Shady Side Holiday Rentals

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Holiday Rentals in Shady Side

The Cottage

10.0 out of 10, Exceptional, (6)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is AU$696
includes taxes & fees
9 July - 10 July
The Cottage

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

10.0 out of 10, Exceptional, (1)
"Stay there while my new home was getting work done, house was clean, perfect size for my family. It’s 50 ft to an ice cream shop and laundry mat. Our hoist even included a gift card to the ice cream shop. Great communication and perfect stay for us, felt like home "
The price is AU$733
includes taxes & fees
10 July - 11 July
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

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

9.6 out of 10, Exceptional, (9)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is AU$654
includes taxes & fees
9 July - 10 July
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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

10.0 out of 10, Exceptional, (12)
"very serene, peaceful home on the bay! Amazing getaway! "
The price is AU$907
includes taxes & fees
9 July - 10 July
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

#2 Egret Cottage Harris Cove

The price is AU$589
includes taxes & fees
27 July - 28 July
#2 Egret Cottage Harris Cove

Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (17)
"Loved the location, the property, and amenities. Would definitely stay again!"
The price is AU$1,288
includes taxes & fees
2 Aug - 3 Aug
Waterfront Sunset Bayview: sleeps 6

Room for an Island getaway

2.0 star property
9.0 out of 10, Wonderful, (2)
"Was a nice place for the night we were there. It had everything we needed for the night"
The price is AU$331
includes taxes & fees
9 July - 10 July
Room for an Island getaway

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

9.6 out of 10, Exceptional, (28)
"Great place and location. Not far from good food and local hot spots. Would definitely rebook and stay here again. "
The price is AU$520
includes taxes & fees
13 July - 14 July
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (37)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is AU$521
includes taxes & fees
14 July - 15 July
Relax on Kent Island in 3 Bedroom Home w/Waterview

Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

10.0 out of 10, Exceptional, (38)
"Easy check-in and access to the property. Clean and stocked with everything we needed. Great rental for families!"
The price is AU$2,142
includes taxes & fees
21 July - 22 July
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

10.0 out of 10, Exceptional, (75)
"Property and Host were exceptional."
The price is AU$2,008
includes taxes & fees
14 July - 15 July
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.

9.4 out of 10, Exceptional, (3)
"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. "
The price is AU$837
includes taxes & fees
4 Aug - 5 Aug
Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.

Charming Pet-Friendly Stay - Near Bay & Beaches.

10.0 out of 10, Exceptional, (1)
"Tons of space with lots of amenities! Super nice neighbor hood and neighbors. Very clean as well!"
The price is AU$804
includes taxes & fees
9 July - 10 July
Charming Pet-Friendly Stay - Near Bay & Beaches.

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

9.2 out of 10, Wonderful, (5)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is AU$759
includes taxes & fees
27 July - 28 July
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Charming Cottage with Hot Tub 1 Block from the Bay

10.0 out of 10, Exceptional, (9)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is AU$1,266
includes taxes & fees
14 July - 15 July
Charming Cottage with Hot Tub 1 Block from the Bay

Neptune by the Water

9.8 out of 10, Exceptional, (9)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
The price is AU$754
includes taxes & fees
9 July - 10 July
Neptune by the Water

Charming Historic Row House in The Heart of Eastport's Horn Point

2.5 star property
10.0 out of 10, Exceptional, (1)
"Gorgeous little house in the heart of Eastport, walking distance to fabulous restaurants and a short hop over the bridge to dwtn Annapolis. The house was clean, well stocked, comfy beds, and the patio was a lovely little oasis to kick back in with a glass of wine at the end of the day. The host was very responsive and accommodating. Highly recommend! "
The price is AU$876
includes taxes & fees
21 July - 22 July
Charming Historic Row House in The Heart of Eastport's Horn Point

Annapolis Retreat - 7 mins from downtown Annapolis!

10.0 out of 10, Exceptional, (2)
"The house was roomy, perfect for a large group and it was very clean and cozy. They also provided everything that was needed to have a comfortable stay."
The price is AU$968
includes taxes & fees
9 July - 10 July
Annapolis Retreat - 7 mins from downtown Annapolis!

Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

10.0 out of 10, Exceptional, (26)
"Everything about our stay was wonderful..the hosts were so quick to respond to any questions amd were very patient with me with all of my questions..I would DEFINITELY stay here again!!"
The price is AU$636
includes taxes & fees
9 July - 10 July
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

Beach Home with King Bed and Beach Passes in a Cute Town

10.0 out of 10, Exceptional, (14)
"We had everything we needed in this townhome in North Beach. Nicely decorated, clean and the beds were comfortable! Perfect spot for our girl's weekend."
The price is AU$480
includes taxes & fees
9 July - 10 July
Beach Home with King Bed and Beach Passes in a Cute Town
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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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?

The Cottage : This highly rated holiday home rental in Shady Side has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals will I find in Shady Side?

Expedia has 10 holiday rentals for your stay in Shady Side.

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

Cultural attractions include Captain Avery Museum, whereas Shadyside Park is a spot to enjoy nature. Franklin Point State Park and London Town are a couple of places you'll find in the wider area.

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.