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

Find the holiday homes that appeal to you the most

The best holiday homes in Saint Michaels

Check out our pick of great holiday homes in Saint Michaels

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Calloway Drive Retreat

Deale (Near Saint Michaels)

Set in Deale, 35 km from Annapolis Harbor and 46 km from Addison Road-Seat Pleasant, Calloway Drive Retreat offers a restaurant. Guests can benefit from a patio and a children's playground.

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 7 reviews
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Grasonville Home with Private Pool on the Water

Grasonville (Near Saint Michaels)

Located 21 km from Sandy Point State Park, 35 km from Annapolis Yacht Basin and 41 km from Annapolis Landing Marina, Grasonville Home with Private Pool on the Water provides accommodation situated in...

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 5 reviews
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All holiday homes in Saint Michaels

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 Saint Michaels and surroundings in the past month

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Holiday Homes with swimming pools in Saint Michaels and nearby

Enjoy breakfast in Saint Michaels and nearby

  • Covey Creek

    Mount Pleasant
    Breakfast options

    Situated in Mount Pleasant in the Maryland region, Covey Creek features accommodation with free WiFi and free private parking.

  • Set in Mount Pleasant, Bankors Aweigh offers accommodation with private pool, free WiFi and free private parking for guests who drive. A hot tub is available for guests.

  • Situated in Mount Pleasant, Hawkeye Point features accommodation with private pool, free WiFi and free private parking for guests who drive.

  • Swan Hollow

    Mount Pleasant
    Breakfast options

    Situated in Mount Pleasant, Swan Hollow features accommodation with private pool, free WiFi and free private parking for guests who drive.

  • Set in Mount Pleasant, Dragonfly Cove offers accommodation with private pool, free WiFi and free private parking for guests who drive. A hot tub is available for guests.

  • Oyster Cottage is located in Mount Pleasant. Featuring complimentary private parking, the holiday home is 26 km from Academy Of The Arts.

  • Situated in Mount Pleasant in the Maryland region, Herons Roost features accommodation with free WiFi and free private parking.

  • Situated in Mount Pleasant in the Maryland region, The Weekender features accommodation with free WiFi and free private parking.

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

  • Sunrise Cove

    Royal Oak
    Budget options available

    Situated in Royal Oak, Sunrise Cove features accommodation with private pool, free WiFi and free private parking for guests who drive. The holiday home is 50 km from Chesapeake Exploration Center.

  • Bayside The Point

    Royal Oak
    Budget options available

    Situated in Royal Oak, Bayside The Point features accommodation with private pool, free WiFi and free private parking for guests who drive. A hot tub is available for guests.

  • Miles Rest

    Royal Oak
    Budget options available

    Situated in Royal Oak, Miles Rest features accommodation with private pool, free WiFi and free private parking for guests who drive. A hot tub is available for guests.

  • Blue Herons Villa

    Royal Oak
    Budget options available

    Situated in Royal Oak in the Maryland region, Blue Herons Villa features accommodation with free WiFi and free private parking.

  • Chesapeake Pines

    Royal Oak
    Budget options available

    Chesapeake Pines is set in Royal Oak. Featuring free private parking, the holiday home is 14 km from Academy Of The Arts.

  • Mill Point

    Neavitt
    Budget options available

    Set in Neavitt, Mill Point offers accommodation with private pool, free WiFi and free private parking for guests who drive. The property is non-smoking and is situated 30 km from Academy Of The Arts.

  • Loon Cottage

    Oxford
    Budget options available

    Located 18 km from Academy Of The Arts, Loon Cottage provides accommodation with free WiFi and free private parking.

  • Neavitt Cottage

    Neavitt
    Budget options available

    Situated 32 km from Academy Of The Arts, Neavitt Cottage features accommodation with free WiFi and free private parking.

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