Vacation Rentals By Owner In Annapolis, MD

Showing 180 Of 450 Vacation Rentals

$552.33

/ Nightly

Private Vacation Home

Elegant 3-bedroom house with EV charger in Downtown Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(18)

$579.69

/ Nightly

Private Vacation Home

Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$559.93

/ Nightly

Private Vacation Home

Sunny and spacious water view/access home in Annapolis.

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(13)

$554.48

/ Nightly

Apartment

Historic Suite 2 Blocks from Main St with On-Site Parking & Dog-Friendly

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(6)

$2008.68

/ Nightly

Private Vacation Home

Spacious Converted Carriage House in Historic District near USNA

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(10)

$610.47

/ Nightly

Private Vacation Home

Escape Villa in Downtown Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$831.32

/ Nightly

Private Vacation Home

Bay Ridge House- Charming 2-Bedroom Home – Large Backyard, Family-Friendly, Clos

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$716.68

/ Nightly

Private Vacation Home

Elegant Townhome Mins to Downtown Annapolis, w Multiple EnSuite Bedrooms & Parking

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(12)

Select Dates for Price

Private Vacation Home

MODERN 2022 NEWLY BUILT TOWNHOME

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(38)

Select Dates for Price

Apartment

Anchor's Away in the Heart of Eastport!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(21)

$483.36

/ Nightly

Private Vacation Home

Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(3)

$172.06

/ Nightly

Guest House

Barefoot Cottage A Quiet Coastal Retreat

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$596.9

/ Nightly

Private Vacation Home

Quiet Woodland Lodge w Community Beach Access & Large Private Deck

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(10)

$987.24

/ Nightly

Private Vacation Home

Annapolis -Eastport - -3 Bedroom- 3 bath with parking

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(3)

$320.86

/ Nightly

Private Vacation Home

Pet Friendly Hideaway for 5 Close to Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(10)

$1744.2

/ Nightly

Private Vacation Home

Spacious Annapolis Abode: 507 Schley Rd Vacation Rental, Minutes from Downtown!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(75)

$639.54

/ Nightly

Private Vacation Home

Sophisticated Charmer with Parking & Views of the USNA Chapel Dome

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$1258.56

/ Nightly

Private Vacation Home

Historic Downtown Luxury • USNA • Waterfront

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(147)

$387.49

/ Nightly

Private Vacation Home

Charming garden row home, easy 4 block walk to the heart of Annapolis.

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(17)

$219.91

/ Nightly

Private Vacation Home

Wright's Cottage- Pet's Welcome & EV Charging

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Rent a place that suits your needs

Private vacation home

View 318 Private vacation home

Most popular vacation rentals in Annapolis

Exceptional(17)

$1926.40

/ Nightly

Private vacation home

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

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(17)

$2008.68

/ Nightly

Private vacation home

Spacious Converted Carriage House in Historic District near USNA

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(17)

$2164.57

/ Nightly

Private vacation home

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

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(17)

$2302.80

/ Nightly

Private vacation home

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

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(17)

$2805.96

/ Nightly

Private vacation home

Downtown Annapolis Duke's House

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(17)

$2853.88

/ Nightly

Private vacation home

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

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(17)

$2974.10

/ Nightly

Private vacation home

Nantucket on the Chesapeake Heated Pool

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(17)

$499.32

/ Nightly

House boat

Welcome Aboard the Kathleen Marie!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(17)

$485.19

/ Nightly

Apartment

Pool Loft Suite | Bay Access & Beach Passes

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(17)

$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

$552.33

$579.69

$559.93

$554.48

$2008.68

$610.47

$831.32

$716.68

$483.36

$172.06

$596.9

$987.24

$320.86

$1744.2

$639.54

$1258.56

$387.49

$219.91

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