Holiday Homes in Shady Side

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Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

Featured Holiday Homes in Shady Side and around

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
10.0 out of 10, Exceptional, (3)
"Very comfortable bedrooms and sitting area. Perfect location for the event we were attending. Very clean. Friendly host. "
United States
Mark E.
The price is €377
includes taxes & fees
23 Oct - 24 Oct
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Marina
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
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
The price is €242
includes taxes & fees
27 Oct - 28 Oct
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Beach nearby
Walk to Beach! King Bed & Free Beach Passes
Walk to Beach! King Bed & Free Beach Passes
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 €306
includes taxes & fees
23 Oct - 24 Oct
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.
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 €369
includes taxes & fees
23 Oct - 24 Oct
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Marina
Relax on Kent Island in 3 Bedroom Home w/Waterview
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (41)
"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 €276
includes taxes & fees
16 Nov - 17 Nov
Relax on Kent Island in 3 Bedroom Home w/Waterview
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
10.0 out of 10, Exceptional, (30)
"Absolutely beautiful and spacious home perfectly located in North Beach. Very peaceful area and close to the beach, restaurants and shopping. We really enjoyed our stay and hope to visit again in the future. "
United States
Vicki K.
The price is €432
includes taxes & fees
25 Oct - 26 Oct
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Property grounds
New! Stylish downtown home w/awesome outdoor area!
New! Stylish downtown home w/awesome outdoor area!
9.8 out of 10, Exceptional, (25)
"The house was spacious, clean, and in a great location. The owners were available, and easy to communicate with."
United States
Marjorie N.
New! Stylish downtown home w/awesome outdoor area!
Microwave, oven, stovetop, dishwasher
Annapolis Retreat - 7 mins from downtown Annapolis!
Annapolis Retreat - 7 mins from downtown Annapolis!
10.0 out of 10, Exceptional, (4)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is €482
includes taxes & fees
4 Nov - 5 Nov
Annapolis Retreat - 7 mins from downtown Annapolis!
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
9.8 out of 10, Exceptional, (11)
"Very clean - well equipped - perfect for our relaxing weekend."
United States
Chris J.
The price is €423
includes taxes & fees
4 Nov - 5 Nov
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Fridge, microwave, oven, stovetop
Cute bungalow blocks to Stadium
Cute bungalow blocks to Stadium
10.0 out of 10, Exceptional, (5)
"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 €458
includes taxes & fees
27 Oct - 28 Oct
Cute bungalow blocks to Stadium
TV, books, offices
Holly Hill Haven - Sleeps 10
Holly Hill Haven - Sleeps 10
10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is €437
includes taxes & fees
5 Nov - 6 Nov
Holly Hill Haven - Sleeps 10
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
9.4 out of 10, Exceptional, (29)
"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 €287
includes taxes & fees
17 Nov - 18 Nov
Large 2 bedroom house with private parking in a nice neighborhood
Marina
Cozy 2br home w/ parking in downtown Annapolis
Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (71)
"The house was clean and all amenities were provided. It was also very walkable to many restuarants and the dock street location in town. Would highly recomment this house for your next stay"
United States
Vincent W.
The price is €272
includes taxes & fees
4 Nov - 5 Nov
Cozy 2br home w/ parking in downtown Annapolis
Pool
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
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.
The price is €434
includes taxes & fees
20 Nov - 21 Nov
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Marina
London Towne Bungalow w/Loft - Walk to the Beach!
London Towne Bungalow w/Loft - Walk to the Beach!
8.0 out of 10, Very good, (2)
"The water that comes out of the house tastes bad."
United States
Mario A.
The price is €406
includes taxes & fees
29 Oct - 30 Oct
London Towne Bungalow w/Loft - Walk to the Beach!
Interior
Historic Row Home 1 Block from Gate 1 at USNA!
Historic Row Home 1 Block from Gate 1 at USNA!
10.0 out of 10, Exceptional, (2)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
Historic Row Home 1 Block from Gate 1 at USNA!
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!
10.0 out of 10, Exceptional, (7)
"Clean and easy "
United States
Robert R.
The price is €326
includes taxes & fees
26 Oct - 27 Oct
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Fridge, microwave, oven, stovetop
Edgewater/Mayo Gateaway w/ Hot Tub
Edgewater/Mayo Gateaway w/ Hot Tub
9.8 out of 10, Exceptional, (23)
"Very clean, had everything we needed for our stay!"
United States
Jackie R.
The price is €488
includes taxes & fees
29 Oct - 30 Oct
Edgewater/Mayo Gateaway w/ Hot Tub
3 bedrooms, iron/ironing board, travel cot, 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.
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.
The price is €362
includes taxes & fees
4 Nov - 5 Nov
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Fridge, microwave, oven, stovetop
Historic Row Home in Downtown Annapolis
Historic Row Home in Downtown Annapolis
Historic Row Home in Downtown Annapolis
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

Hampton Inn & Suites Glenarden/Washington DC

Hampton Inn & Suites Glenarden/Washington DC

10/10 Excellent
"The front desk staff was very friendly. The hotel was really nicely updated. The pool was in great condition and was a good temperature. The area had lots of stores and restaurants within just a couple of minutes of walking. The room was very clean and spacious. My only two complaints would be that 1) I think our room faced a major highway so there was some road noise but it was manageable, and 2) there was only one staff member working the breakfast, which was not sufficient. Items kept running out and she couldn't keep up with all of it on her own."
Patrisha 1-night trip
Posted 2 days ago
Hampton Inn & Suites Glenarden/Washington DC

Find out more about Shady Side

Shady Side Holiday Homes information

Number of reviews
303
Accommodation
653 Holiday Homes
Lowest Price
€242
Highest Price
€488

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