Shady Side Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Shady Side vacation rentals

Smart TV

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

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Shady Side
10.0 out of 10, Exceptional, (4 reviews)
"Would stay here again "
United States
Thomas D.
The price is ￥24,762
￥70,169 total
includes taxes & fees
Feb 10 - Feb 11
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Interior

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
The price is ￥25,155
￥63,988 total
includes taxes & fees
Feb 16 - Feb 17
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
9.8 out of 10, Exceptional, (7 reviews)
"Enjoyed the stay"
United States
Kedra B.
The price is ￥20,635
￥57,579 total
includes taxes & fees
Feb 10 - Feb 11
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Fridge, microwave, oven, stovetop

Annapolis Boat Life - Overnight Stays

Annapolis Boat Life - Overnight Stays
ANNAPOLIS
10.0 out of 10, Exceptional, (1 review)
"Great stay, host was super amazing and we had the best time!!"
United States
Kirstyn I.
The price is ￥33,016
￥41,000 total
includes taxes & fees
Mar 10 - Mar 11
Annapolis Boat Life - Overnight Stays
Marina

Sailboat Experience in Annapolis

Sailboat Experience in Annapolis
Parole
10.0 out of 10, Exceptional, (1 review)
The price is ￥26,413
￥33,321 total
includes taxes & fees
Mar 2 - Mar 3
Sailboat Experience in Annapolis
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)
"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 ￥39,305
￥66,328 total
includes taxes & fees
Feb 10 - Feb 11
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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 ￥32,545
￥65,061 total
includes taxes & fees
Feb 10 - Feb 11
Waterfront Oasis of Annapolis Star
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)
"Amazing news out of the back.Great for kayaking.We brought our own kayaksAnd also use yoursThere were four of usWe also took a nice trip over to Saint Michael’s"
United States
Sandy S.
The price is ￥41,247
￥83,218 total
includes taxes & fees
Feb 10 - Feb 11
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Fridge, microwave, oven, stovetop

Luxury Pool Loft sleeps 4

Luxury Pool Loft sleeps 4
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 ￥19,653
￥61,477 total
includes taxes & fees
Feb 10 - Feb 11
Luxury Pool Loft sleeps 4
Exterior

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (32 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is ￥15,112
￥43,850 total
includes taxes & fees
Feb 18 - Feb 19
Charming Coastal/Country Home w/3 Acres & Sauna!
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, (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 ￥14,433
￥43,130 total
includes taxes & fees
Feb 17 - Feb 18
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Exterior detail

2nd floor Spacious Downtown Getaway- Across from US Naval Academy

2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Historic District
9.6 out of 10, Exceptional, (27 reviews)
"Very nice place, just two of us stayed but would fit 4 comfortably. "
United States
Brad L.
The price is ￥33,016
￥58,429 total
includes taxes & fees
Feb 10 - Feb 11
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Marina

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 ￥27,095
￥76,234 total
includes taxes & fees
Feb 10 - Feb 11
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Fridge, microwave, oven, stovetop

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (8 reviews)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
The price is ￥25,627
￥85,710 total
includes taxes & fees
Feb 10 - Feb 11
Cute bungalow blocks to Stadium
Interior

Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
10.0 out of 10, Exceptional, (5 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
The price is ￥23,897
￥114,887 total
includes taxes & fees
Feb 10 - Feb 11
Historic Row Home | Hot Tub - 1 Block from Gate 1!
Microwave, oven, stovetop, dishwasher

Walk to the stadium! - Lighthouse on Glenwood

Walk to the stadium! - Lighthouse on Glenwood
Annapolis
9.8 out of 10, Exceptional, (7 reviews)
"5 star property with plenty of street parking. Everything was clean and had all of the ammendities"
United States
Tom D.
The price is ￥39,305
￥61,476 total
includes taxes & fees
Feb 10 - Feb 11
Walk to the stadium! - Lighthouse on Glenwood
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, (18 reviews)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
The price is ￥12,853
￥51,498 total
includes taxes & fees
Feb 16 - Feb 17
Walk to Beach! King Bed & Free Beach Passes
Fridge, microwave, oven, stovetop

Annapolis Gem: Stylish and Cozy

Annapolis Gem: Stylish and Cozy
Eastport
10.0 out of 10, Exceptional, (3 reviews)
"Great spot"
United States
Brian F.
The price is ￥38,921
￥76,272 total
includes taxes & fees
Feb 10 - Feb 11
Annapolis Gem: Stylish and Cozy
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
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is ￥37,497
￥84,687 total
includes taxes & fees
Feb 11 - Feb 12
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Interior

Upscale Condo in Annapolis w/Private Parking

Upscale Condo in Annapolis w/Private Parking
Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Great condo! Very clean and convenient to everything in Annapolis. We will definitely be back."
United States
Scott P.
The price is ￥37,016
￥85,036 total
includes taxes & fees
Mar 12 - Mar 13
Upscale Condo in Annapolis w/Private Parking
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

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Clean room. Friendly staff. Good food. "
Claudia 1-night trip
Posted 18 hours ago
Crowne Plaza Annapolis by IHG

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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Frequently asked questions

Are there vacation rentals in Shady Side?

Yes, we have vacation rentals close to well known points of interest in Shady Side, or you can go with a more remote option if you're looking for relaxation. 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 vacation rentals in Shady Side?

The Blue Crab Beach House - Free beach passes : This vacation home rental outside of Shady Side is located near the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a private yard and a selection of games.

How many vacation rentals will I find in Shady Side?

Expedia has 12 vacation rentals for your stay in Shady Side.

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

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

What’s a vacation rental in Shady Side like?

Vacation rentals are private properties where you can stay for a couple of days or more in Shady Side. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for a family getaway.