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Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Our top choices for Shady Side vacation homes

Smart TV

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 ￥25,014
￥71,126 total
includes taxes & fees
Mar 16 - Mar 17
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Interior

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
The price is ￥34,981
￥75,527 total
includes taxes & fees
Apr 14 - Apr 15
Sunset Cottage - West River Access and Views!
Exterior

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 ￥10,184
￥38,394 total
includes taxes & fees
Mar 16 - Mar 17
Charming Coastal/Country Home w/3 Acres & Sauna!
Exterior

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 ￥10,184
￥38,733 total
includes taxes & fees
Mar 16 - Mar 17
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Dining

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 27 - Mar 28
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Interior

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 ￥20,126
￥50,622 total
includes taxes & fees
Mar 15 - Mar 16
Large 2 bedroom house with private parking in a nice neighborhood
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 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 ￥41,792
￥84,319 total
includes taxes & fees
Mar 23 - Mar 24
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Pool

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 ￥27,081
￥69,856 total
includes taxes & fees
Mar 24 - Mar 25
Family Beach House: Spacious Deck, Grill & Views
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, (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 ￥18,281
￥58,116 total
includes taxes & fees
Mar 18 - Mar 19
Walk to Beach! King Bed & Free Beach Passes
Marina

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 ￥27,528
￥77,452 total
includes taxes & fees
Mar 15 - Mar 16
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
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 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is ￥39,613
￥71,281 total
includes taxes & fees
Mar 16 - Mar 17
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Beach nearby, sun loungers, beach towels

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 ￥38,096
￥86,039 total
includes taxes & fees
Mar 17 - Mar 18
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Outdoor dining

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 ￥22,746
￥73,669 total
includes taxes & fees
Mar 15 - Mar 16
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Outdoor pool

Annapolis Garden Suite

Annapolis Garden Suite
Epping Forest
10.0 out of 10, Exceptional, (14 reviews)
"We had a quick overnight stay to attend an event at the Naval Academy! This was the perfect spot!! The accommodations were exactly what we needed!! Thanks for a great stay!!! "
United States
Mary S.
The price is ￥31,398
￥65,577 total
includes taxes & fees
Mar 16 - Mar 17
Annapolis Garden Suite
Fridge, microwave, oven, stovetop

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 ￥25,078
￥85,986 total
includes taxes & fees
Mar 22 - Mar 23
Cute bungalow blocks to Stadium
Smart TV, books

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 ￥32,265
￥61,799 total
includes taxes & fees
Apr 13 - Apr 14
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Microwave, oven, stovetop, dishwasher

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, (2 reviews)
"Cute neighborhood! Wonderful floor plan with a bedroom at each end of the house, very spacious and open. A lot of care obviously went into the update. Conveniently located. Easy access to 97 and points north as well as to Annapolis. Will definitely book again if our travels take us back to the area! Thank you for a wonderful vacation!"
United States
Kara H.
The price is ￥12,234
￥34,831 total
includes taxes & fees
Apr 8 - Apr 9
Cute, Cozy 2-bedroom house in near Annapolis with water access
TV, offices

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 ￥28,058
￥59,117 total
includes taxes & fees
Mar 23 - Mar 24
Wright's Cottage- Pet's Welcome & EV Charging
Outdoor spa tub

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 ￥21,084
￥74,475 total
includes taxes & fees
Mar 16 - Mar 17
London Towne Bungalow w/Loft - Walk to the Beach!
Interior

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is ￥28,592
￥87,222 total
includes taxes & fees
Mar 16 - Mar 17
Annapolis Retreat - 7 mins from 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

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

8/10 Good
"The room was spacious, clean but a little dated. The bathroom was small, haven’t seen a bathtub with curtain in a long time. My biggest peeve is how did they expect people to get to the hotel? There is a charge for parking a car. Not in a garage or covered garage port, but in an outdoor parking spot. Surely nobody is walking to this hotel. Another way o grab another dollar."
Barry 2-night trip
Posted 16 hours ago
Sonesta ES Suites Annapolis

Find out more about Shady Side

Shady Side Vacation Homes information

Number of reviews
230
Accommodation
591 Vacation Homes
Lowest Price
￥34,831
Highest Price
￥87,222