Title: Book the Best Hotels with POOL in Princess Anne in 2026 | Expedia.ca [Hotels in Princess Anne](https://expedia.ca/Princess-Anne-Hotels.d148385.Travel-Guide-Hotels)[Vacation Rentals in Princess Anne](https://expedia.ca/Princess-Anne-Vacation-Rentals.d148385.Travel-Guide-VacationRentals)[Princess Anne Car Rentals](https://expedia.ca/Car-Rentals-In-Princess-Anne.d148385.Car-Rental-Guide)[Princess Anne Vacation Packages](https://expedia.ca/Princess-Anne.d148385.Destination-Travel-Guides) ![Aerial view of Princess Anne, Maryland with marshlands and waterways at sunset](https://images.trvl-media.com/place/148385/205c3bf2-4444-43c8-94c9-aefa6641ff7e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/148385/205c3bf2-4444-43c8-94c9-aefa6641ff7e.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 Princess Anne Hotels with a Pool Tonight [Feb 27 - Feb 28](https://www.expedia.ca/Hotel-Search?regionId=148385&startDate=2026-02-27&endDate=2026-02-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 28 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=148385&startDate=2026-02-28&endDate=2026-03-01&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=148385&startDate=2026-02-27&endDate=2026-03-01&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=148385&startDate=2026-03-06&endDate=2026-03-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Princess Anne hotels with a pool ![Seasonal outdoor pool, open 9 AM to 9 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/26400/26336/d061d423.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/30000/26400/26336/89e61f2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/26400/26336/05a5e8a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9 AM to 9 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/26400/26336/e616b7d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Econo Lodge Princess Anne [](https://www.expedia.ca/Salisbury-Hotels-Econo-Lodge-Princess-Anne.h26336.Hotel-Information) Princess Anne 6.6/10 (672 reviews) - Bask in the sun at this charming motel with a seasonal outdoor pool, loungers for relaxing, and complimentary breakfast. CA $105 CA $116 total includes taxes & fees Mar 5 - Mar 6 [](https://www.expedia.ca/Salisbury-Hotels-Econo-Lodge-Princess-Anne.h26336.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) ![Boating](https://images.trvl-media.com/lodging/7000000/6160000/6157400/6157368/0959dd25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/7000000/6160000/6157400/6157368/59257844.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 (590 reviews) - Splash into spectacular views at this waterfront hotel where poolside serenity meets bay sunsets. CA $150 CA $168 total includes taxes & fees Mar 13 - Mar 14 [](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/1000000/300000/295900/295865/17e42883.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) ![Fishing](https://images.trvl-media.com/lodging/1000000/300000/295900/295865/0c592b6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/300000/295900/295865/0b5ea2de.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) - Sun-kissed indoor and outdoor pools with bayfront views await after a day of coastal fun. CA $143 CA $162 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Chincoteague-Hotels-Comfort-Suites-Chincoteague-Island-Bayfront-Resort.h295865.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) ![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) ![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) ### 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 (761 reviews) - Dive into waterfront tranquility with a heated indoor pool and relaxing hot tub overlooking the wildlife refuge. CA $146 CA $164 total includes taxes & fees Mar 8 - Mar 9 [](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) ![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) ![Oyster Cottage](https://images.trvl-media.com/lodging/22000000/21390000/21381400/21381363/78e32203.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) ### 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) - Dive into poolside bliss with a private beach oasis and refreshing outdoor swimming awaiting you in Chincoteague. [](https://www.expedia.ca/Chincoteague-Hotels-Key-West-Cottages-On-The-Chincoteague-Bay.h21381363.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) - Float away in Chincoteague's downtown marina hotel with a seasonal pool and nautical adventures. [](https://www.expedia.ca/Chincoteague-Hotels-Waterside-Inn.h1615555.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/480000/477500/477474/89421cb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/480000/477500/477474/6b4fb5f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/480000/477500/477474/3e1337a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/480000/477500/477474/f8626115.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Pocomoke City [](https://www.expedia.ca/Pocomoke-City-Hotels-Best-Western-Plus-Pocomoke-City.h477474.Hotel-Information) Pocomoke City 8.6/10 Excellent (901 reviews) - Sparkling indoor pool creates year-round relaxation oasis at this charming rural retreat. CA $132 CA $148 total includes taxes & fees Mar 9 - Mar 10 [](https://www.expedia.ca/Pocomoke-City-Hotels-Best-Western-Plus-Pocomoke-City.h477474.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/16000000/15040000/15030800/15030757/ae01482b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/16000000/15040000/15030800/15030757/41034ad3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/16000000/15040000/15030800/15030757/6b25f927.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) ### Marina Bay Hotel & Suites, an Ascend Collection Hotel [](https://www.expedia.ca/Chincoteague-Hotels-Marina-Bay-Hotel-Suites.h15030757.Hotel-Information) Downtown Chincoteague 9.0/10 Wonderful (1,000 reviews) - Escape to a sun-kissed marina oasis with a seasonal pool and shaded umbrellas for ultimate relaxation. CA $103 CA $137 total includes taxes & fees Mar 22 - Mar 23 [](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) ![Single Room, 1 King Bed | Bathroom](https://images.trvl-media.com/lodging/65000000/64620000/64616700/64616626/0f8c0d24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Room](https://images.trvl-media.com/lodging/65000000/64620000/64616700/64616626/9c5a817a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Birchwood Inn [](https://www.expedia.ca/Chincoteague-Hotels-Birchwood-Inn.h64616626.Hotel-Information) Downtown Chincoteague 7.0/10 Good (389 reviews) - Splash into summer at this downtown retreat with a seasonal pool and scenic terrace garden. CA $80 CA $96 total includes taxes & fees Mar 13 - Mar 14 [](https://www.expedia.ca/Chincoteague-Hotels-Birchwood-Inn.h64616626.Hotel-Information) ![Sports facility](https://images.trvl-media.com/lodging/2000000/1440000/1438800/1438753/2d2de68c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1440000/1438800/1438753/c88ed50f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast served, American cuisine](https://images.trvl-media.com/lodging/2000000/1440000/1438800/1438753/b41ce7f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1440000/1438800/1438753/e1aeb676.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Salisbury [](https://www.expedia.ca/Salisbury-Hotels-Courtyard-Marriott-Salisbury.h1438753.Hotel-Information) Salisbury 8.6/10 Excellent (978 reviews) - Sink into serenity at this modern hotel's indoor pool sanctuary, where bubbling hot tub escapes and extended swimming hours await. CA $165 CA $185 total includes taxes & fees Mar 7 - Mar 8 [](https://www.expedia.ca/Salisbury-Hotels-Courtyard-Marriott-Salisbury.h1438753.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=2026-03-14&endDate=2026-03-15®ionId=148385&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Princess Anne Breakfast included Hot tub 4 stars 5 stars Spa ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AFFINITY_SPRING_PROMO_148385) ## Top Princess Anne Hotel Reviews ![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 "Great room, staff super friendly. Great location as.was walking distance to many restaurants and attractions." [](https://expedia.ca/Chincoteague-Hotels-Fairfield-Inn-Suites-By-Marriott-Chincoteague-Island-Waterfront.h6157368.Hotel-Information) ![Days Inn by Wyndham Salisbury](https://images.trvl-media.com/lodging/1000000/20000/16300/16257/3d6af3ed_y.jpg) ### Days Inn by Wyndham Salisbury 10/10 Excellent "The room was clean, the staff was pleasant, and fulfilled my requests as requested for room service" [](https://expedia.ca/Salisbury-Hotels-Days-Inn-By-Wyndham-Salisbury.h16257.Hotel-Information) ![Hampton Inn & Suites Chincoteague Waterfront](https://images.trvl-media.com/lodging/1000000/900000/899200/899134/72fcaffc_y.jpg) ### Hampton Inn & Suites Chincoteague Waterfront 10/10 Excellent "Great stay. " [](https://expedia.ca/Chincoteague-Hotels-Hampton-Inn-Suites-Chincoteague-Waterfront.h899134.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 "The room and view were beautiful, had a great time. looking forward to going back again this summer. " [](https://expedia.ca/Chincoteague-Hotels-Comfort-Suites-Chincoteague-Island-Bayfront-Resort.h295865.Hotel-Information) ![Wingate by Wyndham Salisbury](https://images.trvl-media.com/lodging/1000000/220000/213700/213687/51d14f46_y.jpg) ### Wingate by Wyndham Salisbury 10/10 Excellent "Yes, everything in our room was great. Nice Breakfast. Staff was Cordial." [](https://expedia.ca/Salisbury-Hotels-Sleep-Inn-Salisbury.h213687.Hotel-Information) ![Country Inn & Suites by Radisson, Salisbury, MD](https://images.trvl-media.com/lodging/2000000/1260000/1250200/1250138/ab94f972_y.jpg) ### Country Inn & Suites by Radisson, Salisbury, MD 10/10 Excellent "I had a great stay and I’m so glad we choose Country Inn!! I want to start off by saying Steven at the front desk was so helpful and mindful as well. He went above and beyond with his service which was highly appreciated. My family loved the pool it was very nice & clean, the rooms were nice and clean as well. House keeping made our beds & took out the trash upon request with no hesitation. I also need to point out the breakfast 10/10\. The food was fresh and tasty and my picky kids enjoyed it both days we were there. With all that being said we will be back next time we are in town! " [](https://expedia.ca/Salisbury-Hotels-Country-Inn-Suites-By-Radisson.h1250138.Hotel-Information) ![Waterside Inn](https://images.trvl-media.com/lodging/2000000/1620000/1615600/1615555/43b08add_y.jpg) ### Waterside Inn 10/10 Excellent "The staff was so friendly and helpful. The view from our room was beautiful and it was clean and had everything- toiletries, fridge, and microwave. Finitely would stay there again!!!" [](https://expedia.ca/Chincoteague-Hotels-Waterside-Inn.h1615555.Hotel-Information) ![Hampton Inn & Suites Salisbury/Fruitland](https://images.trvl-media.com/lodging/3000000/2220000/2212000/2211931/578c88da_y.jpg) ### Hampton Inn & Suites Salisbury/Fruitland 10/10 Excellent "Friendly staff " [](https://expedia.ca/Salisbury-Hotels-Hampton-Inn-Suites-Fruitland.h2211931.Hotel-Information) ![Hampton Inn Salisbury](https://images.trvl-media.com/lodging/1000000/290000/282000/281943/633fd984_y.jpg) ### Hampton Inn Salisbury 10/10 Excellent "The room was very spotless, staff friendly and amazing. The amenities were good. And the continental breakfast was good. " [](https://expedia.ca/Salisbury-Hotels-Hampton-Inn-Salisbury.h281943.Hotel-Information) ## Frequently asked questions ### What are the best hotels in Princess Anne with outdoor pools? > Guests appreciate the comfortable and clean rooms, along with the friendly staff who go the extra mile to ensure a pleasant stay. The hotel also provides a complimentary continental breakfast and free WiFi, making it a convenient choice for families seeking both value and comfort. ### How much does a hotel with outdoor pool in Princess Anne cost? ### Is it cheaper to book flights and a hotel in Princess Anne as a package? ### How can I save on a hotel in Princess Anne with Expedia? ### Can I cancel my hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [4 Star Hotels in Kingston ](https://www.expedia.ca/4Star-Kingston-Hotels.s40-0-d553248635975867875.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in Baltimore ](https://www.expedia.ca/Baltimore-Hotels-Honeymoon-Hotels.0-0-d178235-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Lazy River in Baltimore ](https://www.expedia.ca/Baltimore-Hotels-Hotels-With-A-Lazy-River.0-0-d178235-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Bivalve ](https://www.expedia.ca/Bivalve-Hotels-Hotel-With-Pool.0-0-d553248635975846907-tHotelwithPool.Travel-Guide-Filter-Hotels) - 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