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Our top choices for Shady Side vacation homes

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 reviews)
"Would stay here again "
United States
Thomas D.
The price is ¥24,946
¥70,934 total
includes taxes & fees
Mar 16 - Mar 17
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
The price is ¥28,515
¥68,407 total
includes taxes & fees
Mar 17 - Mar 18
Sunset Cottage - West River Access and Views!

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (34 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is ¥10,939
¥39,288 total
includes taxes & fees
Mar 16 - Mar 17
Charming Coastal/Country Home w/3 Acres & Sauna!

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 reviews)
"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 ¥39,825
¥67,037 total
includes taxes & fees
Mar 16 - Mar 17
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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, (43 reviews)
"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 ¥10,939
¥39,626 total
includes taxes & fees
Mar 16 - Mar 17
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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 reviews)
"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.
The price is ¥41,706
¥84,145 total
includes taxes & fees
Mar 23 - Mar 24
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is ¥27,025
¥69,712 total
includes taxes & fees
Mar 24 - Mar 25
Family Beach House: Spacious Deck, Grill & Views

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, (36 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
United States
Traci L.
The price is ¥20,072
¥50,486 total
includes taxes & fees
Mar 15 - Mar 16
Large 2 bedroom house with private parking in a nice neighborhood

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (19 reviews)
"Delightful one-night stay! Place was clean, quiet, convenient and very comfortable. Especially grateful that our beloved dog was welcomed"
United States
Elaine D.
The price is ¥19,968
¥60,225 total
includes taxes & fees
Mar 18 - Mar 19
Walk to Beach! King Bed & Free Beach Passes

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 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is ¥39,506
¥71,089 total
includes taxes & fees
Mar 16 - Mar 17
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is ¥27,454
¥77,243 total
includes taxes & fees
Mar 15 - Mar 16
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

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, (32 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is ¥18,367
¥68,034 total
includes taxes & fees
Mar 15 - Mar 16
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

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 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is ¥37,993
¥85,807 total
includes taxes & fees
Mar 17 - Mar 18
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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, (5 reviews)
"Our family had a great stay. Thank you!"
United States
Colleen G.
The price is ¥33,931
¥64,335 total
includes taxes & fees
Mar 30 - Mar 31
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (8 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is ¥23,736
¥83,939 total
includes taxes & fees
Mar 16 - Mar 17
Cute bungalow blocks to Stadium

Wright's Cottage- Pet's Welcome & EV Charging

Wright's Cottage- Pet's Welcome & EV Charging
Annapolis
9.2 out of 10, Wonderful, (16 reviews)
"Nice little spot, very quiet "
United States
Susan S.
The price is ¥27,983
¥58,959 total
includes taxes & fees
Mar 23 - Mar 24
Wright's Cottage- Pet's Welcome & EV Charging

Cute, Cozy 2-bedroom house in near Annapolis with water access

Cute, Cozy 2-bedroom house in near Annapolis with water access
Herald Harbor
10.0 out of 10, Exceptional, (1 review)
"Host was wonderful! Enjoyed our weekend in a very clean, comfortable and peaceful place. Look forward to returning in warmer weather."
United States
Katherine P.
The price is ¥12,107
¥34,686 total
includes taxes & fees
Mar 16 - Mar 17
Cute, Cozy 2-bedroom house in near Annapolis with water access

London Towne Bungalow w/Loft - Walk to the Beach!

London Towne Bungalow w/Loft - Walk to the Beach!
Edgewater
9.0 out of 10, Wonderful, (4 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is ¥20,984
¥74,121 total
includes taxes & fees
Mar 18 - Mar 19
London Towne Bungalow w/Loft - Walk to the Beach!

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 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is ¥36,320
¥106,055 total
includes taxes & fees
Apr 13 - Apr 14
Neptune by the Water - Pet Friendly Fenced Yard

Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
10.0 out of 10, Exceptional, (5 reviews)
"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.
The price is ¥23,736
¥115,862 total
includes taxes & fees
Mar 16 - Mar 17
Historic Row Home | Hot Tub - 1 Block from Gate 1!
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

Find out more about Shady Side

Shady Side Vacation Homes information

Number of reviews
225
Accommodation
591 Vacation Homes
Lowest Price
¥34,686
Highest Price
¥115,862