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

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Shady Side holiday homes

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 £185
includes taxes & fees
3 Sept - 4 Sept
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 £398
includes taxes & fees
8 Sept - 9 Sept
Sunset Cottage - West River Access and Views!
Living area

3. 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 £518
includes taxes & fees
2 Sept - 3 Sept
Family Home on Mayo Peninsula | Deck | Sleeps 10
Living area

4. 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 £364
includes taxes & fees
29 Sept - 30 Sept
3-bedroom house in Deale located on Bay many amenities and great views
Private kitchen

5. 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 £417
includes taxes & fees
2 Sept - 3 Sept
Renovated Bungalow | Walk to Beach | Dog-Friendly
Beach

6. 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 £363
includes taxes & fees
8 Sept - 9 Sept
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Exterior

7. 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 £206
includes taxes & fees
2 Sept - 3 Sept
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Beach

8. 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)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is £266
includes taxes & fees
8 Sept - 9 Sept
Beachside Oasis with Beach Passes & King Suite by A Haven Away
Marina

9. 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 £381
includes taxes & fees
2 Sept - 3 Sept
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
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 £450
includes taxes & fees
16 Sept - 17 Sept
Annapolis Retreat - 7 mins from downtown Annapolis!
Beach

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 £545
includes taxes & fees
2 Sept - 3 Sept
Londontowne Home | Beach | 3BR
Outdoor dining

12. 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 £297
includes taxes & fees
2 Sept - 3 Sept
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Outdoor dining

13. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (76 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 £544
includes taxes & fees
2 Sept - 3 Sept
Charming Annapolis WaterVIEW Home
Exterior

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (46 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 £215
includes taxes & fees
2 Sept - 3 Sept
Charming Coastal/Country Home w/3 Acres & Sauna!
Living area

15. 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 £590
includes taxes & fees
14 Sept - 15 Sept
Londontowne Rancher | 3BR | Near Waterfront
Living area

16. 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
Property grounds

17. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
The price is £358
includes taxes & fees
2 Sept - 3 Sept
Rose Haven Coastal Cottage
Private kitchen

18. Luxe Row Home Steps to USNA Gate 3!

Luxe Row Home Steps to USNA Gate 3!
Historic District
10.0 out of 10, Exceptional, (7 reviews)
"Fantastic stay! The VRBO was clean, comfortable and had everything I needed. The backyard/patio area was great for relaxing and communication with the host made everything simple. I plan to stay again and whole-heartedly recommend it to others."
United States
Christine A.
The price is £910
includes taxes & fees
2 Sept - 3 Sept
Luxe Row Home Steps to USNA Gate 3!
Private kitchen

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.
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Marina

20. 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)
"Great place to stay!! Very close to everything in Annapolis and able to walk everywhere."
United States
Matt S.
The price is £325
includes taxes & fees
8 Sept - 9 Sept
Cozy 2br home w/ parking in downtown Annapolis
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

Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

10/10 Excellent
"Nice location, only about 4 miles to downtown Annapolis, an easy bike ride. Breakfast was more than adequate and the hotel and surrounding grounds clean. Lots of shopping nearby and a Whole Foods around the corner that is easily walked to."
George 2-night trip
Posted less than an hour ago
Holiday Inn Express & Suites Annapolis by IHG

Find out more about Shady Side

Shady Side Holiday Homes information

Number of reviews
289
Accommodation
590 Holiday Homes
Lowest Price
£185
Highest Price
£910