breakfast provided was good with plenty of options. The property was located in a convenient place that made walking to downtown dining and shopping easy. Definitely will stay here again " [](https://expedia.ca/Chincoteague-Hotels-Fairfield-Inn-Suites-By-Marriott-Chincoteague-Island-Waterfront.h6157368.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Deep Hole? > [Sunrise Shore - Waterfront; Private pool & hot tub!](https://www.expedia.ca/Chincoteague-Hotels-Sunrise-Shore.h55396796.Hotel-Information): Offers daily, a seasonal outdoor pool, and free self parking. [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): Provides free self parking, a seasonal outdoor pool, and complimentary wireless internet access. [Waterfowl Watch Cottage - Chincoteague Island Quiet area,bikes, Spend Christmas](https://www.expedia.ca/Chincoteague-Hotels-Waterfowl-Watch-New-Listing-Quiet-Area.h104645745.Hotel-Information): Features a seasonal outdoor pool, an indoor pool, and a sauna. [Quaint Cottages Near Everything on Beach Road](https://www.expedia.ca/Chincoteague-Hotels-Quaint-Cottages-Near-Everything-On-Beach-Road.h67544638.Hotel-Information): Offers a private beach, a seasonal outdoor pool, and a snack bar/deli. [Chincoteague Island Home- "Blue Tide Townhome" Kayaks Included!](https://www.expedia.ca/Chincoteague-Hotels-Chincoteague-Island-Home-Blue-Tide-Townhome-BikesKayaks-Included.h92616675.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 that offers an outdoor if you plan to visit 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 visit 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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[Chincoteague Hotels](https://www.expedia.ca/Chincoteague-Hotels.d55637.Travel-Guide-Hotels) - [Inns in Chincoteague](https://www.expedia.ca/Chincoteague-Inns.d55637-aaInns.Travel-Guide-Accommodation) - [Motels in Chincoteague](https://www.expedia.ca/Chincoteague-Motels.d55637-aaMotels.Travel-Guide-Accommodation) - [Hotels near Chincoteague National Wildlife Refuge](https://www.expedia.ca/Chincoteague-National-Wildlife-Refuge-Hotels.0-l553248621533117191-0.Travel-Guide-Filter-Hotels) - [Resorts in Chincoteague](https://www.expedia.ca/Chincoteague-Resort-Hotels.d55637-aaResortHotels.Travel-Guide-Accommodation) - [Gargatha Hotels](https://www.expedia.ca/Gargatha-Hotels.d553248635544227613.Travel-Guide-Hotels) - [Vacation Homes in Gargatha](https://www.expedia.ca/Gargatha-Private-Vacation-Homes.d553248635544227613-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Luxury Hotels in Horntown](https://www.expedia.ca/Horntown-Hotels-Luxury-Hotel.0-0-d3000355159-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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