Shady Side Holiday Rentals

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Holiday Rentals in Shady Side

Rockhold Creek Cottage, Water Front, Vacation Home, Docks
9.8 out of 10, Exceptional, (83)
"The house was clean and comfortable. Walking distance to a local restaurant. Screened porch was great for watching the sunrise in the morning and the boats coming in and out of harbor "
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
10.0 out of 10, Exceptional, (76)
"Lovely house and location! Pat and Ken were rapid and personable with every interaction."
Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (17)
"We had a great stay at the Turning Point! We had a great time playing Cornhole, pickleball, basketball, cooking on the grill, cooling off in the pool, and watching football on the big screen TV. House was very clean and comfortable. Would definitely stay again and would highly recommend it to anyone."
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Waterfront Cottage on the Eastern Shore
9.6 out of 10, Exceptional, (7)
"We rented the house for the weekend and to host a surprise birthday party. We had the party right at the beach and the host/concierge were able to help us with everything we needed. They really went out of their way for us, and it made a huge difference in the party’s success! Plus, you can’t beat the view and the Chesapeake Bay sunsets !!"
The price is AU$1,200
includes taxes & fees
1 Oct - 2 Oct
Waterfront Cottage on the Eastern Shore
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (212)
"As always our stay was amazing from kayaking, bird watching, sunsets. The cove is a special place."
Relaxing Waterfront Cottage Near St Michaels, Maryland
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (47)
"Great house qoth ocean view"
Charming Annapolis WaterVIEW Home
Cass-Away Luxury Houseboat
10.0 out of 10, Exceptional, (87)
"All as advertised Wonderful option to a hotel"
The price is AU$533
includes taxes & fees
1 Oct - 2 Oct
Cass-Away Luxury Houseboat
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (29)
"Perfect for a 3 day visit! "
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (199)
"Couples getaway weekend to Annapolis. This was the perfect place to have our Basecamp. Absolutely beautiful location, quiet, and peaceful and easy to get everywhere!"
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (107)
"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
9.8 out of 10, Exceptional, (32)
"We had a great 10 person family vacation. The house was spacious and clean. The view of the Chesapeake amazing. The pool was very big and deep in comparison to most vacation rentals. They had a paddle board, several kayaks and life jackets in all sizes. The only things I would be aware of is the amount of steps. The house has 4 levels and 3 flights of steps. The driveway has a flight of steps. To get to the pool many steps and steep hill to maneuver. We didn’t mind it because it was good...
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (198)
"While the cottage may have some of the historic/ older quirks, it is a wonderful (and beautiful ) property that we would highly recommend! We loved the walk-ability to downtown Annapolis and the Naval Academy. Despite its close location, it’s quiet at night lending to a good nights sleep 😊. The owner provided us some great insight on the location as well. "
Directly Across from Gate One & Steps from the Waterfront
Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (69)
"Beautiful property and our quarters were perfectly comfortable for us."
The price is AU$706
includes taxes & fees
3 Oct - 4 Oct
Waterfront Oasis of Annapolis Star
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (27)
"We had a great weekend on Kent Island. We loved the area. It was so family friendly. We had lots of young children in our group, and this house worked great for us. The inside was nice with modern, but minimal decor, which was perfect for toddlers. The fenced in backyard was also just what we needed to let them run around."
The price is AU$367
includes taxes & fees
29 Sept - 30 Sept
Relax on Kent Island in 3 Bedroom Home w/Waterview
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, (24)
"We loved everything about the Kent Island House! Would book again in a hot minute"
Pool and Bay Views on wrap around deck in Kent Island
Charming Cottage with Hot Tub 1 Block from the Bay
10.0 out of 10, Exceptional, (7)
"Great property. Close to USNA but away from the craziness of town. House was adorable and very clean. The hot tub was a big hit. "
The price is AU$855
includes taxes & fees
30 Sept - 1 Oct
Charming Cottage with Hot Tub 1 Block from the Bay
Bay View Studio Apartment
10.0 out of 10, Exceptional, (36)
"We are repeat visitors to this property because of the location, the owner, the comfort and the amazing view here. The owner is so nice and has excellent communication. The property has everything you need and more from the kitchen supplies to the water toys including a hot tub! We will be back again! "
Bay View Studio Apartment
The Yellow Cottage on Harness Creek
10.0 out of 10, Exceptional, (150)
"Highly recommend. Beautiful spot and a wonderful cottage. Rhonda does an amazing job of making you feel at home. My son is at the Academy and with all the pressures they have on them, to see him be able to sit out by the water so peacefully and just relax was so enjoyable. We'll be back for sure."
The Yellow Cottage on Harness Creek
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (46)
"Very sweet cottage right in the heart of North Beach. Danielle and Harry were wonderful and so responsive to anything we needed. If you’re lucky you’ll get to meet their adorable dogs. We will be back for sure!"
The Blue Crab Beach House - Free beach passes
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
9.4 out of 10, Exceptional, (10)
"We appreciate the hospitality and responsiveness of our gracious host. We would stay again and look forward to our next visit. Recommend staying to all looking for a tranquil getaway in the Annapolis area."
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
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Other types of properties in Shady Side you may be interested in

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
2.5 star property
6.4 out of 10, (1376)
"Nice hotel for the price! Room was spacious and clean "
The price is AU$134
includes taxes & fees
9 Oct - 10 Oct
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1666)
"In the heart of the historic district. Easy walk to the harbor or Navsl Academy. Lots of shops and restaurants nearby"
The price is AU$284
includes taxes & fees
27 Oct - 28 Oct
Historic Inns of Annapolis
Crowne Plaza Annapolis, an IHG Hotel
3.5 star property
8.8 out of 10, Excellent, (999)
"I used this hotel as our stay hotel for my boys who shipped to bootcamp. It is across from the Annapolis mall and has restaurants in walking distance. The rooms are beautiful and spacious."
The price is AU$173
includes taxes & fees
23 Oct - 24 Oct
Crowne Plaza Annapolis, an IHG Hotel
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.

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.