Search Holiday Rentals in Shady Side

    price find illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Save instantly and earn perks with One Key
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Top Holiday Rentals in Shady Side

The Cottage

10.0 out of 10, Exceptional, (6)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is £339
includes taxes & fees
7 Jul - 8 Jul
The Cottage

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

10.0 out of 10, Exceptional, (210)
"Great views and location. Well furnished and very comfortable. We will definitely be staying here again. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (45)
"This was our 2nd time at the house and it was just as relaxing as we hoped. Nice, quiet location and beautiful home!"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (28)
"Great place for gathering. Plenty of space to hang out. Kitchen is big, well stocked and great for a large crowd. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (61)
"The property was well- maintained and the kitchen was well-equipped for our needs. Short walk to North Beach for dining and Boardwalk strolls. Nice and toasty for our winter stay - really enjoyed the trip."
The Blue Crab Beach House - Free beach passes

Annapolis Condominium in the heart of the historic center

9.8 out of 10, Exceptional, (274)
"The location and amenities are great. The host are very friendly, helpful and easy to make contact with. My family used this location for commission week and could not have asked for more. "
Annapolis Condominium in the heart of the historic center

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (223)
"Perfect Location - Easy Process - Comfortable Home!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (181)
"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (159)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (49)
"This is a lovely historic home that is close to town. It's nicely decorated, has a screened deck out back, and makes for a comfortable stay."
Dollhouse in Central Historic St Michaels

Private Cottage on gated estate

10.0 out of 10, Exceptional, (24)
"Excellent location, Excellent property, Excellent owners!"
Private Cottage on gated estate

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (73)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
The price is £376
includes taxes & fees
24 Jun - 25 Jun
Waterfront Oasis of Annapolis Star

Romantic Two Bedroom Condo

10.0 out of 10, Exceptional, (76)
"Very good "
Romantic Two Bedroom Condo

The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (30)
"Great location, close to the beach and restaurant. Cozy and comfortable, with a beautiful view of sunset. "
Chesapeake Houseboat Getaway on Kent Island, Maryland

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

9.8 out of 10, Exceptional, (9)
"Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!"
The price is £1,233
includes taxes & fees
15 Jul - 16 Jul
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

10.0 out of 10, Exceptional, (5)
"Lovely little rustic cottage full of charm.We arrived over Thanksgiving,the off season was wonderful thank s again"
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (36)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is £271
includes taxes & fees
30 Jun - 1 Jul
Relax on Kent Island in 3 Bedroom Home w/Waterview

Circa 1700 Chesapeake Colonial home on the National Register.

9.8 out of 10, Exceptional, (53)
"Great and comfortable stay! Beautiful historic house and property Owners were so friendly and helpful"
Circa 1700 Chesapeake Colonial home on the National Register.

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

9.0 out of 10, Wonderful, (12)
"This was a wonderful peaceful stay and the host was great. Loved it!!! "
The price is £305
includes taxes & fees
24 Jun - 25 Jun
Wright's Cottage- Pet's Welcome & EV Charging
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

Frequently asked questions

Are there holiday rentals in Shady Side?

Yes, there are holiday rentals close to the most popular sights in Shady Side, or you can select a more secluded option if you're looking for a relaxing stay. Shady Side is known for its shopping and restaurants. Make sure you have time to check out the parks and museums during your trip.

What are some of the best holiday rentals that Shady Side has to offer?

The Cottage : This highly rated holiday home rental in Shady Side has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals will I find in Shady Side?

Expedia has 10 holiday rentals for your stay in Shady Side.

What’s there to see and do in Shady Side?

Cultural attractions include Captain Avery Museum, whereas Shadyside Park is a spot to enjoy nature. Franklin Point State Park and London Town are a couple of places you'll find in the wider area.

What’s a holiday rental in Shady Side like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Shady Side. Holiday rentals feature extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for family gatherings.