Shady Side Vacation Rentals

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Our top choices for Shady Side vacation rentals

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 CA $215
CA $607 total
includes taxes & fees
Feb 10 - Feb 11
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
The price is CA $219
CA $557 total
includes taxes & fees
Feb 16 - Feb 17
Sunset Cottage - West River Access and Views!

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 CA $179
CA $499 total
includes taxes & fees
Feb 10 - Feb 11
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

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 CA $287
CA $366 total
includes taxes & fees
Mar 10 - Mar 11
Annapolis Boat Life - Overnight Stays

Sailboat Experience in Annapolis

Sailboat Experience in Annapolis
Parole
10.0 out of 10, Exceptional, (1 review)
The price is CA $230
CA $296 total
includes taxes & fees
Mar 2 - Mar 3
Sailboat Experience in Annapolis

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 CA $342
CA $574 total
includes taxes & fees
Feb 10 - Feb 11
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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 CA $283
CA $563 total
includes taxes & fees
Feb 10 - Feb 11
Waterfront Oasis of Annapolis Star

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 CA $359
CA $728 total
includes taxes & fees
Feb 11 - Feb 12
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

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 CA $171
CA $532 total
includes taxes & fees
Feb 10 - Feb 11
Luxury Pool Loft sleeps 4

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 CA $131
CA $389 total
includes taxes & fees
Feb 17 - Feb 18
Charming Coastal/Country Home w/3 Acres & Sauna!

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 CA $126
CA $381 total
includes taxes & fees
Feb 17 - Feb 18
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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 CA $287
CA $507 total
includes taxes & fees
Feb 10 - Feb 11
2nd floor Spacious Downtown Getaway- Across from US Naval Academy

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 CA $236
CA $660 total
includes taxes & fees
Feb 10 - Feb 11
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

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 CA $223
CA $742 total
includes taxes & fees
Feb 10 - Feb 11
Cute bungalow blocks to Stadium

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 CA $208
CA $999 total
includes taxes & fees
Feb 10 - Feb 11
Historic Row Home | Hot Tub - 1 Block from Gate 1!

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 CA $274
CA $444 total
includes taxes & fees
Feb 10 - Feb 11
Walk to the stadium! - Lighthouse on Glenwood

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 CA $112
CA $448 total
includes taxes & fees
Feb 16 - Feb 17
Walk to Beach! King Bed & Free Beach Passes

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 CA $339
CA $660 total
includes taxes & fees
Feb 10 - Feb 11
Annapolis Gem: Stylish and Cozy

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 CA $308
CA $709 total
includes taxes & fees
Feb 10 - Feb 11
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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 CA $275
CA $680 total
includes taxes & fees
Mar 2 - Mar 3
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

Find out more about Shady Side

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Shady Side. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.