Home Vacation Rentals By Owner In Annapolis, MD

Showing 400 Of 450 Vacation Rentals
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Exceptional(8)

$462.84

/ Nightly
Private Vacation Home

Charming on Charles Street

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(62)

$625.41

/ Nightly
Private Vacation Home

Walkable to Main Street at Seashell in the City with 2 parking spots

Annapolis, Maryland, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

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(10)

$755.07

/ Nightly
Private Vacation Home

Steps from City Dock w Private Fenced-In Backyard at Historic Dog-Friendly Philip Clayton House

Annapolis, Maryland, United States

Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(7)

$363.79

/ Nightly
Private Vacation Home

Cozy Cottage with Beach Access

Annapolis, Maryland, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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Exceptional(59)

$608.95

/ Nightly
Private Vacation Home

Unwind at Waterfront Annapolis w/swimming pool & pier - July specials!

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(38)

$512.81

/ Nightly
Private Vacation Home

Annapolis Bay House BOAT SHOW & USNA Families 2 Bedroom with Den sleeps 5

Annapolis, Maryland, United States

Bed 2

Bed

Bath 2

Bath

Sleep 5

Sleeps
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Exceptional(15)

$1543.56

/ Nightly
Private Vacation Home

Steps away from the Chesapeake Bay in the unique Bay Ridge community!

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(15)

$748.98

/ Nightly
Private Vacation Home

Charming Home located minutes from the Naval Academy and Downtown Annapolis

Annapolis, Maryland, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(14)

$398.43

/ Nightly
Private Vacation Home

Arts District - Peaceful, Sparkling, 1 Bed/1 Bath, Walk to Navy Stadium and Town

Annapolis, Maryland, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(147)

$547.2

/ Nightly
Private Vacation Home

Historic Downtown Charmer, Water Views and Parking!

Annapolis, Maryland, United States

Bed 2

Bed

Bath 1

Bath

Sleep 5

Sleeps
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Exceptional(42)

$594.95

/ Nightly
Private Vacation Home

Historic Capital Views, w Free Off-Site Parking & Patio

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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$324.44

/ Nightly
Private Vacation Home

2-bedroom house in nice Annapolis with cool AC breeze

Annapolis, Maryland, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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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(262)

$436.62

/ Nightly
Private Vacation Home

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Annapolis, Maryland, United States

Bed 3

Bed

Bath 1

Bath

Sleep 8

Sleeps
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Exceptional(6)

$138.98

/ Nightly
Hotel

Nautical Adventure Awaits in Annapolis Suites! Pets Allowed Here! Free Breakfast

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(19)

$583.01

/ Nightly
Private Vacation Home

Ahoy! Game Room, Screened Porch, Yard Mins to DTA

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 9

Sleeps
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Exceptional(22)

$581.73

/ Nightly
Private Vacation Home

Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(5)

$479.94

/ Nightly
Private Vacation Home

Charming Historic Row House in The Heart of Eastport's Horn Point

Annapolis, Maryland, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(16)

$1692.52

/ Nightly
Private Vacation Home

Waterfront Architectural Masterpiece with private dockage available.

Annapolis, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 10

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(16)

$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(16)

$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(16)

$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(16)

$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(16)

$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(16)

$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(16)

$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(16)

$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(16)

$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(16)

$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