Vacation Rentals By Owner In Annapolis, MD

Showing 450 Of 450 Vacation Rentals

Exceptional(219)

$817.38

/ Nightly

Private Vacation Home

Charming Historic Annapolis Home With Two Off-street Parking Places!

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(16)

$1032.27

/ Nightly

Private Vacation Home

Beautiful Historic Annapolis home just a few minutes walk from Main Street

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(6)

$798.31

/ Nightly

Private Vacation Home

Walk Everywhere From Eastport Cape Cod with Gourmet Kitchen

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(39)

$657.03

/ Nightly

Private Vacation Home

USNA Home Steps to Stadium Dog-Friendly w Parking

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(18)

$352.57

/ Nightly

Private Vacation Home

Naval Academy Gate 1

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(125)

$300.39

/ Nightly

Cottage

Firefly Cottage at the Cape, Hot Tub, Community beach, Boat Show, USNA Football.

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(86)

$434.34

/ Nightly

Private Vacation Home

Cozy 2br home w/ parking in downtown Annapolis

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(1)

$900.36

/ Nightly

Private Vacation Home

BY THE BAY

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(17)

$371.64

/ Nightly

Condo

Annapolis steps to Harbor and Naval Academy

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(97)

$642.58

/ Nightly

Private Vacation Home

Tastefully decorated fully-equipped Eastport Annapolis house with water views

Annapolis, Maryland, United States

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Bath

Sleeps

Rent a place that suits your needs

Private vacation home

View 318 Private vacation home

Most popular vacation rentals in Annapolis

Exceptional(97)

$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(97)

$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(97)

$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(97)

$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(97)

$2805.96

/ Nightly

Private vacation home

Downtown Annapolis Duke's House

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(97)

$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(97)

$2974.10

/ Nightly

Private vacation home

Nantucket on the Chesapeake Heated Pool

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(97)

$499.32

/ Nightly

House boat

Welcome Aboard the Kathleen Marie!

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(97)

$485.19

/ Nightly

Apartment

Pool Loft Suite | Bay Access & Beach Passes

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(97)

$487.67

/ Nightly

Private vacation home

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

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Vacation Rentals By Owner In Annapolis, MD

$817.38

$1032.27

$798.31

$657.03

$352.57

$300.39

$434.34

$900.36

$371.64

$642.58

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