Shady Side Holiday Rentals

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Holiday Rentals in Shady Side

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
9.8 out of 10, Exceptional, 6 reviews
"The property was beautiful. The property manager was available for any inquiries we had. My family and I enjoyed it immensely. The view of the water was wonderful whether sitting on the dock or sitting in the sunroom. We played indoor and outdoor games. Perfect place for family bonding. The weather was perfect for our stay."
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Cozy place close to the city dock
10.0 out of 10, Exceptional, 55 reviews
"We enjoyed our 2 nights at Cozy Place Close to the docks. Easy access and personalized connection with Nathalie were appreciated! We enjoyed the French and sail boating themes in the apartment, aligned the Annapolis maritime history! The docks are a short drive and old Town Annapolis was pleasant and historical! We recommend Cozy Place to others!"
Cozy place close to the city dock
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, 21 reviews
"Everyone really loved the house and the location. The pool was great"
Pool and Bay Views on wrap around deck in Kent Island
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Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, 183 reviews
"We stayed at this property for a week. It was nice and clean and close to the US Naval Academy! The home had everything you could need for a stay away from home. The host provided practically everything you could need as well! The host was very communicative and responded quickly as needed. We really appreciated our stay here. Thank you so much!"
Directly Across from Gate One & Steps from the Waterfront
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, 188 reviews
"Several family members and I went on a fishing trip out of Edgewater. We stayed in this wonderful cottage on the water. The house was immaculate and everything we needed aside from food was provided. The check in and check out were very simple and the host gave us contact information in case we needed anything. The location and overall property could not have been any better. We would definitely stay here again."
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Firefly Cottage at the Cape, community beach, stand alone house, hot tub, pets.
10.0 out of 10, Exceptional, 62 reviews
"This is our second stay and it was just as memorable and lovely as our first stay. Pat and Ken are fantastic hosts. They think of everything! They are super responsive when you have questions/issues. They also let you know about things going on in the community so that you can join if you wish. The house itself is perfect for us. It's very well and generously stocked. Having a washer and dryer on site is a life saver when you travel by plane. I would highly recommend the Firefly Cottage if you...
Firefly Cottage at the Cape, community beach, stand alone house, hot tub, pets.
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, 44 reviews
"This house was perfect for a group of friends celebrating a 50th birthday! The house was so clean and well cared for! The front porch and outdoor backyard space provided even more room for us to gather together. We will be back!"
Recently Renovated Annapolis Home - Conveniently Located
Chesapeake Houseboat Getaway on Kent Island, Maryland
10.0 out of 10, Exceptional, 8 reviews
"My husband and I both LOVED this property!!! The houseboat was beautifully decorated, so relaxing and in a great area. We cant wait to go back!"
Chesapeake Houseboat Getaway on Kent Island, Maryland
Waterfront Cottage on the Eastern Shore
9.4 out of 10, Exceptional, 3 reviews
"Very much as pictured in ad. Convenient to we did venue we were attending"
The price is NZ$1,845
includes taxes & fees
20 June - 21 June
20 Jun - 21 Jun
Waterfront Cottage on the Eastern Shore
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, 43 reviews
"Beautiful house and views. Amenities and grounds were great. Loved the playground and beach. Peace and quiet at its finest in nature."
The price is NZ$1,234
includes taxes & fees
10 July - 11 July
10 Jul - 11 Jul
Charming Annapolis WaterVIEW Home
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, 20 reviews
"My children and grandchildren loved staying together in one house. We were able to play outdoors and there was space to socialize and play indoors. We were a group of 11 and I felt it was a bit small for all of us. Great location for what we were looking for."
The price is NZ$513
includes taxes & fees
26 June - 27 June
26 Jun - 27 Jun
Relax on Kent Island in 3 Bedroom Home w/Waterview
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, 106 reviews
"We love staying at the John Bruff house in St. Michaels. The location is great, right in the heart of town! Our family has been staying here for the past few years and we can’t wait to go back!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
10.0 out of 10, Exceptional, 25 reviews
"I chose to stay at this property for the duration of my wedding weekend. It was really great to be able to spend that extra time with family all together! Getting ready at the house, rather than a hotel was also really nice because we had much more room to space out. The make up artist and hair stylist also complimented the ample natural light and space to work. The pool and hot tub were beautiful! The only downside was a lack of curtains in the master bedroom. The sunrise is beautiful but...
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Gorgeous dog-friendly retreat w/ fireplace, patio, & firepit - centrally located
10.0 out of 10, Exceptional, 6 reviews
"This location was extremely clean and perfect for a weekend get away. It’s located not even 2 miles from downtown Annapolis. 10/10 would recommend"
Gorgeous dog-friendly retreat w/ fireplace, patio, & firepit - centrally located
Indulge or be still near Naval Academy/ Annapolis
9.2 out of 10, Wonderful, 9 reviews
"Great place, super neighborhood!"
Indulge or be still near Naval Academy/ Annapolis
Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, 62 reviews
"My husband and I were traveling to Annapolis for a family reunion with our one year old grandchild. Our hosts, Beth and Andy went above and beyond to make sure that we had a wonderful stay on their beautiful property. We were treated like family the whole time that we were there. Beth was so helpful when it came to questions or concerns that I had in traveling for the first time with our baby granddaughter. To celebrate my Birthday, we took a boat tour with Captain Andy, which was our...
The price is NZ$815
includes taxes & fees
20 June - 21 June
20 Jun - 21 Jun
Waterfront Oasis of Annapolis Star
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, 40 reviews
"Property and home were in excellent condition. Home made us feel welcome and secure. Host provides extras that make your stay convenient. Close to the restaurants and ice cream shop that serves Hershey ice cream. Love the people and neighborhood."
The Blue Crab Beach House - Free beach passes
Bay View Studio Apartment
10.0 out of 10, Exceptional, 28 reviews
"Chespeake Bay waterfront with beautiful views. Very close to Annapolis Sailing School, as well as Annapolis itself."
Bay View Studio Apartment
Cass-Away Luxury Houseboat
10.0 out of 10, Exceptional, 82 reviews
"Class-Away is a very nice property clean and very nice view to watch the sunset.The pictures that are listed are exact.A please Cass-Away experience:)"
The price is NZ$649
includes taxes & fees
24 June - 25 June
24 Jun - 25 Jun
Cass-Away Luxury Houseboat
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, 84 reviews
"The house had everything we needed. Loved the decor. It created a cozy atmosphere. The backyard was amazing with the flowers and pool. The host is super!"
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
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See all available properties in Shady Side
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.

Other types of properties in Shady Side you may be interested in

Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, 1,610 reviews
"Great location. Clean rooms. "
The price is NZ$292
includes taxes & fees
2 July - 3 July
2 Jul - 3 Jul
Historic Inns of Annapolis
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
2.5 star property
6.6 out of 10, 1,288 reviews
"Great hotel"
The price is NZ$199
includes taxes & fees
20 June - 21 June
20 Jun - 21 Jun
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
Graduate Annapolis
4.0 star property
9.4 out of 10, Exceptional, 1,022 reviews
"We had a nice time for our baby moon!"
The price is NZ$330
includes taxes & fees
1 July - 2 July
1 Jul - 2 Jul
Graduate Annapolis
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Shady Side holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Shady Side. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Shady Side. Seeing all the best attractions is bound to make you fall in love with Shady Side. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Shady Side short-term rentals, that won’t be hard to do.

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?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Shady Side offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind.

How many holiday rentals will I find in Shady Side?

Expedia has 12 holiday rentals for your stay in Shady Side.

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

Shadyside Park and Franklin Point State Park are a couple of scenic spots to enjoy the outdoors, whereas Captain Avery Museum is one of the cultural attractions. London Town and Maryland Quiet Waters Park 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.

Recent reviews of Shady Side properties
Expedia verified reviews