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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec
In four months
23 Jan - 25 Jan
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Exterior

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

10.0 out of 10, Exceptional, (2)
"The property is newly renovated and very comfortable. Property owner is responsive to any questions, and we enjoyed our stay here. Would recommend it for anyone staying in Shady Side."
The price is HK$1,121
HK$3,282 total
includes taxes & fees
5 Oct - 6 Oct
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Relax on Kent Island in 3 Bedroom Home w/Waterview
Marina

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (40)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
The price is HK$531
HK$1,932 total
includes taxes & fees
6 Oct - 7 Oct
Relax on Kent Island in 3 Bedroom Home w/Waterview
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Marina

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

9.6 out of 10, Exceptional, (30)
"Nice and peaceful stay for a quick local getaway. "
The price is HK$572
HK$1,967 total
includes taxes & fees
5 Oct - 6 Oct
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Exterior

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

9.6 out of 10, Exceptional, (12)
"Nice stay, would book again. Needs new king mattress, more mirrors in the home and a water filter. Very relaxing clean, makess you want to stay in and gamg out. Close to everything cool."
The price is HK$1,945
HK$3,258 total
includes taxes & fees
4 Nov - 5 Nov
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 nearby, sun-loungers, beach towels

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. "
The price is HK$1,185
HK$3,623 total
includes taxes & fees
5 Oct - 6 Oct
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Pool

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."
The price is HK$1,144
HK$3,198 total
includes taxes & fees
16 Oct - 17 Oct
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Smart TV

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

10.0 out of 10, Exceptional, (13)
"very serene, peaceful home on the bay! Amazing getaway! "
The price is HK$2,358
HK$4,281 total
includes taxes & fees
5 Oct - 6 Oct
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Walk to Beach! King Bed & Free Beach Passes
Beach nearby

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!"
The price is HK$765
HK$2,692 total
includes taxes & fees
6 Oct - 7 Oct
Walk to Beach! King Bed & Free Beach Passes
Charming Pet-Friendly Stay - Near Bay & Beaches.
Interior

Charming Pet-Friendly Stay - Near Bay & Beaches.

10.0 out of 10, Exceptional, (3)
"Tons of space with lots of amenities! Super nice neighbor hood and neighbors. Very clean as well!"
The price is HK$1,893
HK$4,492 total
includes taxes & fees
6 Oct - 7 Oct
Charming Pet-Friendly Stay - Near Bay & Beaches.
Holly Hill Haven - Sleeps 10
TV, books, offices

Holly Hill Haven - Sleeps 10

10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
The price is HK$1,152
HK$3,825 total
includes taxes & fees
27 Oct - 28 Oct
Holly Hill Haven - Sleeps 10
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Terrace/patio

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

10.0 out of 10, Exceptional, (10)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is HK$1,716
HK$4,014 total
includes taxes & fees
15 Oct - 16 Oct
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Annapolis Retreat - 7 mins from downtown Annapolis!
Microwave, oven, stovetop, dishwasher

Annapolis Retreat - 7 mins from downtown Annapolis!

10.0 out of 10, Exceptional, (3)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
The price is HK$1,517
HK$4,409 total
includes taxes & fees
4 Nov - 5 Nov
Annapolis Retreat - 7 mins from downtown Annapolis!
Waterfront Getaway, Dock Your Boat & Play!
Outdoor dining

Waterfront Getaway, Dock Your Boat & Play!

10.0 out of 10, Exceptional, (2)
"Lovely stay, don't let the RV aspect.of it scare you. Nicer than most other bnbs ice stayed in. Quiet, clean and beautiful view of the water. "
The price is HK$903
HK$2,532 total
includes taxes & fees
21 Oct - 22 Oct
Waterfront Getaway, Dock Your Boat & Play!
London Towne Bungalow w/Loft - Walk to the Beach!
Marina

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."
The price is HK$1,136
HK$3,707 total
includes taxes & fees
21 Oct - 22 Oct
London Towne Bungalow w/Loft - Walk to the Beach!
Golden Anchor Retreat; Lux Living! - Sleeps 7
Interior

Golden Anchor Retreat; Lux Living! - Sleeps 7

10.0 out of 10, Exceptional, (2)
"The property was beautiful with plenty of space to have a getaway with friends. The host was super communicative when we had issues with check in. Would highly recommend staying here!"
The price is HK$1,774
HK$5,007 total
includes taxes & fees
21 Oct - 22 Oct
Golden Anchor Retreat; Lux Living! - Sleeps 7
Wright's Cottage- Pet's Welcome & EV Charging
TV, offices

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

9.0 out of 10, Wonderful, (14)
"The property was well cleaned and communication with owner was excellent. Would stay again"
The price is HK$1,602
HK$3,184 total
includes taxes & fees
5 Oct - 6 Oct
Wright's Cottage- Pet's Welcome & EV Charging
Spacious 5 BR house - 5 Min Walk to N-MC Stadium!
Fridge, microwave, oven, stovetop

Spacious 5 BR house - 5 Min Walk to N-MC Stadium!

9.4 out of 10, Exceptional, (3)
"Great location for Navy Football. Quiet neighborhood, great outdoor space. Nice place for family to stay. "
The price is HK$1,549
HK$6,113 total
includes taxes & fees
6 Oct - 7 Oct
Spacious 5 BR house - 5 Min Walk to N-MC Stadium!
Historic Row Home 1 Block from Gate 1 at USNA!
Interior

Historic Row Home 1 Block from Gate 1 at USNA!

10.0 out of 10, Exceptional, (1)
"Wonderful location. Easy walking to downtown restaurants, shops, city docks and USNA. Enjoyed spending time on front porch and swing.Comfortable beds and home like atmosphere.No need for a vehicle, but if you have one, parking garage is just a few blocks away. "
Historic Row Home 1 Block from Gate 1 at USNA!
Annapolis Gem: Stylish and Cozy
Fridge, microwave, oven, stovetop

Annapolis Gem: Stylish and Cozy

10.0 out of 10, Exceptional, (1)
"Clean and nicely decorated. Did not realize it was a basement unit."
The price is HK$1,926
HK$3,775 total
includes taxes & fees
4 Nov - 5 Nov
Annapolis Gem: Stylish and Cozy
Neptune by the Water - Pet Friendly Fenced Yard
Fridge, microwave, oven, stovetop

Neptune by the Water - Pet Friendly Fenced Yard

9.6 out of 10, Exceptional, (10)
"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! "
The price is HK$1,673
HK$4,600 total
includes taxes & fees
29 Oct - 30 Oct
Neptune by the Water - Pet Friendly Fenced Yard
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"So the entire experience was amazing. There was so much in walking distance. It was kind of weird because there were actually 3 inns and we didn't know which one we were in"
Alison Marie 4-night trip
Posted 6 days ago
Historic Inns of Annapolis

Find out more about Shady Side

Find out more about Shady Side

Shady Side Vacation Homes information

Number of reviews
9,543
Accommodation
654 Vacation Homes
Lowest Price
HK$724
Highest Price
HK$3,536