Vacation Home Rentals By Owner In Annapolis, MD

Showing 20 Of 318 Vacation Rentals

Exceptional(7)

$420.28

/ Nightly

Private Vacation Home

Eastport Bungalow | Yard, Grill & Walk Downtown

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(4)

$514.14

/ Nightly

Private Vacation Home

Charming 3-bedroom house in Annapolis Eastport! Beautifully furnished home

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$512.43

/ Nightly

Private Vacation Home

Eastport Cottage Only 4 Blocks to Downtown!

Annapolis, Maryland, United States

Bed

Bath

Exceptional(100)

$502.17

/ Nightly

Private Vacation Home

Cozy Cottage by the Beach - Waterview
Minutes from Downtown Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(5)

$479.94

/ Nightly

Private Vacation Home

Charming Historic Row House in The Heart of Eastport's Horn Point

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(5)

$478.8

/ Nightly

Private Vacation Home

Port of Call: 5BR Modern Nautical Luxury

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(1)

$469.12

/ Nightly

Private Vacation Home

4BR Family Retreat Near Annapolis w/ Large Yard

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(23)

$468.54

/ Nightly

Private Vacation Home

Annapolis Vacation Home: 2 Mi to Quiet Waters Park

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(1)

$440.73

/ Nightly

Private Vacation Home

Restful and Charming Home in Eastport

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$423.51

/ Nightly

Private Vacation Home

Cozy 2-bedroom home with WiFi and huge backyard minutes from downtown Annapolis.

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(9)

$366

/ Nightly

Private Vacation Home

Pet-Friendly Eastport | Yard & Fire Pit

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(13)

$300.39

/ Nightly

Private Vacation Home

Beautiful 2-bedroom water view house in Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$324.44

/ Nightly

Private Vacation Home

2-bedroom house in nice Annapolis with cool AC breeze

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$361.21

/ Nightly

Private Vacation Home

Hidden Wine Cellar | Eastport Retreat

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(7)

$363.79

/ Nightly

Private Vacation Home

Cozy Cottage with Beach Access

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$389.91

/ Nightly

Private Vacation Home

Classic 3 Bedroom Eastport Cottage with Large Yard and Free Parking

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$416.1

/ Nightly

Private Vacation Home

The Harness Creek Retreat in Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(4)

$411.16

/ Nightly

Private Vacation Home

Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(19)

$515.28

/ Nightly

Private Vacation Home

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Annapolis, Maryland, United States

Bed

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

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(6)

$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(6)

$2008.68

/ Nightly

Private vacation home

Spacious Converted Carriage House in Historic District near USNA

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(6)

$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(6)

$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(6)

$2805.96

/ Nightly

Private vacation home

Downtown Annapolis Duke's House

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(6)

$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(6)

$2974.10

/ Nightly

Private vacation home

Nantucket on the Chesapeake Heated Pool

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(6)

$499.32

/ Nightly

House boat

Welcome Aboard the Kathleen Marie!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(6)

$485.19

/ Nightly

Apartment

Pool Loft Suite | Bay Access & Beach Passes

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Exceptional(6)

$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 Home Rentals By Owner In Annapolis, MD

$420.28

$514.14

$512.43

$502.17

$479.94

$478.8

$469.12

$468.54

$440.73

$423.51

$366

$300.39

$324.44

$361.21

$363.79

$389.91

$416.1

$411.16

$515.28

$371.07

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