Title: Shady Side Vacation Home Rentals from CA $458: Search Top Private Vacation Homes for Rent | Expedia.ca

  

[Hotels in Shady Side](https://expedia.ca/Shady-Side-Hotels.d6264943.Travel-Guide-Hotels)[Vacation Rentals in Shady Side](https://expedia.ca/Shady-Side-Vacation-Rentals.d6264943.Travel-Guide-VacationRentals)[Flights to Shady Side](https://expedia.ca/Cheap-Flights-To-Shady-Side.d6264943.Travel-Guide-Flights)[Shady Side Car Rentals](https://expedia.ca/Car-Rentals-In-Shady-Side.d6264943.Car-Rental-Guide)[Shady Side Vacation Packages](https://expedia.ca/Shady-Side.d6264943.Destination-Travel-Guides)

![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Shady Side Vacation Rentals

![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.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

Sign in to save 10% or more on thousands of hotels

[Sign in](https://www.expedia.ca/login)

![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

Next weekend

[Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6264943&startDate=2025-10-03&endDate=2025-10-05&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6264943&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6264943&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6264943&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Shady Side Vacation Homes

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103320000/103319200/103319197/201547af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, printers](https://images.trvl-media.com/lodging/104000000/103320000/103319200/103319197/ba566cbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103320000/103319200/103319197/1629612c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, printers](https://images.trvl-media.com/lodging/104000000/103320000/103319200/103319197/302865e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Cape Saint Claire

10/10

Exceptional

(36)

"Fabulous place. We’ll be booking again next year. "

[](https://www.expedia.ca/Annapolis-Hotels-Turning-Point-On-The-Little-Magothy-Large-Private-Estate.h103319197.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112540000/112534600/112534582/ece781ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/113000000/112540000/112534600/112534582/c9bc7ef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112540000/112534600/112534582/e9d5fa42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/113000000/112540000/112534600/112534582/78cb936a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Waterfront Executive Family Home Annapolis with All Amenities

Annapolis

7.4/10

Good

(3)

"Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. "

[](https://www.expedia.ca/Annapolis-Hotels-Luxury-Waterfront-Executive-Family-Home-Annapolis-With-All-Amenities.h112534582.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119500000/119494200/119494194/2f76af57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player](https://images.trvl-media.com/lodging/120000000/119500000/119494200/119494194/37f6b60c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119500000/119494200/119494194/39be2411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119500000/119494200/119494194/5954935b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 3-bedroom house in Gambrills, in the area of Annapolis, Baltimore, & DC.

Gambrills

10/10

Exceptional

(2)

"Perfect!! We enjoyed staying there and hope to come back next year. Thank you"

[](https://www.expedia.ca/Gambrills-Hotels-3-Bedroom-House-In-Gambrills.h119494194.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82800000/82795000/82794982/cdcfd11d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/83000000/82800000/82795000/82794982/ead949d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/83000000/82800000/82795000/82794982/4970419b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/83000000/82800000/82795000/82794982/764f0419.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Historic Townhouse Steps From USNA

Historic District

10/10

Exceptional

(30)

"It was great!"

[](https://www.expedia.ca/Annapolis-Hotels-Charming-Historic-Townhouse-Steps-From-USNA.h82794982.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/06a8a8c9.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)

![Exterior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/762da084.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/e5c30638.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Large 2 bedroom house with private parking in a nice neighborhood

Arnold

9.4/10

Exceptional

(28)

"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."

CA $184

CA $458 total

includes taxes & fees

Sep 30 - Oct 1

[](https://www.expedia.ca/Arnold-Hotels-Large-2-Bedroom-House-Private-Parking-Nice-Neighborhood.h89057630.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/75000000/74430000/74420700/74420621/41c0fff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/75000000/74430000/74420700/74420621/10cdcc77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/75000000/74430000/74420700/74420621/w1341h900x4y0-5e84ad4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/75000000/74430000/74420700/74420621/fd17942d.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.ca/Riva-Hotels-Riverfront-Retreat-7mil-From-MD-Renaissance-Fest.h74420621.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/35000000/34300000/34297800/34297781/3dba8eb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34300000/34297800/34297781/w696h464x4y4-e7980281.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34300000/34297800/34297781/0c67a974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/35000000/34300000/34297800/34297781/54227098.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Historic District

10/10

Exceptional

(233)

"This was a wonderful historic home to vacation in"

[](https://www.expedia.ca/Annapolis-Hotels-Directly-Across-From-Gate-One-Steps-From-The-Waterfront.h34297781.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/77000000/76260000/76259800/76259762/75c5aef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Golf](https://images.trvl-media.com/lodging/77000000/76260000/76259800/76259762/c73dd104.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76260000/76259800/76259762/6355b849.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76260000/76259800/76259762/f7286f90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### RANCH AT ROYAL OAK- Exclusive waterfront pool pier

Royal Oak

10/10

Exceptional

(26)

"Wow, what a homerun of a vacation house - it had everything we needed and more. We had the best time and hope to be back soon."

[](https://www.expedia.ca/Royal-Oak-Hotels-RANCH-AT-ROYAL-OAK-Exclusive-Waterfront-Pool-Pier.h76259762.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/88000000/87980000/87974300/87974256/8a3a7f1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, free WiFi](https://images.trvl-media.com/lodging/88000000/87980000/87974300/87974256/8e1a496c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/88000000/87980000/87974300/87974256/2f4be5f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87980000/87974300/87974256/e71ba419.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Home in Beautiful Annapolis

Annapolis

10/10

Exceptional

(13)

"Great property and very clean!"

[](https://www.expedia.ca/Annapolis-Hotels-Cozy-Home-In-Beautiful-Annapolis.h87974256.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)

![Outdoor dining](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/ba6b073a.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/43000000/42020000/42019100/42019059/5acb80c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 2br home w/ parking in downtown Annapolis

Historic District

10/10

Exceptional

(71)

"The house was clean and all amenities were provided. It was also very walkable to many restuarants and the dock street location in town. Would highly recomment this house for your next stay"

CA $244

CA $536 total

includes taxes & fees

Sep 29 - Sep 30

[](https://www.expedia.ca/Annapolis-Hotels-Cozy-2br-Home-W-Parking-In-Downtown-Annapolis.h42019059.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99230000/99230000/99229951/5203d265.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/100000000/99230000/99230000/99229951/282c7db2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![6 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/100000000/99230000/99230000/99229951/664908bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99230000/99230000/99229951/e3e394be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Historic District

10/10

Exceptional

(29)

"Great location for our team to stay during Annapolis sail show. "

[](https://www.expedia.ca/Annapolis-Hotels-Historic-AnnapolisNew-Interior5-Parking-Spaces6BR.h99229951.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119480000/119473600/119473518/8535fa00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119480000/119473600/119473518/aeae0806.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119480000/119473600/119473518/a90b515d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach towels](https://images.trvl-media.com/lodging/120000000/119480000/119473600/119473518/75b9bbad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful 2-bedroom water view house in Annapolis

Arundel on the Bay

10/10

Exceptional

(2)

"Very nice rental. Very clean and easy to access"

[](https://www.expedia.ca/Annapolis-Hotels-Beautiful-2-Bedroom-Water-View-House-In-Annapolis.h119473518.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117480000/117470400/117470324/c3d60345.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117480000/117470400/117470324/06e1da47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117480000/117470400/117470324/d3b3d87d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117480000/117470400/117470324/46cf6210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Annapolis Townhome

Historic District

10/10

Exceptional

(1)

"Great and convenient property. The host was really responsive and helped with questions and recommendations. Easy walk to downtown, naval academy and the football stadium. Parking is one block away and a lot easier than many places in the old town. "

CA $512

CA $985 total

includes taxes & fees

Sep 28 - Sep 29

[](https://www.expedia.ca/Annapolis-Hotels-Charming-Annapolis-Townhome.h117470324.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101200000/101190100/101190049/w1646h1094x1y0-5465a8de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![6 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/102000000/101200000/101190100/101190049/7087bd89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101200000/101190100/101190049/w1296h1091x4y3-c34e5260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/102000000/101200000/101190100/101190049/3ae18228.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

Historic District

9.4/10

Exceptional

(14)

"Our group had a great time! This house was super convenient location and easily walkable to Main Street. Thank you!"

CA $978

CA $1,728 total

includes taxes & fees

Oct 13 - Oct 14

[](https://www.expedia.ca/Annapolis-Hotels-Grand.h101190049.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)

![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)

![Smart TV](https://images.trvl-media.com/lodging/98000000/97560000/97553100/97553068/5d59a8a8.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)

"Excellent property, great communication with the hosts. Quite and relaxing"

[](https://www.expedia.ca/Stevensville-Hotels-Chesapeake-Waterfront-With-Hot-Tub.h97553068.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)

![Smart TV](https://images.trvl-media.com/lodging/62000000/61590000/61585600/61585503/8a18018c.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.ca/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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33960000/33951800/33951725/4fac73a5.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)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33960000/33951800/33951725/6fde9999.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis

Oyster Harbor

10/10

Exceptional

(94)

"Great property and great time in Oyster Harbour!"

[](https://www.expedia.ca/Annapolis-Hotels-Cozy-Cottage-By-The-Beach.h33951725.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/31000000/30050000/30045800/30045722/03f77dbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/31000000/30050000/30045800/30045722/ab59427a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/31000000/30050000/30045800/30045722/20159cd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/31000000/30050000/30045800/30045722/bb17f5e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming garden row home, easy 4 block walk to the heart of Annapolis.

Historic District

10/10

Exceptional

(119)

"We felt so comfortable and relaxed in this home away from home - it was beautiful and the location was perfect - so close to downtown - we were able to walk everywhere! "

[](https://www.expedia.ca/Annapolis-Hotels-Charming-Garden-Row-Home.h30045722.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74250000/74249000/74248912/907bdc93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/75000000/74250000/74249000/74248912/7228b0c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/75000000/74250000/74249000/74248912/acc4f9d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/75000000/74250000/74249000/74248912/c3b71378.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Recently Renovated Annapolis Home - Conveniently Located

Murray Hill

10/10

Exceptional

(68)

"House is beautiful and in a great location! "

[](https://www.expedia.ca/Annapolis-Hotels-Recently-Renovated-Annapolis-Home-Conveniently-Located.h74248912.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/84000000/83160000/83151800/83151743/b9a75b2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83160000/83151800/83151743/cfba789b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/84000000/83160000/83151800/83151743/561d8651.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83160000/83151800/83151743/067e07a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

Crofton

9.8/10

Exceptional

(94)

"Very nice home, the pictures don't lie. The home was super clean, had space and i felt really comfortable staying. Would definitely come back if I'm in the area again."

[](https://www.expedia.ca/Crofton-Hotels-Beautiful-Family-Sized-Townhouse-With-Deck-Close-To-Washington-DC-And-Baltimore.h83151743.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-11&endDate=2025-10-12&regionId=6264943&adults=2&lodging=VACATION_HOME&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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FShady-Side-Private-Vacation-Homes.d6264943-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FShady-Side-Private-Vacation-Homes.d6264943-aaPrivateVacationHomes.Travel-Guide-Accommodation)

## Top Shady Side Hotel Reviews

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

### DoubleTree by Hilton Hotel Largo/Washington DC

10/10 Excellent

"Nice"

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

![Hyatt Place Kent Narrows & Marina](//images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/35e0cb86_y.jpg)

### Hyatt Place Kent Narrows & Marina

10/10 Excellent

"Great location and rooms. Great place!"

[](https://expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information)

![Historic Inns of Annapolis](//images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg)

### Historic Inns of Annapolis

10/10 Excellent

"Good"

[](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.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

" evering"

[](https://expedia.ca/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information)

![Comfort Inn Conference Center](//images.trvl-media.com/lodging/1000000/20000/17300/17201/925f7921_y.jpg)

### Comfort Inn Conference Center

10/10 Excellent

"Desk staff was SO friendly and helpful with suggestions on food, coffee, best travel routes in the area, etc. I felt recognized and welcomed as me, not just "another customer". "

[](https://expedia.ca/Annapolis-Hotels-Comfort-Inn-Conference-Center.h17201.Hotel-Information)

![Microtel Inn & Suites by Wyndham Gambrills](//images.trvl-media.com/lodging/53000000/52810000/52802300/52802235/b7d11ace_y.jpg)

### Microtel Inn & Suites by Wyndham Gambrills

10/10 Excellent

"It was great accommodation. The only thing we didn't like was the pillow were not comfortable at all. Too soft and you head just sunk in. Other than that it was great. Room smelled clean and everything was very nice. "

[](https://expedia.ca/Gambrills-Hotels-Microtel-Inn-Suites-By-Wyndham-Gambrills.h52802235.Hotel-Information)

![DoubleTree by Hilton Hotel Annapolis](//images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg)

### DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"Clean room, efficient staff and superb breakfast. Grateful thanks to the hotel staff."

[](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information)

![Crowne Plaza Annapolis by IHG](//images.trvl-media.com/lodging/1000000/10000/7700/7668/6084a9f0_y.jpg)

### Crowne Plaza Annapolis by IHG

10/10 Excellent

"My wife and were away to celebrate our 34th wedding anniversary and the stay was close to home affordable and very comfortable. Hotel staff was very friendly and welcoming "

[](https://expedia.ca/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information)

![Country Inn & Suites by Radisson, Annapolis, MD](//images.trvl-media.com/lodging/1000000/150000/140400/140359/d2b7f950_y.jpg)

### Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent

"It was a very comfortable place, ver nice atmosphere."

[](https://expedia.ca/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information)

## Find out more about Shady Side

## Shady Side Vacation Homes information

| Number of reviews | 929 |
| --- | --- |
| Accommodation | 671 Vacation Homes |
| Lowest Price | CA $458 |
| Highest Price | CA $1,728 |

## Explore a world of travel with Expedia

-   Lodging
-   Flights
-   Packages
-   Cars
-   Vacation Rental
-   Other
-   More ways to book

-   [4 Star Hotels in Anchorage](https://www.expedia.ca/4Star-Anchorage-Annapolis-Hotels.s40-n553248635976473602-0.Travel-Guide-Filter-Hotels)
-   [Adults Only Resorts & in Anchorage](https://www.expedia.ca/Anchorage-Annapolis-Hotels-Adults-Only-Resorts.0-n553248635976473602-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels)
-   [Boutique Hotels in Anchorage](https://www.expedia.ca/Anchorage-Annapolis-Hotels-Boutique-Hotel.0-n553248635976473602-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
-   [Historic Hotels in Anchorage](https://www.expedia.ca/Anchorage-Annapolis-Hotels-Historic-Hotel.0-n553248635976473602-0-tHistoricHotel.Travel-Guide-Filter-Hotels)
-   [Hotels with Bar in Anchorage](https://www.expedia.ca/Anchorage-Annapolis-Hotels-Hotels-With-Bar.0-n553248635976473602-0-tHotelswithBar.Travel-Guide-Filter-Hotels)
-   [Hotels with Hot Tubs in Anchorage](https://www.expedia.ca/Anchorage-Annapolis-Hotels-Hotels-With-Hot-Tubs.0-n553248635976473602-0-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels)
-   [Hotels with an Indoor Pool in Anchorage](https://www.expedia.ca/Anchorage-Annapolis-Hotels-Hotels-With-Indoor-Pool.0-n553248635976473602-0-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels)
-   [Hotels with Kitchenettes in Anchorage](https://www.expedia.ca/Anchorage-Annapolis-Hotels-Hotels-With-Kitchenettes.0-n553248635976473602-0-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels)
-   [Lake Hotels in Anchorage](https://www.expedia.ca/Anchorage-Annapolis-Hotels-Lake-Hotels.0-n553248635976473602-0-tLakeHotels.Travel-Guide-Filter-Hotels)
-   [Luxury Hotels in Anchorage](https://www.expedia.ca/Anchorage-Annapolis-Hotels-Luxury-Hotel.0-n553248635976473602-0-tLuxuryHotel.Travel-Guide-Filter-Hotels)
-   [Pet-Friendly Hotels in Anchorage](https://www.expedia.ca/Anchorage-Annapolis-Hotels-Pet-Friendly-Hotel.0-n553248635976473602-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
-   [Scuba Diving Hotels in Anchorage](https://www.expedia.ca/Anchorage-Annapolis-Hotels-Scuba-Diving-Vacations.0-n553248635976473602-0-tscubadivingvacations.Travel-Guide-Filter-Hotels)
-   [Hotel Wedding Venues Hotels in Anchorage](https://www.expedia.ca/Anchorage-Annapolis-Hotels-Wedding-Hotels.0-n553248635976473602-0-tWeddingHotels.Travel-Guide-Filter-Hotels)
-   [Anchorage Hotels](https://www.expedia.ca/Anchorage-Annapolis-Hotels.0-n553248635976473602-0.Travel-Guide-Filter-Hotels)
-   [Beach Hotel Hotels in Arundel on the Bay](https://www.expedia.ca/Arundel-On-The-Bay-Annapolis-Hotels-Beach-Hotel.0-n553248635976475949-0-tBeachHotel.Travel-Guide-Filter-Hotels)
-   [Golf Hotels in Arundel on the Bay](https://www.expedia.ca/Arundel-On-The-Bay-Annapolis-Hotels-Golf-Hotel.0-n553248635976475949-0-tGolfHotel.Travel-Guide-Filter-Hotels)
-   [Pet-Friendly Hotels in Arundel on the Bay](https://www.expedia.ca/Arundel-On-The-Bay-Annapolis-Hotels-Pet-Friendly-Hotel.0-n553248635976475949-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
-   [Arundel on the Bay Hotels](https://www.expedia.ca/Arundel-On-The-Bay-Annapolis-Hotels.0-n553248635976475949-0.Travel-Guide-Filter-Hotels)
-   [Best Western Hotels in Beverly Beach](https://www.expedia.ca/Beverly-Beach-Hotels-Best-Western.0-0-d553248635975869024--bBestWestern.Travel-Guide-Filter-Hotels)
-   [Inns in Beverly Beach](https://www.expedia.ca/Beverly-Beach-Inns.d553248635975869024-aaInns.Travel-Guide-Accommodation)
-   [Cape Anne Hotels](https://www.expedia.ca/Cape-Anne-Hotels.d553248635976386052.Travel-Guide-Hotels)
-   [Luxury Hotels in Churchton](https://www.expedia.ca/Churchton-Hotels-Luxury-Hotel.0-0-d6247936-tLuxuryHotel.Travel-Guide-Filter-Hotels)
-   [Churchton Hotels](https://www.expedia.ca/Churchton-Hotels.d6247936.Travel-Guide-Hotels)
-   [Motels in Churchton](https://www.expedia.ca/Churchton-Motels.d6247936-aaMotels.Travel-Guide-Accommodation)
-   [Boutique Hotels in Deale](https://www.expedia.ca/Deale-Hotels-Boutique-Hotel.0-0-d55664-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
-   [Cheap Hotels in Deale](https://www.expedia.ca/Deale-Hotels-Cheap-Hotels.0-0-d55664-tCheapHotels.Travel-Guide-Filter-Hotels)
-   [Extended Stay America Hotels in Deale](https://www.expedia.ca/Deale-Hotels-Extended-Stay-America.0-0-d55664--bExtendedStayAmerica.Travel-Guide-Filter-Hotels)
-   [Deale Hotels](https://www.expedia.ca/Deale-Hotels.d55664.Travel-Guide-Hotels)
-   [Apartments in Edgewater](https://www.expedia.ca/Edgewater-Apartments.d6348965-aaApartments.Travel-Guide-Accommodation)
-   [B&B in Edgewater](https://www.expedia.ca/Edgewater-Bed-And-Breakfast.d6348965-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Chalets in Edgewater](https://www.expedia.ca/Edgewater-Chalets.d6348965-aaChalets.Travel-Guide-Accommodation)
-   [Guest Houses in Edgewater](https://www.expedia.ca/Edgewater-Guest-Houses.d6348965-aaGuestHouses.Travel-Guide-Accommodation)
-   [Beach Hotel Hotels in Edgewater](https://www.expedia.ca/Edgewater-Hotels-Beach-Hotel.0-0-d6348965-tBeachHotel.Travel-Guide-Filter-Hotels)
-   [Cheap Hotels in Edgewater](https://www.expedia.ca/Edgewater-Hotels-Cheap-Hotels.0-0-d6348965-tCheapHotels.Travel-Guide-Filter-Hotels)
-   [Luxury Hotels in Edgewater](https://www.expedia.ca/Edgewater-Hotels-Luxury-Hotel.0-0-d6348965-tLuxuryHotel.Travel-Guide-Filter-Hotels)
-   [Spa Hotels in Edgewater](https://www.expedia.ca/Edgewater-Hotels-Spa-Hotel.0-0-d6348965-tSpaHotel.Travel-Guide-Filter-Hotels)
-   [Hotel Wedding Venues Hotels in Edgewater](https://www.expedia.ca/Edgewater-Hotels-Wedding-Hotels.0-0-d6348965-tWeddingHotels.Travel-Guide-Filter-Hotels)
-   [Edgewater Hotels](https://www.expedia.ca/Edgewater-Hotels.d6348965.Travel-Guide-Hotels)
-   [Inns in Edgewater](https://www.expedia.ca/Edgewater-Inns.d6348965-aaInns.Travel-Guide-Accommodation)
-   [Lodges in Edgewater](https://www.expedia.ca/Edgewater-Lodges.d6348965-aaLodges.Travel-Guide-Accommodation)
-   [Motels in Edgewater](https://www.expedia.ca/Edgewater-Motels.d6348965-aaMotels.Travel-Guide-Accommodation)
-   [Rv Parks in Edgewater](https://www.expedia.ca/Edgewater-RV-Parks.d6348965-aaRVParks.Travel-Guide-Accommodation)
-   [Resorts in Edgewater](https://www.expedia.ca/Edgewater-Resort-Hotels.d6348965-aaResortHotels.Travel-Guide-Accommodation)
-   [Townhomes in Edgewater](https://www.expedia.ca/Edgewater-Townhomes.d6348965-aaTownhomes.Travel-Guide-Accommodation)
-   [Inns in Friendship](https://www.expedia.ca/Friendship-Inns.d3000440601-aaInns.Travel-Guide-Accommodation)
-   [Galesville Hotels](https://www.expedia.ca/Galesville-Hotels.d6264947.Travel-Guide-Hotels)
-   [B&B in Harwood](https://www.expedia.ca/Harwood-Bed-And-Breakfast.d553248635975850804-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Condo Rentals in Harwood](https://www.expedia.ca/Harwood-Condos.d553248635975850804-aaCondos.Travel-Guide-Accommodation)
-   [Luxury Hotels in Harwood](https://www.expedia.ca/Harwood-Hotels-Luxury-Hotel.0-0-d553248635975850804-tLuxuryHotel.Travel-Guide-Filter-Hotels)
-   [Harwood Hotels](https://www.expedia.ca/Harwood-Hotels.d553248635975850804.Travel-Guide-Hotels)
-   [Condo Rentals in Highland Beach](https://www.expedia.ca/Highland-Beach-Condos.d553248634998823058-aaCondos.Travel-Guide-Accommodation)
-   [Guest Houses in Highland Beach](https://www.expedia.ca/Highland-Beach-Guest-Houses.d553248634998823058-aaGuestHouses.Travel-Guide-Accommodation)
-   [Cheap Hotels in Highland Beach](https://www.expedia.ca/Highland-Beach-Hotels-Cheap-Hotels.0-0-d553248634998823058-tCheapHotels.Travel-Guide-Filter-Hotels)
-   [Luxury Hotels in Highland Beach](https://www.expedia.ca/Highland-Beach-Hotels-Luxury-Hotel.0-0-d553248634998823058-tLuxuryHotel.Travel-Guide-Filter-Hotels)
-   [Highland Beach Hotels](https://www.expedia.ca/Highland-Beach-Hotels.d553248634998823058.Travel-Guide-Hotels)
-   [Spa Hotels in Hillsmere](https://www.expedia.ca/Hillsmere-Annapolis-Hotels-Spa-Hotel.0-n553248635976473205-0-tSpaHotel.Travel-Guide-Filter-Hotels)
-   [Hotels near London Town](https://www.expedia.ca/London-Town-Hotels.0-l553248621532662270-0.Travel-Guide-Filter-Hotels)
-   [Hostels in Lothian](https://www.expedia.ca/Lothian-Hostels.d3000440697-aaHostels.Travel-Guide-Accommodation)
-   [Lothian Hotels](https://www.expedia.ca/Lothian-Hotels.d3000440697.Travel-Guide-Hotels)
-   [Resorts in Lothian](https://www.expedia.ca/Lothian-Resort-Hotels.d3000440697-aaResortHotels.Travel-Guide-Accommodation)
-   [Hotels near Maryland Quiet Waters Park](https://www.expedia.ca/Maryland-Quiet-Waters-Park-Hotels.0-l6172639-0.Travel-Guide-Filter-Hotels)
-   [B&B in Mayo](https://www.expedia.ca/Mayo-Bed-And-Breakfast.d553248634998988486-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Cabin Rentals in Mayo](https://www.expedia.ca/Mayo-Cabins.d553248634998988486-aaCabins.Travel-Guide-Accommodation)
-   [Guest Houses in Mayo](https://www.expedia.ca/Mayo-Guest-Houses.d553248634998988486-aaGuestHouses.Travel-Guide-Accommodation)
-   [Mayo Hotels](https://www.expedia.ca/Mayo-Hotels.d553248634998988486.Travel-Guide-Hotels)
-   [Motels in Mayo](https://www.expedia.ca/Mayo-Motels.d553248634998988486-aaMotels.Travel-Guide-Accommodation)
-   [Spa Hotels in Oyster Harbor](https://www.expedia.ca/Oyster-Harbor-Annapolis-Hotels-Spa-Hotel.0-n553248635976482330-0-tSpaHotel.Travel-Guide-Filter-Hotels)
-   [Apartments in Rose Haven](https://www.expedia.ca/Rose-Haven-Apartments.d153066-aaApartments.Travel-Guide-Accommodation)
-   [B&B in Rose Haven](https://www.expedia.ca/Rose-Haven-Bed-And-Breakfast.d153066-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Guest Houses in Rose Haven](https://www.expedia.ca/Rose-Haven-Guest-Houses.d153066-aaGuestHouses.Travel-Guide-Accommodation)
-   [Rose Haven Hotels](https://www.expedia.ca/Rose-Haven-Hotels.d153066.Travel-Guide-Hotels)
-   [Inns in Rose Haven](https://www.expedia.ca/Rose-Haven-Inns.d153066-aaInns.Travel-Guide-Accommodation)
-   [Aparthotels in Selby-on-the-Bay](https://www.expedia.ca/Selby-On-The-Bay-Apart-Hotels.d553248634999271692-aaApartHotels.Travel-Guide-Accommodation)
-   [Selby-On-The-Bay Hotels](https://www.expedia.ca/Selby-On-The-Bay-Hotels.d553248634999271692.Travel-Guide-Hotels)
-   [Aparthotels in Tracys Landing](https://www.expedia.ca/Tracys-Landing-Apart-Hotels.d3000440927-aaApartHotels.Travel-Guide-Accommodation)
-   [Tracys Landing Hotels](https://www.expedia.ca/Tracys-Landing-Hotels.d3000440927.Travel-Guide-Hotels)
-   [Motels in Tracys Landing](https://www.expedia.ca/Tracys-Landing-Motels.d3000440927-aaMotels.Travel-Guide-Accommodation)
-   [West River Hotels](https://www.expedia.ca/West-River-Hotels.d553248635975860906.Travel-Guide-Hotels)

-   [Flights to Deale](https://www.expedia.ca/Cheap-Flights-To-Deale.d55664.Travel-Guide-Flights)
-   [Flights to Edgewater](https://www.expedia.ca/Cheap-Flights-To-Edgewater.d6348965.Travel-Guide-Flights)
-   [Flights from Allentown (ABE) to Annapolis (ANP)](https://www.expedia.ca/lp/flights/abe/anp/allentown-to-annapolis)
-   [Flights from Buffalo (BUF) to Annapolis (ANP)](https://www.expedia.ca/lp/flights/buf/anp/buffalo-to-annapolis)
-   [Flights from Detroit (DTW) to Annapolis (ANP)](https://www.expedia.ca/lp/flights/dtw/anp/detroit-to-annapolis)
-   [Flights from Frankfurt (FRA) to Annapolis (ANP)](https://www.expedia.ca/lp/flights/fra/anp/frankfurt-to-annapolis)
-   [Flights from New York (JFK) to Annapolis (ANP)](https://www.expedia.ca/lp/flights/jfk/anp/new-york-to-annapolis)
-   [Flights from Edmonton (YEG) to Annapolis (ANP)](https://www.expedia.ca/lp/flights/yeg/anp/edmonton-to-annapolis)
-   [Flights from Montreal (YUL) to Annapolis (ANP)](https://www.expedia.ca/lp/flights/yul/anp/montreal-to-annapolis)
-   [Flights from Calgary (YYC) to Annapolis (ANP)](https://www.expedia.ca/lp/flights/yyc/anp/calgary-to-annapolis)
-   [Flights from Toronto (YYZ) to Annapolis (ANP)](https://www.expedia.ca/lp/flights/yyz/anp/toronto-to-annapolis)

-   [Visit Arundel on the Bay](https://www.expedia.ca/Annapolis-Arundel-On-The-Bay.dx553248635976475949)
-   [Visit Churchton](https://www.expedia.ca/Churchton.dx6247936)
-   [Visit Deale](https://www.expedia.ca/Deale.dx55664)
-   [Maryland Quiet Waters Park](https://www.expedia.ca/Maryland-Quiet-Waters-Park-Hillsmere.d6172639.Vacation-Attraction)
-   [Visit Selby-on-the-Bay](https://www.expedia.ca/Selby-On-The-Bay.dx553248634999271692)
-   [Shadyside Park](https://www.expedia.ca/Shadyside-Park-Shady-Side.d6263308.Vacation-Attraction)

-   [Car rental Deale](https://www.expedia.ca/Car-Rentals-In-Deale.d55664.Car-Rental-Guide)
-   [Car rental Highland Beach](https://www.expedia.ca/Car-Rentals-In-Highland-Beach.d553248634998823058.Car-Rental-Guide)
-   [Sixt Ni Rental Cars in Selby-on-the-Bay](https://www.expedia.ca/Sixt-Ni-Car-Rentals-In-Selby-On-The-Bay.d553248634999271692-c1126.Car-Rental-Guide-Suppliers)

-   [Edgewater Vacation Rentals](https://www.expedia.ca/Edgewater-Vacation-Rentals.d6348965.Travel-Guide-VacationRentals)

-   [Things to do in Edgewater](https://www.expedia.ca/Things-To-Do-In-Edgewater.d6348965.Travel-Guide-Activities)

-   [Book Vacation Homes in Shady Side on Expedia.com](https://www.expedia.com/Shady-Side-Private-Vacation-Homes.d6264943-aaPrivateVacationHomes.Travel-Guide-Accommodation)