Title: Shady Side Holiday Homes from £181: Search Holiday Homes in Shady Side | Expedia.co.uk [Shady Side Travel Guide](https://expedia.co.uk/Shady-Side.dx6264943)[Hotels in Shady Side](https://expedia.co.uk/Shady-Side-Hotels.d6264943.Travel-Guide-Hotels)[Holiday Rentals in Shady Side](https://expedia.co.uk/Shady-Side-Holiday-Rentals.d6264943.Travel-Guide-HolidayRentals)[Shady Side Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Shady-Side.d6264943.Car-Hire-Guide)[Shady Side Holidays](https://expedia.co.uk/Shady-Side.d6264943.Holidays-City-Breaks) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](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) - ![](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 In two weeks [27 Feb - 1 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=6264943&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [10 Apr - 12 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=6264943&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [8 May - 10 May](https://www.expedia.co.uk/Hotel-Search?regionId=6264943&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [5 Jun - 7 Jun](https://www.expedia.co.uk/Hotel-Search?regionId=6264943&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Shady Side holiday homes ![Interior](https://images.trvl-media.com/lodging/123000000/122690000/122684200/122684164/w1199h797x1y1-f2a2d97f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/123000000/122690000/122684200/122684164/w1199h798x1y1-faa90d52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/123000000/122690000/122684200/122684164/w1199h797x1y1-df143cd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122690000/122684200/122684164/w1200h797x0y1-0a79f7be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunset Cottage - West River Access and Views! [](https://www.expedia.co.uk/Shady-Side-Hotels-Sunset-Cottage-West-River-Access-And-Views.h122684164.Hotel-Information) Shady Side £293 includes taxes & fees 16 Feb - 17 Feb [](https://www.expedia.co.uk/Shady-Side-Hotels-Sunset-Cottage-West-River-Access-And-Views.h122684164.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/0100abcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/681a375c.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) ![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) ### Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side [](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) Shady Side 10/10 Exceptional (4 reviews) "Would stay here again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas D. £319 includes taxes & fees 22 Feb - 23 Feb [](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) ![Exterior](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/a71c8e39.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/85000000/84070000/84063900/84063895/w1024h678x0y5-f3e384c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/c53ddff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/e9f923a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Coastal/Country Home w/3 Acres & Sauna! [](https://www.expedia.co.uk/Stevensville-Hotels-Charming-CoastalCountry-Home-W3-Acres-Sauna.h84063895.Hotel-Information) Stevensville 9.6/10 Exceptional (32 reviews) "Great stay, would do it again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandon D. £181 includes taxes & fees 16 Feb - 17 Feb [](https://www.expedia.co.uk/Stevensville-Hotels-Charming-CoastalCountry-Home-W3-Acres-Sauna.h84063895.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) ![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/80cf0fdf.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) ![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/c77382da.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.co.uk/Stevensville-Hotels-Relax-On-Kent-Island-In-3-Bedroom-Home-WWaterview.h84063656.Hotel-Information) Stevensville 9.8/10 Exceptional (43 reviews) "We had a great stay! The property has everything we needed and host was easy to communicate with " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie S. £181 includes taxes & fees 17 Feb - 18 Feb [](https://www.expedia.co.uk/Stevensville-Hotels-Relax-On-Kent-Island-In-3-Bedroom-Home-WWaterview.h84063656.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/2a64ee56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/737f2153.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/23f1d475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/30ebd57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 2 bedroom duplex located conveniently near Route 50 East and West. [](https://www.expedia.co.uk/Spacious-2-Bedroom-Duplex-Located-Conveniently-Near-Route-50-East-And-West.h99830322.Hotel-Information) Grasonville 9.6/10 Exceptional (12 reviews) "Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joe C. £310 includes taxes & fees 16 Feb - 17 Feb [](https://www.expedia.co.uk/Spacious-2-Bedroom-Duplex-Located-Conveniently-Near-Route-50-East-And-West.h99830322.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/f79dd58b.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.co.uk/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 £354 includes taxes & fees 16 Feb - 17 Feb [](https://www.expedia.co.uk/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) ![Dining](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/457a4a48.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/70000000/69550000/69541400/69541327/28005d62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk to Beach! King Bed & Free Beach Passes [](https://www.expedia.co.uk/North-Beach-Hotels-Plant-Filled-Oasis-Near-Beach-Town-With-Passes-Tips.h69541327.Hotel-Information) North Beach 10/10 Exceptional (18 reviews) "We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer B. £231 includes taxes & fees 16 Feb - 17 Feb [](https://www.expedia.co.uk/North-Beach-Hotels-Plant-Filled-Oasis-Near-Beach-Town-With-Passes-Tips.h69541327.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) ![Smart TV](https://images.trvl-media.com/lodging/84000000/83070000/83066200/83066154/d0df96b9.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) ![3 bedrooms, travel cot, 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) ### WATERFRONT!! \*\*HOT TUB\*\* 3 bedroom Oasis on 2+ acres - Sleeps 8 [](https://www.expedia.co.uk/Cambridge-Hotels-WATERFRONT-3-Bed-Oasis-On-2-Acres-Sleeps-8.h83066154.Hotel-Information) Cambridge 10/10 Exceptional (14 reviews) "Amazing news out of the back.Great for kayaking.We brought our own kayaksAnd also use yoursThere were four of usWe also took a nice trip over to Saint Michael’s" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sandy S. £380 includes taxes & fees 17 Feb - 18 Feb [](https://www.expedia.co.uk/Cambridge-Hotels-WATERFRONT-3-Bed-Oasis-On-2-Acres-Sleeps-8.h83066154.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/125000000/124830000/124829800/124829757/a2bc20d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/125000000/124830000/124829800/124829757/4624c991.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/125000000/124830000/124829800/124829757/f552eabe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/125000000/124830000/124829800/124829757/af565df9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cute, Cozy 2-bedroom house in near Annapolis with water access [](https://www.expedia.co.uk/Crownsville-Hotels-Cute.h124829757.Hotel-Information) Herald Harbor £162 includes taxes & fees 16 Mar - 17 Mar [](https://www.expedia.co.uk/Crownsville-Hotels-Cute.h124829757.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101900000/101897400/101897342/dc0187f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101900000/101897400/101897342/ea596829.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101900000/101897400/101897342/3f9288e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/102000000/101900000/101897400/101897342/bb91d7f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Neptune by the Water - Pet Friendly Fenced Yard [](https://www.expedia.co.uk/Annapolis-Hotels-Neptune-By-The-Water.h101897342.Hotel-Information) Cape Saint Claire 9.8/10 Exceptional (11 reviews) "Very nice home, location, close to our family and activities. Enjoyed our stay and would recommend to other renters looking for spaciousness and holiness that a hotel cannot provide! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa S. £408 includes taxes & fees 16 Feb - 17 Feb [](https://www.expedia.co.uk/Annapolis-Hotels-Neptune-By-The-Water.h101897342.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/e5c30638.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/3a482076.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/86c425c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/a5c24734.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Large 2 bedroom house with private parking in a nice neighborhood [](https://www.expedia.co.uk/Arnold-Hotels-Large-2-Bedroom-House-Private-Parking-Nice-Neighborhood.h89057630.Hotel-Information) Arnold 9.4/10 Exceptional (36 reviews) "This house was perfect for my husband and I, plus two daughters! We loved the location and how clean the unit was. The beds were comfortable and there were plenty of towels and all the things we needed for our weekend. We will definitely stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emily B. £245 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Arnold-Hotels-Large-2-Bedroom-House-Private-Parking-Nice-Neighborhood.h89057630.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) ![3 bedrooms, iron/ironing board, travel cot, free WiFi](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522263/9a42128d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522263/4429fbeb.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) ### Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space. [](https://www.expedia.co.uk/Prince-Frederick-Hotels-Kick-Back-And-Enjoy-The-Chesapeake-This-3-Bedroom.h113522263.Hotel-Information) Prince Frederick 9.6/10 Exceptional (5 reviews) "We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carrie K. £281 includes taxes & fees 16 Mar - 17 Mar [](https://www.expedia.co.uk/Prince-Frederick-Hotels-Kick-Back-And-Enjoy-The-Chesapeake-This-3-Bedroom.h113522263.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) ![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) ![Smart TV, books](https://images.trvl-media.com/lodging/104000000/103640000/103638100/103638094/b10c421b.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) ### 2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt! [](https://www.expedia.co.uk/Prince-Frederick-Hotels-2-Blocks-From-Dares-Beach-On-The-Chesapeake-Bay-Beach-And-Boat-Access.h103638094.Hotel-Information) Prince Frederick 10/10 Exceptional (8 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. £300 includes taxes & fees 16 Mar - 17 Mar [](https://www.expedia.co.uk/Prince-Frederick-Hotels-2-Blocks-From-Dares-Beach-On-The-Chesapeake-Bay-Beach-And-Boat-Access.h103638094.Hotel-Information) ![Beach nearby, sun-loungers, beach towels](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/8a8d7f46.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) ![Outdoor spa tub](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/825e8c03.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.co.uk/Annapolis-Hotels-Charming-Cottage-With-Hot-Tub-1-Block-From-The-Bay.h91033683.Hotel-Information) Arundel on the Bay 9.8/10 Exceptional (11 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. £402 includes taxes & fees 26 Feb - 27 Feb [](https://www.expedia.co.uk/Annapolis-Hotels-Charming-Cottage-With-Hot-Tub-1-Block-From-The-Bay.h91033683.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) ![Exterior detail](https://images.trvl-media.com/lodging/106000000/105550000/105549100/105549011/bc27c0ac.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) ### Wright's Cottage- Pet's Welcome & EV Charging [](https://www.expedia.co.uk/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. £257 includes taxes & fees 9 Mar - 10 Mar [](https://www.expedia.co.uk/Annapolis-Hotels-Wrights-Cottage-Pets-Welcome-EV-Charging.h105549011.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100210000/100202700/100202663/f3add354.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100210000/100202700/100202663/7efcfe99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/101000000/100210000/100202700/100202663/465f6a52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100210000/100202700/100202663/ab2cfa42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cute bungalow blocks to Stadium [](https://www.expedia.co.uk/Annapolis-Hotels-Cute-Bungalow-Blocks-To-Stadium.h100202663.Hotel-Information) Admiral Heights 9.8/10 Exceptional (8 reviews) "We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tammy L. £388 includes taxes & fees 16 Feb - 17 Feb [](https://www.expedia.co.uk/Annapolis-Hotels-Cute-Bungalow-Blocks-To-Stadium.h100202663.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) ![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) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/a72fcd9c.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) ### Annapolis Retreat - 7 mins from downtown Annapolis! [](https://www.expedia.co.uk/Annapolis-Hotels-Annapolis-Retreat-7-Mins-From-Downtown-Annapolis.h99470706.Hotel-Information) Hillsmere 10/10 Exceptional (5 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. £376 includes taxes & fees 16 Feb - 17 Feb [](https://www.expedia.co.uk/Annapolis-Hotels-Annapolis-Retreat-7-Mins-From-Downtown-Annapolis.h99470706.Hotel-Information) ![Smart TV, fireplace, table football, ping pong](https://images.trvl-media.com/lodging/76000000/75720000/75710800/75710733/084c9639.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/76000000/75720000/75710800/75710733/0431981f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/76000000/75720000/75710800/75710733/1b3af336.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75720000/75710800/75710733/ce9756b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown [](https://www.expedia.co.uk/Annapolis-Hotels-Charming-Historic-Home-15-Miles-To-USNA-And-1-Mile-To-Marine-Corps-Stadium.h75710733.Hotel-Information) Homewood 9.8/10 Exceptional (9 reviews) "Our family gathered for a special celebration and loved the home! It was roomy and had everything we needed for our stay. The location was perfect for getting around." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeanie W. £342 includes taxes & fees 17 Feb - 18 Feb [](https://www.expedia.co.uk/Annapolis-Hotels-Charming-Historic-Home-15-Miles-To-USNA-And-1-Mile-To-Marine-Corps-Stadium.h75710733.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305193/8bc5c09a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305193/bff50623.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305193/75c4ec47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305193/28989db9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### London Towne Bungalow w/Loft - Walk to the Beach! [](https://www.expedia.co.uk/Edgewater-Hotels-London-Towne-Bungalow-WLoft-Walk-To-The-Beach.h96305193.Hotel-Information) Edgewater 8.8/10 Excellent (3 reviews) "Very cute house. It was exactly what I was looking for. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Collin G. £340 includes taxes & fees 17 Feb - 18 Feb [](https://www.expedia.co.uk/Edgewater-Hotels-London-Towne-Bungalow-WLoft-Walk-To-The-Beach.h96305193.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/fc34c762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/081c863e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/c9b926ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/4de85be2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 2br home w/ parking in downtown Annapolis [](https://www.expedia.co.uk/Annapolis-Hotels-Cozy-2br-Home-W-Parking-In-Downtown-Annapolis.h42019059.Hotel-Information) Historic District 10/10 Exceptional (74 reviews) "Welcoming host, great location and easy parking " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris B. £252 includes taxes & fees 19 Feb - 20 Feb [](https://www.expedia.co.uk/Annapolis-Hotels-Cozy-2br-Home-W-Parking-In-Downtown-Annapolis.h42019059.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=2026-03-01&endDate=2026-03-02®ionId=6264943&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Holiday Sale Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save. [Book now](https://expedia.co.uk/cheap-deals?rfrr=AA_SPRING_PROMO_6264943) ## Find holiday rentals that suit your style Aparthotels [](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=APART_HOTEL) Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=APARTMENT) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=VACATION_HOME) Villas [](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=VILLA) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=CONDO) Houseboats [](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=HOUSE_BOAT) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=COTTAGE) ![](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%2FShady-Side-Private-Holiday-Homes.d6264943-aaPrivateHolidayHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FShady-Side-Private-Holiday-Homes.d6264943-aaPrivateHolidayHomes.Travel-Guide-Accommodation) ## Top Shady Side Hotel Reviews ![Hilton Garden Inn Annapolis Downtown](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/4fdee6d5_y.jpg) ### Hilton Garden Inn Annapolis Downtown 10/10 Excellent "The staff was.very welcoming and so helpful with go to information. I have stayed their before and would again! Thankyou" [](https://expedia.co.uk/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information) ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Great hotel, across from State House. Restaurants within walking distance. Great little town, can’t wait to visit again . " [](https://expedia.co.uk/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Sonesta ES Suites Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe_y.jpg) ### Sonesta ES Suites Annapolis 10/10 Excellent "Great place. Perfect." [](https://expedia.co.uk/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 10/10 Excellent "The staff were so nice and helpful and the amenities were great. The restaurant and bar were great especially the breakfast and of course the cookies. The shuttle was so convenient, fast, and super polite. Great stay. I recommend and will stay again next time I'm in town. " [](https://expedia.co.uk/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Microtel Inn & Suites by Wyndham Gambrills](https://images.trvl-media.com/lodging/53000000/52810000/52802300/52802235/b7d11ace_y.jpg) ### Microtel Inn & Suites by Wyndham Gambrills 10/10 Excellent "Our room was clean and the staff was friendly. We plan to stay here again on future visits." [](https://expedia.co.uk/Gambrills-Hotels-Microtel-Inn-Suites-By-Wyndham-Gambrills.h52802235.Hotel-Information) ![Crowne Plaza Annapolis by IHG](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/6084a9f0_y.jpg) ### Crowne Plaza Annapolis by IHG 10/10 Excellent "Great stay. Room was great, staff were very friendly and helpful. " [](https://expedia.co.uk/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ![Rod 'N' Reel Resort](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/4803b1f5_y.jpg) ### Rod 'N' Reel Resort 10/10 Excellent "Newly remodeled rooms. Very clean. Staff was so friendly and courteous! I love the fact there are two restaurants on site. " [](https://expedia.co.uk/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information) ![Comfort Inn Largo-Washington DC East](https://images.trvl-media.com/lodging/1000000/20000/19400/19389/428ef9f4_y.jpg) ### Comfort Inn Largo-Washington DC East 10/10 Excellent "Staff was absolutely GREAT,very professional even the housekeepers were nice My family and I only stayed one night but enjoyed ourselves,pool was super fun for us and breakfast was good as well,most def will be booking again! Thank you for a great stay " [](https://expedia.co.uk/Upper-Marlboro-Hotels-Comfort-Inn.h19389.Hotel-Information) ![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg) ### Graduate by Hilton Annapolis 10/10 Excellent "Clean comfortable room!" [](https://expedia.co.uk/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ## Find out more about Shady Side ## Shady Side Holiday Homes information | Number of reviews | 307 | | ----------------- | ----------------- | | Accommodation | 591 Holiday Homes | | Lowest Price | £181 | | Highest Price | £408 | ## Explore a world of travel with Expedia - More ways to book - [Book Holiday Homes in Shady Side on Expedia.com ](https://www.expedia.com/Shady-Side-Private-Vacation-Homes.d6264943-aaPrivateVacationHomes.Travel-Guide-Accommodation)