Home Vacation Rentals By Owner In Annapolis, MD

Showing 340 Of 450 Vacation Rentals
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$2571.27

/ Nightly
Private Vacation Home

The Harness Creek House

Annapolis, Maryland, United States

Bed 6

Bed

Bath 5

Bath

Sleep 12

Sleeps
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$1578.33

/ Nightly
Private Vacation Home

18th Century 4bdrm Luxury Historic Home in Downtown Annapolis

Annapolis, Maryland, United States

Bed 3

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(3)

$1692.9

/ Nightly
Private Vacation Home

Annapolis History In Style Next to City Dock with Street Parking

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 5

Sleeps
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Exceptional(87)

$396.15

/ Nightly
Apartment

Waterfront Oasis of Annapolis Star

Annapolis, Maryland, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(45)

$648.63

/ Nightly
Private Vacation Home

Walk to Waterfront from Eastport Gem w Fire Pit, Porch & Fenced-In Yard

Annapolis, Maryland, United States

Bed 2

Bed

Bath 1

Bath

Sleep 7

Sleeps
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$1463.08

/ Nightly
Private Vacation Home

This thoughtfully styled home overlooks the Bay and is perfect for your Annapolis escape.

Annapolis, Maryland, United States

Bed 5

Bed

Bath 5

Bath

Sleep 14

Sleeps
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Exceptional(203)

$224.01

/ Nightly
Condo

Renovated Apt In Historic Dist w/2 Parking Spots

Annapolis, Maryland, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(8)

$587.14

/ Nightly
Private Vacation Home

Historic Annapolis Retreat Steps to the Statehouse & City Dock w Parking & Private Patio

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(7)

$558.89

/ Nightly
Condo

Waterfront Suite with Views of Annapolis from Prime Eastport Location

Annapolis, Maryland, United States

Bed 2

Bed

Bath 1

Bath

Sleep 5

Sleeps
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Exceptional(1)

$568.99

/ Nightly
Condo

Chapel Gate 3BR Steps to City Dock & Naval Academy

Annapolis, Maryland, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(21)

$459.14

/ Nightly
Private Vacation Home

Walking distance to Navy Stadium! No cleaning fees!

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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$1179.16

/ Nightly
Private Vacation Home

Eastport 4 Bedroom Spacious Gem on Jefferson

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(69)

$1016.91

/ Nightly
Private Vacation Home

Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(4)

$1007.88

/ Nightly
Private Vacation Home

Annapolis Area Gem for Family and Friends

Annapolis, Maryland, United States

Bed 6

Bed

Bath 4

Bath

Sleep 12

Sleeps
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Exceptional(73)

$638.35

/ Nightly
Private Vacation Home

Walk to USNA, Main St w Parking Historic Wisteria

Annapolis, Maryland, United States

Bed 3

Bed

Bath 4

Bath

Sleep 8

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(12)

$1000.92

/ Nightly
Private Vacation Home

Stadium-Side Annapolis | Chef Kitchen | Sleeps 10

Annapolis, Maryland, United States

Bed 3

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(7)

$386.09

/ Nightly
Private Vacation Home

Historic District 2BR + Parking | Walk to City Dock & USNA

Annapolis, Maryland, United States

Bed 2

Bed

Bath 1

Bath

Sleep 3

Sleeps
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Exceptional(7)

$732.29

/ Nightly
Private Vacation Home

3 BR charming home sits in the heart of Annapolis with rooftop deck

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(3)

$505.78

/ Nightly
Private Vacation Home

Historic Downtown Annapolis | 2BR En Suites | Walk to USNA & City Dock

Annapolis, Maryland, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

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(3)

$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(3)

$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(3)

$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(3)

$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(3)

$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(3)

$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(3)

$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(3)

$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(3)

$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(3)

$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