Holiday rentals near Shadyside Park
We found 566 holiday rentals — enter your dates for availability
Take a look at private holiday rentals within easy reach of Shadyside Park that can be your home away from home. Whether you're travelling with your children and pets, with friends or just your children, holiday rentals have the amenities that you need and want for your stay, which might include a garden and Wi-Fi. Whatever you're looking for, you'll be able to choose a property to rent that has what everyone needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Shadyside Park
Showing deals for:10 Oct - 17 Oct
Image gallery for Spacious 4 Bedroom Home w/ Hot Tub
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Spacious 4 Bedroom Home w/ Hot Tub
Edgewater, MD
7% off
Price is AU$8,143
AU$8,143
AU$1,163 per night
includes taxes & fees
Image gallery for Bay views with kayaks, bikes, fire pit, crabbing and more
9.69.6 out of 10 rating
Exceptional
(21 reviews)
Bay views with kayaks, bikes, fire pit, crabbing and more
Shady Side, MD
33% off
Price is AU$3,822
AU$3,822
AU$546 per night
includes taxes & fees
Image gallery for Annapolis Area Private, 3 Bedroom Pool, Jacuzzi & Sauna & Casino-Like Game Room
9.69.6 out of 10 rating
Exceptional
(33 reviews)
Annapolis Area Private, 3 Bedroom Pool, Jacuzzi & Sauna & Casino-Like Game Room
Davidsonville, MD
7% off
Price is AU$12,338
AU$12,338
AU$1,763 per night
includes taxes & fees
Image gallery for Charming Annapolis WaterVIEW Home
9.69.6 out of 10 rating
Exceptional
(51 reviews)
Charming Annapolis WaterVIEW Home
Annapolis, MD
8% off
Price is AU$6,216
AU$6,216
AU$888 per night
includes taxes & fees
Image gallery for Spacious 6-bedroom country house on the water in beautiful Shady Side with WiFi
1010 out of 10 rating
Exceptional
(6 reviews)
Spacious 6-bedroom country house on the water in beautiful Shady Side with WiFi
Shady Side, MD
8% off
Price is AU$13,087
AU$13,087
AU$1,870 per night
includes taxes & fees
Image gallery for Captain's Retreat! Newly Renovated - few steps from the beach!
9.89.8 out of 10 rating
Exceptional
(17 reviews)
Captain's Retreat! Newly Renovated - few steps from the beach!
Annapolis, MD
16% off
Price is AU$11,039
AU$11,039
AU$1,577 per night
includes taxes & fees
Image gallery for Modern Bay Dream
1010 out of 10 rating
Exceptional
(15 reviews)
Modern Bay Dream
Deale, MD
8% off
Price is AU$5,832
AU$5,832
AU$833 per night
includes taxes & fees
Image gallery for Water Views - Close to Downtown Annapolis
1010 out of 10 rating
Exceptional
(45 reviews)
Water Views - Close to Downtown Annapolis
Annapolis, MD
12% off
Price is AU$6,346
AU$6,346
AU$907 per night
includes taxes & fees
Image gallery for Walk to Bay, Family + Dog Friendly, Fenced Yard, Beach Passes - 3BD/2BA
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Walk to Bay, Family + Dog Friendly, Fenced Yard, Beach Passes - 3BD/2BA
North Beach, MD
8% off
Price is AU$2,821
AU$2,821
AU$403 per night
includes taxes & fees
Image gallery for Cute Bay Home/Fantastic View and Sandy Beach
9.49.4 out of 10 rating
Exceptional
(28 reviews)
Cute Bay Home/Fantastic View and Sandy Beach
Tracys Landing, MD
7% off
Price is AU$3,285
AU$3,285
AU$469 per night
includes taxes & fees
Image gallery for Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
9.89.8 out of 10 rating
Exceptional
(38 reviews)
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
West River, MD
12% off
Price is AU$1,934
AU$1,934
AU$276 per night
includes taxes & fees
Image gallery for Cute bungalow blocks to Stadium
1010 out of 10 rating
Exceptional
(5 reviews)
Cute bungalow blocks to Stadium
Annapolis, Maryland
8% off
Price is AU$11,528
AU$11,528
AU$1,647 per night
includes taxes & fees
Image gallery for Cozy Annapolis Cottage
1010 out of 10 rating
Exceptional
(11 reviews)
Cozy Annapolis Cottage
Annapolis, MD
8% off
Price is AU$6,373
AU$6,373
AU$910 per night
includes taxes & fees
Image gallery for Enchanting West River Retreat
1010 out of 10 rating
Exceptional
(8 reviews)
Enchanting West River Retreat
West River, MD
7% off
Price is AU$4,940
AU$4,940
AU$706 per night
includes taxes & fees
Image gallery for Chesapeake Bay Getaway | New Waterfront With Private Pier | Near Annapolis /USNA
1010 out of 10 rating
Exceptional
(21 reviews)
Chesapeake Bay Getaway | New Waterfront With Private Pier | Near Annapolis /USNA
Edgewater, MD
8% off
Price is AU$5,796
AU$5,796
AU$828 per night
includes taxes & fees
Image gallery for Riverview Retreat on Warehouse Creek - sleeps 6
1010 out of 10 rating
Exceptional
(23 reviews)
Riverview Retreat on Warehouse Creek - sleeps 6
Edgewater, MD
8% off
Price is AU$6,934
AU$6,934
AU$991 per night
includes taxes & fees
Image gallery for Private Waterfront Home w/ Pier and 2+ Acres!
1010 out of 10 rating
Exceptional
(84 reviews)
Private Waterfront Home w/ Pier and 2+ Acres!
Deale, MD
8% off
Price is AU$5,535
AU$5,535
AU$791 per night
includes taxes & fees
Image gallery for Freshly renovated 3-story home 1 block from USNA!
9.89.8 out of 10 rating
Exceptional
(34 reviews)
Freshly renovated 3-story home 1 block from USNA!
Annapolis, Maryland
8% off
Price is AU$13,522
AU$13,522
AU$1,932 per night
includes taxes & fees
Image gallery for Waterfront, Private Beach, Peaceful Family Getaway
9.89.8 out of 10 rating
Exceptional
(54 reviews)
Waterfront, Private Beach, Peaceful Family Getaway
North Beach, MD
8% off
Price is AU$4,554
AU$4,554
AU$651 per night
includes taxes & fees
Image gallery for Dog friendly! Next to Navy Stadium and DTA Shuttle!
1010 out of 10 rating
Exceptional
(7 reviews)
Dog friendly! Next to Navy Stadium and DTA Shuttle!
Annapolis, MD
12% off
Price is AU$6,003
AU$6,003
AU$858 per night
includes taxes & fees
Image gallery for The Liberty House- Pristine Renovation with parking
1010 out of 10 rating
Exceptional
(42 reviews)
The Liberty House- Pristine Renovation with parking
Annapolis, MD
8% off
Price is AU$5,922
AU$5,922
AU$846 per night
includes taxes & fees
Image gallery for Pristine Waterfront Home with Expansive Views.
1010 out of 10 rating
Exceptional
(24 reviews)
Pristine Waterfront Home with Expansive Views.
Deale, MD
8% off
Price is AU$6,196
AU$6,196
AU$885 per night
includes taxes & fees
Image gallery for ★ Midcentury Modern Getaway ★ Prime Location ★
1010 out of 10 rating
Exceptional
(33 reviews)
★ Midcentury Modern Getaway ★ Prime Location ★
Annapolis, MD
8% off
Price is AU$11,714
AU$11,714
AU$1,673 per night
includes taxes & fees
Image gallery for 3 BR Pet Friendly Beverly Beach Cottage
9.89.8 out of 10 rating
Exceptional
(7 reviews)
3 BR Pet Friendly Beverly Beach Cottage
Edgewater, MD
7% off
Price is AU$4,969
AU$4,969
AU$710 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Shadyside Park
Private Waterview Estate with 4 Suites, Hot Tub, Gourmet Kitchen and Game Room
Sleeps 14 · 6 bedrooms · 5 bathrooms
9.89.8 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
91 reviews(91 reviews)
Waterfront Camper with Dock
Sleeps 6 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Chesapeake Bay Cottage
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
80 reviews(80 reviews)
Waterfront Oasis in Eastport-Easy Walk to Downtown
Sleeps 10 · 5 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
87 reviews(87 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value