Shady Side Rentals

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123 Houses

180-degree water views at unique round house

Shady Side house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$424

Private Waterview Estate with 4 bedroom Suites & Hot Tub

Shady Side house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

Price per night from

$429

Great rentals within 20 miles that match your search

Beautiful Murray Hill Home (Annapolis)

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

“Comfortable and secure in a great home - almost as good as at ho” The house is set is a terrific neighborhood of annapolis within easy walking distance to two small parks on the water and to town. We all found the house a delight - the design, decorating, furnishings are tasteful and match the age and the imagery of the house. It is well equipped with comfortable bedrooms, adequate bathrooms and linens, utensils and staple supplies. We certainly will attempt to stay at this house again if we ever return to annapolis.

Price per night from

$487

2. Private 20 acre waterfront estate - studio apt

Annapolis apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$344

Vintage Bungalow-cozy, walk to shops, water, free pkg.

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$476

Waterfront Property, Kayaks, Private Dock, Near Town

St. Michaels house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$859

Love Point Waterfront

Kent Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

“Love Point Retreat” I stayed at Paula's property 3 times so far. We stayed once in October 2014 and twice in April 2015. Here is how I would break it up: Owner: Paula is very nice, accommodating and extremely responsive. She was easy to deal with, answered all of our questions and concerns timely. Property (Interior): The property is really clean and very well maintained considering its age. I also feel that it is properly stocked with all the necessities. Property (Outdoor Space / View): We spend the majority of our time there outside. The deck / backyard area is very well maintained and stocked with adequate furniture. We used the gas grill every day of our stay. The dock is set up nicely for fishing including rod holders and a light for night fishing. The view from the dock is to die for, the Bay is so wide and the Bay Bridge is a nice backdrop to the view specially during sunset. Fishing: Fishing is the best I have ever experienced (compared to all other rentals I tried). I caught numerous species from the dock including Spot, White Perch and of course Striped Bass (Rockfish). I caught my biggest Rockfish ever from the dock there (39 inch fish, roughly 30 pounds) in April. Overall, I love the property, the view and the peaceful surroundings. A great bonus for me is the short one hour commute to get there. We will definitely be back to Love Point for an encore.

Price per night from

$458

One Beautiful home come relax

Cheltenham house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 6

Price per night from

$201

KENT ISLAND-OCEAN VIEW Home for rent-4 bedrooms EASTERN SHORE sleeps 10-12

Kent Island house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Price per night from

$1,947

DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12

Chester house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$1,947

2 Bedroom Condo minutes away from DC & VA

Largo condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Price per night from

$201

The Heart of Historic Cool in Annapolis

Annapolis house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$1,145

Stunning Waterfront Home in Round Bay

Severna Park house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$1,451

Walk to waterfront & USNA with Parking at Historic Wisteria

Annapolis house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$465

Popular Historic Firehouse fully renovated with Parking and Pet Friendly

Annapolis house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$465

Steps to Gate 1 and Free Parking at Naval-Academy Themed Home

Annapolis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 11

Price per night from

$610

Available 2024 Commissioning Week 13 mins to USNA Big Family Space

Severna Park house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 14

Price per night from

$127

Price per night from

$370

Sprawling Family home on a Cul De Sac sleeps 10-14!

Severna Park house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Price per night from

$382

Cottage by the Bay on one level in family-friendly community

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$367

Escape to this Cape Cod home close to everything!

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$414

"Around the corner" from everything, private backyard and parking!

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$426

Private deck, backyard and dog-friendly just 12 minutes to Annapolis

Severna Park house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$338

Hanover House across from USNA Gate 3 with private back patio

Annapolis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$465

Pool and Bay Views on wrap around deck in Kent Island

Stevensville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

Price per night from

$321

2 parking spots and Walkable to Main Street at Seashell in the City

Annapolis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$465

Price per night from

$465

Stay at Lux Red Door Gem with 3 Parking Spots

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$382

Deep in the Heart of Annapolis; Parking for days!

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 6

Price per night from

$518

Free Parking at Randall House in Downtown Annapolis

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 11

Price per night from

$729

Waterfront Jolly Roger with Private Pier mins to Annapolis

Crownsville house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

Price per night from

$454

Steps from the water, Easy parking and private backyard patio

Annapolis house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$378

Private pier at Waterfront Kent Island home with Hot Tub (Open!)

Stevensville house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$416

1 Block to USNA with Chapel Views big back patio and off-site parking!

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$465

Quiet Home Close to Downtown Annapolis and Parks

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$400

Price per night from

$315

St. Michael's Premier in Town Summer Cottage now with private pool!

St. Michaels house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$716

Free Parking with private fenced-in backyard with pool table at Weekender

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$292

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