Title: Holiday Rentals Shady Side from £956: Find Short-Term Rentals & Holiday Accommodations | 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)[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)

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## 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 rentals

![Smart TV](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/0100abcb.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/117000000/116010000/116005700/116005601/1bc5d356.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

[](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.

£327

includes taxes & fees

10 Feb - 11 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)

![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)

![Terrace/patio](https://images.trvl-media.com/lodging/123000000/122690000/122684200/122684164/d2005c57.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

£298

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)

![Terrace/patio](https://images.trvl-media.com/lodging/100000000/99520000/99518900/99518844/4b955546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/100000000/99520000/99518900/99518844/14020520.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/100000000/99520000/99518900/99518844/9c7dbc30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, stereo](https://images.trvl-media.com/lodging/100000000/99520000/99518900/99518844/d131334a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

[](https://www.expedia.co.uk/Arnold-Hotels-Bung-A-Flo-Tiny-Bohemian-Designed-Floating-Home-W-360-Waterfront-Views.h99518844.Hotel-Information)

Arnold

9.8/10

Exceptional

(7 reviews)

"Enjoyed the stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kedra B.

£266

includes taxes & fees

10 Feb - 11 Feb

[](https://www.expedia.co.uk/Arnold-Hotels-Bung-A-Flo-Tiny-Bohemian-Designed-Floating-Home-W-360-Waterfront-Views.h99518844.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102770000/102761900/102761818/f435d690.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102770000/102761900/102761818/7c9eec10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102770000/102761900/102761818/c718db9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi](https://images.trvl-media.com/lodging/103000000/102770000/102761900/102761818/ece96a3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Annapolis Boat Life - Overnight Stays

[](https://www.expedia.co.uk/Annapolis-Hotels-Annapolis-Boat-Life-Overnight-Stays.h102761818.Hotel-Information)

ANNAPOLIS

10/10

Exceptional

(1 review)

"Great stay, host was super amazing and we had the best time!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kirstyn I.

£195

includes taxes & fees

10 Mar - 11 Mar

[](https://www.expedia.co.uk/Annapolis-Hotels-Annapolis-Boat-Life-Overnight-Stays.h102761818.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/103000000/102760000/102759300/102759203/1b7ace28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102760000/102759300/102759203/0c843e91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/103000000/102760000/102759300/102759203/9891f005.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102760000/102759300/102759203/e1e4be63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sailboat Experience in Annapolis

[](https://www.expedia.co.uk/Annapolis-Hotels-Sailboat-Experience-In-Annapolis.h102759203.Hotel-Information)

Parole

10/10

Exceptional

(1 review)

£159

includes taxes & fees

2 Mar - 3 Mar

[](https://www.expedia.co.uk/Annapolis-Hotels-Sailboat-Experience-In-Annapolis.h102759203.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)

![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)

![Smart TV, table football](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/44a64359.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)

### 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.

£311

includes taxes & fees

10 Feb - 11 Feb

[](https://www.expedia.co.uk/Spacious-2-Bedroom-Duplex-Located-Conveniently-Near-Route-50-East-And-West.h99830322.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/b2a36b22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/8c6112e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/95f44d8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/8e1aa433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront Oasis of Annapolis Star

[](https://www.expedia.co.uk/Annapolis-Hotels-Waterfront-Oasis-Sleep-4-Close-To-Downtown.h68986275.Hotel-Information)

Annapolis

10/10

Exceptional

(81 reviews)

"Owners were great hosts. Loved this property!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Thomas

£298

includes taxes & fees

10 Feb - 11 Feb

[](https://www.expedia.co.uk/Annapolis-Hotels-Waterfront-Oasis-Sleep-4-Close-To-Downtown.h68986275.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)

![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)

![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.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.

£381

includes taxes & fees

10 Feb - 11 Feb

[](https://www.expedia.co.uk/Cambridge-Hotels-WATERFRONT-3-Bed-Oasis-On-2-Acres-Sleeps-8.h83066154.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117370000/117360200/117360157/8d73bbbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117370000/117360200/117360157/a19fc40c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/118000000/117370000/117360200/117360157/45c5363e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117370000/117360200/117360157/28c9186e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Pool Loft sleeps 4

[](https://www.expedia.co.uk/Annapolis-Hotels-New-The-Pool-Loft-At-Poplar-Hill.h117360157.Hotel-Information)

Cape Saint Claire

10/10

Exceptional

(4 reviews)

"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ana S.

£282

includes taxes & fees

10 Feb - 11 Feb

[](https://www.expedia.co.uk/Annapolis-Hotels-New-The-Pool-Loft-At-Poplar-Hill.h117360157.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)

![Dining](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/7d796cd2.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.

£209

includes taxes & fees

17 Feb - 18 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)

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/c77382da.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.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.

£199

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)

![Exterior detail](https://images.trvl-media.com/lodging/77000000/76590000/76586000/76585906/1af81f7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76590000/76586000/76585906/7d32385a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/77000000/76590000/76586000/76585906/0ff4c45c.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/77000000/76590000/76586000/76585906/8e972348.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2nd floor Spacious Downtown Getaway- Across from US Naval Academy

[](https://www.expedia.co.uk/Annapolis-Hotels-Spacious-Downtown-Getaway-Across-From-US-Naval-Academy.h76585906.Hotel-Information)

Historic District

9.6/10

Exceptional

(27 reviews)

"Very nice place, just two of us stayed but would fit 4 comfortably. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Brad L.

£277

includes taxes & fees

10 Feb - 11 Feb

[](https://www.expedia.co.uk/Annapolis-Hotels-Spacious-Downtown-Getaway-Across-From-US-Naval-Academy.h76585906.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)

![Dining](https://images.trvl-media.com/lodging/102000000/101090000/101083600/101083507/f2ba56b9.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)

![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

£355

includes taxes & fees

10 Feb - 11 Feb

[](https://www.expedia.co.uk/Annapolis-Hotels-Bay-Ridge-Unit-By-Downtown-Annapolis-And-Quiet-Waters-Park.h101083507.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)

![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)

![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100210000/100202700/100202663/98bec3d6.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)

### 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.

£389

includes taxes & fees

10 Feb - 11 Feb

[](https://www.expedia.co.uk/Annapolis-Hotels-Cute-Bungalow-Blocks-To-Stadium.h100202663.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/1aa587de_edited_b1ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/w1359h906x3y0-7a94439d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/w1514h908x8y2-08d635bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/w1359h908x3y0-283a58db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Row Home | Hot Tub - 1 Block from Gate 1!

[](https://www.expedia.co.uk/Annapolis-Hotels-Historic-Row-Home-Hot-Tub-1-Block-From-Gate-1.h117588789.Hotel-Information)

Historic District

10/10

Exceptional

(5 reviews)

"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tracie B.

£523

includes taxes & fees

10 Feb - 11 Feb

[](https://www.expedia.co.uk/Annapolis-Hotels-Historic-Row-Home-Hot-Tub-1-Block-From-Gate-1.h117588789.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/119000000/118090000/118087600/118087589/c54c30fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118090000/118087600/118087589/1a8667d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118090000/118087600/118087589/97972db8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/119000000/118090000/118087600/118087589/3de2c820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk to the stadium! - Lighthouse on Glenwood

[](https://www.expedia.co.uk/Annapolis-Hotels-Walk-To-The-Stadium-Lighthouse-On-Glenwood.h118087589.Hotel-Information)

Annapolis

9.8/10

Exceptional

(7 reviews)

"5 star property with plenty of street parking. Everything was clean and had all of the ammendities"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tom D.

£243

includes taxes & fees

10 Feb - 11 Feb

[](https://www.expedia.co.uk/Annapolis-Hotels-Walk-To-The-Stadium-Lighthouse-On-Glenwood.h118087589.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)

![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)

![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)

### 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.

£236

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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630212/c38145a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630212/8fb2f231.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630212/2d43a6e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630212/94a88eae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Annapolis Gem: Stylish and Cozy

[](https://www.expedia.co.uk/Annapolis-Hotels-Annapolis-Gem-Stylish-And-Cozy.h117630212.Hotel-Information)

Eastport

10/10

Exceptional

(3 reviews)

"Great spot"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Brian F.

£350

includes taxes & fees

10 Feb - 11 Feb

[](https://www.expedia.co.uk/Annapolis-Hotels-Annapolis-Gem-Stylish-And-Cozy.h117630212.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)

![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)

![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)

### 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.

£370

includes taxes & fees

10 Feb - 11 Feb

[](https://www.expedia.co.uk/Annapolis-Hotels-Charming-Cottage-With-Hot-Tub-1-Block-From-The-Bay.h91033683.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/119000000/118830000/118824200/118824130/964bce68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118830000/118824200/118824130/70b0ea71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118830000/118824200/118824130/4940f0a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118830000/118824200/118824130/3ab90a95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Upscale Condo in Annapolis w/Private Parking

[](https://www.expedia.co.uk/Annapolis-Hotels-Upscale-Condo-In-Annapolis.h118824130.Hotel-Information)

Historic District

10/10

Exceptional

(2 reviews)

"Great condo! Very clean and convenient to everything in Annapolis. We will definitely be back."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Scott P.

£365

includes taxes & fees

1 Mar - 2 Mar

[](https://www.expedia.co.uk/Annapolis-Hotels-Upscale-Condo-In-Annapolis.h118824130.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=2026-02-23&endDate=2026-02-24&regionId=6264943&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## 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&regionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America&regionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=APARTMENT)

Private holiday homes

[](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America&regionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=VACATION_HOME)

Villas

[](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America&regionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=VILLA)

Cottages

[](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America&regionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=COTTAGE)

Condos

[](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America&regionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=CONDO)

Houseboats

[](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America&regionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=HOUSE_BOAT)

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## 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 room was ready early and very clean..staff was very friendly "

[](https://expedia.co.uk/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.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

"Wonderful stay! Automatic checkout 2pm. Thank you!!"

[](https://expedia.co.uk/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.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

"Room was spotless. Staff was very courteous. Would highly recommended."

[](https://expedia.co.uk/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.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

"We were happy to stay at this place. Very beautiful, warm, comfortable ❤️❤️❤️"

[](https://expedia.co.uk/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.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

"Staff was courteous "

[](https://expedia.co.uk/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information)

![DoubleTree by Hilton Hotel Largo/Washington DC](https://images.trvl-media.com/lodging/1000000/30000/21500/21463/aa92a5c8_y.jpg)

### DoubleTree by Hilton Hotel Largo/Washington DC

10/10 Excellent

"Staff was super friendly and helpful - rooms had good sound proofing. I could hear a party going on while I was in the hallway but didn’t hear it at all in my room. My daughter had a competition the next day so the peace and quiet was important. "

[](https://expedia.co.uk/Waldorf-Hotels-DoubleTree-By-Hilton-Hotel-Largo-Washington-DC.h21463.Hotel-Information)

![Holiday Inn Express I-95 Capitol Beltway-Largo by IHG](https://images.trvl-media.com/lodging/2000000/1360000/1357100/1357084/faf6da25_y.jpg)

### Holiday Inn Express I-95 Capitol Beltway-Largo by IHG

10/10 Excellent

"Nice and clean. Pleasant staff."

[](https://expedia.co.uk/Waldorf-Hotels-Holiday-Inn-Express-I-95-Capitol-Beltway-Largo.h1357084.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

"Very convenient location, clean and nice staff. "

[](https://expedia.co.uk/Gambrills-Hotels-Microtel-Inn-Suites-By-Wyndham-Gambrills.h52802235.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

"Everything about this beautiful historic hotel was beautiful and perfect—I can’t wait to come back!"

[](https://expedia.co.uk/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information)

## Find out more about Shady Side

**Everything you need to know about** **Shady Side** **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 Shady Side 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 Shady Side holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Shady Side holiday rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Shady Side. 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 Shady Side 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 Shady Side holiday rentals we have selected for you start as low as £956 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Shady Side rentals**

At Expedia, we put the best Shady Side 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 Shady Side 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 Shady Side 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 Shady Side. 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

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- [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

### Are there holiday rentals in Shady Side?

### What are some of the best holiday rentals that Shady Side has to offer?

### How many holiday rentals will I find in Shady Side?

### What’s there to see and do in Shady Side?

### What’s a holiday rental in Shady Side like?

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