Shady Side Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

This weekend
Next weekend

Our top choices for Shady Side vacation rentals

10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
$402 nightly
The price is $458
Jan 3 - Jan 4, 2026
Total with taxes and fees
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
2.0 star property
$439 nightly
The price is $445
Dec 30 - Dec 31
Total with taxes and fees
Sunset Cottage - West River Access and Views!
10.0 out of 10, Exceptional, (1)
$189 nightly
The price is $192
Jan 21 - Jan 22, 2026
Total with taxes and fees
Sailboat Experience in Annapolis
10.0 out of 10, Exceptional, (1)
"Great stay, host was super amazing and we had the best time!!"
United States
Kirstyn I.
$264 nightly
The price is $269
Jan 21 - Jan 22, 2026
Total with taxes and fees
Annapolis Boat Life - Overnight Stays
9.8 out of 10, Exceptional, (7)
"Enjoyed the stay"
United States
Kedra B.
$320 nightly
The price is $365
Dec 30 - Dec 31
Total with taxes and fees
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Condo in Historic District

Upscale Condo in Annapolis
10.0 out of 10, Exceptional, (1)
"The host family was incredible to work with. Patient with details. Easy location walking distance to USNA and the stadium. "
United States
Jennifer H.
$459 nightly
The price is $524
Jan 20 - Jan 21, 2026
Total with taxes and fees
Upscale Condo in Annapolis
10.0 out of 10, Exceptional, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
$369 nightly
The price is $407
Jan 4 - Jan 5, 2026
Total with taxes and fees
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
10.0 out of 10, Exceptional, (17)
"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.
$292 nightly
The price is $322
Jan 11 - Jan 12, 2026
Total with taxes and fees
Walk to Beach! King Bed & Free Beach Passes
9.6 out of 10, Exceptional, (32)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
$269 nightly
The price is $285
Jan 5 - Jan 6, 2026
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
9.6 out of 10, Exceptional, (4)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
$260 nightly
The price is $276
Jan 1 - Jan 2, 2026
Total with taxes and fees
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
9.6 out of 10, Exceptional, (12)
"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.
$388 nightly
The price is $411
Dec 26 - Dec 27
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
9.8 out of 10, Exceptional, (42)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
$260 nightly
The price is $275
Jan 5 - Jan 6, 2026
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Condo in Arundel on the Bay

Cozy Retreat w/Private Beach Access
2.0 star property
Cozy Retreat w/Private Beach Access
9.6 out of 10, Exceptional, (5)
"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. "
United States
Carrie K.
$367 nightly
The price is $389
Jan 4 - Jan 5, 2026
Total with taxes and fees
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
10.0 out of 10, Exceptional, (34)
"This is our second stay here and we love it. Very clean and close to everything. "
United States
Francesca K.
$321 nightly
The price is $366
Dec 29 - Dec 30
Total with taxes and fees
New Downtown Annapolis Condo With Free Parking
10.0 out of 10, Exceptional, (48)
"We love this place!"
United States
Joan K.
$268 nightly
The price is $284
Dec 26 - Dec 27
Total with taxes and fees
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
10.0 out of 10, Exceptional, (8)
"Everything was amazing. "
United States
Lorie S.
$377 nightly
The price is $400
Jan 14 - Jan 15, 2026
Total with taxes and fees
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
United States
shannan t.
$802 nightly
The price is $885
Dec 28 - Dec 29
Total with taxes and fees
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Vacation Home in Chesapeake Beach

Family Beach House: Spacious Deck, Grill & Views
9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
$448 nightly
The price is $473
Jan 25 - Jan 26, 2026
Total with taxes and fees
Family Beach House: Spacious Deck, Grill & Views

Vacation Home in Historic District

Historic Row Home in Downtown Annapolis
$637 nightly
The price is $726
Dec 29 - Dec 30
Total with taxes and fees
Historic Row Home in Downtown Annapolis
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Shady Side Hotel Reviews

Find out more about Shady Side

Everything you need to know about Shady Side vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Shady Side vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Shady Side vacation 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 low season months. For more hustle and bustle, you may prefer to visit Shady Side in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $458 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Shady Side rentals

At Expedia, we put the best Shady Side vacation 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 vacation.

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 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?

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA: This vacation home rental outside of Shady Side is located in the city center and offers a selection of games, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Shady Side?

Expedia has 11 vacation 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 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.