Vacation Rentals By Owner In Annapolis, MD

Showing 280 Of 450 Vacation Rentals

Exceptional(42)

$616.42

/ Nightly

Private Vacation Home

Luxury Annapolis Oasis: Hot Tub, Fire Pit, Fully Fenced, Pet Friendly

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(33)

$716.49

/ Nightly

Private Vacation Home

All-stop. Rental Midships.

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$184.8

/ Nightly

Hotel

Enjoy a Hassle-Free Stay! Pet-Friendly, Close to William Paca Garden

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(34)

$807.69

/ Nightly

Private Vacation Home

Sailor's Retreat! Perfect home for the getaway weekend. Best location!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(117)

$498.18

/ Nightly

Private Vacation Home

Historic Renovated Home in the Heart of Downtown

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$430.92

/ Nightly

Private Vacation Home

8 Bells Bungalow - Cozy, Stylish, Prime Location

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(15)

$749.85

/ Nightly

Private Vacation Home

The General's House-Spacious Home w/Pool & Hot Tub

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$429.21

/ Nightly

Private Vacation Home

Spacious 5-bedroom house with AC in gorgeous Annapolis historic district capital

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$394.82

/ Nightly

Private Vacation Home

Spacious 4-bedroom house with AC in brilliant Annapolis

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(26)

$974.7

/ Nightly

Private Vacation Home

Cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(3)

$806.03

/ Nightly

Apartment

Prime Spot Stay–Simple Comfort, Perfect Location

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(23)

$1111.66

/ Nightly

Private Vacation Home

Walk to Downtown Annapolis & Spa Creek from Stunning Craftsman with Game Room, Parking and Backyard

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(14)

$401.85

/ Nightly

Private Vacation Home

1 Block to USNA Stadium: Modern Annapolis Home!

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(1)

$726.49

/ Nightly

Private Vacation Home

Eastport 3 bedroom Cottage: Walk to Downtown

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$325.66

/ Nightly

Apartment

Custom Studio Efficiency apartment with AC easy accces to Annapolis and USNA.

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(3)

$488.49

/ Nightly

Private Vacation Home

Walk to DTA & USNA | Pet-Friendly Home

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(21)

$744.31

/ Nightly

Private Vacation Home

Captain's Retreat! Newly Renovated - few steps from the beach!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(5)

$1169.23

/ Nightly

Private Vacation Home

Historic Luxury Steps to USNA + Vibrant Waterfront

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(10)

$501.68

/ Nightly

Private Vacation Home

Your Annapolis Retreat near the Naval Academy and downtown

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$455.72

/ Nightly

Apartment

Waterfront private In-law apartment, 10 minutes from Downtown Annapolis.

Annapolis, Maryland, United States

Bed

Bath

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Rent a place that suits your needs

Bed

Bath

Sleeps

Vacation Rentals By Owner In Annapolis, MD

$616.42

$716.49

$184.8

$807.69

$498.18

$430.92

$749.85

$429.21

$394.82

$974.7

$806.03

$1111.66

$401.85

$726.49

$325.66

$488.49

$744.31

$1169.23

$501.68

$455.72

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