Home Vacation Home Rentals By Owner In Annapolis, MD

Showing 300 Of 318 Vacation Rentals
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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(1)

$1571.49

/ Nightly
Private Vacation Home

Luxury Waterfront Annapolis home with your very own Private Beach & Dock

Annapolis, Maryland, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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$1593.69

/ Nightly
Private Vacation Home

3-story, dog-friendly home near beaches with home theatre, grill & gaming tables

Annapolis, Maryland, United States

Bed 6

Bed

Bath 5

Bath

Sleep 15

Sleeps
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Exceptional(1)

$1628.6

/ Nightly
Private Vacation Home

Lakeside on the Chesapeake! Serene Waterfront home in charming Annapolis

Annapolis, Maryland, United States

Bed 6

Bed

Bath 7

Bath

Sleep 14

Sleeps
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Exceptional(11)

$1660.07

/ Nightly
Private Vacation Home

Annapolis Waterfront Oasis with Pool, Hot Tub & Piers with L2 EV Charger

Annapolis, Maryland, United States

Bed 7

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Exceptional(1)

$1886.7

/ Nightly
Private Vacation Home

Spacious Waterfront 5-bedroom house in charming Annapolis with Hot Tub

Annapolis, Maryland, United States

Bed 5

Bed

Bath 3

Bath

Sleep 16

Sleeps
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$1916.72

/ Nightly
Private Vacation Home

Waterfront Gem w/ Dock: 2 Mi to Dwtn Annapolis!

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(1)

$1926.4

/ 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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$2142.36

/ Nightly
Private Vacation Home

Beautiful waterfront home on The Chesapeake Bay with private dock & beach access

Annapolis, Maryland, United States

Bed 5

Bed

Bath 3

Bath

Sleep 10

Sleeps
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$2571.27

/ Nightly
Private Vacation Home

The Harness Creek House

Annapolis, Maryland, United States

Bed 6

Bed

Bath 5

Bath

Sleep 12

Sleeps
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Exceptional(27)

$2974.1

/ 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(4)

$246.85

/ Nightly
Private Vacation Home

Walk to Lake & Boat Ramp: Annapolis Extended Stay

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(6)

$361.68

/ Nightly
Private Vacation Home

Private 2BR Apartment with Parking for Corporate, Medical & Military Stays

Annapolis, Maryland, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(3)

$386.46

/ Nightly
Private Vacation Home

Renovated 3BR | Near Sandy Point Beach

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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$421.14

/ Nightly
Private Vacation Home

Unique A-Frame Home Near Downtown Annapolis & USNA

Annapolis, Maryland, United States

Bed 3

Bed

Bath 1

Bath

Sleep 7

Sleeps
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Exceptional(9)

$453.5

/ Nightly
Private Vacation Home

Peaceful Pet-Friendly Stay - Near USNA and Beaches

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(4)

$469

/ Nightly
Private Vacation Home

Beautiful Annapolis Home Near the Beach with a fitness room

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 11

Sleeps
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Exceptional(10)

$501.68

/ Nightly
Private Vacation Home

Your Annapolis Retreat near the Naval Academy and downtown

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 16

Sleeps
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Exceptional(2)

$516.93

/ Nightly
Private Vacation Home

Annapolis Spacious Family Retreat

Annapolis, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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$546.06

/ Nightly
Private Vacation Home

Annapolis Retreat

Annapolis, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Private vacation home

Private vacation home

View 318 Private vacation home

Home Most popular vacation rentals in Annapolis

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$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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$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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$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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$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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$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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$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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$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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$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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$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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$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