Home Vacation Home Rentals By Owner In Annapolis, MD

Showing 260 Of 318 Vacation Rentals
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Exceptional(174)

$640.3

/ Nightly
Private Vacation Home

4-Bedroom Eastport Haven + Walk to Downtown & USNA + Rare Multi-Car Parking!

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(50)

$640.3

/ Nightly
Private Vacation Home

Water Views - Close to Downtown Annapolis

Annapolis, Maryland, United States

Bed 5

Bed

Bath 2

Bath

Sleep 12

Sleeps
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Exceptional(97)

$642.58

/ Nightly
Private Vacation Home

Tastefully decorated fully-equipped Eastport Annapolis house with water views

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$646.08

/ Nightly
Private Vacation Home

Welcome to Getaway on the Bay | Your Waterfront Annapolis Escape

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(45)

$648.63

/ Nightly
Private Vacation Home

Walk to Waterfront from Eastport Gem w Fire Pit, Porch & Fenced-In Yard

Annapolis, Maryland, United States

Bed 2

Bed

Bath 1

Bath

Sleep 7

Sleeps
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$666.99

/ Nightly
Private Vacation Home

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(2)

$672.03

/ 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(150)

$681.15

/ Nightly
Private Vacation Home

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

Annapolis, Maryland, United States

Bed 2

Bed

Bath 2

Bath

Sleep 5

Sleeps
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Exceptional(1)

$682.29

/ Nightly
Private Vacation Home

2-story downtown home with enclosed yard, deck, firepit, gas grill & fireplace

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(11)

$684

/ Nightly
Private Vacation Home

Modern Styled Home in Historic Annapolis Eastport Neighborhood

Annapolis, Maryland, United States

Bed 2

Bed

Bath 2

Bath

Sleep 5

Sleeps
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$684

/ Nightly
Private Vacation Home

Charming Eastport CapeCod

Annapolis, Maryland, United States

Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(95)

$684.57

/ Nightly
Private Vacation Home

Waterfront Oasis in Eastport-Easy Walk to Downtown

Annapolis, Maryland, United States

Bed 5

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(6)

$704.87

/ Nightly
Private Vacation Home

Sing Second Stays—Spacious Annapolis Home Near USNA & Navy Stadium

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 12

Sleeps
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Exceptional(6)

$709.54

/ Nightly
Private Vacation Home

Oasis by the Bay - Waterfront Heated Pool Hot Tub!

Annapolis, Maryland, United States

Bed 6

Bed

Bath 5

Bath

Sleep 18

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)

$726.49

/ Nightly
Private Vacation Home

Eastport 3 bedroom Cottage: Walk to Downtown

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(19)

$731.5

/ Nightly
Private Vacation Home

Chesapeake Bay single family home

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(21)

$744.31

/ Nightly
Private Vacation Home

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

Annapolis, Maryland, United States

Bed 4

Bed

Bath 2

Bath

Sleep 12

Sleeps
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$751.07

/ Nightly
Private Vacation Home

New Waterfront Thomas Point Retreat with Private Beach, Dock, Billiards & Parking

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 7

Sleeps
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Exceptional(59)

$764.94

/ Nightly
Private Vacation Home

Nautical Feel to This Beautiful Eastport Home

Annapolis, Maryland, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

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(59)

$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(59)

$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(59)

$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(59)

$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(59)

$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(59)

$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(59)

$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(59)

$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(59)

$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(59)

$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