Vacation Rentals By Owner In Annapolis, MD

Showing 60 Of 450 Vacation Rentals

Exceptional(5)

$641.82

/ Nightly

Private Vacation Home

Mins to DTA - King Beds - Parking

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(39)

$819.62

/ Nightly

Private Vacation Home

Serene Sunsets at Historic Waterfront Home

Annapolis, Maryland, United States

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Exceptional(67)

$535.12

/ Nightly

Private Vacation Home

ACROSS FROM STADIUM - walk to downtown Annapolis.

Annapolis, Maryland, United States

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Sleeps

Exceptional(8)

$1269.62

/ Nightly

Private Vacation Home

USNA Stay w Private Pool, Hot Tub, King Beds, Child Safe & Stocked, Pet Friendly

Annapolis, Maryland, United States

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Bath

Sleeps

$480.98

/ Nightly

Private Vacation Home

Historic 2BR + Loft Home in Downtown Annapolis

Annapolis, Maryland, United States

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Bath

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Exceptional(75)

$385.89

/ Nightly

Apartment

Bay View Studio Apartment

Annapolis, Maryland, United States

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Bath

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Exceptional(41)

$633.22

/ Nightly

Private Vacation Home

Historic Hanover House Across from USNA Gate 3 w Private Patio

Annapolis, Maryland, United States

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Bath

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Exceptional(16)

$501.03

/ Nightly

Private Vacation Home

Go Navy! Steps to USNA, City Dock & Street Parking

Annapolis, Maryland, United States

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Bath

Sleeps

$1916.72

/ Nightly

Private Vacation Home

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

Annapolis, Maryland, United States

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Exceptional(8)

$505.02

/ Nightly

Private Vacation Home

Cozy Stay in Downtown Naptown -Located in the heart of Annapolis - 3BR, 2 BA

Annapolis, Maryland, United States

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Bath

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Exceptional(13)

$526.5

/ Nightly

Private Vacation Home

Cute bungalow blocks to Stadium

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(148)

Select Dates for Price

Private Vacation Home

Your Annapolis Adventure Starts Here!!

Annapolis, Maryland, United States

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Bath

Sleeps

$512.43

/ Nightly

Private Vacation Home

Eastport Cottage Only 4 Blocks to Downtown!

Annapolis, Maryland, United States

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Bath

Exceptional(33)

$618.45

/ Nightly

Private Vacation Home

Charm & Style in this Renovated Eastport Home

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(33)

$478.13

/ Nightly

Condo

Prime Eastport Location Walk Everywhere from Waterfront Condo w Pool & Parking

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(64)

$732.45

/ Nightly

Private Vacation Home

Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$420.81

/ Nightly

Private Vacation Home

Amazing townhome in Annapolis, near Restaurants, USNA, Shopping centers, & more

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(6)

$371.07

/ Nightly

Private Vacation Home

Annapolis-Eastport Cottage Home - Walk Everywhere - RV Van Parking & Hook-up too

Annapolis, Maryland, United States

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Bath

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Exceptional(6)

$993.09

/ Nightly

Private Vacation Home

Brilliantly Updated Multi-Level Walkable to Navy Stadium & Close to Historic Downtown Annapolis

Annapolis, Maryland, United States

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Exceptional(11)

$432.63

/ Nightly

Apartment

Perfect Eastport Location, walk everywhere, 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(11)

$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(11)

$2008.68

/ Nightly

Private vacation home

Spacious Converted Carriage House in Historic District near USNA

Annapolis, Maryland, United States

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Bath

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Exceptional(11)

$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(11)

$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

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Exceptional(11)

$2805.96

/ Nightly

Private vacation home

Downtown Annapolis Duke's House

Annapolis, Maryland, United States

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Bath

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Exceptional(11)

$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

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Exceptional(11)

$2974.10

/ Nightly

Private vacation home

Nantucket on the Chesapeake Heated Pool

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(11)

$499.32

/ Nightly

House boat

Welcome Aboard the Kathleen Marie!

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(11)

$485.19

/ Nightly

Apartment

Pool Loft Suite | Bay Access & Beach Passes

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(11)

$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

$641.82

$819.62

$535.12

$1269.62

$480.98

$385.89

$633.22

$501.03

$1916.72

$505.02

$526.5

$512.43

$618.45

$478.13

$732.45

$420.81

$371.07

$993.09

$432.63

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