Home Vacation Home Rentals By Owner In Annapolis, MD

Showing 60 Of 318 Vacation Rentals
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Exceptional(78)

$1074.45

/ Nightly
Private Vacation Home

Charming Annapolis Victorian

Annapolis, Maryland, United States

Bed 6

Bed

Bath 4

Bath

Sleep 12

Sleeps
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Exceptional(4)

$1325.66

/ Nightly
Private Vacation Home

Clean, Spacious Family House

Annapolis, Maryland, United States

Bed 5

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(44)

$1318.6

/ Nightly
Private Vacation Home

Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway!

Annapolis, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 10

Sleeps
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Exceptional(8)

$1269.62

/ Nightly
Private Vacation Home

USNA Stay w Private Pool, Hot Tub, King Beds, Child Safe & Stocked, Pet Friendly

Annapolis, Maryland, United States

Bed 5

Bed

Bath 3

Bath

Sleep 15

Sleeps
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Exceptional(2)

$1258.56

/ Nightly
Private Vacation Home

Historic Downtown Luxury • USNA • Waterfront

Annapolis, Maryland, United States

Bed 5

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(7)

$1251.72

/ Nightly
Private Vacation Home

Luxe Row Home Steps to USNA Gate 3!

Annapolis, Maryland, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(5)

$1169.23

/ Nightly
Private Vacation Home

Historic Luxury Steps to USNA + Vibrant Waterfront

Annapolis, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 10

Sleeps
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Exceptional(3)

$1143.99

/ Nightly
Private Vacation Home

5BR, 3 King Beds, Near Downtown & USNA

Annapolis, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 10

Sleeps
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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

Bed 6

Bed

Bath 4

Bath

Sleep 18

Sleeps
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Exceptional(24)

$1124.61

/ Nightly
Private Vacation Home

Beautiful Blend of Restoration and Renovation in this Downtown Home

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(4)

$1007.88

/ Nightly
Private Vacation Home

Annapolis Area Gem for Family and Friends

Annapolis, Maryland, United States

Bed 6

Bed

Bath 4

Bath

Sleep 12

Sleeps
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Exceptional(39)

$986.52

/ Nightly
Private Vacation Home

West Annapolis Cottage- 6BR Walk to Navy Stadium

Annapolis, Maryland, United States

Bed 6

Bed

Bath 5

Bath

Sleep 14

Sleeps
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Exceptional(6)

$993.09

/ Nightly
Private Vacation Home

Brilliantly Updated Multi-Level Walkable to Navy Stadium & Close to Historic Downtown Annapolis

Annapolis, Maryland, United States

Bed 6

Bed

Bath 3

Bath

Sleep 13

Sleeps
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Exceptional(12)

$1000.92

/ Nightly
Private Vacation Home

Stadium-Side Annapolis | Chef Kitchen | Sleeps 10

Annapolis, Maryland, United States

Bed 3

Bed

Bath 3

Bath

Sleep 10

Sleeps
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$1006.85

/ Nightly
Private Vacation Home

Updated historic home with parking; near Academy, college & harbor - central AC

Annapolis, Maryland, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(69)

$1016.91

/ Nightly
Private Vacation Home

Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(16)

$1032.27

/ Nightly
Private Vacation Home

Beautiful Historic Annapolis home just a few minutes walk from Main Street

Annapolis, Maryland, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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$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

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(7)

$1331.52

/ Nightly
Private Vacation Home

Historic Annapolis Charmer <1Mile to NMC Stadium

Annapolis, Maryland, United States

Bed 7

Bed

Bath 4

Bath

Sleep 20

Sleeps
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Exceptional(73)

$1010.04

/ Nightly
Private Vacation Home

Beautiful Downtown Annapolis Townhome!

Annapolis, Maryland, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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View 318 Private vacation home

Home Most popular vacation rentals in Annapolis

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Exceptional(73)

$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(73)

$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(73)

$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(73)

$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(73)

$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(73)

$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(73)

$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(73)

$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(73)

$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(73)

$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