A river with boats, a marina, and a town with houses and buildings.

Shady Side Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Shady Side holiday rentals

A deck with outdoor furniture, a red door, and a house with windows.

1. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
9.0 out of 10, Wonderful, (2 reviews)
"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"
United States
David S.
The price is AU$528
includes taxes & fees
27 Oct - 28 Oct
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

2. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is AU$700
includes taxes & fees
10 Nov - 11 Nov
Sunset Cottage - West River Access and Views!
A house with a yellow door and a window with a lamp outside.

3. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is AU$515
includes taxes & fees
15 Nov - 16 Nov
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

4. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (13 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is AU$782
includes taxes & fees
27 Oct - 28 Oct
Renovated Bungalow | Walk to Beach | Dog-Friendly
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

5. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (56 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is AU$434
includes taxes & fees
2 Nov - 3 Nov
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

6. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (25 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is AU$479
includes taxes & fees
2 Nov - 3 Nov
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

7. 3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views
Deale
The price is AU$612
includes taxes & fees
27 Oct - 28 Oct
3-bedroom house in Deale located on Bay many amenities and great views
A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

8. The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach
9.6 out of 10, Exceptional, (30 reviews)
"Wonderful place to visit "
United States
James L.
The price is AU$432
includes taxes & fees
27 Oct - 28 Oct
The Cozy Crab- Your Charming Haven in Lovely North Beach!
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

9. Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (6 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is AU$1,016
includes taxes & fees
27 Oct - 28 Oct
Family Home on Mayo Peninsula | Deck | Sleeps 10
A beach with chairs and a pier in the background.

10. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
"Super clean, well furnished and in a nice quiet neighborhood close to downtown Annapolis. Great place to stay!"
United States
Ryan C.
The price is AU$678
includes taxes & fees
9 Nov - 10 Nov
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

11. Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is AU$789
includes taxes & fees
9 Nov - 10 Nov
Annapolis Retreat - 7 mins from downtown Annapolis!
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

12. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (40 reviews)
"This property and host were excellent. Property was as advertised. Lovely, clean, quiet and comfortable. Owner was super responsive and check in and check out was easy. 100% recommend."
United States
Sarah
The price is AU$646
includes taxes & fees
30 Oct - 31 Oct
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

13. Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.8 out of 10, Exceptional, (28 reviews)
"Lovely place to stay. Very nice area and the host was very accommodating."
United States
Jax H.
The price is AU$297
includes taxes & fees
1 Nov - 2 Nov
Cute, Cozy 2-bedroom house near Annapolis with water access
A lighthouse with a white exterior, a balcony, and a metal roof.

14. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (49 reviews)
"Great stay"
United States
Michael V.
The price is AU$464
includes taxes & fees
2 Nov - 3 Nov
Charming Coastal/Country Home w/3 Acres & Sauna!
A waterfront patio with outdoor seating and umbrellas, overlooking a river with boats and a bridge in the background.

15. Cass-Away Luxury Houseboat

Cass-Away Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (109 reviews)
"Wonderful stay. House boat was amazing and hosts helpful and responsive! "
United States
Jamie L.
The price is AU$441
includes taxes & fees
27 Oct - 28 Oct
Cass-Away Luxury Houseboat
A deck with a view of a marina, including boats and docks.

16. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (54 reviews)
"Love This rental. One of our favorites. Small but everything needed. And the view is absolutely wonderful."
United States
Yamilet
The price is AU$399
includes taxes & fees
12 Nov - 13 Nov
Cass-N-Reel Luxury Houseboat
A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

17. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
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$770
includes taxes & fees
27 Oct - 28 Oct
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
A calm lake with a sandy shore, surrounded by trees and houses.

18. Londontowne Home | Beach | 3BR

Londontowne Home | Beach | 3BR
Edgewater
9.4 out of 10, Exceptional, (3 reviews)
"The property was beautiful with plenty of space to have a getaway with friends. The host was super communicative when we had issues with check in. Would highly recommend staying here!"
United States
Sam A.
The price is AU$1,068
includes taxes & fees
27 Oct - 28 Oct
Londontowne Home | Beach | 3BR
Aft deck with spiral staircase to the rooftop, sliding glass doors, and an unobstructed sunset view across the Magothy River from Ferry Point Marina.

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

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Arnold
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful location! Amazing restaurant down the street. Best crab dip and cream of crab soup you’ll ever have."
United States
Anonymous traveller
The price is AU$521
includes taxes & fees
28 Oct - 29 Oct
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
A living room with a beige sofa, two framed floral pictures, a wooden cabinet, and a small table with a lamp.

20. Cozy 1-bedroom studio in pleasant Crofton with AC

Cozy 1-bedroom studio in pleasant Crofton with AC
Crofton
9.0 out of 10, Wonderful, (2 reviews)
"Host was very friendly and accommodating. The location is wonderful. Lots of shops and festivities nearby could not have asked for better. Her cat was also very friendly "
United States
Michaela C.
The price is AU$210
includes taxes & fees
31 Oct - 1 Nov
Cozy 1-bedroom studio in pleasant Crofton with AC
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

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Great location, friendly staff."
Joel 3-night trip
Posted 6 hours ago
Hilton Garden Inn Annapolis Downtown

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$256 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?

Lovely bay views with kayaks, bikes, fire pit, crabbing & more: This highly rated holiday home rental in Shady Side offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 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 garden and a selection of games.

How many holiday rentals will I find in Shady Side?

Expedia has 12 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.