Shady Side Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Browse Select Shady Side Vacation 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 CA $280
CA $695 total
includes taxes & fees
Aug 28 - Aug 29
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 CA $137
CA $430 total
includes taxes & fees
Sep 1 - Sep 2
Waterfront Getaway, Dock Your Boat & Play!

The Cottage

10.0 out of 10, Exceptional, (7)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is CA $299
CA $650 total
includes taxes & fees
Sep 1 - Sep 2
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 CA $144
CA $424 total
includes taxes & fees
Sep 1 - Sep 2
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 CA $109
CA $380 total
includes taxes & fees
Aug 28 - Aug 29
❤️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 CA $346
CA $579 total
includes taxes & fees
Aug 28 - Aug 29
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 CA $262
CA $698 total
includes taxes & fees
Aug 28 - Aug 29
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!"
The price is CA $213
CA $738 total
includes taxes & fees
Sep 1 - Sep 2
Cute bungalow blocks to Stadium

Holly Hill Haven - Sleeps 10

10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
The price is CA $173
CA $635 total
includes taxes & fees
Sep 1 - Sep 2
Holly Hill Haven - Sleeps 10

Family Beach House: Spacious Deck, Grill & Views

9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is CA $209
CA $575 total
includes taxes & fees
Sep 16 - Sep 17
Family Beach House: Spacious Deck, Grill & Views

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 CA $466
CA $829 total
includes taxes & fees
Aug 28 - Aug 29
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."
The price is CA $311
CA $718 total
includes taxes & fees
Sep 9 - Sep 10
Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier

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

The price is CA $162
CA $837 total
includes taxes & fees
Sep 1 - Sep 2
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 CA $227
CA $731 total
includes taxes & fees
Aug 28 - Aug 29
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. "
The price is CA $216
CA $1,019 total
includes taxes & fees
Sep 1 - Sep 2
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"
The price is CA $427
CA $1,017 total
includes taxes & fees
Sep 2 - Sep 3
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 CA $220
CA $924 total
includes taxes & fees
Sep 1 - Sep 2
Freshly renovated 3-story home 1 block from USNA!

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

The price is CA $280
CA $453 total
includes taxes & fees
Aug 28 - Aug 29
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. "
The price is CA $560
CA $1,071 total
includes taxes & fees
Aug 31 - Sep 1
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!"
The price is CA $210
CA $815 total
includes taxes & fees
Sep 1 - Sep 2
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Shady Side Hotel Reviews

Find out more about Shady Side

Find out more about Shady Side

Shady Side Vacation Homes information

Number of reviews
605
Accommodation
643 Vacation Homes
Lowest Price
CA $237
Highest Price
CA $237

Explore a world of travel with Expedia

Explore a world of travel with Expedia