Holiday Homes in Shady Side

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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Shady Side holiday 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 €380
includes taxes & fees
25 Jan - 26 Jan
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!
2.0 star property
Shady Side
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, (32 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is €235
includes taxes & fees
28 Jan - 29 Jan
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 €224
includes taxes & fees
28 Jan - 29 Jan
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
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, (31 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is €375
includes taxes & fees
4 Feb - 5 Feb
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
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, (18 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 €281
includes taxes & fees
27 Jan - 28 Jan
Walk to Beach! King Bed & Free Beach Passes
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 €364
includes taxes & fees
23 Jan - 24 Jan
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Interior

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 €441
includes taxes & fees
25 Jan - 26 Jan
Annapolis Retreat - 7 mins from downtown Annapolis!
TV, books, offices

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 €482
includes taxes & fees
2 Feb - 3 Feb
Holly Hill Haven - Sleeps 10
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)
"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 €443
includes taxes & fees
23 Jan - 24 Jan
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
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)
"Just as advertised. Clean and quiet."
United States
Robert B.
The price is €265
includes taxes & fees
25 Jan - 26 Jan
Large 2 bedroom house with private parking in a nice neighborhood
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 €415
includes taxes & fees
25 Jan - 26 Jan
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Smart TV, fireplace, table football, ping pong

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, (9 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 €407
includes taxes & fees
26 Jan - 27 Jan
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
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 €419
includes taxes & fees
3 Feb - 4 Feb
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Marina

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (74 reviews)
"Great location!"
United States
Burton S.
The price is €307
includes taxes & fees
9 Feb - 10 Feb
Cozy 2br home w/ parking in downtown Annapolis
Fridge, microwave, oven, stovetop

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 €463
includes taxes & fees
26 Jan - 27 Jan
Cute bungalow blocks to Stadium
Interior

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 €619
includes taxes & fees
25 Jan - 26 Jan
Historic Row Home | Hot Tub - 1 Block from Gate 1!
Fridge, microwave, oven, stovetop

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 €520
includes taxes & fees
4 Feb - 5 Feb
Neptune by the Water - Pet Friendly Fenced Yard
Outdoor spa tub

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 €421
includes taxes & fees
17 Feb - 18 Feb
London Towne Bungalow w/Loft - Walk to the Beach!
TV

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

Cute, Cozy 2-bedroom house in near Annapolis with water access
Herald Harbor
The price is €198
includes taxes & fees
23 Jan - 24 Jan
Cute, Cozy 2-bedroom house in near Annapolis with water access
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

Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"Very clean view was amazing "
Treva 1-night trip
Posted 22 hours ago
Rod 'N' Reel Resort

Find out more about Shady Side

Shady Side Holiday Homes information

Number of reviews
310
Accommodation
591 Holiday Homes
Lowest Price
€224
Highest Price
€619