Home Vacation Rentals By Owner In Annapolis, MD

Showing 220 Of 451 Vacation Rentals
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Exceptional(7)

$1002.31

/ Nightly
Private Vacation Home

Historic Downtown 3BR Crabby Patty-∙Walk to USNA

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(48)

$629.4

/ Nightly
Private Vacation Home

Historic Annapolis Getaway - 45 steps to Downtown and 150 steps to USNA!

Annapolis, Maryland, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(1)

$699.96

/ Nightly
Private Vacation Home

Historic Parish House 2-Bedroom Condo Steps to Naval Academy

Annapolis, Maryland, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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Exceptional(3)

$957.6

/ Nightly
Private Vacation Home

Charming Annapolis Escape!!

Annapolis, Maryland, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(18)

$670.13

/ Nightly
Private Vacation Home

Navy Weekend Haven, Family-Friendly Luxury Home w Fenced-in Backyard & Parking

Annapolis, Maryland, United States

Bed 5

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(23)

$465.12

/ Nightly
Private Vacation Home

Annapolis Vacation Home: 2 Mi to Quiet Waters Park

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(2)

$735.87

/ Nightly
Private Vacation Home

5 bedroom house with EV charger Near Downtown Annapolis

Annapolis, Maryland, United States

Bed 5

Bed

Bath 2

Bath

Sleep 12

Sleeps
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Exceptional(10)

$536.13

/ Nightly
Apartment

Walk to Shops & Dining from Dog-Friendly Apartment w Parking & Private Backyard

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(4)

$383.65

/ Nightly
Private Vacation Home

West Annapolis Cottage | Porch, Walk to USNA

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(45)

$315.21

/ Nightly
Apartment

Pristine Downtown 1-Bedroom Steps from State House

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(13)

$355.11

/ Nightly
Apartment

Downtown furnished apartment - walking distance to restaurants

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(1)

$163.96

/ Nightly
Hotel

Unique Victorian Stay | Steps from Waterfront | 0.1mi to State House

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(12)

$173.08

/ Nightly
Hotel

Maryland Inn King, Historic Inns, Elegant Dining, Waterfront Proximity

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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$163.96

/ Nightly
Hotel

Robert Johnson 2 Double Beds | Historic Inns | 0.8 miles to Cheston Avenue Wharf

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(1)

$181.06

/ Nightly
Hotel

Robert Johnson King | Historic Inns | Near Top Dining & City Attractions

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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$336.1

/ Nightly
Hotel

Robert Johnson Townhouse | 0.2mi to Main Street Shops & 0.3mi to Waterfront

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(2)

$181.06

/ Nightly
Hotel

Just Steps from Waterfront | Robert Johnson King | 0.3mi to US Naval Academy

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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$389.68

/ Nightly
Hotel

Robert Johnson Townhouse | 0.1mi State House | 0.3mi Naval Academy

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(1)

$173.08

/ Nightly
Hotel

Authentic 18th Century Hotel Near US Naval Academy - Walking Distance

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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Exceptional(15)

$173.08

/ Nightly
Hotel

Charming Downtown Hotel Room w/ Vintage Character + Historic Site

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

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(15)

$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(15)

$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(15)

$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(15)

$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(15)

$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(15)

$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(15)

$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(15)

$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(15)

$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(15)

$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