Home Vacation Rentals By Owner In Annapolis, MD

Showing 160 Of 450 Vacation Rentals
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Exceptional(6)

$709.54

/ Nightly
Private Vacation Home

Oasis by the Bay - Waterfront Heated Pool Hot Tub!

Annapolis, Maryland, United States

Bed 6

Bed

Bath 5

Bath

Sleep 18

Sleeps
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Exceptional(30)

$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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$219.82

/ Nightly
Hotel

Boutique Historic Stay Near USNA & Annapolis City Dock | 1 King Bed

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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$218.68

/ Nightly
Hotel

Robert Johnson 1 Queen Bed Pure Wellness Room at Historic Inns of Annapolis

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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$218.68

/ Nightly
Hotel

Maryland Inn | Victorian Charm | Queen Room | 0.1mi State House

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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$218.68

/ Nightly
Hotel

Robert Johnson 1 King Bed Pure Wellness Room at Historic Inns of Annapolis

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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$173.08

/ Nightly
Hotel

Maryland Inn Queen at Historic Inns of Annapolis | Pets are Allowed

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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$173.08

/ Nightly
Hotel

Elegant Historic Flat: Near State House & Naval Academy | Pets Are Allowed

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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$380.56

/ Nightly
Hotel

Pet-friendly Accommodation at Historic Inns of Annapolis | 0.3 mi to State House

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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$380.56

/ Nightly
Hotel

Maryland Inn Suite at Historic Inns of Annapolis | Pets Are Allowed

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(63)

$638.4

/ Nightly
Private Vacation Home

Eastport Cottage .5 mi from Downtown Annapolis

Annapolis, Maryland, United States

Bed 2

Bed

Bath 1

Bath

Sleep 3

Sleeps
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Exceptional(7)

$420.28

/ Nightly
Private Vacation Home

Eastport Bungalow | Yard, Grill & Walk Downtown

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(28)

$575.9

/ Nightly
Private Vacation Home

Scenic One-Level Waterfront Retreat Mins to Annapolis w Panoramic Bay/Bridge Views & Fenced-In Yard

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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$181.06

/ Nightly
Hotel

Robert Johnson Queen at Historic Inns of Annapolis | 0.1mi State Circle

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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$385.12

/ Nightly
Hotel

Robert Johnson Suite | 0.2mi to William Paca House & 0.3mi to USNA

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(1)

$219.82

/ Nightly
Hotel

Robert Johnson 2 Double Beds Pure Wellness Room at Historic Inns of Annapolis

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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$181.06

/ Nightly
Hotel

Explore Local Attractions | Across Maryland State House | 0.2mi to City Dock

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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$380.56

/ Nightly
Hotel

Robert Johnson Suite at Historic Inns of Annapolis | Pet-Friendly + Free Shuttle

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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$218.68

/ Nightly
Hotel

Close to Naval Academy & State House | Robert Johnson 2 Doubles

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(1)

$601.57

/ Nightly
Private Vacation Home

Green on Fleet 1 Block to City Dock & USNA w Parking

Annapolis, Maryland, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Home Most popular vacation rentals in Annapolis

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Exceptional(1)

$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(1)

$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(1)

$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(1)

$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(1)

$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(1)

$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(1)

$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(1)

$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(1)

$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(1)

$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