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

  • Red Barn Farm

    Mount Pleasant
    Budget options available

    Situated in Mount Pleasant, Red Barn Farm features accommodation with private pool, free WiFi and free private parking for guests who drive.

  • Covey Creek

    Mount Pleasant
    Budget options available

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

  • Bankors Aweigh

    Mount Pleasant
    Budget options available

    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.

  • Hawkeye Point

    Mount Pleasant
    Budget options available

    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
    Budget options available

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

  • Featuring air-conditioned accommodation with a private pool, Brand-New Pool! Waterfront Bozman Village Home is set in Bozman.

  • Dragonfly Cove

    Mount Pleasant
    Budget options available

    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

    Mount Pleasant
    Budget options available

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

Enjoy breakfast in Saint Michaels and nearby

  • 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.

  • Sunrise Cove

    Royal Oak
    Breakfast options

    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.

  • 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
    Breakfast options

    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.

  • Featuring air-conditioned accommodation with a patio, 25 Bedrooms - Retreat Center Waterfront Renovated is located in Royal Oak. The holiday home is 21 km from Academy Of The Arts.

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

  • Chesapeake Pines

    Royal Oak
    Breakfast options

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

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