Title: Chesapeake Beach Vacation Rentals from $286: Search Short-Term Rentals | Expedia.com [Chesapeake Beach Travel Guide](https://expedia.com/Chesapeake-Beach.dx88967)[Hotels in Chesapeake Beach](https://expedia.com/Chesapeake-Beach-Hotels.d88967.Travel-Guide-Hotels)[Flights to Chesapeake Beach](https://expedia.com/Cheap-Flights-To-Chesapeake-Beach.d88967.Travel-Guide-Flights)[Things to do in Chesapeake Beach](https://expedia.com/Things-To-Do-In-Chesapeake-Beach.d88967.Travel-Guide-Activities)[Car Rentals in Chesapeake Beach](https://expedia.com/Car-Rentals-In-Chesapeake-Beach.d88967.Car-Rental-Guide)[Chesapeake Beach Vacation Packages](https://expedia.com/Chesapeake-Beach.d88967.Destination-Travel-Guides) ![Aerial view of Chesapeake Beach marina with luxury sail boats, beach house apartments, fishing boats near the water park popular vacation spot for Washington residents in Calvery county Maryland](https://images.trvl-media.com/place/88967/88834884-dfa0-472f-8984-918630335b80.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/88967/88834884-dfa0-472f-8984-918630335b80.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ## Check prices for these dates In two weeks [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=88967&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=88967&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=88967&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 24 - Jul 26](https://www.expedia.com/Hotel-Search?regionId=88967&startDate=2026-07-24&endDate=2026-07-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chesapeake Beach vacation rentals ![Pool](https://images.trvl-media.com/lodging/97000000/96350000/96341600/96341595/w952h953x0y0-b52c439e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/97000000/96350000/96341600/96341595/ae401628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96350000/96341600/96341595/b3688b5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/97000000/96350000/96341600/96341595/abb760b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Beach House: Spacious Deck, Grill & Views [](https://www.expedia.com/Chesapeake-Beach-Hotels-Family-Beach-House-Spacious-Deck.h96341595.Hotel-Information) Chesapeak beach 9.0/10 Wonderful (6 reviews) "Everything was great. The owner was extremely helpful. Couldn't ask for anything better." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bryan P. $417 nightly $439 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Chesapeake-Beach-Hotels-Family-Beach-House-Spacious-Deck.h96341595.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96640000/96637800/96637704/df7451da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96640000/96637800/96637704/d31a8fd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/97000000/96640000/96637800/96637704/b3cbb2b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/97000000/96640000/96637800/96637704/89e18a15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch. [](https://www.expedia.com/Benedict-Hotels-Peaceful-Suite-On-The-Water-Osprey-Sunrise-Over-The-River-From-Your-Porch.h96637704.Hotel-Information) Benedict 9.0/10 Wonderful (8 reviews) "The location was perfect. It was quiet and clean with a wonderful view of the water, especially the sunrise through the bedroom window in the morning. The host kept in touch to answer any questions we had, and made sure our stay was great. We will absolutely be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Coulter L. $243 nightly $268 total Apr 3 - Apr 4 Total with taxes and fees [](https://www.expedia.com/Benedict-Hotels-Peaceful-Suite-On-The-Water-Osprey-Sunrise-Over-The-River-From-Your-Porch.h96637704.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/57f188cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/99582f9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/80cf0fdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/12356e9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relax on Kent Island in a 4 Bedroom Home w/Waterview! [](https://www.expedia.com/Stevensville-Hotels-Relax-On-Kent-Island-In-3-Bedroom-Home-WWaterview.h84063656.Hotel-Information) Stevensville 9.8/10 Exceptional (43 reviews) "We had a wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Supriya V. $270 nightly $286 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Stevensville-Hotels-Relax-On-Kent-Island-In-3-Bedroom-Home-WWaterview.h84063656.Hotel-Information) ![Sun loungers](https://images.trvl-media.com/lodging/38000000/37270000/37269100/37269068/9371a02d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/38000000/37270000/37269100/37269068/42c55f30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/38000000/37270000/37269100/37269068/f7c493ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/38000000/37270000/37269100/37269068/eb65ebc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage Located on the Patuxent River! [](https://www.expedia.com/Prince-Frederick-Hotels-Cottage-Located-On-The-Patuxent-River.h37269068.Hotel-Information) Prince Frederick 10/10 Exceptional (42 reviews) "The accommodations were superb and being on the water was amazing!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel P. $303 nightly $321 total Apr 3 - Apr 4 Total with taxes and fees [](https://www.expedia.com/Prince-Frederick-Hotels-Cottage-Located-On-The-Patuxent-River.h37269068.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/102000000/101090000/101083600/101083507/0cad4612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101090000/101083600/101083507/3334515c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/102000000/101090000/101083600/101083507/f2ba56b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101090000/101083600/101083507/0cab7732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bay Ridge unit by Downtown Annapolis and Quiet Waters Park [](https://www.expedia.com/Annapolis-Hotels-Bay-Ridge-Unit-By-Downtown-Annapolis-And-Quiet-Waters-Park.h101083507.Hotel-Information) Annapolis 8.8/10 Excellent (3 reviews) "The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William $425 nightly $485 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-Bay-Ridge-Unit-By-Downtown-Annapolis-And-Quiet-Waters-Park.h101083507.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/3f3bd4d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/bf60932b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/42bbbfcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/28005d62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk to Beach! King Bed & Free Beach Passes [](https://www.expedia.com/North-Beach-Hotels-Plant-Filled-Oasis-Near-Beach-Town-With-Passes-Tips.h69541327.Hotel-Information) North Beach 10/10 Exceptional (19 reviews) "Delightful one-night stay! Place was clean, quiet, convenient and very comfortable. Especially grateful that our beloved dog was welcomed" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elaine D. $335 nightly $370 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/North-Beach-Hotels-Plant-Filled-Oasis-Near-Beach-Town-With-Passes-Tips.h69541327.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/104000000/103640000/103638100/103638094/5aeb926e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103640000/103638100/103638094/7d735d64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103640000/103638100/103638094/f8f86577.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103640000/103638100/103638094/dd4e694d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt! [](https://www.expedia.com/Prince-Frederick-Hotels-2-Blocks-From-Dares-Beach-On-The-Chesapeake-Bay-Beach-And-Boat-Access.h103638094.Hotel-Information) Prince Frederick 10/10 Exceptional (10 reviews) "Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Olivia M. $468 nightly $496 total Apr 7 - Apr 8 Total with taxes and fees [](https://www.expedia.com/Prince-Frederick-Hotels-2-Blocks-From-Dares-Beach-On-The-Chesapeake-Bay-Beach-And-Boat-Access.h103638094.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522263/0806f7bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522263/a1c3089f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522263/9a42128d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522263/4a570741.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space. [](https://www.expedia.com/Prince-Frederick-Hotels-Kick-Back-And-Enjoy-The-Chesapeake-This-3-Bedroom.h113522263.Hotel-Information) Prince Frederick 9.8/10 Exceptional (6 reviews) "Our family had a great stay. Thank you!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Colleen G. $401 nightly $425 total Apr 14 - Apr 15 Total with taxes and fees [](https://www.expedia.com/Prince-Frederick-Hotels-Kick-Back-And-Enjoy-The-Chesapeake-This-3-Bedroom.h113522263.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/64000000/63650000/63641700/63641659/a9c3170d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/64000000/63650000/63641700/63641659/2b76d904.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/64000000/63650000/63641700/63641659/f39074a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, stereo](https://images.trvl-media.com/lodging/64000000/63650000/63641700/63641659/ba3c3f81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunset Breezes - quiet waterfront retreat [](https://www.expedia.com/Cambridge-Hotels-Sunset-Breezes-Quiet-Waterfront-Retreat.h63641659.Hotel-Information) Dorchester County 10/10 Exceptional (43 reviews) "Clean, quiet, comfy" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Deborah V. $352 nightly $389 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Cambridge-Hotels-Sunset-Breezes-Quiet-Waterfront-Retreat.h63641659.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/128000000/127800000/127792300/127792237/8b19534f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/128000000/127800000/127792300/127792237/1d3660fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bathroom](https://images.trvl-media.com/lodging/128000000/127800000/127792300/127792237/4b46a2dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/128000000/127800000/127792300/127792237/0a803417.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 1-bedroom cottage with AC in cozy Harwood [](https://www.expedia.com/Charming-1-Bedroom-Cottage-With-AC-In-Cozy-Harwood.h127792237.Hotel-Information) Harwood $295 nightly $336 total Apr 8 - Apr 9 Total with taxes and fees [](https://www.expedia.com/Charming-1-Bedroom-Cottage-With-AC-In-Cozy-Harwood.h127792237.Hotel-Information) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/35e98514.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/5c5b72be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/8a80c02f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, printers](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/c2958ab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach [](https://www.expedia.com/Annapolis-Hotels-Charming-Cottage-With-Hot-Tub-1-Block-From-The-Bay.h91033683.Hotel-Information) Arundel on the Bay 9.6/10 Exceptional (13 reviews) "Great communication with the host, easy check in.. nice property. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Henry P. $550 nightly $627 total Apr 28 - Apr 29 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-Charming-Cottage-With-Hot-Tub-1-Block-From-The-Bay.h91033683.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/84000000/83070000/83066200/83066154/3f6b4c84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83070000/83066200/83066154/d811e5a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/84000000/83070000/83066200/83066154/960e2739.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83070000/83066200/83066154/fcc4baa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### WATERFRONT!! \*\*HOT TUB\*\* 3 bedroom Oasis on 2+ acres - Sleeps 8 [](https://www.expedia.com/Cambridge-Hotels-WATERFRONT-3-Bed-Oasis-On-2-Acres-Sleeps-8.h83066154.Hotel-Information) Cambridge 10/10 Exceptional (14 reviews) "Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jill C. $552 nightly $585 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Cambridge-Hotels-WATERFRONT-3-Bed-Oasis-On-2-Acres-Sleeps-8.h83066154.Hotel-Information) ![Oven, stovetop](https://images.trvl-media.com/lodging/121000000/120860000/120855800/120855751/009658d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/121000000/120860000/120855800/120855751/f21ef3f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/121000000/120860000/120855800/120855751/f5323c3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120860000/120855800/120855751/df58aec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 40' Bristol sailboat with spectacular views [](https://www.expedia.com/Stevensville-Hotels-40-Bristol-Sailboat-With-Spectacular-Views.h120855751.Hotel-Information) Stevensville $409 nightly $434 total Apr 3 - Apr 4 Total with taxes and fees [](https://www.expedia.com/Stevensville-Hotels-40-Bristol-Sailboat-With-Spectacular-Views.h120855751.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/d00ee2e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/9df6bc62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/48c7542a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/8156a7b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Annapolis Retreat - 7 mins from downtown Annapolis! [](https://www.expedia.com/Annapolis-Hotels-Annapolis-Retreat-7-Mins-From-Downtown-Annapolis.h99470706.Hotel-Information) Hillsmere 10/10 Exceptional (6 reviews) "Great house in cute neighborhood. Thanks for a very comfortable stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul C. $479 nightly $546 total Apr 7 - Apr 8 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-Annapolis-Retreat-7-Mins-From-Downtown-Annapolis.h99470706.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120840000/120836100/120836005/6d192d96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120840000/120836100/120836005/3e37b615.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120840000/120836100/120836005/ed18b7e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120840000/120836100/120836005/2f8e6449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakefront Log Cabin Retreat w/ Hot tub + Kayaks! [](https://www.expedia.com/Lusby-Hotels-Hot-Tub-Beach-Access-Lakefront-Getaway-In-Lusby.h120836005.Hotel-Information) Lusby $627 nightly $696 total Apr 13 - Apr 14 Total with taxes and fees [](https://www.expedia.com/Lusby-Hotels-Hot-Tub-Beach-Access-Lakefront-Getaway-In-Lusby.h120836005.Hotel-Information) ![TV, offices](https://images.trvl-media.com/lodging/106000000/105550000/105549100/105549011/b24c0f35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/106000000/105550000/105549100/105549011/f0fc07ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105550000/105549100/105549011/b705d36c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/106000000/105550000/105549100/105549011/bc27c0ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wright's Cottage- Pet's Welcome & EV Charging [](https://www.expedia.com/Annapolis-Hotels-Wrights-Cottage-Pets-Welcome-EV-Charging.h105549011.Hotel-Information) Annapolis 9.2/10 Wonderful (16 reviews) "Nice little spot, very quiet " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan S. $365 nightly $416 total May 3 - May 4 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-Wrights-Cottage-Pets-Welcome-EV-Charging.h105549011.Hotel-Information) ![Smart TV, fireplace, computer monitors, printers](https://images.trvl-media.com/lodging/97000000/96850000/96845700/96845663/e5e72f1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96850000/96845700/96845663/672659cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96850000/96845700/96845663/a631d41e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96850000/96845700/96845663/w1024h680x0y3-d4aa18cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tranquil Modern Farmhouse [](https://www.expedia.com/Waldorf-Hotels-Tranquil-Modern-Farmhouse.h96845663.Hotel-Information) Waldorf 9.2/10 Wonderful (7 reviews) "This property was super gorgeous and spacious so we were able to relax. Guests had more than enough space and didn’t feel like they were on top of each other sleeping wise! We were able to just have dinner and feel safe! The owner answered any questions we had within 15 minutes, which was super helpful! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) khaddija j. $559 nightly $617 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Waldorf-Hotels-Tranquil-Modern-Farmhouse.h96845663.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/d0edf916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/e5b3706d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/b40492dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/c0808af9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants [](https://www.expedia.com/North-Beach-Hotels-Huge-Beach-Bungalow-WYard.h83966408.Hotel-Information) North Beach 10/10 Exceptional (32 reviews) "Perfect place to spend quality time with our three adult children and their significant others. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Malarkey F. $436 nightly $482 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/North-Beach-Hotels-Huge-Beach-Bungalow-WYard.h83966408.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/60e252be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/e06d3ac6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/63fb220b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/54c5a0dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Unit | Dock, Kayaks & SUPs Included [](https://www.expedia.com/Edgewater-Hotels-Waterfront-Getaway.h96305189.Hotel-Information) Edgewater 10/10 Exceptional (3 reviews) "Great place to stay. It is clean, comfortable, and not lacking convenience.Quick communication with the host. We would definitely recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel K. $309 nightly $352 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/Edgewater-Hotels-Waterfront-Getaway.h96305189.Hotel-Information) ![Game room](https://images.trvl-media.com/lodging/120000000/119720000/119717100/119717086/d290777f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/120000000/119720000/119717100/119717086/41573385.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119720000/119717100/119717086/57cd3b54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119720000/119717100/119717086/462c5778.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2BR, 1BA Boutique Brick Beauty located in historic Eastport. [](https://www.expedia.com/Annapolis-Hotels-2BR.h119717086.Hotel-Information) Eastport $389 nightly $443 total Apr 27 - Apr 28 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-2BR.h119717086.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.com/Hotel-Search?startDate=2026-04-16&endDate=2026-04-17®ionId=88967&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Chesapeake+Beach%2C+Maryland%2C+United+States+of+America®ionId=88967&latLong=38.694%2C-76.53376&adults=2&startDate=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=VACATION_HOME) Cottages [](https://www.expedia.com/Hotel-Search?destination=Chesapeake+Beach%2C+Maryland%2C+United+States+of+America®ionId=88967&latLong=38.694%2C-76.53376&adults=2&startDate=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=COTTAGE) Houseboats [](https://www.expedia.com/Hotel-Search?destination=Chesapeake+Beach%2C+Maryland%2C+United+States+of+America®ionId=88967&latLong=38.694%2C-76.53376&adults=2&startDate=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=HOUSE_BOAT) Condos [](https://www.expedia.com/Hotel-Search?destination=Chesapeake+Beach%2C+Maryland%2C+United+States+of+America®ionId=88967&latLong=38.694%2C-76.53376&adults=2&startDate=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=CONDO) Apartments [](https://www.expedia.com/Hotel-Search?destination=Chesapeake+Beach%2C+Maryland%2C+United+States+of+America®ionId=88967&latLong=38.694%2C-76.53376&adults=2&startDate=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=APARTMENT) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChesapeake-Beach-Vacation-Rentals.d88967.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChesapeake-Beach-Vacation-Rentals.d88967.Travel-Guide-VacationRentals) ## Top Chesapeake Beach Hotel Reviews ![The Wildset](https://images.trvl-media.com/lodging/65000000/64420000/64410600/64410566/391fbabf_y.jpg) ### The Wildset 10/10 Excellent "The Wildset is an OUTSTANDING hotel in terms of the fine finishings of the place itself, and the kindness of the staff. And you cannot do better than to eat at their in-house restaurant, Ruse. I had mentioned, when I made my reservations to both establishments, that my wife and I were there celebrating our 35th anniversary, and we were treated like royalty! We were assigned an upgraded room, which happened to be on the second floor. This was fine for us, but be aware that there is no elevator if this could be an issue for you." [](https://expedia.com/St-Michaels-Hotels-The-Wildset.h64410566.Hotel-Information) ![Sonesta ES Suites Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/eac8c079_y.jpg) ### Sonesta ES Suites Annapolis 10/10 Excellent "Great hotel, good breakfast, clean" [](https://expedia.com/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ![Candlewood Suites Annapolis by IHG](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/aabb28e6_y.jpg) ### Candlewood Suites Annapolis by IHG 10/10 Excellent "Everything looked crisp and new in my room including the kitchen, which had all appliances and some counter space.I only stayed one night for a conference nearby, but it would be a great place to spend several days in Annapolis. " [](https://expedia.com/Annapolis-Hotels-Homestyle-Suites.h1160798.Hotel-Information) ![Courtyard Marriott Waldorf](https://images.trvl-media.com/lodging/3000000/2310000/2301400/2301328/5e52a70b_y.jpg) ### Courtyard Marriott Waldorf 6/10 Okay "Clean room Staff always seen preoccupied or under staffed" [](https://expedia.com/Waldorf-Hotels-Courtyard-Marriott-Waldorf.h2301328.Hotel-Information) ![Econo Lodge Andrews Air Force Base](https://images.trvl-media.com/lodging/1000000/30000/20400/20372/a41591ab_y.jpg) ### Econo Lodge Andrews Air Force Base 2/10 Terrible "Refund. Disgusting room. Roaches everywhere, unsecured door. Broken locks. Toilet did not flush. Cold water. Dirty bed sheets. " [](https://expedia.com/Waldorf-Hotels-Econo-Lodge-Andrews-Air-Force-Base.h20372.Hotel-Information) ![Spark by Hilton Waldorf](https://images.trvl-media.com/lodging/1000000/30000/26400/26379/094f0724_y.jpg) ### Spark by Hilton Waldorf 6/10 Okay "Breakfast was good and fresh. Big mall nearby." [](https://expedia.com/Waldorf-Hotels-Spark-By-Hilton-Waldorf.h26379.Hotel-Information) ![Hilton Garden Inn Solomons](https://images.trvl-media.com/lodging/2000000/1650000/1644700/1644617/0b056987_y.jpg) ### Hilton Garden Inn Solomons 10/10 Excellent "The buffet breakfast was not up because they were short staff on March 28th ,2026 so that was disappointing but the breakfast was ok it was microwaved " [](https://expedia.com/Solomons-Hotels-Hilton-Garden-Inn-Solomons.h1644617.Hotel-Information) ![Rod 'N' Reel Resort](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/43373394_y.jpg) ### Rod 'N' Reel Resort 10/10 Excellent "love the property for location and now that restaurant and lovely lobby and sitting areas it's quite nice (nicer!)" [](https://expedia.com/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information) ![Fairfield by Marriott Inn & Suites Clinton](https://images.trvl-media.com/lodging/1000000/20000/11400/11332/9c73520c_y.jpg) ### Fairfield by Marriott Inn & Suites Clinton 6/10 Okay "Clean room, sheets felt cheap and not soft, no soap in dispensers in shower. " [](https://expedia.com/Waldorf-Hotels-Comfort-Inn-At-Joint-Base-Andrews.h11332.Hotel-Information) ## Find out more about Chesapeake Beach **Everything you need to know about Chesapeake Beach vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake Beach vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on. There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesapeake Beach vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. **Chesapeake Beach vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Chesapeake Beach. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chesapeake Beach in high season. Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $286 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals! **How to find incredible deals on Chesapeake Beach rentals** At Expedia, we put the best Chesapeake Beach vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. To find some top Chesapeake Beach rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesapeake Beach vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesapeake Beach. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. ## Explore a world of travel with Expedia - Trending destinations on Expedia.com - All accommodation types in Chesapeake Beach ### Trending destinations on Expedia.com - [Destin Vacation Rentals ](https://www.expedia.com/Destin-Vacation-Rentals.d6906.Travel-Guide-VacationRentals) - [Panama City Vacation Rentals ](https://www.expedia.com/Panama-City-Beach-Vacation-Rentals.d8021.Travel-Guide-VacationRentals) - [Hilton Head Vacation Rentals ](https://www.expedia.com/Hilton-Head-Island-Vacation-Rentals.d601684.Travel-Guide-VacationRentals) - [Gulf Shores Vacation Rentals ](https://www.expedia.com/Gulf-Shores-Vacation-Rentals.d603078.Travel-Guide-VacationRentals) - [Key West Vacation Rentals ](https://www.expedia.com/Key-West-Vacation-Rentals.d1187.Travel-Guide-VacationRentals) - [Gatlinburg Vacation Rentals ](https://www.expedia.com/Gatlinburg-Vacation-Rentals.d7474.Travel-Guide-VacationRentals) - [Maui Vacation Rentals ](https://www.expedia.com/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Orlando Vacation Rentals ](https://www.expedia.com/Orlando-Vacation-Rentals.d178294.Travel-Guide-VacationRentals) - [Myrtle Beach Vacation Rentals ](https://www.expedia.com/Myrtle-Beach-Vacation-Rentals.d601685.Travel-Guide-VacationRentals) - [Orange Beach Vacation Rentals ](https://www.expedia.com/Orange-Beach-Vacation-Rentals.d9136.Travel-Guide-VacationRentals) - [Pigeon Forge Vacation Rentals ](https://www.expedia.com/Pigeon-Forge-Vacation-Rentals.d8264.Travel-Guide-VacationRentals) - [Ocean City Vacation Rentals ](https://www.expedia.com/Ocean-City-Vacation-Rentals.d9151.Travel-Guide-VacationRentals) - [Outer Banks Vacation Rentals ](https://www.expedia.com/Outer-Banks-Vacation-Rentals.d602135.Travel-Guide-VacationRentals) - [San Diego Vacation Rentals ](https://www.expedia.com/San-Diego-Vacation-Rentals.d3073.Travel-Guide-VacationRentals) - [Siesta Key Vacation Rentals ](https://www.expedia.com/Siesta-Key-Vacation-Rentals.d6881.Travel-Guide-VacationRentals) - [Galveston Vacation Rentals ](https://www.expedia.com/Galveston-Vacation-Rentals.d1341.Travel-Guide-VacationRentals) - [Clearwater Beach Vacation Rentals ](https://www.expedia.com/Clearwater-Beach-Vacation-Rentals.d10759.Travel-Guide-VacationRentals) - [Palm Springs Vacation Rentals ](https://www.expedia.com/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals) - [Florida Keys Vacation Rentals ](https://www.expedia.com/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals) - [Lake Tahoe Vacation Rentals ](https://www.expedia.com/South-Lake-Tahoe-Vacation-Rentals.d10150.Travel-Guide-VacationRentals) - [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals) - [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations) - [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations) - [Vacation Homes in Chesapeake Beach ](https://expedia.com/Chesapeake-Beach-Private-Vacation-Homes.d88967-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Cottages in Chesapeake Beach ](https://expedia.com/Chesapeake-Beach-Cottages.d88967-aaCottages.Travel-Guide-Accommodation) - [Apartments in Chesapeake Beach ](https://expedia.com/Chesapeake-Beach-Apartments.d88967-aaApartments.Travel-Guide-Accommodation) - [B&B in Chesapeake Beach ](https://expedia.com/Chesapeake-Beach-Bed-And-Breakfast.d88967-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Houseboats in Chesapeake Beach ](https://expedia.com/Chesapeake-Beach-Houseboats.d88967-aaHouseboats.Travel-Guide-Accommodation) - [Farmstay in Chesapeake Beach ](https://expedia.com/Chesapeake-Beach-Agritourism.d88967-aaAgritourism.Travel-Guide-Accommodation) - [Cabin Rentals in Chesapeake Beach ](https://expedia.com/Chesapeake-Beach-Cabins.d88967-aaCabins.Travel-Guide-Accommodation) - [Motels in Chesapeake Beach ](https://expedia.com/Chesapeake-Beach-Motels.d88967-aaMotels.Travel-Guide-Accommodation) - [Inns in Chesapeake Beach ](https://expedia.com/Chesapeake-Beach-Inns.d88967-aaInns.Travel-Guide-Accommodation) - [Guest Houses in Chesapeake Beach ](https://expedia.com/Chesapeake-Beach-Guest-Houses.d88967-aaGuestHouses.Travel-Guide-Accommodation) - [Condo Rentals in Chesapeake Beach ](https://expedia.com/Chesapeake-Beach-Condos.d88967-aaCondos.Travel-Guide-Accommodation) - [Villas in Chesapeake Beach ](https://expedia.com/Chesapeake-Beach-Villas.d88967-aaVillas.Travel-Guide-Accommodation) ## Frequently asked questions ### Can I find a vacation rental in Chesapeake Beach? ### What are some of the best vacation home rentals that Chesapeake Beach has to offer? ### How many vacation rentals will I find in Chesapeake Beach? ### What’s there to see and do in Chesapeake Beach? ### What’s a vacation rental in Chesapeake Beach like? ### Expedia's Latest Trends Hotels - [Top Hotels in Waldorf](https://expedia.com/Waldorf-Hotels.d6057464.Travel-Guide-Hotels) - [Ocean City Pet-friendly Hotels](https://expedia.com/Ocean-City-Hotels-Pet-Friendly-Hotel.0-0-d9151-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Top Hotels in Hagerstown](https://expedia.com/Hagerstown-Hotels.d6057475.Travel-Guide-Hotels) - [Top Hotels in Silver Spring](https://expedia.com/Silver-Spring-Hotels.d6891.Travel-Guide-Hotels) - [Top Hotels in Ocean City](https://expedia.com/Ocean-City-Hotels.d9151.Travel-Guide-Hotels) - [Ocean City Oceanfront Hotels](https://expedia.com/Ocean-City-Hotels-Oceanfront-Hotels.0-0-d9151-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Ocean City Cheap Hotels](https://expedia.com/Ocean-City-Hotels-Cheap-Hotels.0-0-d9151-tCheapHotels.Travel-Guide-Filter-Hotels) - [Top Hotels in Bowie](https://expedia.com/Bowie-Hotels.d6278.Travel-Guide-Hotels) - [Top Hotels in Rockville](https://expedia.com/Rockville-Hotels.d6353.Travel-Guide-Hotels) - [Top Hotels in Salisbury](https://expedia.com/Salisbury-Hotels.d6057491.Travel-Guide-Hotels) - [Top Hotels in Aberdeen](https://expedia.com/Aberdeen-Hotels.d6044.Travel-Guide-Hotels) - [Top Hotels in Annapolis](https://expedia.com/Annapolis-Hotels.d6034082.Travel-Guide-Hotels) - [Top Hotels in St. Michaels](https://expedia.com/St-Michaels-Hotels.d5940.Travel-Guide-Hotels) - [Top Hotels in Cumberland](https://expedia.com/Cumberland-Hotels.d6057474.Travel-Guide-Hotels) - [Top Hotels in College Park](https://expedia.com/College-Park-Hotels.d6057494.Travel-Guide-Hotels) - [Top Hotels in Frederick](https://expedia.com/Frederick-Hotels.d6057476.Travel-Guide-Hotels) - [Annapolis Oceanfront Hotels](https://expedia.com/Annapolis-Hotels-Oceanfront-Hotels.0-0-d6034082-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Top Hotels in Bel Air](https://expedia.com/Bel-Air-Hotels.d6023736.Travel-Guide-Hotels) - [Ocean City Luxury Hotels](https://expedia.com/Ocean-City-Hotels-Luxury-Hotel.0-0-d9151-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Top Hotels in Gaithersburg](https://expedia.com/Gaithersburg-Hotels.d7427.Travel-Guide-Hotels) Flights - [Flights to SBY](https://expedia.com/Cheap-Flights-To-Ocean-City.d9151.Travel-Guide-Flights) Cars - [Car rentals in Rockville](https://expedia.com/Car-Rentals-In-Rockville.d6353.Car-Rental-Guide) - [Car rentals in Silver Spring](https://expedia.com/Car-Rentals-In-Silver-Spring.d6891.Car-Rental-Guide) - [Car rentals in Frederick](https://expedia.com/Car-Rentals-In-Frederick.d6057476.Car-Rental-Guide) Activities - [Things to do in Annapolis](https://expedia.com/Things-To-Do-In-Annapolis.d6034082.Travel-Guide-Activities) - [Things to do in Ocean City](https://expedia.com/Things-To-Do-In-Ocean-City.d9151.Travel-Guide-Activities) Packages - [Holiday in Ocean City](https://expedia.com/Ocean-City.d9151.Destination-Travel-Guides) Vacation Rentals - [Ocean City Vacation Rental](https://expedia.com/Ocean-City-Vacation-Rentals.d9151.Travel-Guide-VacationRentals) General - [Visit Ocean City](https://expedia.com/Ocean-City.dx9151) - [Visit Chesapeake City](https://expedia.com/Chesapeake-City.dx177517)