Home Vacation Rentals By Owner In Annapolis, MD

Showing 120 Of 450 Vacation Rentals
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$262.66

/ Nightly
Apartment

Walk to Navy Stadium | Private Studio w/ Parking

Annapolis, Maryland, United States

Bath 1

Bath

Sleep 2

Sleeps
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Exceptional(126)

$600.15

/ Nightly
Private Vacation Home

Waterfront Retreat in Riva· Pool, Pier & Kayaks · Sleeps 9 · 15 Min to Annapolis

Annapolis, Maryland, United States

Bed 4

Bed

Bath 2

Bath

Sleep 9

Sleeps
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$347.7

/ Nightly
Bed & Breakfast

Charming Living room in beautiful Annapolis with AC discount long stay

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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$278.54

/ Nightly
Private Vacation Home

Charming barn in Annapolis for a relaxing getaway not a room just a mattress

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 6

Sleeps
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$559.68

/ Nightly
Private Vacation Home

Annapolis Retreat | Outdoor Kitchen + Fire Pit

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(26)

$222.42

/ Nightly
Guest House

A Serene Tiny Home Experience

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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Exceptional(9)

$1066.7

/ Nightly
Private Vacation Home

Luxury Home w Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis

Annapolis, Maryland, United States

Bed 3

Bed

Bath 3

Bath

Sleep 12

Sleeps
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Exceptional(3)

$584.93

/ Nightly
Private Vacation Home

Charming 3-bedroom house in Annapolis two blocks from the Navy Stadium

Annapolis, Maryland, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Hotel

Historic Inn Stay | 1 Unit | Heart of Annapolis at State Circle

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 1

Sleeps
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Hotel

Historic Inn | Steps from Naval Academy & State House

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 1

Sleeps
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Exceptional(1)

$512.15

/ Nightly
Private Vacation Home

Cozy Townhome in Downtown Annapolis

Annapolis, Maryland, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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Exceptional(66)

$450.3

/ Nightly
Apartment

CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS

Annapolis, Maryland, United States

Bed 2

Bed

Bath 1

Bath

Sleep 5

Sleeps
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Exceptional(27)

$2974.1

/ 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(100)

$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(2)

$455.32

/ Nightly
Private Vacation Home

Charming 1926 Four Bedroom Home w Ample Parking

Annapolis, Maryland, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(4)

$1325.66

/ Nightly
Private Vacation Home

Clean, Spacious Family House

Annapolis, Maryland, United States

Bed 5

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(4)

$514.14

/ Nightly
Private Vacation Home

Charming 3-bedroom house in Annapolis Eastport! Beautifully furnished home

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(35)

$813.96

/ Nightly
Private Vacation Home

Adorable cottage! Walking distance to USNA & downtown! (VRBO only)

Annapolis, Maryland, United States

Bed 3

Bed

Bath 1

Bath

Sleep 5

Sleeps
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Exceptional(9)

$560.78

/ Nightly
Apartment

Historic dog-friendly home 2 blocks to Main St

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

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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Private vacation home

Private vacation home

View 318 Private vacation home

Home Most popular vacation rentals in Annapolis

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$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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$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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$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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$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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$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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$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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$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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$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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$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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$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