Home Vacation Rentals By Owner In Annapolis, MD

Showing 260 Of 450 Vacation Rentals
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Exceptional(16)

$502.17

/ Nightly
Private Vacation Home

Downtown Pinkney House w/Parking

Annapolis, Maryland, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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Exceptional(31)

$331.17

/ Nightly
Private Vacation Home

Historic Home with Parking Steps From Capital & USNA

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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$619.02

/ Nightly
Cottage

Walk to everything! Downtown Historic Annapolis “Arts District”

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(1)

$713.33

/ Nightly
Private Vacation Home

Newly-Renovated Waterfront Home w Private Pier in Annapolis & Dog-Friendly

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 12

Sleeps
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Exceptional(1)

$1571.49

/ Nightly
Private Vacation Home

Luxury Waterfront Annapolis home with your very own Private Beach & Dock

Annapolis, Maryland, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(9)

$417.81

/ Nightly
Private Vacation Home

Vintage Retreat: 5 minute walk to downtown, Naval Academy, Stadium and more.

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 5

Sleeps
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Exceptional(12)

$383.04

/ Nightly
Private Vacation Home

Modern Gem Near Historic Annapolis & Naval Academy

Annapolis, Maryland, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
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Exceptional(12)

$547.2

/ Nightly
Private Vacation Home

Dog friendly! Next to Navy Stadium and DTA Shuttle!

Annapolis, Maryland, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(1)

$520.24

/ Nightly
Private Vacation Home

Mins to Downtown in Waterfront community at Pet-Friendly Pinecrest Bungalow

Annapolis, Maryland, United States

Bed 2

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(10)

$911.43

/ Nightly
Cottage

Charming Bay Ridge Cottage with Chesapeake Bay Views – Just Steps to the Beach

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$323.19

/ Nightly
Cottage

The Red Door Cottage in Eastport - Pet-Friendly!

Annapolis, Maryland, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(139)

$260.2

/ Nightly
Apartment

Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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$132.41

/ Nightly
Hotel

Annapolis Adventure: Room w/ Outdoor Pool + Easy Access to Historic Sites

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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$138.06

/ Nightly
Hotel

Experience Historical Annapolis + Complimentary Breakfast! Outdoor Pool!

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(1)

$152.75

/ Nightly
Hotel

Our Welcoming Suite in Annapolis Near Historic Downtown

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 5

Sleeps
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Exceptional(3)

$132.41

/ Nightly
Hotel

Minutes from History: Room w/ Free Breakfast Near Downtown Annapolis

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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Exceptional(1)

$1886.7

/ Nightly
Private Vacation Home

Spacious Waterfront 5-bedroom house in charming Annapolis with Hot Tub

Annapolis, Maryland, United States

Bed 5

Bed

Bath 3

Bath

Sleep 16

Sleeps
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Exceptional(5)

$542.32

/ Nightly
Private Vacation Home

Eastport Charmer Summ

Annapolis, Maryland, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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Exceptional(56)

$827.94

/ Nightly
Private Vacation Home

Parking at Randall House Across from USNA Gate 1

Annapolis, Maryland, United States

Bed 4

Bed

Bath 4

Bath

Sleep 11

Sleeps
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Exceptional(12)

$517.68

/ Nightly
Private Vacation Home

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis, Maryland, United States

Bed 5

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Home Rent a place that suits your needs

Private vacation home

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View 318 Private vacation home

Home Most popular vacation rentals in Annapolis

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Exceptional(12)

$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(12)

$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(12)

$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(12)

$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(12)

$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(12)

$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(12)

$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(12)

$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(12)

$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(12)

$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