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Check prices for these dates

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

Vacation Homes in Shady Side

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

Vacation Home in Shady Side

10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
The price is AED 588
AED 1,650 total
includes taxes & fees
9 Dec - 10 Dec
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

2.0 star property
The price is AED 841
AED 1,761 total
includes taxes & fees
2 Dec - 3 Dec
Sunset Cottage - West River Access and Views!
Marina
Charming Coastal/Country Home w/3 Acres & Sauna!

Vacation Home in 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 AED 251
AED 912 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!

Vacation Home in 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 AED 251
AED 912 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

Vacation Home in 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 AED 313
AED 1,206 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

Vacation Home in 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 AED 452
AED 1,607 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

Vacation Home in 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 AED 628
AED 1,658 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.

Vacation Home in 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 AED 661
AED 1,339 total
includes taxes & fees
4 Dec - 5 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.

Vacation Home in 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 AED 918
AED 1,538 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!

Vacation Home in Prince Frederick

10.0 out of 10, Exceptional, (8)
"Clean and easy "
United States
Robert R.
The price is AED 621
AED 1,293 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

Vacation Home in 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 AED 430
AED 1,118 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

Vacation Home in 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 AED 479
AED 1,200 total
includes taxes & fees
1 Dec - 2 Dec
Large 2 bedroom house with private parking in a nice neighborhood
Interior
Charming Pet-Friendly Stay - Near Bay & Beaches.

Vacation Home in 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 AED 818
AED 2,026 total
includes taxes & fees
2 Dec - 3 Dec
Charming Pet-Friendly Stay - Near Bay & Beaches.
Fridge, microwave, oven, stovetop
Cute bungalow blocks to Stadium

Vacation Home in 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.
Cute bungalow blocks to Stadium
Fridge, microwave, oven, stovetop
Neptune by the Water - Pet Friendly Fenced Yard

Vacation Home in 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 AED 562
AED 1,860 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

Vacation Home in 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.
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Property grounds
New! Stylish downtown home w/awesome outdoor area!

Vacation Home in 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 AED 900
AED 1,954 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!

Vacation Home in 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.
Historic Row Home 1 Block from Gate 1 at USNA!
Fridge, microwave, oven, stovetop
Stunning 4 BR Home - Walking Distance to Stadium

Vacation Home in 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.
Stunning 4 BR Home - Walking Distance to Stadium
TV
Golden Anchor Retreat; Lux Living! - Sleeps 7

Vacation Home in 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 AED 731
AED 2,219 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 16 hours ago
Graduate by Hilton Annapolis

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