Vacation Rentals in Annapolis, Maryland

50 Properties Available

Private vacation home

Nantucket on the Chesapeake Heated Pool

$2994 / night

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Private vacation home

Stunning remodel in Murray Hill- Available Commissioning Week 2025, 2026

$2907 / night

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Private vacation home

Premium Home in West Annapolis: Perfect for Navy Events, Boat Shows, Walkable!

$2622 / night

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Private vacation home

Elegant Eastport Entertaining Dream House

$2230 / night

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Private vacation home

Beautiful waterfront home on The Chesapeake Bay with private dock & beach access

$2076 / night

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Private vacation home

Spacious Waterfront 5-bedroom house in charming Annapolis with Hot Tub

$1887 / night

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$Spacious home with an outdoor pool, screened porch, washer\/dryer & central AC$ Private vacation home

Spacious home with an outdoor pool, screened porch, washer\/dryer & central AC

$1706 / night

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Private vacation home

Renovated historic home with courtyard, balcony, grill, great downtown location

$1650 / night

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Private vacation home

Marvelous Home with Backyard Living Room in Murray Hill

$1549 / night

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Private vacation home

Luxury Waterfront Annapolis home with your very own Private Beach & Dock

$1504 / night

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Private vacation home

Eastport Oasis 4 BR 2 BA fully renovated home on quiet street with parking

$1422 / night

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Private vacation home

3-story, dog-friendly home near beaches with home theatre, grill & gaming tables

$1335 / night

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Private vacation home

5 BDRM across from the USNA Stadium

$1300 / night

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Private vacation home

Beautiful colonial only 3 miles to the Naval Academy!

$1264 / night

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Private vacation home

Renovated dog-friendly bayfront home with private hot tub & pool, grill, & dock

$1191 / night

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Private vacation home

Waterfront Estate Annapolis - Beautiful Views - Dock & Boat Slip - Pet Friendly

$1167 / night

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Private vacation home

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

$1081 / night

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Private vacation home

Historic Annapolis With Parking

$1077 / night

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Private vacation home

Deep in the Heart of Annapolis; Parking for days!

$1049 / night

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$Dog-friendly house with yard, deck, firepit, washer\/dryer & AC - near golf$ Private vacation home

Dog-friendly house with yard, deck, firepit, washer\/dryer & AC - near golf

$1042 / night

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Private vacation home

Huge deck overlooking water

$1032 / night

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Private vacation home

Private 4-bedroom house in Annapolis, great location!

$944 / night

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Private vacation home

Beautiful Downtown Annapolis Townhome!

$915 / night

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Cottage

Charming Bay Ridge Cottage with Chesapeake Bay Views – Just Steps to the Beach

$911 / night

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Private vacation home

Cottage for Rent

$896 / night

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Private vacation home

Updated historic home with parking; near Academy, college & harbor - central AC

$884 / night

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Private vacation home

Perfect weekend getaway

$884 / night

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Private vacation home

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

$868 / night

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Private vacation home

Stately Brick Ranch On Corner Lot with Private Backyard for Entertaining

$844 / night

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Private vacation home

WATERFRONT Historic Home on the Chesapeake Bay

$837 / night

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$Spacious beachfront home with decks, gas grill, wet bar, gas fireplace, and W\/D$ Private vacation home

Spacious beachfront home with decks, gas grill, wet bar, gas fireplace, and W\/D

$829 / night

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Private vacation home

Parking at Randall House Across from USNA Gate 1

$828 / night

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Private vacation home

Newly-Renovated Waterfront Home w Private Pier in Annapolis & Dog-Friendly

$813 / night

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Private vacation home

Stay just steps from the Waterfront in the Historic Fleet's Inn

$803 / night

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Private vacation home

West Annapolis Cottage

$795 / night

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Private vacation home

3-bedroom Home Away From Home. More than a rental — it's an experience.

$780 / night

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$Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis\n$ Private vacation home

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

$771 / night

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Private vacation home

BAY RIDGE MODERN HOME WITH VINTAGE CHARM

$750 / night

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Private vacation home

Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard

$740 / night

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$Historic district home, View of the Capital, WALK Downtown, w\/ Outdoor Dining!$ Private vacation home

Historic district home, View of the Capital, WALK Downtown, w\/ Outdoor Dining!

$732 / night

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$Charming 3-bedroom house with AC and WiFi in enchanting Annapolis\/Eastport$ Private vacation home

Charming 3-bedroom house with AC and WiFi in enchanting Annapolis\/Eastport

$717 / night

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Private vacation home

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

$700 / night

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Private vacation home

BY THE BAY

$695 / night

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Private vacation home

Beautifully Renovated Historic District Home

$685 / night

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$Charming 235-yo former tavern 1 block to water\/shops$ Private vacation home

Charming 235-yo former tavern 1 block to water\/shops

$685 / night

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Private vacation home

Charming Eastport CapeCod

$684 / night

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Private vacation home

Hanover House across from USNA Gate 3 with private back patio

$681 / night

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Cottage

WATERFRONT COTTAGE ON SEVERN - STUNNING VIEWS - MINUTES FROM DOWNTOWN ANNAPOLIS

$679 / night

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Private vacation home

Fox Hollow House- The perfect Annapolis Getaway

$666 / night

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Private vacation home

Naptown Villa- Fun, Family and Relaxation

$652 / night

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