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Shady Side Rentals

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Price range

Per night

$10 - $500

Rental types

Shady Side Rentals

78 Houses

Shady Side House on Chesapeake Bay Near Marina!

Shady Side house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 9 minutes

Price per night from

$184

1 / 24

Great rentals within 20 miles that match your search

Halos'Haven Vacation Rental

McDaniel house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$695

1 / 15

Seahorse Guest Cottage near the Bay, dog friendly

North Beach cottage

1 bedroom / 1 bathroom / sleeps 5

Responds fast! avg. 12 minutes

Price per night from

$159

1 / 17

Annapolis Crows Nest Cottage: Chesapeake Bay View

Annapolis villa

5 bedrooms / 3 bathrooms / sleeps 20

Price per night from

$686

1 / 26

Love Point Luxury Waterfront in Stevensville

Stevensville house

3 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$1,389

1 / 26

Huge Stevensville House Overlooking Eastern Shore!

Stevensville house

3 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 9 minutes

Price per night from

$397

1 / 26

Waterfront Stevensville House w/ Pier & 2 Decks!

Stevensville house

5 bedrooms / 2 bathrooms / sleeps 12

Responds fast! avg. 10 minutes

Price per night from

$373

1 / 25

St. Michaels Waterfront Home W/Dock for 2 boats

Neavitt house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$224

1 / 18

Tilghman Island Cottage for Six - Near Marina and Knapps Narrows Drawbridge

Tilghman cottage

3 bedrooms / 2 bathrooms / sleeps 6

“We loved it!” We had a great (albeit too short!) family getaway at the Roost! The cottage is extremely clean, comfortable, well-maintained, and spacious. The kids (ages 6 and 20 months) loved it -- especially the bunk beds and the nice backyard, and t

Price per night from

$199

1 / 20

C/ean & Cozy

Annapolis room

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$59

1 / 10

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

“Crabtastic Great Escape” This cottage is the perfect great escape. Conveniently located in the middle of quaint St Michael's close to the harbor, restaurants, and shops. The property is clean and well-maintained with beautiful landscaping. The buildin

Responds fast! avg. 3 hours 32 minutes

Price per night from

$148

1 / 27

St. Michaels Area Cottage - Walk to Water & Marina

Neavitt house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 12 minutes

Price per night from

$174

1 / 28

Upscale House/12 MINUTES FROM DC

Bowie house

5 bedrooms / 3 bathrooms / sleeps 16

Price per night from

$487

1 / 33

Best sunrise in St. Michaels....Broadview Bay House

St. Michaels house

6 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$596

1 / 24

Cottage 1a at Grandview Pleasure Point

Bozman house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$244

1 / 8

Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)

Chester house

4 bedrooms / 2 bathrooms / sleeps 8

“Unbelievable value” We were a family group of 3 couples plus an infant traveling to a wedding at the Usna chapel. The home was just wonderful, had a great view, was very clean, and was well equipped for the cooking being planned. Stores, restaurants,

Price per night from

$283

1 / 21

Renovated Luxury Waterview House

North Beach house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$296

1 / 9

Cottage 2 at Grandview Pleasure Point

Bozman house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$383

1 / 9

Annapolis Area Waterfront Home

Annapolis house

5 bedrooms / 4 bathrooms / sleeps 11

Price per night from

$543

1 / 21

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, ans

Price per night from

$249

1 / 19

Charming and Spacious Annapolis Victorian

Annapolis house

6 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 1 hour 34 minutes

Price per night from

$740

1 / 19

Location,location,location,walk to city dock,free

Annapolis apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$179

1 / 15

Clean & Spacious

Cape Saint Claire house

4 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$348

1 / 12

Harris Cove Cottages LLC

St. Michaels cottage

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$199

1 / 12

Walk to Shops/Eateries Charming Cottage. Dogs Wel.

Annapolis house

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 49 minutes

Price per night from

$249

1 / 52

Perfect Annapolis with Lots of Parking & Hot Tub

Annapolis townhouse

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$492

1 / 4

St. Michael's Premier in Town Summer Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$283

1 / 7

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, decor

Price per night from

$422

1 / 30

St. Michaels award-winning waterfront BayCottage, pool, docks, sundeck, grounds

St. Michaels villa

6 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 1 hour 1 minutes

Price per night from

$839

1 / 38

Metromax Lovely Private Studio!

Gambrills apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$60

1 / 6

The Yellow House- Gorgeous Southern Colonial

Annapolis house

6 bedrooms / 6 bathrooms / sleeps 14

Responds fast! avg. 1 hour 30 minutes

Price per night from

$982

1 / 43

Lochhaven house for rent

Edgewater house

3 bedrooms / 1 bathroom / sleeps 2

Price per night from

$100

1 / 4

One Beautiful home come relax

Cheltenham house

6 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$174

1 / 6

NEW! Charming Annapolis Home w/ Yard-5 Mins to DT!

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 12 minutes

Price per night from

$317

1 / 24

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

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,489

1 / 32

Luxury vacation condominum with private beach

Chester house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$437

1 / 35

KI Golf House-A PAR for the Course & Mile to Beach

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$596

1 / 17

Kent Island Beach House II:Chesapeake Bay Fisherman's Village at Kentmorr Marina

Stevensville house

4 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$645

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