The 10 best holiday homes in Annapolis, USA | Booking.com
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Holiday Homes in Annapolis

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Holiday Homes for every style

Find the right holiday home for you in Annapolis

The best holiday homes in Annapolis

Check out our pick of great holiday homes in Annapolis

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Looking for a holiday home?

Great for families or large parties, holiday homes are privately owned accommodation, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities for self-catering, although breakfast may be offered as an add-on. These properties have their own independent front door, which makes them different to apartments.

Most booked holiday homes in Annapolis and surroundings in the past month

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Save money on holiday homes in Annapolis and nearby – budget options available

  • Westside Storied

    Annapolis
    Budget options available

    Set 2.3 km from Annapolis Harbor, 47 km from Sports Legends Museum At Camden Yards and 48 km from Baltimore Convention Center, Westside Storied offers accommodation situated in Annapolis.

  • Downtown Annapolis

    Annapolis
    Budget options available

    Boasting air-conditioned accommodation with a patio, Downtown Annapolis is set in Annapolis.

  • Scored out of 10, guest rating 7.0
    Good - What previous guests thought, 4 reviews

    Set in Annapolis, 2.2 km from Annapolis Harbor and 48 km from Sports Legends Museum At Camden Yards, Cozy 2br home w/ parking in downtown Annapolis offers a garden and air conditioning.

  • The Little House

    Annapolis
    Budget options available
    Scored out of 10, guest rating 4.0
    Disappointing - What previous guests thought, 1 review

    Boasting air-conditioned accommodation with a patio, The Little House is set in Annapolis.

  • St Johns Adjacent

    Annapolis
    Budget options available

    Boasting air-conditioned accommodation with a patio, St Johns Adjacent is situated in Annapolis.

  • Offering barbecue facilities and garden view, 1879 Downtown Annapolis Home with Koi Ponds and Gardens is set in Annapolis, 48 km from Sports Legends Museum At Camden Yards and 48 km from Baltimore...

  • Situated in Annapolis, 2.5 km from Annapolis Harbor and 48 km from Sports Legends Museum At Camden Yards, Timeless Charm, Modern Comfort features spacious air-conditioned accommodation with a patio...

  • Naval Academy Gate 1

    Annapolis
    Budget options available

    Located in Annapolis, 1.8 km from Annapolis Harbor and 41 km from Inner Harbor, Naval Academy Gate 1 provides air-conditioned accommodation with a patio and free WiFi.

Great access to the city centre. Check these holiday homes in Annapolis and nearby

  • Located in Annapolis, 1.8 km from Annapolis Harbor and 48 km from Sports Legends Museum At Camden Yards, Historic Row Home in Downtown Annapolis provides air-conditioned accommodation with a patio and...

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 2 reviews

    Featuring air-conditioned accommodation with a patio, Skyline Sanctuary is located in Annapolis.

  • Anchors Aweigh

    Annapolis
    Central location
    Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Featuring air-conditioned accommodation with a patio, Anchors Aweigh is set in Annapolis.

  • Seas The Bay

    Annapolis
    Central location
    Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 1 review

    Boasting air-conditioned accommodation with a patio, Seas The Bay is situated in Annapolis.

  • Located in Annapolis, 2.6 km from Annapolis Harbor and 41 km from Inner Harbor, Newly Renovated In Dta W Parking provides spacious air-conditioned accommodation with a patio and free WiFi.

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 2 reviews

    Situated in Annapolis, 1.8 km from Annapolis Harbor and 48 km from Sports Legends Museum At Camden Yards, Historic Row Home 1 Block from Gate 1 at USNA features air-conditioned accommodation with a...

  • Crew's Quarters

    Annapolis
    Central location

    Situated in Annapolis, 2.6 km from Annapolis Harbor and 48 km from Sports Legends Museum At Camden Yards, Crew's Quarters offers air conditioning.

  • Boasting air-conditioned accommodation with a balcony, The Master Shipwright is situated in Annapolis. Guests staying at this holiday home have access to a patio.

Enjoy breakfast in Annapolis and nearby

  • Situated in Annapolis in the Maryland region, Unique And Central In Eastport has a patio.

  • Eden on Adams

    Annapolis
    Breakfast options

    Eden on Adams is situated in Annapolis, 1.4 km from Annapolis Harbor, 43 km from Addison Road-Seat Pleasant, and 49 km from Sports Legends Museum At Camden Yards.

  • Harrison Hall

    Annapolis
    Breakfast options
    Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Boasting air-conditioned accommodation with a patio, Harrison Hall is set in Annapolis.

  • Boasting air-conditioned accommodation with a patio, Beautiful 4BR - Walking Distance to Stadium is situated in Annapolis.

  • Lighthouse Inn

    Annapolis
    Breakfast options

    Lighthouse Inn is set in Annapolis, less than 1 km from Annapolis Harbor, 49 km from Sports Legends Museum At Camden Yards, and 50 km from Baltimore Convention Center.

  • Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 9 reviews

    Located in Annapolis, 4.4 km from Annapolis Harbor and 45 km from Sports Legends Museum At Camden Yards, Stylish + fresh bungalow 2 blocks from N-MC Stadium provides spacious air-conditioned...

  • Located 40 km from Inner Harbor, 40 km from Power Plant and 41 km from Baltimore Convention Center, 1 Block to USNA Stadium Modern Annapolis Home! provides accommodation set in Annapolis.

  • Featuring air-conditioned accommodation with a patio, Brand New Spacious Luxury Home is located in Annapolis. This property offers access to a terrace, free private parking and free WiFi.

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