Annapolis: Vacation Rental By Owner

Showing 20 Of 194 Vacation Rentals
  • Property-1 Image 1
    House Select Dates for Price
    • 5 Bed
    • 4 Baths
    Annapolis, MD

    Located in safe residential neighborhood. Our backyard is a private wooded Oasis! Close to shopping, restaurants and the Chesapeake Bay. Minutes drive to... ...more

  • Property-2 Image 1
    House $1,013 / Nightly
    • 5 Bed
    • 4 Baths
    Annapolis, MD

    This Vintage 1930's Bay Front Beach House overlooks the Chesapeake Bay and Thomas Point Light House all the way to Kent Island! The sunrise colors and sounds of... ...more

  • Property-3 Image 1
    House $390 / Nightly
    • 3 Bed
    • 3 Baths
    • (46) Excellent
    Annapolis, MD

    This home is spacious and clean and will make your vacation plans a breeze from this central location. Many families, groups of friends, reunions, wedding... ...more

  • Property-4 Image 1
    Townhome $640 / Nightly
    • 3 Bed
    • 3 Baths
    Annapolis, MD

    Come and enjoy this very cozy little Historic District house fully furnished just waiting for you! This three bedrooms, two and a half bath, with a garage for 2... ...more

  • Property-5 Image 1
    Apartment Select Dates for Price
    • 1 Bed
    • 1 Baths
    Annapolis, MD

    This quaint little cottage is the perfect getaway retreat for a week. It has just what you need to stay there and enjoy your time in Annapolis. This unit is in... ...more

  • Property-6 Image 1
    Condo Select Dates for Price
    • 2 Bed
    • 2 Baths
    Annapolis, MD

    An Annapolis dream unit! This great garden-style condo is located in the gated Shearwater Community in Eastport with a fabulous deck overlooking Spa Creek. It is... ...more

  • Property-7 Image 1
    House Select Dates for Price
    • 3 Bed
    • 2 Baths
    • (5) Exceptional
    Annapolis, MD

    Delightful Arts and Crafts/ Coastal style home. Main Level is open space concept with 9 ft ceilings and plenty of natural light, walk out to large yard and... ...more

  • Property-8 Image 1
    House Select Dates for Price
    • 3 Bed
    • 3 Baths
    • (19) Exceptional
    Annapolis, MD

    Visit this expanded & completely renovated home at the end of a cul-de-sac featuring an open floor plan and large, private backyard with standalone bar & grill!... ...more

  • Property-9 Image 1
    Townhome $561 / Nightly
    • 3 Bed
    • 4 Baths
    • (62)
    Annapolis, MD

    Five Star quality private home in the historic Murray Hill neighborhood of Annapolis, around the corner from the town center but in a quiet, quaint neighborhood.... ...more

  • Property-10 Image 1
    Hotel Select Dates for Price
    • 1 Baths
    Annapolis, MD

    EPS Location 1 and 2 With a stay at Extended Stay America Annapolis - Admiral Cochrane Drive in Annapolis, you'll be within a 15-minute drive of U.S. Naval... ...more

  • Property-11 Image 1
    Apartment Select Dates for Price
    • 2 Bed
    • 1 Baths
    • (31)
    Annapolis, MD

    This luxiourious apartment sits right off Main Street and is so centrally located...you can park your car in the city garage and walk to everything. Great place... ...more

  • Property-12 Image 1
    House $448 / Nightly
    • 2 Bed
    • 1 Baths
    • (68)
    Annapolis, MD

    A Gorgeous, Waterfront setting in the Sailing Capital of the World! Charm, Detail, and Hospitality were not spared in this newly-remodeled and totally upgraded... ...more

  • Property-13 Image 1
    House $1,347 / Nightly
    • 5 Bed
    • 4 Baths
    • (6) Exceptional
    Annapolis, MD

    The William Anderson House invites you, your family and friends to enjoy this stunning renovation of a semi-detached home located in the heart of Historic... ...more

  • Property-14 Image 1
    House Select Dates for Price
    • 5 Bed
    • 5 Baths
    Annapolis, MD

    0514 THE CREW HOUSE Nantucket meets Martha's Vineyard in this charming, recently renovated Eastport home impeccably decorated by a US Naval Academy family in the... ...more

  • Property-15 Image 1
    House Select Dates for Price
    • 4 Bed
    • 3 Baths
    Annapolis, MD

    0180 ANCHORS AWEIGH Perfect 4 Bedroom Historic Home. Located within a block of the William Paca House and Gardens and two blocks to Annapolis Harbor, St. Johns... ...more

  • Property-16 Image 1
    House Select Dates for Price
    • 2 Bed
    • 2 Baths
    Annapolis, MD

    Charming 3 bedroom home in quiet neighborhood next to stadium, city dock and walking trails. The home is 1.5 miles away from the Naval Academy Campus and 0.5... ...more

  • Property-17 Image 1
    House Select Dates for Price
    • 6 Bed
    • 6 Baths
    • (4)
    Annapolis, MD

    WATERSIDE with IT ALL. Private Pier, Pool & Hot Tub 6 Bedrooms, 5 1/2 Baths, 2 Fireplaces and ???????finished lower level walk out with In law Suite, 2 Full... ...more

  • Property-18 Image 1
    House Select Dates for Price
    • 6 Bed
    • 5 Baths
    • (10) Excellent
    Annapolis, MD

    0025 BELLA CHATEAU ???????Lot's of space! Entertaining space, dining space, outdoor space and sleeping space. Warm and inviting social rooms for gathering and... ...more

  • Property-19 Image 1
    House Select Dates for Price
    • 5 Bed
    • 3 Baths
    • (26) Exceptional
    Annapolis, MD

    MAGICAL WATERFRONT Beautifully restored, turn of the century, beach cottage located on an acre of landscaped property with magnificent views of the Chesapeake... ...more

  • Property-20 Image 1
    House Select Dates for Price
    • 5 Bed
    • 4 Baths
    • (5) Exceptional
    Annapolis, MD

    Historic Grandeur in the Heart of Downtown. Upscale historic residence situated on one of the most sought-after streets in downtown Annapolis. 5 large bedrooms... ...more

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Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Annapolis. Many accommodations in Annapolis provide "Pets Not Allowed", there are 227, or there are 191 of Vacation Rentals in Annapolis with a "Non Smoking Only", there are also 137 with "Children Welcome", which is another great reason to visit Annapolis.

We analyzed price data and rendered them in this graph, which shows vacation rental prices for the next twelve months in Annapolis. The most expensive month of the next 12 months is in June, where prices hit an average of $392 a night. In July, prices will hit an average low of $257 per night.