Shady Side Holiday Rentals

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Our top choices for Shady Side holiday rentals

10.0 out of 10, Exceptional, (4 reviews)
"Would stay here again "
United States
Thomas D.
The price is AU$607
includes taxes & fees
8 Mar - 9 Mar
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
The price is AU$619
includes taxes & fees
8 Mar - 9 Mar
Sunset Cottage - West River Access and Views!
10.0 out of 10, Exceptional, (14 reviews)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is AU$745
includes taxes & fees
3 Mar - 4 Mar
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
9.6 out of 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
Joe C.
The price is AU$580
includes taxes & fees
3 Mar - 4 Mar
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is AU$733
includes taxes & fees
3 Mar - 4 Mar
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is AU$563
includes taxes & fees
3 Mar - 4 Mar
Waterfront Oasis of Annapolis Star
9.6 out of 10, Exceptional, (34 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is AU$345
includes taxes & fees
4 Mar - 5 Mar
Charming Coastal/Country Home w/3 Acres & Sauna!
9.8 out of 10, Exceptional, (43 reviews)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is AU$345
includes taxes & fees
3 Mar - 4 Mar
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
9.6 out of 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
Carrie K.
The price is AU$538
includes taxes & fees
30 Mar - 31 Mar
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
9.4 out of 10, Exceptional, (36 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
United States
Traci L.
The price is AU$448
includes taxes & fees
3 Mar - 4 Mar
Large 2 bedroom house with private parking in a nice neighborhood
The price is AU$595
includes taxes & fees
3 Mar - 4 Mar
40' Bristol sailboat with spectacular views
10.0 out of 10, Exceptional, (4 reviews)
"Great location, easy check in/out. Everything we needed was available! Very comfortable bed, super cute property. "
United States
MJ S.
The price is AU$500
includes taxes & fees
3 Mar - 4 Mar
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Apartment in Eastport

Annapolis Gem: Stylish and Cozy
10.0 out of 10, Exceptional, (3 reviews)
"Great spot"
United States
Brian F.
The price is AU$663
includes taxes & fees
3 Mar - 4 Mar
Annapolis Gem: Stylish and Cozy
9.8 out of 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
Jeanie W.
The price is AU$699
includes taxes & fees
3 Mar - 4 Mar
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
9.2 out of 10, Wonderful, (5 reviews)
The price is AU$811
includes taxes & fees
3 Mar - 4 Mar
Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is AU$663
includes taxes & fees
3 Mar - 4 Mar
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
10.0 out of 10, Exceptional, (8 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is AU$623
includes taxes & fees
16 Mar - 17 Mar
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Holiday Home in Historic District

Fisher House: Steps From USNA + Covered Parking!
10.0 out of 10, Exceptional, (14 reviews)
"Great house and location. Great communication. We had a great time there!"
United States
Barbara S.
The price is AU$1,011
includes taxes & fees
10 Mar - 11 Mar
Fisher House: Steps From USNA + Covered Parking!

Cottage in Historic District

Secluded Cozy Cottage in Historic Downtown
9.6 out of 10, Exceptional, (16 reviews)
"This cottage is a hidden gem. Beautiful decor, perfect for our family of 4 & right in the center of all the main attractions. Jennifer was an amazing host!"
United States
Linda Q.
The price is AU$787
includes taxes & fees
10 Mar - 11 Mar
Secluded Cozy Cottage in Historic Downtown
8.0 out of 10, Very good, (3 reviews)
"Great location to walk to Navy game. Good space and great communication with property owner."
United States
Rebecca G.
The price is AU$579
includes taxes & fees
3 Mar - 4 Mar
Fabulous 5-bedroom house with AC in charming Annapolis
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.

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Top Shady Side Hotel Reviews

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, cottages, cabins, 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 favourite 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 depend 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 AU$345 per night. Entering your travel dates in the search wizard might find you 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. 

Frequently asked questions

Are there holiday rentals in Shady Side?

Yes, there are holiday rentals close to the most popular sights in Shady Side, or you can select a more secluded option if you're looking for a relaxing stay. Shady Side is known for its shopping and restaurants. Make sure you have time to check out the parks and museums during your trip.

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

Charming Annapolis WaterVIEW Home: This holiday home rental outside of Shady Side is located on the waterfront, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals will I find in Shady Side?

Expedia has 11 holiday rentals for your stay in Shady Side.

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

Northern Chesapeake Bay and Chesapeake Bay are a couple of scenic spots to enjoy the outdoors, whereas Captain Avery Museum is one of the cultural attractions. Shadyside Park and Franklin Point State Park are other places to visit while you're in town.

What’s a holiday rental in Shady Side like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Shady Side. Holiday rentals feature extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for family gatherings.