A river with boats, a marina, and a town with houses and buildings.

Shady Side Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Shady Side vacation rentals

A modern kitchen with a large window, a dishwasher, and a ceiling fan.

1. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
9.8 out of 10, Exceptional, (6 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is ￥33,072
￥69,621 total
includes taxes & fees
Dec 1 - Dec 2
Sunset Cottage - West River Access and Views!
A deck with outdoor furniture, a red door, and a house with windows.

2. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
9.4 out of 10, Exceptional, (3 reviews)
"the house was clean and fully stocked with all linens. there are some staples in the refrigerator and cabinets. All cookware and eatery are provided. there is only one grocery store in the area, so plan ahead. Fast food is not readily available. Nick responded quickly and thoroughly to all messages, that was great. It's a quiet neighborhood. It was the perfect place for a family and pet. we will return"
United States
Jenny A.
The price is ￥27,321
￥57,556 total
includes taxes & fees
Nov 16 - Nov 17
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

3. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (25 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is ￥14,066
￥49,510 total
includes taxes & fees
Nov 16 - Nov 17
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A house with a yellow door and a window with a lamp outside.

4. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is ￥20,866
￥50,217 total
includes taxes & fees
Nov 15 - Nov 16
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

5. 3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views
Deale
10.0 out of 10, Exceptional, (2 reviews)
"Everything at this location was as shown on the listing and it was very clean. We were very satisfied with all elements of this stay. We were there for a weekend and did not use the place heavily, but it suited our needs. It's a quiet location. They had all the major points covered. The only negative comment I have is that the water out of the tap was smelly. I suggest bringing a couple of bottles of water and not drinking the water out of the taps. This is obviously a well maintained home...
United States
Amelia
The price is ￥28,780
￥69,811 total
includes taxes & fees
Nov 14 - Nov 15
3-bedroom house in Deale located on Bay many amenities and great views
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

6. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (14 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is ￥30,772
￥84,805 total
includes taxes & fees
Nov 14 - Nov 15
Renovated Bungalow | Walk to Beach | Dog-Friendly
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

7. Relax on Kent Island in 4 Bedroom Home w/Waterview

Relax on Kent Island in 4 Bedroom Home w/Waterview
Stevensville
9.8 out of 10, Exceptional, (57 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is ￥13,421
￥45,212 total
includes taxes & fees
Nov 15 - Nov 16
Relax on Kent Island in 4 Bedroom Home w/Waterview
A lighthouse with a white exterior, a balcony, and a metal roof.

8. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (50 reviews)
"Great stay"
United States
Michael V.
The price is ￥22,048
￥55,974 total
includes taxes & fees
Nov 29 - Nov 30
Charming Coastal/Country Home w/3 Acres & Sauna!
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

9. Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (6 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is ￥38,680
￥107,480 total
includes taxes & fees
Nov 14 - Nov 15
Family Home on Mayo Peninsula | Deck | Sleeps 10
A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

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

The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach
9.6 out of 10, Exceptional, (30 reviews)
"Wonderful place to visit "
United States
James L.
The price is ￥23,167
￥49,452 total
includes taxes & fees
Nov 15 - Nov 16
The Cozy Crab- Your Charming Haven in Lovely North Beach!
A calm lake with a sandy shore, surrounded by trees and houses.

11. Londontowne Home | Beach | 3BR

Londontowne Home | Beach | 3BR
Edgewater
9.4 out of 10, Exceptional, (3 reviews)
"The property was beautiful with plenty of space to have a getaway with friends. The host was super communicative when we had issues with check in. Would highly recommend staying here!"
United States
Sam A.
The price is ￥38,680
￥113,126 total
includes taxes & fees
Nov 15 - Nov 16
Londontowne Home | Beach | 3BR
A beach with chairs and a pier in the background.

12. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
"Super clean, well furnished and in a nice quiet neighborhood close to downtown Annapolis. Great place to stay!"
United States
Ryan C.
The price is ￥33,072
￥75,405 total
includes taxes & fees
Nov 16 - Nov 17
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

13. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (41 reviews)
"This property and host were excellent. Property was as advertised. Lovely, clean, quiet and comfortable. Owner was super responsive and check in and check out was easy. 100% recommend."
United States
Sarah
The price is ￥17,625
￥62,951 total
includes taxes & fees
Nov 16 - Nov 17
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

14. Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is ￥33,552
￥84,877 total
includes taxes & fees
Nov 30 - Dec 1
Annapolis Retreat - 7 mins from downtown Annapolis!
A sandy beach with a boat docked on the left and calm water.

15. Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.8 out of 10, Exceptional, (31 reviews)
"Great stay"
United States
Guillaume P.
The price is ￥10,505
￥31,662 total
includes taxes & fees
Nov 15 - Nov 16
Cute, Cozy 2-bedroom house near Annapolis with water access
A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

16. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
9.0 out of 10, Wonderful, (4 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is ￥35,948
￥84,147 total
includes taxes & fees
Nov 24 - Nov 25
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
A spacious living room with a high ceiling, large windows, and a ceiling fan.

17. The Harness Creek Retreat in Annapolis

The Harness Creek Retreat in Annapolis
Hillsmere
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay! The property was beautiful, exceptionally clean, and in a perfect location for enjoying everything Annapolis has to offer. The beds were very comfortable, and the home had wonderful amenities that made our stay even more enjoyable. We couldn’t have asked for a better place to stay and would absolutely return. Highly recommend!"
United States
Dayna A.
The price is ￥43,138
￥67,755 total
includes taxes & fees
Nov 15 - Nov 16
The Harness Creek Retreat in Annapolis
A deck with a view of a marina, including boats and docks.

18. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (54 reviews)
"Love This rental. One of our favorites. Small but everything needed. And the view is absolutely wonderful."
United States
Yamilet
Cass-N-Reel Luxury Houseboat
A spacious living room with a sofa set, a coffee table, and a chair. There is a painting on the wall and a window providing natural light.

19. Londontowne Rancher | 3BR | Near Waterfront

Londontowne Rancher | 3BR | Near Waterfront
Edgewater
7.0 out of 10, Good, (2 reviews)
"The house was much smaller then it originally appeared to be in the listing photos and what they had available was the bare minimum. The neighborhood was rowdy and there was screaming late into the night. The shower also sprayed water all over the floor and caused a massive puddle. The house was overall nice and clean but not worth the price that it was listed for. A hotel would have much better accommodated our needs. "
United States
rebekah h.
Londontowne Rancher | 3BR | Near Waterfront
A modern kitchen with a central island, built-in oven, and microwave.

20. Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.4 out of 10, Exceptional, (13 reviews)
"Great location, very clean, and the host was very responsive!"
United States
Heather B.
The price is ￥35,647
￥92,114 total
includes taxes & fees
Nov 30 - Dec 1
Cute bungalow blocks to 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.
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Top Shady Side Hotel Reviews

Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"Beautiful view from my room! Amazing sunrise! Overall great room and stay!!"
Lori 3-night trip
Posted 7 hours ago
Rod 'N' Reel Resort

Find out more about Shady Side

Search for holiday rentals in Shady Side on Expedia! You can easily find your home rentals, villas, holiday apartments in Shady Side using one of the methods below:

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Look no further and take a look at our great range of rental properties in Shady Side!

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?

Lovely bay views with kayaks, bikes, fire pit, crabbing & more: Visitors like this Shady Side vacation home rental. It offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Shady Side?

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

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

Northern Chesapeake Bay and Chesapeake Bay are a couple of scenic spots to enjoy the outdoors, whereas Captain Avery Museum is one of the cultural attractions. Shadyside Park and Franklin Point State Park are other places to visit while you're in town.

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.