Shady Side Vacation Rentals

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Check prices for these dates

In two weeks
Oct 31 - Nov 2
In two months
Dec 12 - Dec 14
In three months
Jan 9 - Jan 11
In four months
Feb 6 - Feb 8

Vacation Rentals in Shady Side

Exterior
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
10.0 out of 10, Exceptional, (3)
"Very comfortable bedrooms and sitting area. Perfect location for the event we were attending. Very clean. Friendly host. "
The price is ￥21,936
￥65,122 total
includes taxes & fees
Oct 16 - Oct 17
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (121)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (36)
"Fabulous place. We’ll be booking again next year. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Marina
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
10.0 out of 10, Exceptional, (236)
"This was a wonderful historic home to vacation in"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Fridge, microwave, oven, stovetop
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
10.0 out of 10, Exceptional, (14)
"Everything was exactly as described on the listing. It’s the perfect spot for a peaceful and relaxing getaway, all while being close to a charming town. The hosts were very pleasant and easy to communicate with. I highly recommend this place! "
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Outdoor dining
The Cozy Crab- Your Charming Haven in Lovely North Beach!
The Cozy Crab- Your Charming Haven in Lovely North Beach!
9.8 out of 10, Exceptional, (11)
"Great place. Just a short drive to town with shops, restaurants, and boardwalk."
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Marina
Floating 2 bed 2 bath condo stunning views of the bay
Floating 2 bed 2 bath condo stunning views of the bay
2.0 star property
7.0 out of 10, Good, (6)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
Floating 2 bed 2 bath condo stunning views of the bay
Outdoor dining
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
9.8 out of 10, Exceptional, (49)
"Our large family of adults and two one-year-olds and a dog had a perfect week. The hosts were kind and responsive, and the home was spacious with lots of room for privacy and being all together. Looking forward to going again!"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Outdoor dining
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
10.0 out of 10, Exceptional, (194)
"We all had wonderful stay at Love point! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Outdoor dining
Waterfront Getaway, Dock Your Boat & Play!
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 ￥17,306
￥49,198 total
includes taxes & fees
Oct 28 - Oct 29
Waterfront Getaway, Dock Your Boat & Play!
Marina
Cass-N-Reel Luxury Houseboat
Cass-N-Reel Luxury Houseboat
10.0 out of 10, Exceptional, (42)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat
Interior
Charming townhome with AC and WiFi in delightful Annapolis
Charming townhome with AC and WiFi in delightful Annapolis
3.0 out of 10, (2)
"This is a room, property owner will be there during your stay. Mattress on The floor. Single pillow, comforter, no top sheet. No curtans, and in a mildly questionable part of town. Owner was very "
The price is ￥7,266
￥11,757 total
includes taxes & fees
Nov 12 - Nov 13
Charming townhome with AC and WiFi in delightful Annapolis
Marina
Relax on Kent Island in 3 Bedroom Home w/Waterview
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (41)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
The price is ￥13,595
￥41,538 total
includes taxes & fees
Oct 19 - Oct 20
Relax on Kent Island in 3 Bedroom Home w/Waterview
Outdoor dining
Luxury Waterfront Executive Family Home Annapolis with All Amenities
Luxury Waterfront Executive Family Home Annapolis with All Amenities
7.6 out of 10, Good, (4)
"Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. "
Luxury Waterfront Executive Family Home Annapolis with All Amenities
Dining
Million Dollar View of the Chesapeake Bay
Million Dollar View of the Chesapeake Bay
9.8 out of 10, Exceptional, (129)
"We just enjoyed our fourth year at Million Dollar View of the Chesapeake Bay and already look forward to our next vacation at this wonderful home!"
Million Dollar View of the Chesapeake Bay
Exterior
Top Location | Free Breakfast + Fitness Center
Top Location | Free Breakfast + Fitness Center
2.0 star property
10.0 out of 10, Exceptional, (1)
"Very nice!"
Top Location | Free Breakfast + Fitness Center
Smart TV, books
Large 2 bedroom house with private parking in a nice neighborhood
Large 2 bedroom house with private parking in a nice neighborhood
9.4 out of 10, Exceptional, (28)
"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."
The price is ￥19,735
￥49,496 total
includes taxes & fees
Nov 12 - Nov 13
Large 2 bedroom house with private parking in a nice neighborhood
Exterior
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (219)
"We had a wonderful time. Hosts were very kind and responsive! Beautiful property "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Fridge, microwave, oven, stovetop
Edgewater/Mayo Gateaway w/ Hot Tub
Edgewater/Mayo Gateaway w/ Hot Tub
9.8 out of 10, Exceptional, (23)
"Very clean, had everything we needed for our stay!"
The price is ￥33,246
￥92,314 total
includes taxes & fees
Nov 11 - Nov 12
Edgewater/Mayo Gateaway w/ Hot Tub
Outdoor dining
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8 out of 10, Exceptional, (191)
"Excellent accommodations. Comfortable, good location.One way you could improve is to furnish wash cloths and hand towels. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
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

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills

10/10 Excellent
"The property was clean and safe, and the room was clean and safe."
kenneth 2-night trip
Posted 1 day ago
Microtel Inn & Suites by Wyndham Gambrills

Find out more about Shady Side

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Frequently asked questions

Are there vacation rentals in Shady Side?

Yes, we have vacation rentals close to well known points of interest in Shady Side, or you can go with a more remote option if you're looking for relaxation. 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 vacation rentals in Shady Side?

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side: Visitors like this Shady Side vacation home rental. It has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities like a stovetop and a microwave can make your vacation run smoothly.

How many vacation rentals will I find in Shady Side?

Expedia has 10 vacation 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 Smithsonian Environmental Research Center are a couple of places you'll find in the larger area.

What’s a vacation rental in Shady Side like?

Vacation rentals are private properties where you can stay for a couple of days or more in Shady Side. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for a family getaway.