Holiday Homes in Shady Side

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Featured Holiday Homes in Shady Side and around

Our top choices for Shady Side holiday homes

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 €461
includes taxes & fees
26 Sept - 27 Sept
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

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 €275
includes taxes & fees
27 Aug - 28 Aug
Waterfront Getaway, Dock Your Boat & Play!

The Cottage

10.0 out of 10, Exceptional, (7)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The Cottage

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (39)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is €242
includes taxes & fees
27 Aug - 28 Aug
Relax on Kent Island in 3 Bedroom Home w/Waterview

❤️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 €290
includes taxes & fees
8 Sept - 9 Sept
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

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

9.8 out of 10, Exceptional, (11)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is €369
includes taxes & fees
8 Sept - 9 Sept
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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 €448
includes taxes & fees
27 Aug - 28 Aug
Charming Pet-Friendly Stay - Near Bay & Beaches.

Cute bungalow blocks to Stadium

10.0 out of 10, Exceptional, (5)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
Cute bungalow blocks to Stadium

Holly Hill Haven - Sleeps 10

10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
Holly Hill Haven - Sleeps 10

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."
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

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 €525
includes taxes & fees
28 Aug - 29 Aug
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

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

10.0 out of 10, Exceptional, (9)
"Very clean - well equipped - perfect for our relaxing weekend."
Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier

Historic 3 BR Home - 15 Min Walk to N-MC Stadium

Historic 3 BR Home - 15 Min Walk to N-MC Stadium

Edgewater/Mayo Gateaway w/ Hot Tub

9.8 out of 10, Exceptional, (21)
"We had a very good time. Fenced backyard for the pet was a great added value. We could relax and visit the beach and the towns around. We really enjoyed our stay."
The price is €658
includes taxes & fees
25 Sept - 26 Sept
Edgewater/Mayo Gateaway w/ Hot Tub

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 Baystone House

10.0 out of 10, Exceptional, (1)
"The Annapolis bayside house is fully equipped with everything you would need while away from your home. Nicely decorated, clean, high tech features , plenty of games nice bedding, convenient location. It’s a townhouse with three floors so not conducive for elderly people . I would Definately rent this house again"
Annapolis Baystone House

Freshly renovated 3-story home 1 block from USNA!

9.8 out of 10, Exceptional, (37)
"Remodeled kitchen is well equipped and beautiful. "
The price is €570
includes taxes & fees
27 Aug - 28 Aug
Freshly renovated 3-story home 1 block from USNA!

2BR, 1BA Boutique Brick Beauty located in historic Eastport.

2BR, 1BA Boutique Brick Beauty located in historic Eastport.

Charming Annapolis WaterVIEW Home

9.6 out of 10, Exceptional, (54)
"It was a great home. We cooked and held the whole family sleeping comfortable. It gave us a nice place to stay close enough to the Naval Academy. My kids really enjoyed the kayaks and hot tub. They had a great view of the Chesapeake Bay. "
Charming Annapolis WaterVIEW Home

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

9.0 out of 10, Wonderful, (2)
"My mom and I visited with 8 grandchildren as part of their Christmas present. We checked out the Naval Academy, monuments in DC, and a football bowl game. The kids enjoyed the new adventures!"
Spacious 5 BR house - 5 Min Walk to N-MC Stadium!
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

Find out more about Shady Side

Shady Side Holiday Homes information

Number of reviews
644
Accommodation
654 Holiday Homes
Lowest Price
€335
Highest Price
€335

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