Vacation Rentals By Owner In Annapolis, MD

Showing 100 Of 450 Vacation Rentals

Exceptional(75)

$604.63

/ Nightly

Private Vacation Home

Eastport Historic Firehouse with Parking, Dogs OK

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$574.01

/ Nightly

Private Vacation Home

Downtown Annapolis Charming 2 BDR Townhome

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(11)

$1139.24

/ Nightly

Private Vacation Home

Unique Listing! Entire Downtown Triplex w/Private Parking! Sleeps 12-18. Pets ok

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(19)

$515.28

/ Nightly

Private Vacation Home

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(5)

$548.75

/ Nightly

Apartment

Walk To Main St & City Dock from Historic Downtown Dog-Friendly Apartment

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(80)

$455.15

/ Nightly

Private Vacation Home

Recently Renovated Annapolis Home - Conveniently Located

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(18)

$542.98

/ Nightly

Apartment

Spectacular Location: State Circle Apartment

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(3)

$654.36

/ Nightly

Private Vacation Home

Downtown Fleet St home with garage parking EV Walk to USNA

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(49)

$392.16

/ Nightly

Cottage

Waterfront Annapolis Cottage: Fire Pit & Pier

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(45)

$672.51

/ Nightly

Cottage

Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(7)

$1251.72

/ Nightly

Private Vacation Home

Luxe Row Home Steps to USNA Gate 3!

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(1)

$884.64

/ Nightly

Private Vacation Home

Two Historic Rowhomes in Downtown Annapolis

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(2)

$661.56

/ Nightly

Condo

Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(50)

$906.39

/ Nightly

Private Vacation Home

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(102)

$498.18

/ Nightly

Private Vacation Home

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$270.27

/ Nightly

Hotel

Minutes from History: 2 Relaxing Units w/ Free Breakfast Near Downtown Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$262.43

/ Nightly

Hotel

Annapolis Adventure: 2 Cozy Units, Outdoor Pool + Easy Access to Historic Sites!

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(14)

$641.94

/ Nightly

Private Vacation Home

Boutique Cedar Home 2 blocks from City Dock, USNA & Main Street w Parking

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$677.92

/ Nightly

Private Vacation Home

Upscale One-Level Home Near West Annapolis w Resort-Style Outdoor Spaces

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$585.82

/ Nightly

Private Vacation Home

Apartment Near Downtown Annapolis with Private Outdoor Space and Parking

Annapolis, Maryland, United States

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Bath

Sleeps

Rent a place that suits your needs

Bed

Bath

Sleeps

Vacation Rentals By Owner In Annapolis, MD

$604.63

$574.01

$1139.24

$515.28

$548.75

$455.15

$542.98

$654.36

$392.16

$672.51

$1251.72

$884.64

$661.56

$906.39

$498.18

$270.27

$262.43

$641.94

$677.92

$585.82

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