Vacation Home Rentals By Owner In Annapolis, MD

Showing 200 Of 318 Vacation Rentals

Exceptional(60)

$1399.92

/ Nightly

Private Vacation Home

Stunning Annapolis Home! Across from the library, walk to Naval Graduation

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1578.33

/ Nightly

Private Vacation Home

18th Century 4bdrm Luxury Historic Home in Downtown Annapolis

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(16)

$1692.52

/ Nightly

Private Vacation Home

Waterfront Architectural Masterpiece with private dockage available.

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(3)

$1692.9

/ Nightly

Private Vacation Home

Annapolis History In Style Next to City Dock with Street Parking

Annapolis, Maryland, United States

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Bath

Sleeps

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(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

$1923.56

/ Nightly

Private Vacation Home

Submariner's Gate - Historic 4-bedroom home in charming Annapolis with parking

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1925.92

/ Nightly

Private Vacation Home

Dog-friendly riverfront home with dock, 2 balconies, waterside patio, & grill

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

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Bath

Sleeps

$2147.79

/ Nightly

Private Vacation Home

Marvelous Home with Backyard Living Room in Murray Hill

Annapolis, Maryland, United States

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Bath

Sleeps

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

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

$2573.29

/ Nightly

Private Vacation Home

3-story home near river with patio, firepit, Ping-Pong, grill and wood fireplace

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(3)

$2805.96

/ Nightly

Private Vacation Home

Downtown Annapolis Duke's House

Annapolis, Maryland, United States

Bath

Sleeps

Exceptional(30)

$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(12)

Select Dates for Price

Private Vacation Home

MODERN 2022 NEWLY BUILT TOWNHOME

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

Bed

Bath

Sleeps

Exceptional(7)

Select Dates for Price

Private Vacation Home

Steps to Marinas & Shops w Parking in Eastport

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

Exceptional(5)

$287.06

/ Nightly

Private Vacation Home

Bay Ridge house by Quiet Waters Park, Thomas Point Park

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(5)

$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(5)

$2008.68

/ Nightly

Private vacation home

Spacious Converted Carriage House in Historic District near USNA

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(5)

$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(5)

$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(5)

$2805.96

/ Nightly

Private vacation home

Downtown Annapolis Duke's House

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(5)

$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(5)

$2974.10

/ Nightly

Private vacation home

Nantucket on the Chesapeake Heated Pool

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(5)

$499.32

/ Nightly

House boat

Welcome Aboard the Kathleen Marie!

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(5)

$485.19

/ Nightly

Apartment

Pool Loft Suite | Bay Access & Beach Passes

Annapolis, Maryland, United States

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Bath

Sleeps

Exceptional(5)

$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 Home Rentals By Owner In Annapolis, MD

$1399.92

$1578.33

$1692.52

$1692.9

$1738.5

$1744.2

$1923.56

$1925.92

$2008.68

$2147.79

$2164.57

$2302.8

$2573.29

$2805.96

$2853.88

$281.01

$287.06

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