Shady Side Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

Tonight
Nov 9 - Nov 10
Tomorrow
Nov 10 - Nov 11
Next weekend
Nov 14 - Nov 16
In two weeks
Nov 21 - Nov 23

Vacation Rentals in Shady Side

Exterior
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)
"Very comfortable bedrooms and sitting area. Perfect location for the event we were attending. Very clean. Friendly host. "
United States
Mark E.
$376 nightly
The price is $429
Nov 11 - Nov 12
Total with taxes and fees
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Property grounds
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.

Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.

Edgewater
$2,691 nightly
The price is $3,068
Nov 11 - Nov 12
Total with taxes and fees
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
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
10.0 out of 10, Exceptional, (5)
"Great visit! Outstanding experience, beautiful houseboat, great views!"
United States
Nathan M.
$352 nightly
The price is $401
Nov 11 - Nov 12
Total with taxes and fees
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Outdoor dining
Waterfront Getaway, Dock Your Boat & Play!

Waterfront Getaway, Dock Your Boat & Play!

Edgewater
10.0 out of 10, Exceptional, (3)
"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.
$291 nightly
The price is $311
Nov 11 - Nov 12
Total with taxes and fees
Waterfront Getaway, Dock Your Boat & Play!
Terrace/patio
Historic Downtown Luxury • USNA • Waterfront

Historic Downtown Luxury • USNA • Waterfront

Historic District
$573 nightly
The price is $583
Nov 11 - Nov 12
Total with taxes and fees
Historic Downtown Luxury • USNA • Waterfront
Marina
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

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

Stevensville
9.6 out of 10, Exceptional, (31)
"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
$240 nightly
The price is $254
Nov 12 - Nov 13
Total with taxes and fees
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Marina
Relax on Kent Island in 3 Bedroom Home w/Waterview

Relax on Kent Island in 3 Bedroom Home w/Waterview

Stevensville
9.8 out of 10, Exceptional, (41)
"This is a great place for a small family and friends' weekend reunion."
United States
Paul G.
$253 nightly
The price is $268
Nov 16 - Nov 17
Total with taxes and fees
Relax on Kent Island in 3 Bedroom Home w/Waterview
Terrace/patio
Upscale Condo in Annapolis

Upscale Condo in Annapolis

Historic District
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.
$530 nightly
The price is $604
Nov 17 - Nov 18
Total with taxes and fees
Upscale Condo in Annapolis
Exterior
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)
"I was impressed with how spacious and clean the house was."
United States
Susan M.
$395 nightly
The price is $419
Nov 11 - Nov 12
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Beach nearby, sun loungers, beach towels
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

North Beach
10.0 out of 10, Exceptional, (30)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
$378 nightly
The price is $417
Nov 11 - Nov 12
Total with taxes and fees
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Microwave, oven, stovetop, dishwasher
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

2.0 star property
North Beach
10.0 out of 10, Exceptional, (1)
"Great location! Everything was on hand and it was an easy sweet little cottage to be in.It was clean and very functional with the added bonus of being so close to all the activity in North Beach.Heather was responsive and obviously cares about her guests and their stay.Highly recommend! "
United States
Georgina P.
$261 nightly
The price is $277
Nov 21 - Nov 22
Total with taxes and fees
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Outdoor pool
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Owings
10.0 out of 10, Exceptional, (48)
"Lovely property."
United States
Melissa W.
$241 nightly
The price is $255
Nov 13 - Nov 14
Total with taxes and fees
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Marina
#2 Egret Cottage Harris Cove

#2 Egret Cottage Harris Cove

Saint Michaels
10.0 out of 10, Exceptional, (1)
$355 nightly
The price is $384
Nov 16 - Nov 17
Total with taxes and fees
#2 Egret Cottage Harris Cove
3 bedrooms, iron/ironing board, travel crib, free WiFi
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

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

Prince Frederick
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. "
United States
Carrie K.
$367 nightly
The price is $389
Nov 11 - Nov 12
Total with taxes and fees
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Microwave, oven, stovetop, dishwasher
Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere
10.0 out of 10, Exceptional, (4)
"Property was perfect for my regatta crew. Loved it."
United States
Michael Q.
$483 nightly
The price is $551
Nov 23 - Nov 24
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown Annapolis!
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, (16)
"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.
$321 nightly
The price is $354
Dec 1 - Dec 2
Total with taxes and fees
Walk to Beach! King Bed & Free Beach Passes
Smart TV, books
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, (31)
"This was a great place to stay with everything you needed. I loved the furniture in the house and it was well decorated, not to mention the neighborhood was quiet and close to all these good restaurants. Parking was a breeze for us since we drove in two cars. We parked in the wrap around driveway. There is a small fenced in back yard so it was perfect to let the dog run around and do his business. The host was great and couldn’t have asked for a better stay. "
United States
Mateusz K.
$271 nightly
The price is $309
Nov 11 - Nov 12
Total with taxes and fees
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)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
$513 nightly
The price is $544
Nov 16 - Nov 17
Total with taxes and fees
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Fridge, microwave, oven, stovetop
Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium

Admiral Heights
10.0 out of 10, Exceptional, (5)
"We had a great stay in this property. The inside looks just like the pictures and feels like it was newly renovated. The kitchen and baths were spectacular. The location was great, it is less than 1/4 mile to the USNA Marine Corps Stadium and also has great access to West Street and all that has to offer. It's a nice quiet neighborhood, jogging trail right in front of the house, close to shopping and dining. The beds and linens were fresh and comfortable. The open floor plan layout...
United States
Tim G.
$477 nightly
The price is $539
Nov 11 - Nov 12
Total with taxes and fees
Cute bungalow blocks to Stadium
Fridge, microwave, oven, stovetop
Edgewater/Mayo Gateaway w/ Hot Tub

Edgewater/Mayo Gateaway w/ Hot Tub

Edgewater
9.8 out of 10, Exceptional, (24)
"We had a very good time. Fenced backyard for the pet was a great added value. We could relax and visit the beach and the towns around. We really enjoyed our stay."
United States
Mireia A.
$494 nightly
The price is $526
Nov 11 - Nov 12
Total with taxes and fees
Edgewater/Mayo Gateaway w/ Hot Tub
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Shady Side Hotel Reviews

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Great location. Every employee was so friendly and seemed happy to be there. Room was clean. Everything in the room was in good, working order. "
Courtney 2-night trip
Posted 1 day ago
Hilton Garden Inn Annapolis Downtown

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 $268 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.

Explore a world of travel with Expedia

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?

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres. : This vacation home rental outside of Shady Side is located next to a golf course and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a pool table.

How many vacation rentals will I find in Shady Side?

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

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

Shadyside Park and Chesapeake Bay are a couple of scenic spots to enjoy the outdoors, whereas Captain Avery Museum is one of the cultural attractions. Franklin Point State Park and Northern Chesapeake Bay 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.