Title: Holiday Rentals Chesapeake Beach from £182: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk [Chesapeake Beach Travel Guide](https://expedia.co.uk/Chesapeake-Beach.dx88967)[Hotels in Chesapeake Beach](https://expedia.co.uk/Chesapeake-Beach-Hotels.d88967.Travel-Guide-Hotels)[Flights to Chesapeake Beach](https://expedia.co.uk/Cheap-Flights-To-Chesapeake-Beach.d88967.Travel-Guide-Flights)[Chesapeake Beach Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chesapeake-Beach.d88967.Car-Hire-Guide)[Chesapeake Beach Holidays](https://expedia.co.uk/Chesapeake-Beach.d88967.Holidays-City-Breaks) ![](https://mediaim.expedia.com/destination/2/a9547e3e3a06984ae8df1712c3d277fb.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Ronanne Vinson # Search Holiday Rentals in Chesapeake Beach ![price find illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Tonight [19 Sept - 20 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=88967&startDate=2025-09-19&endDate=2025-09-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [20 Sept - 21 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=88967&startDate=2025-09-20&endDate=2025-09-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [19 Sept - 21 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=88967&startDate=2025-09-19&endDate=2025-09-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [26 Sept - 28 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=88967&startDate=2025-09-26&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Holiday Rentals in Chesapeake Beach ## Our top choices for Chesapeake Beach holiday rentals ![Exterior](https://images.trvl-media.com/lodging/34000000/33510000/33506200/33506110/1dc9ddc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor banquet area](https://images.trvl-media.com/lodging/34000000/33510000/33506200/33506110/d6f3062d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33510000/33506200/33506110/438bfc90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/34000000/33510000/33506200/33506110/c5d1df22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family and Pet-Friendly, Waterfront with Pier Cambridge 10/10 Exceptional (257) "It is a perfect spot to relax and enjoy the water. We will book again if we are back that way. " [](https://www.expedia.co.uk/Cambridge-Hotels-Family-And-Pet-Friendly.h33506110.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/106000000/105760000/105758700/105758639/9f651e90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105760000/105758700/105758639/5a48c8aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/106000000/105760000/105758700/105758639/30aed7f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/106000000/105760000/105758700/105758639/57c49178.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Floating 2 bed 2 bath condo stunning views of the bay Stevensville 6.8/10 (5) "Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. " [](https://www.expedia.co.uk/Stevensville-Hotels-Floating-2-Bed-2-Bath-Condo-Stunning-Views-Of-The-Bay.h105758639.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/83000000/82950000/82943900/82943888/7d8af0d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/83000000/82950000/82943900/82943888/b541b7f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82950000/82943900/82943888/cbbbb52d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/83000000/82950000/82943900/82943888/d807abc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Flat in the Heart of St. Michaels – Walk Everywhere Saint Michaels 10/10 Exceptional (49) "Highly recommend this apt. Beautifully renovated and very spacious! Location is centrally located and very quiet on the inside. I ended up staying another night because we enjoyed so much!" [](https://www.expedia.co.uk/St-Michaels-Hotels-The-Heart-Of-St-Michaels-Awaits.h82943888.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/75000000/74430000/74420700/74420621/b7c6ac78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, ping pong](https://images.trvl-media.com/lodging/75000000/74430000/74420700/74420621/e506c5ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/75000000/74430000/74420700/74420621/e95d1273.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/75000000/74430000/74420700/74420621/958880a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverfront Retreat 7mil from MD Renaissance Fest! Riva 9.2/10 Wonderful (17) "It was a beautiful and private setting for a family reunion." [](https://www.expedia.co.uk/Riva-Hotels-Riverfront-Retreat-7mil-From-MD-Renaissance-Fest.h74420621.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) ![Exterior](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/7e1ea789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/8fd48299.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/a4a9eedd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Getaway, Dock Your Boat & Play! Edgewater 10/10 Exceptional (2) "Lovely stay, don't let the RV aspect.of it scare you. Nicer than most other bnbs ice stayed in. Quiet, clean and beautiful view of the water. " £238 includes taxes & fees 21 Sept - 22 Sept [](https://www.expedia.co.uk/Edgewater-Hotels-Waterfront-Getaway.h96305189.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/24000000/23930000/23921900/23921839/7094a412.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/24000000/23930000/23921900/23921839/4f65749e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/24000000/23930000/23921900/23921839/c21d2141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun-loungers](https://images.trvl-media.com/lodging/24000000/23930000/23921900/23921839/060f4535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay Port Republic 10/10 Exceptional (179) "Cottage was just as pictured. Lots of character and charm. Host, Brett was easy to work with and very helpful!" [](https://www.expedia.co.uk/Port-Republic-Hotels-Stunning-Views-From-Waterfront-Log-Cabin-With-Fireplace-On-The-Chesapeake-Bay.h23921839.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/33000000/32570000/32562400/32562385/c5bdec51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/33000000/32570000/32562400/32562385/0d1878e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/33000000/32570000/32562400/32562385/c9d30e18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/33000000/32570000/32562400/32562385/afb23ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels! Saint Michaels 9.6/10 Exceptional (119) "We once again enjoyed our stay here. Perfect location to every where you’d want to go in St. Michael’s! Loved sitting out front looking at the water and park and enjoying music from our front yard. Highly recommend this cottage." [](https://www.expedia.co.uk/St-Michaels-Hotels-John-Bruff-Waterview-Cottage-On-Harbor-And-On-Park-In-Town-St-Michaels.h32562385.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107130000/107125200/107125181/1b7f2d33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107130000/107125200/107125181/e37ba28e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun-loungers, beach towels](https://images.trvl-media.com/lodging/108000000/107130000/107125200/107125181/a0ab8a51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107130000/107125200/107125181/1e6435f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4BDRM River front house with Private Beach in Hollywood Hollywood 9.8/10 Exceptional (14) "This house was just what we needed for our business associates. " [](https://www.expedia.co.uk/Hollywood-Hotels-4BDRM-River-Front-House-With-Private-Beach-In-Hollywood.h107125181.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/c77382da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/b482bb5d.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 3 Bedroom Home w/Waterview Stevensville 9.8/10 Exceptional (40) "We had a great stay! The property has everything we needed and host was easy to communicate with " £182 includes taxes & fees 21 Sept - 22 Sept [](https://www.expedia.co.uk/Stevensville-Hotels-Relax-On-Kent-Island-In-3-Bedroom-Home-WWaterview.h84063656.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/93000000/92010000/92008700/92008639/0809820d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/93000000/92010000/92008700/92008639/1a21e043.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92010000/92008700/92008639/d6081e49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/93000000/92010000/92008700/92008639/0310a691.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly) Cambridge 10/10 Exceptional (11) "Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. " [](https://www.expedia.co.uk/Cambridge-Hotels-Cozy-Cottage-With-Private-Dock-Chesapeake-Bay-Cambridge.h92008639.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/98000000/97560000/97553100/97553068/c2f460cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/98000000/97560000/97553100/97553068/5d59a8a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97560000/97553100/97553068/22d8a3b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/98000000/97560000/97553100/97553068/033d6fd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 25-50% Off~Private Beach~Hot Tub~Fire Table~ Stevensville 10/10 Exceptional (29) "Cute little cottage with great views and very comfortable for a small family. " [](https://www.expedia.co.uk/Chesapeake-Waterfront-With-Hot-Tub.h97553068.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/116000000/115920000/115915900/115915900/w1290h1714x0y14-f0c33c6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115920000/115915900/115915900/b47b0948.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115920000/115915900/115915900/7a22672e_edited_eae3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115920000/115915900/115915900/w1280h955x0y7-8f5da894.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Cozy Crab- Your Charming Haven in Lovely North Beach! North Beach 9.6/10 Exceptional (9) "Great place. Just a short drive to town with shops, restaurants, and boardwalk." [](https://www.expedia.co.uk/Owings-Hotels-The-Cozy-Crab-Your-Charming-Haven-In-Lovely-North-Beach.h115915900.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/62000000/61590000/61585600/61585503/31813fa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/62000000/61590000/61585600/61585503/cc07a31f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/62000000/61590000/61585600/61585503/b09248c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/62000000/61590000/61585600/61585503/e6532040.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dollhouse in Central Historic St Michaels St Michaels 9.6/10 Exceptional (54) "This is a lovely historic home that is close to town. It's nicely decorated, has a screened deck out back, and makes for a comfortable stay." [](https://www.expedia.co.uk/St-Michaels-Hotels-Dollhouse-In-Central-Historic-St-Michaels.h61585503.Hotel-Information) ![Beach nearby, sun-loungers, beach towels](https://images.trvl-media.com/lodging/34000000/33960000/33951800/33951725/ff3c2b90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33960000/33951800/33951725/29be39b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33960000/33951800/33951725/6fde9999.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33960000/33951800/33951725/2275c590.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cottage by the Beach - Waterview
Minutes from Downtown Annapolis Oyster Harbor 10/10 Exceptional (94) "Great property and great time in Oyster Harbour!" [](https://www.expedia.co.uk/Annapolis-Hotels-Cozy-Cottage-By-The-Beach.h33951725.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/49000000/48380000/48378600/48378570/b94b1ba5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/49000000/48380000/48378600/48378570/38fa4ea8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/49000000/48380000/48378600/48378570/7c8f8b76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/49000000/48380000/48378600/48378570/7c62e911.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife St. Michaels 9.8/10 Exceptional (42) "Wonderful home in excellent location!!" [](https://www.expedia.co.uk/St-Michaels-Hotels-Carpenter-Alley-Newly-Renovated-Cottage-In-Center-Of-Historic-St-Michaels.h48378570.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33710000/33706000/33705957/9bbf68fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, travel cot, free WiFi](https://images.trvl-media.com/lodging/34000000/33710000/33706000/33705957/w800h599x0y1-c77560c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video games, DVD player, video library](https://images.trvl-media.com/lodging/34000000/33710000/33706000/33705957/fced1e30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33710000/33706000/33705957/fb9738e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW Cambridge 9.8/10 Exceptional (132) "Beautiful property with gorgeous view. The owner was helpful and accommodating. Everything was clean and the amenities were superb. An evening of kayaking on the water was amazing. Great location for the half Ironman as well! " [](https://www.expedia.co.uk/Cambridge-Hotels-Waterfront-Family-Retreat-With-Gorgeous-Views-And-A-Large-Deepwater-Dock-5-MLW.h33705957.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/5eca3b46_edited_e784.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/0100abcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/10e31f36_edited_f301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/8aaef683.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side Shady Side 10/10 Exceptional (2) "The property is newly renovated and very comfortable. Property owner is responsive to any questions, and we enjoyed our stay here. Would recommend it for anyone staying in Shady Side." £323 includes taxes & fees 29 Sept - 30 Sept [](https://www.expedia.co.uk/Shady-Side-Hotels-Peaceful-2-Bedroom-2-Bathroom-House-With-WiFi-And-AC-In-Serene-Shady-Side.h116005601.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/86000000/85390000/85383900/85383832/4ec52bf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/86000000/85390000/85383900/85383832/bc027eb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/86000000/85390000/85383900/85383832/ad4965a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/86000000/85390000/85383900/85383832/42f3eb31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Thorneton Point Estate Easton 9.6/10 Exceptional (20) "Beautiful, well-maintained property in a gorgeous waterside setting. " [](https://www.expedia.co.uk/Easton-Hotels-Thorneton-Point-Estate.h85383832.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33970000/33965500/33965405/a1d6df97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33970000/33965500/33965405/15d1eccc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33970000/33965500/33965405/41b1486b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, video library](https://images.trvl-media.com/lodging/34000000/33970000/33965500/33965405/827849fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA Edgewater 10/10 Exceptional (218) "We had a wonderful time. Hosts were very kind and responsive! Beautiful property " [](https://www.expedia.co.uk/Annapolis-Hotels-Charming-Waterfront-Cottage-With-Private-Dock-Close-To-Annapolis-Usna.h33965405.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/58000000/57940000/57931900/57931801/47c309cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/58000000/57940000/57931900/57931801/c472e480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/58000000/57940000/57931900/57931801/86338eda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/58000000/57940000/57931900/57931801/4d3b692f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk to Everything House Saint Michaels 10/10 Exceptional (83) "Clean and nice place to stay" [](https://www.expedia.co.uk/St-Michaels-Hotels-Walk-To-Everything-House.h57931801.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.co.uk/Hotel-Search?startDate=2025-10-03&endDate=2025-10-04®ionId=88967&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChesapeake-Beach-Holiday-Rentals.d88967.Travel-Guide-HolidayRentals)[Sign up, it's free](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChesapeake-Beach-Holiday-Rentals.d88967.Travel-Guide-HolidayRentals) ## Top Chesapeake Beach Hotel Reviews ![Candlewood Suites Annapolis by IHG](//images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/9088c5e1_y.jpg) ### Candlewood Suites Annapolis by IHG 10/10 Excellent "Friendly clean and secure place " [](https://expedia.co.uk/Annapolis-Hotels-Homestyle-Suites.h1160798.Hotel-Information) ![Springhill Suites by Marriott Prince Frederick](//images.trvl-media.com/lodging/2000000/1670000/1662000/1661950/39882431_y.jpg) ### Springhill Suites by Marriott Prince Frederick 10/10 Excellent "Remodeled room are very nice." [](https://expedia.co.uk/Prince-Frederick-Hotels-Springhill-Suites-By-Marriott-Prince-Frederick.h1661950.Hotel-Information) ![Sonesta ES Suites Annapolis](//images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe_y.jpg) ### Sonesta ES Suites Annapolis 10/10 Excellent "The room was very nice" [](https://expedia.co.uk/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ![Residence Inn by Marriott Waldorf](//images.trvl-media.com/lodging/3000000/2680000/2675800/2675705/7669562a_y.jpg) ### Residence Inn by Marriott Waldorf 10/10 Excellent "Would definitely stay here again. Rooms were clean. Great accommodations." [](https://expedia.co.uk/Waldorf-Hotels-Residence-Inn-By-Marriott-Waldorf.h2675705.Hotel-Information) ![Holiday Inn Express Waldorf by IHG](//images.trvl-media.com/lodging/1000000/30000/25500/25493/9a1d7d08_y.jpg) ### Holiday Inn Express Waldorf by IHG 10/10 Excellent "Easy access to everything I needed to do." [](https://expedia.co.uk/Waldorf-Hotels-Holiday-Inn-Express-Waldorf.h25493.Hotel-Information) ![Rod 'N' Reel Resort](//images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/4803b1f5_y.jpg) ### Rod 'N' Reel Resort 10/10 Excellent "Excellent stay" [](https://expedia.co.uk/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information) ![St Michaels Inn](//images.trvl-media.com/lodging/1000000/20000/10300/10281/6601016b_y.jpg) ### St Michaels Inn 10/10 Excellent "Easy Check In & quite area" [](https://expedia.co.uk/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) ![Spark by Hilton Waldorf](//images.trvl-media.com/lodging/1000000/30000/26400/26379/701212c7_y.jpg) ### Spark by Hilton Waldorf 10/10 Excellent "Great experience.. no issues !! Quiet love it !!" [](https://expedia.co.uk/Waldorf-Hotels-Spark-By-Hilton-Waldorf.h26379.Hotel-Information) ![The Wildset](//images.trvl-media.com/lodging/65000000/64420000/64410600/64410566/38a42051_y.jpg) ### The Wildset 10/10 Excellent "fantastic location, great bouboun selection at the bar and wonderful staff" [](https://expedia.co.uk/St-Michaels-Hotels-The-Wildset.h64410566.Hotel-Information) ## Find out more about Chesapeake Beach **Everything you need to know about** **Chesapeake Beach** **holiday rentals** Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake Beach holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/Villas)... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **Chesapeake Beach holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in .  Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesapeake Beach holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesapeake Beach holiday rentals we have selected for you start as low as £182 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Chesapeake Beach rentals** At Expedia, we put the best Chesapeake Beach holiday 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 holiday. 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.co.uk ### Trending destinations on Expedia.co.uk - [Holiday Rentals in the Cotswold](https://www.expedia.co.uk/lp/b/vr/cotswold) - [Holiday Rentals in Lake District](https://www.expedia.co.uk/lp/b/vr/lake-district) - [Devon Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Devon.d6046196.Holiday-Rental-Destinations) - [Norfolk Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Norfolk.d6046223.Holiday-Rental-Destinations) - [Bedfordshire Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Bedfordshire.d6046189.Holiday-Rental-Destinations) - [Dorset Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Dorset.d6046198.Holiday-Rental-Destinations) - [Northumberland Holiday Rentals](https://www.expedia.com/Destinations-In-Northumberland.d6046225.Vacation-Rental-Destinations) - [Herefordshire Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Herefordshire.d6046203.Holiday-Rental-Destinations) - [Essex Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Essex.d6046201.Holiday-Rental-Destinations) - [Cumbria Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Cumbria.d6046194.Holiday-Rental-Destinations) - [Yorkshire Holiday Rentals](https://www.expedia.co.uk/Yorkshire-Holiday-Rentals.d6342462.Travel-Guide-HolidayRentals) - [South Wales Holiday Rentals](https://www.expedia.co.uk/South-Wales-Holiday-Rentals.d6054274.Travel-Guide-HolidayRentals) - [North Wales Holiday Rentals](https://www.expedia.co.uk/North-Wales-Holiday-Rentals.d6054276.Travel-Guide-HolidayRentals) - [London Holiday Rentals](https://www.expedia.co.uk/London-Holiday-Rentals.d178279.Travel-Guide-HolidayRentals) - [York Holiday Rentals](https://www.expedia.co.uk/York-Holiday-Rentals.d5489.Travel-Guide-HolidayRentals) - [Blackpool Holiday Rentals](https://www.expedia.co.uk/Blackpool-Holiday-Rentals.d619.Travel-Guide-HolidayRentals) - [Isle of Wight Holiday Rentals](https://www.expedia.com/Destinations-In-Isle-Of-Wight.d6046218.Vacation-Rental-Destinations) - [Scarborough Holiday Rentals](https://www.expedia.co.uk/Scarborough-Holiday-Rentals.d5680.Travel-Guide-HolidayRentals) - [Edinburgh Holiday Rentals](https://www.expedia.co.uk/Edinburgh-Holiday-Rentals.d6069845.Travel-Guide-HolidayRentals) - [Bath Holiday Rentals](https://www.expedia.co.uk/Bath-Holiday-Rentals.d6084496.Travel-Guide-HolidayRentals) - [Bournemouth Holiday Rentals](https://www.expedia.co.uk/Bournemouth-Holiday-Rentals.d654.Travel-Guide-HolidayRentals) - [England Holiday Rentals](https://www.expedia.co.uk/Destinations-In-England.d11218.Holiday-Rental-Destinations) - [Scotland Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Scotland.d11219.Holiday-Rental-Destinations) - [Cornwall Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Cornwall.d6046193.Holiday-Rental-Destinations) - [Wales Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Wales.d11220.Holiday-Rental-Destinations) - [Northern Ireland Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Northern-Ireland.d11221.Holiday-Rental-Destinations) ## Frequently asked questions ### Can I find a holiday rental in Chesapeake Beach? > Yes, there are holiday rentals in Chesapeake Beach close to Chesapeake Beach Water Park, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Chesapeake Beach is known for its spas and beaches. While you're here, grab a bite or have a drink at the restaurants. ### What are some of the best holiday rentals that Chesapeake Beach has to offer? > [Riverfront Retreat 7mil from MD Renaissance Fest!](https://www.expedia.co.uk/Riva-Hotels-Riverfront-Retreat-7mil-From-MD-Renaissance-Fest.h74420621.Hotel-Information): This holiday home rental outside of Chesapeake Beach is located on a lake, and has a garden, a pool table and a BBQ to put you at ease in your new surroundings. It has 10 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. ### How many holiday rentals will I find in Chesapeake Beach? > With 8 Expedia holiday rentals, you're guaranteed to find just the right place for your Chesapeake Beach stay. ### What’s there to see and do in Chesapeake Beach? > Family-friendly attractions include Chesapeake Beach Water Park and Chesapeake Beach Railway Museum, whereas Breezy Point Beach is a spot to enjoy the outdoors. Other places in town to visit include Rod n Reel Charter Fishing and Bruce Gabrielson's Surf Art Gallery and Museum. ### What’s a holiday rental in Chesapeake Beach like? > Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chesapeake Beach. Holiday rentals provide amenities like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for small groups. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)