Search Vacation Homes in Shady Side

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Vacation Homes 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 8 - Nov 9
Total with taxes and fees
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Terrace/patio
Historic Downtown Luxury • USNA • Waterfront

Historic Downtown Luxury • USNA • Waterfront

Historic District
$576 nightly
The price is $586
Nov 9 - Nov 10
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
$246 nightly
The price is $261
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.
$264 nightly
The price is $280
Nov 16 - Nov 17
Total with taxes and fees
Relax on Kent Island in 3 Bedroom Home w/Waterview
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.
$323 nightly
The price is $356
Dec 2 - Dec 3
Total with taxes and fees
Walk to Beach! King Bed & Free Beach Passes
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 10 - Nov 11
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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.
$478 nightly
The price is $545
Nov 23 - Nov 24
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown Annapolis!
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
Terrace/patio
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)
"Very clean - well equipped - perfect for our relaxing weekend."
United States
Chris J.
$416 nightly
The price is $474
Nov 12 - Nov 13
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
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.
$267 nightly
The price is $304
Nov 9 - Nov 10
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood
Pool
Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views

Chesapeake Beach
9.0 out of 10, Wonderful, (6)
"This house could not have a better location. There’s a gorgeous beach right across the street. My family and I spent many hours walking the beach looking for beach glass and shark teeth, which were surprisingly plentiful. There was even a nice dock to fish on. The house is very well kept. The upstairs table on the patio was a favorite of mine. The owner was in constant contact. We had a blast."
United States
Jeff B.
$386 nightly
The price is $404
Dec 8 - Dec 9
Total with taxes and fees
Family Beach House: Spacious Deck, Grill & Views
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.
$473 nightly
The price is $535
Nov 9 - Nov 10
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.
$485 nightly
The price is $515
Nov 12 - Nov 13
Total with taxes and fees
Edgewater/Mayo Gateaway w/ Hot Tub
Fridge, microwave, oven, stovetop
Neptune by the Water - Pet Friendly Fenced Yard

Neptune by the Water - Pet Friendly Fenced Yard

Cape Saint Claire
9.8 out of 10, Exceptional, (11)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
United States
Kelly D.
$472 nightly
The price is $502
Nov 12 - Nov 13
Total with taxes and fees
Neptune by the Water - Pet Friendly Fenced Yard
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.
$408 nightly
The price is $451
Nov 9 - Nov 10
Total with taxes and fees
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Interior
Historic Row Home 1 Block from Gate 1 at USNA!

Historic Row Home 1 Block from Gate 1 at USNA!

Historic District
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.
$635 nightly
The price is $724
Nov 10 - Nov 11
Total with taxes and fees
Historic Row Home 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.

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.
Marina
Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis

Historic District
10.0 out of 10, Exceptional, (71)
"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.
$270 nightly
The price is $308
Nov 17 - Nov 18
Total with taxes and fees
Cozy 2br home w/ parking in downtown Annapolis
TV, books, offices
Holly Hill Haven - Sleeps 10

Holly Hill Haven - Sleeps 10

Edgewater
10.0 out of 10, Exceptional, (3)
"Only thing is I would better stock the kitchen. Other than that NO COMPLAINTS! Great location, great clean and comfortable home to host thanksgiving "
United States
Brittany B.
$482 nightly
The price is $514
Nov 17 - Nov 18
Total with taxes and fees
Holly Hill Haven - Sleeps 10
Beach
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Prince Frederick
10.0 out of 10, Exceptional, (7)
"This house was extremely clean and a comfortable choice for 4 older adults attending a family wedding in St Leonard. "
United States
Susan W.
$386 nightly
The price is $409
Nov 10 - Nov 11
Total with taxes and fees
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
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

Comfort Inn Conference Center

Comfort Inn Conference Center

10/10 Excellent
"Except for a hardwater stain in the toilet, the room appeared clean and smelled fresh. I did my usual strip the beds, clean the bathroom, wipe down ALL surfaces (counters, tables, remote control, telephone, handles, light fixtures, and the leatherettte chair), and sprayed Lysol. The wipes came back clean. Breakfast included a variety of food, the attendants were attentive, and the food was very good. I would stay there again. The only problem we had was with the directions; we couldn't find the hotel and had to call for assistance."
Mozetta 1-night trip
Posted 20 hours ago
Comfort Inn Conference Center

Find out more about Shady Side

Shady Side Vacation Homes information

Number of reviews
316
Accommodation
645 Vacation Homes
Lowest Price
$261
Highest Price
$724

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