Vacation Rentals By Owner In Annapolis, MD

Showing 40 Of 450 Vacation Rentals

Exceptional(36)

$639.26

/ Nightly

Apartment

Large Luxury Apartment In Downtown Annapolis

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(183)

$585.96

/ Nightly

Private Vacation Home

Heart of Historic District!

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(236)

$520.41

/ Nightly

Private Vacation Home

PERFECT LOCATION in the heart of history

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(95)

$684.57

/ Nightly

Private Vacation Home

Waterfront Oasis in Eastport-Easy Walk to Downtown

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(175)

$302.1

/ Nightly

Condo

Beautiful Condo - Water View Near City Dock

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(11)

$572.68

/ Nightly

Private Vacation Home

Restriction Retreat - Relax & walk to Main St

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(7)

$485.19

/ Nightly

Apartment

Pool Loft Suite | Bay Access & Beach Passes

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(21)

$591.03

/ Nightly

Private Vacation Home

Historic Annapolis Home | 2 Blocks to Main St

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(24)

$1124.61

/ Nightly

Private Vacation Home

Beautiful Blend of Restoration and Renovation in this Downtown Home

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(3)

$2805.96

/ Nightly

Private Vacation Home

Downtown Annapolis Duke's House

Annapolis, Maryland, United States

Bath

Sleeps

Exceptional(9)

$695.84

/ Nightly

Private Vacation Home

Spacious Historic Home with Private Parking in the Heart of Downtown Annapolis

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(1)

$471.2

/ Nightly

Cottage

Peaceful Escape: Bay Ridge Cottage by the Bay

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(7)

Select Dates for Price

Private Vacation Home

Steps to Marinas & Shops w Parking in Eastport

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(176)

$416.67

/ Nightly

Private Vacation Home

A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(35)

$546.06

/ Nightly

Private Vacation Home

Gem in Downtown Annapolis, close to USNA, St. John's College

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(2)

$518.62

/ Nightly

Private Vacation Home

Spacious 4BR | Pet-Friendly, Sleeps 10

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(60)

$769.32

/ Nightly

Private Vacation Home

Prime Location Modern Comfort Steps to City Dock, Gate 1 w Bar & Parking

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(50)

$640.3

/ Nightly

Private Vacation Home

Water Views - Close to Downtown Annapolis

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(150)

$681.15

/ Nightly

Private Vacation Home

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

Annapolis, Maryland, United States

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Bath

Sleeps

$1025.26

/ Nightly

Private Vacation Home

Welcome to Robin's Nest a downtown Annapolis Retreat Newly Renovated Primary Suite Walk Everywhere

Annapolis, Maryland, United States

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Bath

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Rent a place that suits your needs

Private vacation home

View 318 Private vacation home

Most popular vacation rentals in Annapolis

$1926.40

/ Nightly

Private vacation home

Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D

Annapolis, Maryland, United States

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Bath

Sleeps

$2008.68

/ Nightly

Private vacation home

Spacious Converted Carriage House in Historic District near USNA

Annapolis, Maryland, United States

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Bath

Sleeps

$2164.57

/ Nightly

Private vacation home

Welcoming Waterfront Luxury Estate for Family, Friends, and Pets in Annapolis

Annapolis, Maryland, United States

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Bath

Sleeps

$2302.80

/ Nightly

Private vacation home

Fantastic house with lots of parking in downtown Annapolis, steps to the USNA!

Annapolis, Maryland, United States

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Bath

Sleeps

$2805.96

/ Nightly

Private vacation home

Downtown Annapolis Duke's House

Annapolis, Maryland, United States

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Bath

Sleeps

$2853.88

/ Nightly

Private vacation home

Cool 1870's home anchored in the Historic District with modern amenities.

Annapolis, Maryland, United States

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Bath

Sleeps

$2974.10

/ Nightly

Private vacation home

Nantucket on the Chesapeake Heated Pool

Annapolis, Maryland, United States

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Bath

Sleeps

$499.32

/ Nightly

House boat

Welcome Aboard the Kathleen Marie!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$485.19

/ Nightly

Apartment

Pool Loft Suite | Bay Access & Beach Passes

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$487.67

/ Nightly

Private vacation home

Parking. Short Uber Ride. Townhouse in Annapolis! 3 Miles from USNA and Downtown

Annapolis, Maryland, United States

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Bath

Sleeps

Vacation Rentals By Owner In Annapolis, MD

$639.26

$585.96

$520.41

$684.57

$302.1

$572.68

$485.19

$591.03

$1124.61

$2805.96

$695.84

$471.2

$416.67

$546.06

$518.62

$769.32

$640.3

$681.15

$1025.26

Rent a place that suits your needs

Most popular vacation rentals in Annapolis

$1926.40

$2008.68

$2164.57

$2302.80

$2805.96

$2853.88

$2974.10

$499.32

$485.19

$487.67

Most Popular Cities in Maryland