Vacation Rentals By Owner In Annapolis, MD

Showing 420 Of 450 Vacation Rentals

Exceptional(1)

$469.12

/ Nightly

Private Vacation Home

4BR Family Retreat Near Annapolis w/ Large Yard

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(13)

$332.54

/ Nightly

Private Vacation Home

Walk to the stadium! - Lighthouse on Glenwood

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(3)

$374.49

/ Nightly

Cottage

Pet Friendly Annapolis Cottage that Backs Up to Stunning Quiet Waters Park

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(271)

$174.99

/ Nightly

Cottage

Annapolis waterfront tiny house in garden setting

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(174)

$640.3

/ Nightly

Private Vacation Home

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

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(130)

$176.13

/ Nightly

Apartment

Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(5)

$253.65

/ Nightly

Apartment

Five Star Charmer! Great Location Downtown & Stadium! Parking too!

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(94)

$429.92

/ Nightly

Cottage

Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(32)

$517.09

/ Nightly

Private Vacation Home

Historic 3 Bedroom Downtown Annapolis Townhome

Annapolis, Maryland, United States

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Bath

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Exceptional(28)

$1738.5

/ Nightly

Private Vacation Home

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(18)

$559.74

/ Nightly

Private Vacation Home

Winter Retreat Near Naval Academy+ Hot Tub!

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(38)

$281.01

/ Nightly

Private Vacation Home

Private Cottage on gated estate

Annapolis, Maryland, United States

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Bath

Sleeps

$530.1

/ Nightly

Private Vacation Home

DTA 2 bdrm w/parking, pet friendly, great location with all of the amenities!

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(45)

$601.35

/ Nightly

Private Vacation Home

Historic DistrictCrab Cakes and Football

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(27)

$2302.8

/ Nightly

Private Vacation Home

Fantastic house with lots of parking in downtown Annapolis, steps to the USNA!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$929.91

/ Nightly

Private Vacation Home

Waterfront home in Annapolis MD with private pier

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(3)

$482.46

/ Nightly

Apartment

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(145)

$882.36

/ Nightly

Private Vacation Home

Beautiful Waterfront Townhome In Historic Annapolis

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(100)

$502.17

/ Nightly

Private Vacation Home

Cozy Cottage by the Beach - Waterview
Minutes from Downtown Annapolis

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(103)

$976.41

/ Nightly

Private Vacation Home

103 5-star Reviews located inside the City of Annapolis in walkable Murray Hill.

Annapolis, Maryland, United States

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Bath

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Rent a place that suits your needs

Private vacation home

View 318 Private vacation home

Most popular vacation rentals in Annapolis

Exceptional(103)

$1926.40

/ Nightly

Private vacation home

Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(103)

$2008.68

/ Nightly

Private vacation home

Spacious Converted Carriage House in Historic District near USNA

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(103)

$2164.57

/ Nightly

Private vacation home

Welcoming Waterfront Luxury Estate for Family, Friends, and Pets in Annapolis

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(103)

$2302.80

/ Nightly

Private vacation home

Fantastic house with lots of parking in downtown Annapolis, steps to the USNA!

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(103)

$2805.96

/ Nightly

Private vacation home

Downtown Annapolis Duke's House

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(103)

$2853.88

/ Nightly

Private vacation home

Cool 1870's home anchored in the Historic District with modern amenities.

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(103)

$2974.10

/ Nightly

Private vacation home

Nantucket on the Chesapeake Heated Pool

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(103)

$499.32

/ Nightly

House boat

Welcome Aboard the Kathleen Marie!

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(103)

$485.19

/ Nightly

Apartment

Pool Loft Suite | Bay Access & Beach Passes

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(103)

$487.67

/ Nightly

Private vacation home

Parking. Short Uber Ride. Townhouse in Annapolis! 3 Miles from USNA and Downtown

Annapolis, Maryland, United States

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Bath

Sleeps

Vacation Rentals By Owner In Annapolis, MD

$469.12

$332.54

$374.49

$174.99

$640.3

$176.13

$253.65

$429.92

$517.09

$1738.5

$559.74

$281.01

$530.1

$601.35

$2302.8

$929.91

$482.46

$882.36

$502.17

$976.41

Rent a place that suits your needs

Most popular vacation rentals in Annapolis

$1926.40

$2008.68

$2164.57

$2302.80

$2805.96

$2853.88

$2974.10

$499.32

$485.19

$487.67

Most Popular Cities in Maryland