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Check prices for these dates

Next weekend
5 Dec - 7 Dec
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12 Dec - 14 Dec
In one month
26 Dec - 28 Dec
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23 Jan - 25 Jan

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)
"Would stay here again "
United States
Thomas D.
The price is SAR 540
SAR 1,608 total
includes taxes & fees
30 Nov - 1 Dec
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Property grounds
Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!

2.0 star property
Shady Side
The price is SAR 859
SAR 1,799 total
includes taxes & fees
2 Dec - 3 Dec
Sunset Cottage - West River Access and Views!
Marina
Charming Coastal/Country Home w/3 Acres & Sauna!

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

Stevensville
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
The price is SAR 295
SAR 977 total
includes taxes & fees
30 Nov - 1 Dec
Charming Coastal/Country Home w/3 Acres & Sauna!
Marina
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, (42)
"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 SAR 256
SAR 932 total
includes taxes & fees
30 Nov - 1 Dec
Relax on Kent Island in a 4 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.
The price is SAR 320
SAR 1,232 total
includes taxes & fees
1 Dec - 2 Dec
Walk to Beach! King Bed & Free Beach Passes
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, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is SAR 462
SAR 1,641 total
includes taxes & fees
30 Nov - 1 Dec
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
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.
The price is SAR 642
SAR 1,694 total
includes taxes & fees
1 Dec - 2 Dec
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
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
9.6 out of 10, Exceptional, (4)
"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.
The price is SAR 675
SAR 1,368 total
includes taxes & fees
7 Dec - 8 Dec
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
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)
"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 SAR 938
SAR 1,571 total
includes taxes & fees
1 Dec - 2 Dec
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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, (8)
"Clean and easy "
United States
Robert R.
The price is SAR 634
SAR 1,320 total
includes taxes & fees
30 Nov - 1 Dec
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
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, (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.
The price is SAR 439
SAR 1,142 total
includes taxes & fees
30 Nov - 1 Dec
Cozy 2br home w/ parking in downtown Annapolis
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, (33)
"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.
The price is SAR 490
SAR 1,217 total
includes taxes & fees
30 Nov - 1 Dec
Large 2 bedroom house with private parking in a nice neighborhood
Interior
Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Pet-Friendly Stay - Near Bay & Beaches.

Annapolis
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
The price is SAR 836
SAR 2,069 total
includes taxes & fees
2 Dec - 3 Dec
Charming Pet-Friendly Stay - Near Bay & Beaches.
Fridge, microwave, oven, stovetop
Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium

Admiral Heights
9.8 out of 10, Exceptional, (6)
"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 SAR 642
SAR 2,071 total
includes taxes & fees
30 Nov - 1 Dec
Cute bungalow blocks to Stadium
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)
"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.
The price is SAR 574
SAR 1,900 total
includes taxes & fees
3 Dec - 4 Dec
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

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Homewood
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.
The price is SAR 672
SAR 1,733 total
includes taxes & fees
1 Dec - 2 Dec
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Property grounds
New! Stylish downtown home w/awesome outdoor area!

New! Stylish downtown home w/awesome outdoor area!

Stevensville
9.8 out of 10, Exceptional, (26)
"The house was spacious, clean, and in a great location. The owners were available, and easy to communicate with."
United States
Marjorie N.
The price is SAR 919
SAR 1,996 total
includes taxes & fees
25 Dec - 26 Dec
New! Stylish downtown home w/awesome outdoor area!
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.
The price is SAR 597
SAR 2,776 total
includes taxes & fees
30 Nov - 1 Dec
Historic Row Home 1 Block from Gate 1 at USNA!
Fridge, microwave, oven, stovetop
Stunning 4 BR Home - Walking Distance to Stadium

Stunning 4 BR Home - Walking Distance to Stadium

Homewood
10.0 out of 10, Exceptional, (1)
"This house was a TEN! We booked it for family and friends to stay with us for a military retirement over homecoming weekend. The location was great. Perfect for walking to and from the stadium with kids. Easy few minutes drive or Uber to the Academy. The house was well equipped and perfect for a big group. The yard was amazing! Wish we’d planned on a family flag football game! Plenty of space in the kitchen and living room. Management was super responsive when we needed something or had a...
United States
Catherine S.
The price is SAR 915
SAR 3,434 total
includes taxes & fees
30 Nov - 1 Dec
Stunning 4 BR Home - Walking Distance to Stadium
TV
Golden Anchor Retreat; Lux Living! - Sleeps 7

Golden Anchor Retreat; Lux Living! - Sleeps 7

Edgewater
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.
The price is SAR 747
SAR 2,267 total
includes taxes & fees
2 Dec - 3 Dec
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.
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Top Shady Side Hotel Reviews

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Clean rooms, comfortable beds, friendly staff."
Nancy 2-night trip
Posted 17 hours ago
Graduate by Hilton Annapolis