1227+ Vacation Rentals & Holiday Homes in Annapolis |
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Annapolis Accommodations - Hotels & Rentals

About Annapolis Vacation Rentals

Discover More than 1227 Incredible Getaway Rentals Available in Annapolis. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Annapolis.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Annapolis, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Annapolis. The Average Size of Places to Stay Near Annapolis is 919.12 ft², with Prices Averaging US $591 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Annapolis. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Annapolis

Type Count
Vacation Homes 878
Holiday Apartments 120
Cottages 30
Villas 7

Use these Quick Filters to Find a Vacation Rental in Annapolis

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Annapolis with Online Reservations.

Weather in Annapolis, MD

View the weather forecast for Annapolis before booking your Annapolis Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Activities AnnapolisGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World AnnapolisGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


U.S. Naval Academy
Six Flags America
Westfield Annapolis Mall
Annapolis City Dock
Chesapeake Bay Bridge
Sandy Point State Park
Bowie State University
Anne Arundel Medical Center
Maryland State House
Navy-Marine Corps Memorial Stadium
Annapolis Harbour Center
Kunta Kinte–Alex Haley Memorial
Annapolis Maritime Museum
Allen Pond Park
Maryland Quiet Waters Park
St John's College
Bay Hills Golf Club
Maryland World War II Memorial
William Paca House
The Kunta Kinte Alex Haley Memorial

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Northern Chesapeake Bay 10,273 Properties
Murray Hill 427 Properties
Historic District 409 Properties
Parole 75 Properties
Kent Island 69 Properties
Bowie 65 Properties
Eastport 60 Properties
Stevensville 53 Properties
Edgewater 47 Properties
Selby-on-the-Bay 38 Properties
Arnold 31 Properties
Lake Arbor 26 Properties

Frequently Asked Questions About Annapolis?

What are the top hotels, lake houses & vacation rentals in Annapolis?

We provide an array of great vacation destinations in Annapolis. If you are looking to stay in or around the Annapolis area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Annapolis:

How many Hotels & Vacation Rentals have private pools in Annapolis?

We have 60 Hotels & Vacation Rentals featuring a private pool in and near Annapolis. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel, lake house, or vacation rental in Annapolis is best for families?

Searching for a family-friendly getaway in Annapolis? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Annapolis?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 1227 in the Annapolis area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Annapolis.

Nearby Neighborhood (16) 
Neighborhood Property Count
Historic District Vacation Rentals in Annapolis, Maryland 409
Eastport Vacation Rentals in Annapolis, Maryland 60
Murray Hill Vacation Rentals in Annapolis, Maryland 427
Hillsmere Vacation Rentals in Annapolis, Maryland 718
West Annapolis Vacation Rentals in Annapolis, Maryland 710
Arundel on the Bay Vacation Rentals in Annapolis, Maryland 155
Homewood Vacation Rentals in Annapolis, Maryland 722
Epping Forest Vacation Rentals in Annapolis, Maryland 329
Oyster Harbor Vacation Rentals in Annapolis, Maryland 220
Atlantis Vacation Rentals in Annapolis, Maryland 89
Anchorage Vacation Rentals in Annapolis, Maryland 631
Cape St. John Vacation Rentals in Annapolis, Maryland 176
Hunt Meadows Vacation Rentals in Annapolis, Maryland 776
Kingsport Vacation Rentals in Annapolis, Maryland 737
Winchester-on-the-Severn Vacation Rentals in Annapolis, Maryland 505
Downs on the Severn Vacation Rentals in Annapolis, Maryland 149

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