Vacation Rentals By Owner In Annapolis, MD

Showing 440 Of 450 Vacation Rentals

Exceptional(30)

$764.94

/ Nightly

Private Vacation Home

Lots free parking, hot tub, outdoor oasis - NOT party house

Annapolis, Maryland, United States

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Exceptional(59)

$764.94

/ Nightly

Private Vacation Home

Nautical Feel to This Beautiful Eastport Home

Annapolis, Maryland, United States

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Exceptional(5)

$287.06

/ Nightly

Private Vacation Home

Bay Ridge house by Quiet Waters Park, Thomas Point Park

Annapolis, Maryland, United States

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Sleeps

$2147.79

/ Nightly

Private Vacation Home

Marvelous Home with Backyard Living Room in Murray Hill

Annapolis, Maryland, United States

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Exceptional(14)

$425.34

/ Nightly

Apartment

18th Cent. Charm in Historic Downtown Annapolis

Annapolis, Maryland, United States

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Exceptional(2)

$225.91

/ Nightly

Cottage

Cozy 1-bedroom cottage in adorable Annapolis on a private wooded area

Annapolis, Maryland, United States

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Exceptional(22)

$847.02

/ Nightly

Cottage

Secluded Cozy Cottage in Historic Downtown

Annapolis, Maryland, United States

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Bath

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Exceptional(37)

$576.18

/ Nightly

Private Vacation Home

Historic Happy Home Steps from Main Street w Private Yard, Screened-In Porch & Parking

Annapolis, Maryland, United States

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Exceptional(39)

$843.2

/ Nightly

Private Vacation Home

Gather, Relax & Explore — Townhome 1 Block from State Capitol Building with Backyard & Parking

Annapolis, Maryland, United States

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Exceptional(53)

$665.48

/ Nightly

Private Vacation Home

Walk to the Naval Academy and Historic Annapolis. Private parking at the home.

Annapolis, Maryland, United States

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Exceptional(1)

Select Dates for Price

Private Vacation Home

The Corner House-Annapolis

Annapolis, Maryland, United States

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Exceptional(9)

$472.53

/ Nightly

Private Vacation Home

Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Annapolis, Maryland, United States

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Exceptional(4)

$441.73

/ Nightly

Apartment

Dean Street's Lower Deck House!

Annapolis, Maryland, United States

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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

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Sleeps

Exceptional(5)

$650.94

/ Nightly

Private Vacation Home

3 bdrm close to city center, great yard & parking! Perfect for cooks and pets!

Annapolis, Maryland, United States

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Bath

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Exceptional(10)

$484.5

/ Nightly

Private Vacation Home

Historic Row Home | Hot Tub - 1 Block from Gate 1!

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(58)

$737.96

/ Nightly

Cottage

WATERFRONT COTTAGE ON SEVERN - STUNNING VIEWS - MINUTES FROM DOWNTOWN ANNAPOLIS

Annapolis, Maryland, United States

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Exceptional(77)

$748.98

/ Nightly

Private Vacation Home

Beautifully Renovated Historic District Home

Annapolis, Maryland, United States

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Bath

Sleeps

$389.91

/ Nightly

Private Vacation Home

Classic 3 Bedroom Eastport Cottage with Large Yard and Free Parking

Annapolis, Maryland, United States

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Exceptional(26)

$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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Rent a place that suits your needs

Private vacation home

View 318 Private vacation home

Most popular vacation rentals in Annapolis

Exceptional(26)

$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

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Exceptional(26)

$2008.68

/ Nightly

Private vacation home

Spacious Converted Carriage House in Historic District near USNA

Annapolis, Maryland, United States

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Exceptional(26)

$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

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Exceptional(26)

$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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Exceptional(26)

$2805.96

/ Nightly

Private vacation home

Downtown Annapolis Duke's House

Annapolis, Maryland, United States

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Exceptional(26)

$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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Exceptional(26)

$2974.10

/ Nightly

Private vacation home

Nantucket on the Chesapeake Heated Pool

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(26)

$499.32

/ Nightly

House boat

Welcome Aboard the Kathleen Marie!

Annapolis, Maryland, United States

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Sleeps

Exceptional(26)

$485.19

/ Nightly

Apartment

Pool Loft Suite | Bay Access & Beach Passes

Annapolis, Maryland, United States

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Sleeps

Exceptional(26)

$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

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Vacation Rentals By Owner In Annapolis, MD

$764.94

$764.94

$287.06

$2147.79

$425.34

$225.91

$847.02

$576.18

$843.2

$665.48

$472.53

$441.73

$1628.6

$650.94

$484.5

$737.96

$748.98

$389.91

$2164.57

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