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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 ¥24,762
¥70,410 total
includes taxes & fees
Jan 26 - Jan 27
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!
2.0 star property
Shady Side
The price is ¥27,829
¥65,443 total
includes taxes & fees
Jan 20 - Jan 21
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, (32 reviews)
"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 ¥11,954
¥40,327 total
includes taxes & fees
Jan 21 - Jan 22
Charming Coastal/Country Home w/3 Acres & Sauna!

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 ¥8,368
¥35,856 total
includes taxes & fees
Jan 19 - Jan 20
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (17 reviews)
"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 ¥12,871
¥51,059 total
includes taxes & fees
Jan 20 - Jan 21
Walk to Beach! King Bed & Free Beach Passes

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 ¥39,530
¥66,708 total
includes taxes & fees
Jan 19 - Jan 20
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is ¥15,828
¥64,627 total
includes taxes & fees
Jan 21 - Jan 22
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

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)
"Amazing news out of the back.Great for kayaking.We brought our own kayaksAnd also use yoursThere were four of usWe also took a nice trip over to Saint Michael’s"
United States
Sandy S.
The price is ¥41,483
¥83,527 total
includes taxes & fees
Jan 20 - Jan 21
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

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

Cute, Cozy 2-bedroom house in near Annapolis with water access
2.0 star property
Herald Harbor
The price is ¥12,903
¥36,161 total
includes taxes & fees
Jan 19 - Jan 20
Cute, Cozy 2-bedroom house in near Annapolis with water access

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (5 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is ¥26,722
¥84,360 total
includes taxes & fees
Jan 19 - Jan 20
Annapolis Retreat - 7 mins from downtown Annapolis!

Holly Hill Haven - Sleeps 10

Holly Hill Haven - Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (3 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is ¥23,086
¥87,966 total
includes taxes & fees
Feb 9 - Feb 10
Holly Hill Haven - Sleeps 10

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)
"Just as advertised. Clean and quiet."
United States
Robert B.
The price is ¥18,500
¥48,489 total
includes taxes & fees
Jan 19 - Jan 20
Large 2 bedroom house with private parking in a nice neighborhood

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 reviews)
"Our family gathered for a special celebration and loved the home! It was roomy and had everything we needed for our stay. The location was perfect for getting around."
United States
Jeanie W.
The price is ¥32,019
¥77,781 total
includes taxes & fees
Jan 19 - Jan 20
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

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 ¥27,250
¥76,670 total
includes taxes & fees
Jan 19 - Jan 20
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (8 reviews)
"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 ¥27,039
¥88,004 total
includes taxes & fees
Jan 19 - Jan 20
Cute bungalow blocks to Stadium

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 ¥25,141
¥116,987 total
includes taxes & fees
Jan 19 - Jan 20
Historic Row Home | Hot Tub - 1 Block from Gate 1!

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (73 reviews)
"Great location!"
United States
Burton S.
The price is ¥19,133
¥49,391 total
includes taxes & fees
Jan 20 - Jan 21
Cozy 2br home w/ parking in downtown Annapolis

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

London Towne Bungalow w/Loft - Walk to the Beach!
Edgewater
8.8 out of 10, Excellent, (3 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is ¥23,560
¥76,790 total
includes taxes & fees
Feb 17 - Feb 18
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)
"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 ¥24,983
¥90,849 total
includes taxes & fees
Jan 19 - Jan 20
Neptune by the Water - Pet Friendly Fenced Yard

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 ¥34,865
¥81,566 total
includes taxes & fees
Feb 1 - Feb 2
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
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

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Shady Side Vacation Homes information

Number of reviews
308
Accommodation
591 Vacation Homes
Lowest Price
¥35,856
Highest Price
¥116,987