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Wireless Internet
Air conditioning
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Private pool

Heated pool
Private indoor pool
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Cot available
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Staffed property
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Swing set or jungle gym
Bicycles available
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Pets allowed
Parking
Car not required
Children under 5

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Beach or lakeside relaxation
Walking trips
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78 villas

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Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms
2 bathrooms

sleeps 5

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Price per night from

$352

Waterfront Property, Kayaks, Private Dock, Near Town

St. Michaels house

3 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$859

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

St. Michaels house

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$716

TRUE ST MICHAELS 6 ACRE WATERFRONT

St. Michaels house

5 bedrooms
3 bathrooms

sleeps 8

Responds fast! avg. 38 minutes

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Price per night from

$2,295

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

St. Michaels house

6 bedrooms
6 bathrooms

sleeps 12

Responds fast! avg. 38 minutes

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Price per night from

$2,295

Ship's Cove Inn and Resort in St. Michaels, MD

St. Michaels house

6 bedrooms
6 bathrooms

sleeps 12

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Price per night from

$1,890

Great rentals within 20 miles that match your search

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms
3 bathrooms

sleeps 10

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Price per night from

$1,148

Quiet Home Close to Downtown Annapolis and Parks

Annapolis house

4 bedrooms
3 bathrooms

sleeps 7

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Price per night from

$401

CHESAPEAKE MANSION - NEW POOL/12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Sherwood house

8 bedrooms
10 bathrooms

sleeps 12

Responds fast! avg. 38 minutes

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Price per night from

$2,868

Warwick River Retreat

East New Market house

5 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$1,262

Ferry Bridge House

Easton house

3 bedrooms
5 bathrooms

sleeps 6

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Price per night from

$798

Gourmet Kitchen, Family and Pet Friendly Residence!

Mayo house

3 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$402

Huge Beach Bungalow- Yard, Beach Pass, King Beds

North Beach house

4 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$631

Beautiful Waterfront Home, Private Pool and Water Amenities- Sleeps 16

Cambridge house

5 bedrooms
3 bathrooms

sleeps 18

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Price per night from

$861

Waterfront Getaway, Dock Your Boat and Play!

Mayo camper van

1 bedroom
1 bathroom

sleeps 6

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Price per night from

$343

Captain Quarters - Eastport!

Annapolis house

4 bedrooms
3 bathrooms

sleeps 10

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Price per night from

$573

Fisher House - Downtown Annapolis!

Annapolis house

3 bedrooms
2 bathrooms

sleeps 9

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Price per night from

$683

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Annapolis apartment

2 bedrooms
1 bathroom

sleeps 6

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Price per night from

$224

Edgewater/Mayo Getaway!

Edgewater house

4 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$457

Bay Ridge house by Quiet Waters Park, Thomas Point Park

Annapolis apartment

2 bedrooms
1 bathroom

sleeps 5

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Price per night from

$224

Luxury Waterfront - 40 Acre Estate - Swimming, Boating, Activities

Royal Oak manor house

25 bedrooms
25 bathrooms

sleeps 50

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Price per night from

$7,443

Annapolis Charm™ Waterfront Chesapeake Bay Getaway - Private Pier - Near USNA

Cape Saint Claire house

2 bedrooms
1 bathroom

sleeps 6

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Price per night from

$401

Chesapeake Bay Getaway™ | Waterfront Experience with Pier!

Edgewater house

2 bedrooms
1 bathroom

sleeps 8

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Price per night from

$573

King George Downtown Annapolis Getaway

Annapolis apartment

2 bedrooms
1 bathroom

sleeps 6

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Price per night from

$430

Breathtaking Waterfront Cambridge Getaway

Cambridge house

3 bedrooms
2 bathrooms

sleeps 12

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Price per night from

$682

Deep in the Heart of Annapolis; Parking for days!

Annapolis house

4 bedrooms
4 bathrooms

sleeps 6

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Price per night from

$518

Steps to Main Street w View of the Capital private back patio & free off-site pa

Annapolis house

4 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$324

Eastport Bungalow - Popular house Walk to Downtown & USNA

Annapolis house

3 bedrooms
2 bathrooms

sleeps 7

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Price per night from

$400

Popular Historic Firehouse fully renovated with Parking and Pet Friendly

Annapolis house

3 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$465

Hanover House across from USNA Gate 3 with private back patio

Annapolis house

4 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$465

Parking at Stunning On Cloud 9 with private patio pet-friendly

Annapolis house

4 bedrooms
4 bathrooms

sleeps 10

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Price per night from

$500

Private Waterfront Retreat with Pool, Hot Tub and Game Room

Tracys Landing house

5 bedrooms
4 bathrooms

sleeps 14

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Price per night from

$727

Steps from the water, Easy parking and private backyard patio

Annapolis house

2 bedrooms
2 bathrooms

sleeps 7

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Price per night from

$355

Spacious Townhouse 1 block to Capital Bldg, Parking Multiple gathering spaces

Annapolis house

3 bedrooms
4 bathrooms

sleeps 6

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Price per night from

$355

Free Parking at Randall House in Downtown Annapolis

Annapolis house

4 bedrooms
4 bathrooms

sleeps 11

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Price per night from

$729

Pool and Bay Views on wrap around deck in Kent Island

Stevensville house

3 bedrooms
3 bathrooms

sleeps 12

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Price per night from

$321

Take your Leave of Absence around gardens with driveway parking

Annapolis house

3 bedrooms
2 bathrooms

sleeps 9

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Price per night from

$426

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

Annapolis house

4 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$465

Viewing 38 of 78
rentals in St. Michaels

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Vacation Rentals & Villas in St. Michaels

Per night

78 villas

Viewing 38 of 78rentals in St. Michaels

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Viewing 38 of 78
rentals in St. Michaels