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

Holiday Homes in Shady Side

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Shady Side holiday homes

A deck with outdoor furniture, a red door, and a house with windows.

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
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 NZ$435
includes taxes & fees
22 Sept - 23 Sept
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

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 NZ$964
includes taxes & fees
6 Oct - 7 Oct
Sunset Cottage - West River Access and Views!
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

3. 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 NZ$527
includes taxes & fees
21 Sept - 22 Sept
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

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 NZ$865
includes taxes & fees
30 Sept - 1 Oct
3-bedroom house in Deale located on Bay many amenities and great views
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

5. 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)
"We enjoyed our stay in North Beach at this lovely residence. It was spacious, clean, nicely furnished and only a few minutes walk to the bay. The beds were so comfortable too!!"
United States
Penny N.
The price is NZ$802
includes taxes & fees
23 Sept - 24 Sept
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

6. 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 NZ$1,247
includes taxes & fees
20 Sept - 21 Sept
Family Home on Mayo Peninsula | Deck | Sleeps 10
A beach with chairs and a pier in the background.

7. 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)
"Almost everything that you might need is provided, but if not there is shopping close by. Hot tub was nice. Very clean home."
United States
Sharon Z.
The price is NZ$849
includes taxes & fees
22 Sept - 23 Sept
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

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, (23 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is NZ$680
includes taxes & fees
28 Sept - 29 Sept
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A house with a brick exterior, a front porch with a bench, and hanging flower baskets.

9. The Harness Creek Retreat in Annapolis

The Harness Creek Retreat in Annapolis
Hillsmere
The price is NZ$769
includes taxes & fees
17 Sept - 18 Sept
The Harness Creek Retreat in Annapolis
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.

10. 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 NZ$1,199
includes taxes & fees
17 Sept - 18 Sept
Londontowne Rancher | 3BR | Near Waterfront
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

11. 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 NZ$1,132
includes taxes & fees
23 Sept - 24 Sept
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.

12. 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 NZ$877
includes taxes & fees
12 Oct - 13 Oct
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
A calm lake with a sandy shore, surrounded by trees and houses.

13. 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 NZ$1,311
includes taxes & fees
17 Sept - 18 Sept
Londontowne Home | Beach | 3BR
A covered outdoor area with a view of the water, a wicker chair, a table with a plant, and a sofa with pillows.

14. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (77 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 NZ$1,312
includes taxes & fees
22 Sept - 23 Sept
Charming Annapolis WaterVIEW Home
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

15. 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 NZ$1,101
includes taxes & fees
4 Oct - 5 Oct
Renovated Bungalow | Walk to Beach | Dog-Friendly
A laundry room with a washing machine and dryer, wooden cabinets above, and a shelf with a bottle.

16. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
"Great place to stay! Location was nice and close to water views. House was charming and CLEAN. Owners went above and beyond to make the stay welcoming and convenient. Price was reasonable until additional Vrbo fees were added."
United States
Sharon t.
The price is NZ$744
includes taxes & fees
21 Sept - 22 Sept
Rose Haven Coastal Cottage
A lighthouse with a white exterior, a balcony, and a metal roof.

17. 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 NZ$527
includes taxes & fees
21 Sept - 22 Sept
Charming Coastal/Country Home w/3 Acres & Sauna!
A spacious living room with a fireplace, a television, and a dining area with a table and chairs.

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

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is NZ$1,080
includes taxes & fees
29 Sept - 30 Sept
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
A modern kitchen with a central island, built-in oven, and microwave.

19. Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.4 out of 10, Exceptional, (11 reviews)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
The price is NZ$891
includes taxes & fees
29 Sept - 30 Sept
Cute bungalow blocks to Stadium
A wooden dock extending into a calm body of water with boats docked at the end.

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)
"Location, amenities, cleanliness, parking all great!"
United States
Nancy N.
The price is NZ$775
includes taxes & fees
22 Sept - 23 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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

8/10 Good
"Clean rooms beautiful property!"
Heather 1-night trip
Posted 9 hours ago
DoubleTree by Hilton Hotel Annapolis

Find out more about Shady Side

Shady Side Holiday Homes information

Number of reviews
209
Accommodation
593 Holiday Homes
Lowest Price
NZ$435
Highest Price
NZ$1,312