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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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
10.0 out of 10, Exceptional, (5 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 AED 966
AED 1,919 total
includes taxes & fees
15 Nov - 16 Nov
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
9.0 out of 10, Wonderful, (2 reviews)
"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"
United States
David S.
The price is AED 628
AED 1,394 total
includes taxes & fees
21 Oct - 22 Oct
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

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 661
AED 1,604 total
includes taxes & fees
18 Oct - 19 Oct
3-bedroom house in Deale located on Bay many amenities and great views
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

4. 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 AED 970
AED 2,705 total
includes taxes & fees
21 Oct - 22 Oct
Family Home on Mayo Peninsula | Deck | Sleeps 10
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

5. 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)
"Our host Adam was wonderful and very communicative. We love the house and the location was just great. It was close to everything and had water views. We will certainly come back again."
United States
Rebecca B.
The price is AED 333
AED 1,071 total
includes taxes & fees
19 Oct - 20 Oct
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

6. 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, (24 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is AED 353
AED 1,229 total
includes taxes & fees
19 Oct - 20 Oct
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A dining table with a wine bottle, glasses, and a red bowl with a leaf pattern.

7. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (94 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
The price is AED 1,082
AED 1,623 total
includes taxes & fees
5 Nov - 6 Nov
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A beach with chairs and a pier in the background.

8. 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)
"The perfect off-season get-away! "
United States
Pamela B.
The price is AED 694
AED 1,734 total
includes taxes & fees
20 Oct - 21 Oct
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

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

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (13 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
19 Oct - 20 Oct
Renovated Bungalow | Walk to Beach | Dog-Friendly
A bunk bed with a wooden frame, white bedding, and a blue pillow with a floral design.

10. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay at this home in North Beach, MD! The house was clean, comfortable, and conveniently located near The Inn at Herrington Harbour, making it a great choice for our visit. Everything worked well for our stay, and we appreciated having a nice place to relax. We would happily recommend this property to anyone looking for a comfortable and convenient place to stay in the area!"
United States
Jeremy P.
The price is AED 826
AED 1,591 total
includes taxes & fees
18 Oct - 19 Oct
Rose Haven Coastal Cottage
A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

11. 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 AED 437
AED 1,059 total
includes taxes & fees
16 Oct - 17 Oct
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Three birds perched on a wooden structure by the water.

12. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (75 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is AED 2,755
AED 4,865 total
includes taxes & fees
18 Oct - 19 Oct
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

13. 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 815
AED 2,211 total
includes taxes & fees
3 Nov - 4 Nov
Annapolis Retreat - 7 mins from downtown Annapolis!
A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

14. 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 826
AED 2,035 total
includes taxes & fees
21 Oct - 22 Oct
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
A two-story house with a covered patio, a garage, and a well-maintained lawn.

15. Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Admiral Heights
10.0 out of 10, Exceptional, (55 reviews)
"Yes! Enjoyed our stay. Perfect setting and location to enjoy are time in Annapolis."
United States
Maureen D.
The price is AED 1,405
AED 1,832 total
includes taxes & fees
19 Oct - 20 Oct
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
A wooden dock extending into a calm body of water with boats docked at the end.

16. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (86 reviews)
"Location, amenities, cleanliness, parking all great!"
United States
Nancy N.
The price is AED 918
AED 1,763 total
includes taxes & fees
20 Oct - 21 Oct
Cozy 2br home w/ parking in downtown Annapolis
A calm lake with a sandy shore, surrounded by trees and houses.

17. 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 1,058
AED 2,956 total
includes taxes & fees
18 Oct - 19 Oct
Londontowne Home | Beach | 3BR
A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

18. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is AED 2,571
AED 4,630 total
includes taxes & fees
19 Oct - 20 Oct
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
A marina with multiple boats docked, a building with a distinctive yellow roof, and a clear sky.

19. Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (22 reviews)
"The host was amazing, the house was perfect and well equipped, and the location was amazing!!! "
United States
Tim G.
The price is AED 1,837
AED 2,990 total
includes taxes & fees
8 Nov - 9 Nov
Secluded Cozy Cottage in Historic Downtown
A lighthouse with a white exterior, a balcony, and a metal roof.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is AED 315
AED 1,046 total
includes taxes & fees
18 Oct - 19 Oct
Charming Coastal/Country Home w/3 Acres & Sauna!
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

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Perfect place to stay! Classy. Clean comfortable amazing staff"
Nila 2-night trip
Posted 14 hours ago
Annapolis Waterfront Hotel, Autograph Collection

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.