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
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Shady Side vacation rentals

Interior

1. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Lovely place and neighborhood! "
United States
Marci M.
The price is AED 1,065
AED 2,052 total
includes taxes & fees
7 Sep - 8 Sep
Sunset Cottage - West River Access and Views!
Terrace/patio

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
10.0 out of 10, Exceptional, (1 review)
"Jut as described. Easy in easy out. Great for a few days with the family."
United States
Joshua T.
The price is AED 324
AED 993 total
includes taxes & fees
8 Sep - 9 Sep
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Smart TV

3. 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
The price is AED 820
AED 1,893 total
includes taxes & fees
10 Sep - 11 Sep
3-bedroom house in Deale located on Bay many amenities and great views
Exterior detail

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 AED 479
AED 1,225 total
includes taxes & fees
31 Aug - 1 Sep
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
TV, offices

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

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (5 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is AED 889
AED 2,601 total
includes taxes & fees
28 Aug - 29 Aug
Family Home on Mayo Peninsula | Deck | Sleeps 10
Outdoor dining

6. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (75 reviews)
"Our family had a wonderful stay at your beautiful home! The views are to die for! House was very clean with all equipment and kitchen appliances all available! Very happy with our stay! "
United States
Whitney M.
The price is AED 1,234
AED 2,512 total
includes taxes & fees
14 Sep - 15 Sep
Charming Annapolis WaterVIEW Home
Coffee/tea maker, fridge, microwave, oven

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

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (12 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 AED 768
AED 2,144 total
includes taxes & fees
2 Sep - 3 Sep
Renovated Bungalow | Walk to Beach | Dog-Friendly
Beach

8. 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 AED 970
AED 2,843 total
includes taxes & fees
31 Aug - 1 Sep
Londontowne Home | Beach | 3BR
TV

9. 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.
The price is AED 970
AED 2,705 total
includes taxes & fees
30 Aug - 31 Aug
Londontowne Rancher | 3BR | Near Waterfront
Interior

10. 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 AED 826
AED 2,228 total
includes taxes & fees
9 Sep - 10 Sep
Annapolis Retreat - 7 mins from downtown Annapolis!
Marina

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

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is AED 703
AED 1,874 total
includes taxes & fees
30 Aug - 31 Aug
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Living area

12. Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Exterior

13. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
Stevensville
6.8 out of 10, (3 reviews)
"The place was very clean and Host was ok the shopping was six miles away, not in walking distance, we had no pets on this trip."
United States
Anonymous traveler
The price is AED 2,645
AED 3,858 total
includes taxes & fees
28 Aug - 29 Aug
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
Exterior

14. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is AED 407
AED 1,133 total
includes taxes & fees
30 Aug - 31 Aug
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Coffee/tea maker, fridge, microwave, oven

15. Eastport 3 bedroom Cottage: Walk to Downtown

Eastport 3 bedroom Cottage: Walk to Downtown
Eastport
10.0 out of 10, Exceptional, (1 review)
"We had a nice stay. All was fine."
United States
william c.
Eastport 3 bedroom Cottage: Walk to Downtown
Interior

16. Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.

Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.
Eastport
10.0 out of 10, Exceptional, (2 reviews)
"Excellent place to stay!"
United States
Michaell M.
The price is AED 1,274
AED 2,894 total
includes taxes & fees
30 Aug - 31 Aug
Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.
Beach nearby

17. 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, (22 reviews)
"Lovely ! "
United States
Ellen B.
The price is AED 393
AED 1,321 total
includes taxes & fees
30 Aug - 31 Aug
Beachside Oasis with Beach Passes & King Suite by A Haven Away
Outdoor dining

18. 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, (37 reviews)
"Such a great house! "
United States
Stephanie V.
The price is AED 480
AED 1,661 total
includes taxes & fees
30 Aug - 31 Aug
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Coffee/tea maker, fridge, microwave, oven

19. Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive to questions and very easy to communicate with. The house was amazing and so close to downtown. Would definitely stay again!"
United States
Colleen W.
The price is AED 962
AED 2,668 total
includes taxes & fees
31 Aug - 1 Sep
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Coffee/tea maker, fridge, microwave, oven

20. Historic Downtown 3BR Crabby Patty-∙Walk to USNA

Historic Downtown 3BR Crabby Patty-∙Walk to USNA
Historic District
10.0 out of 10, Exceptional, (7 reviews)
"House is perfect for weekend get away with family. Walking distance to everything. "
United States
Nathan A.
The price is AED 1,529
AED 3,142 total
includes taxes & fees
30 Aug - 31 Aug
Historic Downtown 3BR Crabby Patty-∙Walk to USNA
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

St Michaels Inn

St Michaels Inn

8/10 Good
"My room was wonderful! Great comfort of the bed. Peaceful. The breakfast was lack luster with all carbs. Nothing sugar free for diabetics. Lots of construction and painting during my stay. Would stay here again, however!"
Kris 3-night trip
Posted 2 hours ago
St Michaels Inn

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?

Steps to Chesapeake Bay! 'Callaway Drive Retreat': This highly rated vacation home rental in Shady Side is equipped with a patio, laundry facilities, and cable TV to help you feel comfortable during your stay. 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. Another good choice for your trip to Shady Side is Lovely bay views with kayaks, bikes, fire pit, crabbing & more.

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.