Home Vacation Rentals By Owner In Annapolis, MD

Showing 300 Of 450 Vacation Rentals
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Exceptional(22)

$330.03

/ Nightly
Apartment

Annapolis Tree House Apartment- luxury shower, separate space

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 3

Sleeps
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$898.78

/ Nightly
Cottage

Wonderful Cottage Nestled On Chesapeake Bay

Annapolis, Maryland, United States

Bed 3

Bed

Bath 3

Bath

Sleep 7

Sleeps
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Exceptional(28)

$666.15

/ Nightly
Private Vacation Home

Historic Annapolis Hideaway Steps to USNA and Main St w Private Patio & Parking

Annapolis, Maryland, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(34)

$608.93

/ Nightly
Private Vacation Home

Historic Annapolis Union House with Private Patio & Free Off-Site Parking

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(7)

$497.61

/ Nightly
Private Vacation Home

Spacious 5 BR house - 5 Min Walk to N-MC Stadium!

Annapolis, Maryland, United States

Bed 3

Bed

Bath 3

Bath

Sleep 15

Sleeps
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Exceptional(4)

$503.69

/ Nightly
Private Vacation Home

Belle By The Bay Summ

Annapolis, Maryland, United States

Bed 3

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(19)

$302.48

/ Nightly
Private Vacation Home

Annapolis Garden Suite

Annapolis, Maryland, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(56)

$1376.74

/ Nightly
Private Vacation Home

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Annapolis, Maryland, United States

Bed 6

Bed

Bath 4

Bath

Sleep 18

Sleeps
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Exceptional(60)

$850.82

/ Nightly
Private Vacation Home

Brand New.1.5 blocks to Westin. 1st floor bed & bath. Walkable Convenience

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(5)

Select Dates for Price
Private Vacation Home

Annapolis gem with beautiful outdoor dining! Near U.S. Naval Academy

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(3)

$475.38

/ Nightly
Private Vacation Home

Historic district home, View of the Capital, WALK Downtown, w/ Outdoor Dining!

Annapolis, Maryland, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(1)

$720.56

/ Nightly
Private Vacation Home

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis, Maryland, United States

Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(6)

$634.35

/ Nightly
Private Vacation Home

Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 7

Sleeps
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Exceptional(45)

$278.73

/ Nightly
Condo

New Downtown Annapolis Condo With Free Parking

Annapolis, Maryland, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

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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$616.46

/ Nightly
Private Vacation Home

Charming Coastal Retreat w Community Beach Dog-Friendly & Mins to Downtown Annapolis

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 9

Sleeps
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Exceptional(60)

$1399.92

/ Nightly
Private Vacation Home

Stunning Annapolis Home! Across from the library, walk to Naval Graduation

Annapolis, Maryland, United States

Bed 4

Bed

Bath 4

Bath

Sleep 12

Sleeps
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$578.55

/ Nightly
Apartment

Cozy apartment in Historic Annapolis with WiFi, AC

Annapolis, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(16)

$514.14

/ Nightly
Condo

Waterfront 2-Bedroom Condo on Spa Creek

Annapolis, Maryland, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(1)

$1723.68

/ Nightly
Private Vacation Home

Beautiful colonial only 3 miles to the Naval Academy!

Annapolis, Maryland, United States

Bed 6

Bed

Bath 2

Bath

Sleep 12

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(1)

$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(1)

$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(1)

$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(1)

$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(1)

$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(1)

$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(1)

$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(1)

$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(1)

$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(1)

$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