Home Vacation Home Rentals By Owner In Annapolis, MD

Showing 120 Of 318 Vacation Rentals
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Exceptional(13)

$736.44

/ Nightly
Private Vacation Home

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(1)

$1723.68

/ Nightly
Private Vacation Home

Beautiful colonial only 3 miles to the Naval Academy!

Annapolis, Maryland, United States

Bed 6

Bed

Bath 2

Bath

Sleep 12

Sleeps
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Exceptional(56)

$1376.74

/ Nightly
Private Vacation Home

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Annapolis, Maryland, United States

Bed 6

Bed

Bath 4

Bath

Sleep 18

Sleeps
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$1210.91

/ Nightly
Private Vacation Home

GREENNEST is an ENVIRONMENTALLY FRIENDLY Waterfront home close to Annapolis

Annapolis, Maryland, United States

Bed 4

Bed

Bath 4

Bath

Sleep 12

Sleeps
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Exceptional(32)

$1097.44

/ Nightly
Private Vacation Home

Newer Waterfront Home on the Chesapeake Bay

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(48)

$1015.74

/ Nightly
Private Vacation Home

Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

Annapolis, Maryland, United States

Bed 7

Bed

Bath 4

Bath

Sleep 15

Sleeps
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Exceptional(2)

$943.92

/ Nightly
Private Vacation Home

Private 4-bedroom house in Annapolis, great location!

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 11

Sleeps
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$929.91

/ Nightly
Private Vacation Home

Waterfront home in Annapolis MD with private pier

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(4)

$772.92

/ Nightly
Private Vacation Home

Annapolis Baystone House

Annapolis, Maryland, United States

Bath 4

Bath

Sleep 8

Sleeps
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Exceptional(15)

$748.98

/ Nightly
Private Vacation Home

Charming Home located minutes from the Naval Academy and Downtown Annapolis

Annapolis, Maryland, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(18)

$579.69

/ Nightly
Private Vacation Home

Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Annapolis, Maryland, United States

Bed 4

Bed

Bath 2

Bath

Sleep 12

Sleeps
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$546.06

/ Nightly
Private Vacation Home

Annapolis Retreat

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(24)

$550.28

/ Nightly
Private Vacation Home

Annapolis Charm Waterfront Private Fishing Dock Pier Near Beach & Naval Academy

Annapolis, Maryland, United States

Bed 3

Bed

Bath 1

Bath

Sleep 8

Sleeps
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Exceptional(1)

$558.57

/ Nightly
Private Vacation Home

Bay Home in Annapolis with Private Dock

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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$562.73

/ Nightly
Private Vacation Home

Waterfront View of Severn, 6 Bedrooms, Sleeps 11

Annapolis, Maryland, United States

Bed 6

Bed

Bath 3

Bath

Sleep 16

Sleeps
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Exceptional(42)

$616.42

/ Nightly
Private Vacation Home

Luxury Annapolis Oasis: Hot Tub, Fire Pit, Fully Fenced, Pet Friendly

Annapolis, Maryland, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(64)

$732.45

/ Nightly
Private Vacation Home

Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(6)

$662.66

/ Nightly
Private Vacation Home

Spacious 4BR Annapolis Home | Near Navy Stadium & Downtown | Sleeps 9

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 9

Sleeps
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Exceptional(4)

$1466.42

/ Nightly
Private Vacation Home

Stunning Waterfront Retreat w/Pool, Private Dock & Sauna Near Downtown Annapolis

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(59)

$608.95

/ Nightly
Private Vacation Home

Unwind at Waterfront Annapolis w/swimming pool & pier - July specials!

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Private vacation home

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View 318 Private vacation home

Home Most popular vacation rentals in Annapolis

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Exceptional(59)

$1926.40

/ Nightly
Private vacation home

Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D

Annapolis, Maryland, United States

Bed 6

Bed

Bath 4

Bath

Sleep 12

Sleeps
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Exceptional(59)

$2008.68

/ Nightly
Private vacation home

Spacious Converted Carriage House in Historic District near USNA

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(59)

$2164.57

/ Nightly
Private vacation home

Welcoming Waterfront Luxury Estate for Family, Friends, and Pets in Annapolis

Annapolis, Maryland, United States

Bed 6

Bed

Bath 6

Bath

Sleep 14

Sleeps
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Exceptional(59)

$2302.80

/ Nightly
Private vacation home

Fantastic house with lots of parking in downtown Annapolis, steps to the USNA!

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(59)

$2805.96

/ Nightly
Private vacation home

Downtown Annapolis Duke's House

Annapolis, Maryland, United States

Bed 0

Bed

Bath 4

Bath

Sleep 9

Sleeps
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Exceptional(59)

$2853.88

/ Nightly
Private vacation home

Cool 1870's home anchored in the Historic District with modern amenities.

Annapolis, Maryland, United States

Bed 5

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(59)

$2974.10

/ Nightly
Private vacation home

Nantucket on the Chesapeake Heated Pool

Annapolis, Maryland, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(59)

$499.32

/ Nightly
House boat

Welcome Aboard the Kathleen Marie!

Annapolis, Maryland, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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Exceptional(59)

$485.19

/ Nightly
Apartment

Pool Loft Suite | Bay Access & Beach Passes

Annapolis, Maryland, United States

Bed 1

Bed

Bath 3

Bath

Sleep 4

Sleeps
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Exceptional(59)

$487.67

/ Nightly
Private vacation home

Parking. Short Uber Ride. Townhouse in Annapolis! 3 Miles from USNA and Downtown

Annapolis, Maryland, United States

Bed 4

Bed

Bath 4

Bath

Sleep 9

Sleeps

Most Popular Cities in Maryland