Shady Side Holiday Rentals

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Shady Side holiday rentals

Interior

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (4 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 HK$2,422
HK$4,446 total
includes taxes & fees
16 Jun - 17 Jun
Sunset Cottage - West River Access and Views!
Terrace/patio

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
9.6 out of 10, Exceptional, (10 reviews)
"Great place!"
United States
Chris A.
The price is HK$1,555
HK$3,515 total
includes taxes & fees
16 Jun - 17 Jun
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Marina

Sailboat Experience in Annapolis

Sailboat Experience in Annapolis
Parole
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,686
HK$2,147 total
includes taxes & fees
4 Jun - 5 Jun
Sailboat Experience in Annapolis
Outdoor dining

Waterfront Unit | Dock, Kayaks & SUPs Included

Waterfront Unit | Dock, Kayaks & SUPs Included
Edgewater
10.0 out of 10, Exceptional, (3 reviews)
"Great place to stay. It is clean, comfortable, and not lacking convenience.Quick communication with the host. We would definitely recommend!"
United States
Daniel K.
The price is HK$1,520
HK$3,627 total
includes taxes & fees
31 May - 1 Jun
Waterfront Unit | Dock, Kayaks & SUPs Included
Exterior

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, (45 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is HK$853
HK$2,259 total
includes taxes & fees
2 Jun - 3 Jun
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Dining

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (12 reviews)
"Great overnight stay for a wedding nearby. Would highly recommend!"
United States
Kevin F.
The price is HK$1,959
HK$3,281 total
includes taxes & fees
1 Jun - 2 Jun
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Exterior

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (35 reviews)
"Great response time, the place is quite, house is huge and a lot of sleeping places."
United States
Luccas C.
The price is HK$970
HK$2,382 total
includes taxes & fees
3 Jun - 4 Jun
Charming Coastal/Country Home w/3 Acres & Sauna!
Interior

Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (40 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 HK$987
HK$2,474 total
includes taxes & fees
7 Jun - 8 Jun
Large 2 bedroom house with private parking in a nice neighborhood
Smart TV

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
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 HK$2,661
HK$4,889 total
includes taxes & fees
2 Jun - 3 Jun
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Beach nearby

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (20 reviews)
"Everything was exceptional! We will be back. "
United States
Kimberly F.
The price is HK$1,230
HK$3,279 total
includes taxes & fees
14 Jun - 15 Jun
Walk to Beach! King Bed & Free Beach Passes
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is HK$1,904
HK$3,609 total
includes taxes & fees
1 Jun - 2 Jun
Waterfront Oasis of Annapolis Star
Microwave, oven, stovetop, dishwasher

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

Cute, Cozy 2-bedroom house in near Annapolis with water access
Herald Harbor
9.8 out of 10, Exceptional, (7 reviews)
"Host was wonderful! Enjoyed our weekend in a very clean, comfortable and peaceful place. Look forward to returning in warmer weather."
United States
Katherine P.
The price is HK$677
HK$1,835 total
includes taxes & fees
10 Jun - 11 Jun
Cute, Cozy 2-bedroom house in near Annapolis with water access
Pool

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is HK$2,186
HK$4,922 total
includes taxes & fees
4 Jun - 5 Jun
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Outdoor dining

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (70 reviews)
"The host was very welcoming and responsive before and during the stay for my questions. The house was clean and comfortable. The hot tub was lovely for a soak. We enjoyed the walk to and sitting on the peaceful community beach. Thank you!"
United States
Kathy S.
The price is HK$2,108
HK$4,591 total
includes taxes & fees
10 Jun - 11 Jun
Charming Annapolis WaterVIEW Home
Fridge, microwave, oven, stovetop

Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (4 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is HK$1,638
HK$3,868 total
includes taxes & fees
10 Jun - 11 Jun
Pool Loft Suite | Bay Access & Beach Passes
Interior

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 HK$1,802
HK$4,672 total
includes taxes & fees
8 Jun - 9 Jun
Annapolis Retreat - 7 mins from downtown Annapolis!
Private kitchen

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 HK$1,918
HK$4,242 total
includes taxes & fees
29 Jun - 30 Jun
3-bedroom house in Deale located on Bay many amenities and great views
Fridge, microwave, oven, stovetop

Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.4 out of 10, Exceptional, (6 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is HK$1,637
HK$4,492 total
includes taxes & fees
6 Jun - 7 Jun
Renovated Bungalow | Walk to Beach | Dog-Friendly
Fridge, microwave, oven, stovetop

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.8 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is HK$2,069
HK$5,655 total
includes taxes & fees
6 Jun - 7 Jun
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Beach nearby, sun-loungers, beach towels

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, (14 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is HK$2,751
HK$5,369 total
includes taxes & fees
2 Jun - 3 Jun
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
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

Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"Always a great location and nice staff. Only reason I did not give a 5 star is because the coffee maker in the room did not work."
Lewis 1-night trip
Posted 1 hour ago
Historic Inns of Annapolis

Find out more about Shady Side

Search for holiday rentals in Shady Side on Expedia! You can easily find your home rentals, villas, holiday apartments in Shady Side using one of the methods below:

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Look no further and take a look at our great range of rental properties in Shady Side!

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.