Search Vacation Homes in Shady Side

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

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Shady Side vacation homes

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

Vacation Home in Shady Side

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
$376 nightly
The price is $429
Dec 11 - Dec 12
Total with taxes and fees
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Property grounds
Sunset Cottage - West River Access and Views!

Vacation Home in Shady Side

Sunset Cottage - West River Access and Views!
2.0 star property
$460 nightly
The price is $466
Dec 15 - Dec 16
Total with taxes and fees
Sunset Cottage - West River Access and Views!
Marina
Charming Coastal/Country Home w/3 Acres & Sauna!

Vacation Home in Stevensville

Charming Coastal/Country Home w/3 Acres & Sauna!
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
$234 nightly
The price is $248
Dec 11 - Dec 12
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
Beach nearby
Walk to Beach! King Bed & Free Beach Passes

Vacation Home in North Beach

Walk to Beach! King Bed & Free Beach Passes
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.
$288 nightly
The price is $317
Dec 11 - Dec 12
Total with taxes and fees
Walk to Beach! King Bed & Free Beach Passes
Marina
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Vacation Home in Stevensville

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
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.
$229 nightly
The price is $242
Dec 11 - Dec 12
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Beach nearby, sun loungers, beach towels
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Vacation Home in North Beach

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
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.
$371 nightly
The price is $410
Dec 11 - Dec 12
Total with taxes and fees
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Fridge, microwave, oven, stovetop
Neptune by the Water - Pet Friendly Fenced Yard

Vacation Home in Cape Saint Claire

Neptune by the Water - Pet Friendly Fenced Yard
9.8 out of 10, Exceptional, (11)
"Very nice home, location, close to our family and activities. Enjoyed our stay and would recommend to other renters looking for spaciousness and holiness that a hotel cannot provide! "
United States
Lisa S.
$512 nightly
The price is $548
Dec 16 - Dec 17
Total with taxes and fees
Neptune by the Water - Pet Friendly Fenced Yard
4 bedrooms, desk, iron/ironing board, travel crib
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Vacation Home in Homewood

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
9.8 out of 10, Exceptional, (8)
"This house was perfect for us! We love the ease of getting into town without having to drive and park in a parking garage. I would 10/10 recommend this house!"
United States
Elaina H.
$408 nightly
The price is $465
Dec 16 - Dec 17
Total with taxes and fees
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Marina
Cozy 2br home w/ parking in downtown Annapolis

Vacation Home in Historic District

Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (72)
"Great little house easy to walk to West St, Main St & the Yard (USNA). Has parking included which is nice. Great communication we owner. Will stay again. "
United States
Sheldon E.
$353 nightly
The price is $402
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cozy 2br home w/ parking in downtown Annapolis
Smart TV
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Vacation Home in Cambridge

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
10.0 out of 10, Exceptional, (14)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
$498 nightly
The price is $528
Dec 12 - Dec 13
Total with taxes and fees
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Smart TV, books
Large 2 bedroom house with private parking in a nice neighborhood

Vacation Home in Arnold

Large 2 bedroom house with private parking in a nice neighborhood
9.4 out of 10, Exceptional, (36)
"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."
United States
Jim G.
$285 nightly
The price is $324
Dec 11 - Dec 12
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood
Fridge, microwave, oven, stovetop
Cute bungalow blocks to Stadium

Vacation Home in Admiral Heights

Cute bungalow blocks to Stadium
9.8 out of 10, Exceptional, (7)
"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.
$460 nightly
The price is $520
Dec 15 - Dec 16
Total with taxes and fees
Cute bungalow blocks to Stadium
Exterior
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Vacation Home in Grasonville

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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.
$395 nightly
The price is $419
Dec 11 - Dec 12
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Pool
Family Beach House: Spacious Deck, Grill & Views

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.
$462 nightly
The price is $488
Jan 8 - Jan 9, 2026
Total with taxes and fees
Family Beach House: Spacious Deck, Grill & Views
Interior
Historic Row Home with Hot Tub- 1 Block from Gate 1 at USNA!

Vacation Home in Historic District

Historic Row Home with Hot Tub- 1 Block from Gate 1 at USNA!
10.0 out of 10, Exceptional, (5)
"Wonderful location. Easy walking to downtown restaurants, shops, city docks and USNA. Enjoyed spending time on front porch and swing.Comfortable beds and home like atmosphere.No need for a vehicle, but if you have one, parking garage is just a few blocks away. "
United States
Katie S.
$617 nightly
The price is $703
Dec 15 - Dec 16
Total with taxes and fees
Historic Row Home with Hot Tub- 1 Block from Gate 1 at USNA!
3 bedrooms, iron/ironing board, travel crib, free WiFi
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Vacation Home in Prince Frederick

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
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.
$344 nightly
The price is $365
Dec 17 - Dec 18
Total with taxes and fees
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
TV, offices
Wright's Cottage- Pet's Welcome & EV Charging

Vacation Home in Annapolis

Wright's Cottage- Pet's Welcome & EV Charging
9.2 out of 10, Wonderful, (16)
"Great location, cozy cottage, good for dogs, lots to do in and around Annapolis. "
United States
Mike F.
$336 nightly
The price is $383
Dec 15 - Dec 16
Total with taxes and fees
Wright's Cottage- Pet's Welcome & EV Charging
Fridge, microwave, oven, stovetop
Fisher House: Steps From USNA + Covered Parking!

Vacation Home in Historic District

Fisher House: Steps From USNA + Covered Parking!
10.0 out of 10, Exceptional, (13)
"Great house and location. Great communication. We had a great time there!"
United States
Barbara S.
$663 nightly
The price is $718
Dec 11 - Dec 12
Total with taxes and fees
Fisher House: Steps From USNA + Covered Parking!
Interior
Charming Pet-Friendly Stay - Near Bay & Beaches.

Vacation Home in Annapolis

Charming Pet-Friendly Stay - Near Bay & Beaches.
10.0 out of 10, Exceptional, (6)
"The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here."
United States
Kristina
$494 nightly
The price is $563
Dec 15 - Dec 16
Total with taxes and fees
Charming Pet-Friendly Stay - Near Bay & Beaches.
TV
Golden Anchor Retreat; Lux Living! - Sleeps 7

Vacation Home in Edgewater

Golden Anchor Retreat; Lux Living! - Sleeps 7
10.0 out of 10, Exceptional, (2)
"The property was beautiful with plenty of space to have a getaway with friends. The host was super communicative when we had issues with check in. Would highly recommend staying here!"
United States
Sam A.
$593 nightly
The price is $636
Dec 16 - Dec 17
Total with taxes and fees
Golden Anchor Retreat; Lux Living! - Sleeps 7
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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Great"
stephen 3-night trip
Posted 1 day ago
DoubleTree by Hilton Hotel Annapolis

Find out more about Shady Side

Shady Side Vacation Homes information

Number of reviews
322
Accommodation
645 Vacation Homes
Lowest Price
$242
Highest Price
$718

Explore a world of travel with Expedia