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
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Shady Side vacation rentals

Terrace/patio

1. 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 ￥25,691
￥58,376 total
includes taxes & fees
Aug 30 - Aug 31
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Interior

2. 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 ￥44,450
￥86,890 total
includes taxes & fees
Sep 9 - Sep 10
Sunset Cottage - West River Access and Views!
Exterior detail

3. 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 ￥16,505
￥47,539 total
includes taxes & fees
Aug 17 - Aug 18
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
TV, offices

4. 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 ￥38,571
￥112,808 total
includes taxes & fees
Aug 16 - Aug 17
Family Home on Mayo Peninsula | Deck | Sleeps 10
Beach nearby, sun loungers, beach towels

5. 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, (18 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is ￥58,948
￥113,152 total
includes taxes & fees
Sep 14 - Sep 15
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Outdoor dining

6. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (74 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 ￥56,399
￥112,789 total
includes taxes & fees
Sep 14 - Sep 15
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 ￥36,803
￥97,533 total
includes taxes & fees
Sep 1 - Sep 2
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 ￥38,571
￥118,801 total
includes taxes & fees
Aug 16 - Aug 17
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 ￥45,884
￥122,233 total
includes taxes & fees
Aug 20 - Aug 21
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 ￥28,518
￥86,816 total
includes taxes & fees
Sep 15 - Sep 16
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 ￥27,483
￥77,325 total
includes taxes & fees
Aug 17 - Aug 18
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
The price is ￥39,256
￥102,871 total
includes taxes & fees
Sep 8 - Sep 9
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Exterior

13. 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, (53 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is ￥22,305
￥53,637 total
includes taxes & fees
Aug 24 - Aug 25
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Coffee/tea maker, fridge, microwave, oven

14. 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.
The price is ￥54,382
￥122,659 total
includes taxes & fees
Aug 16 - Aug 17
Eastport 3 bedroom Cottage: Walk to Downtown
Interior

15. 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 ￥47,796
￥114,150 total
includes taxes & fees
Aug 16 - Aug 17
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

16. 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 ￥17,912
￥58,153 total
includes taxes & fees
Sep 8 - Sep 9
Beachside Oasis with Beach Passes & King Suite by A Haven Away
Outdoor dining

17. 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 ￥24,973
￥77,376 total
includes taxes & fees
Sep 8 - Sep 9
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Coffee/tea maker, fridge, microwave, oven

18. 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 ￥41,742
￥115,708 total
includes taxes & fees
Aug 17 - Aug 18
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Coffee/tea maker, fridge, microwave, oven

19. 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 ￥69,174
￥139,885 total
includes taxes & fees
Aug 16 - Aug 17
Historic Downtown 3BR Crabby Patty-∙Walk to USNA
Interior

20. Dean Street's Lower Deck House!

Dean Street's Lower Deck House!
Historic District
10.0 out of 10, Exceptional, (4 reviews)
"We had a great time—the location is fantastic and our dog loved the backyard! A great base to rest and recover between adventures in Annapolis. "
United States
Nathaniel R.
The price is ￥34,960
￥74,726 total
includes taxes & fees
Aug 31 - Sep 1
Dean Street's Lower Deck House!
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

8/10 Good
"My room was really nice and very clean. The house keeping lady was so nice and very helpful she kept my room clean with fresh towels and clean sheet. My family and I had a really nice stay at this resort ."
Elizabeth 2-night trip
Posted 1 hour 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:

  • View our selection of featured holiday rentals in Shady Side
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  • Enter your travel dates to view the best deals on holiday rentals in Shady Side while they last

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?

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 13 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.