You have sent
a request for
information to
this owner.
Advertisement

St. Michaels Vacation Rentals, Maryland(65)

USA >
ST. MICHAELS
Sort Properties By: 
Compare Selected
1 2 3
Historic Waterfront Home in St. Michaels, w/Wi-Fi, Dock & Pet Friendly
    4 Bedrooms,
  • 2 Bathrooms, 
  • 1 Half Bath
    • , Sleeps 8
  • Viewed

Historic Waterfront Home in St. Michaels, w/Wi-Fi, Dock & Pet Friendly

4 Bedrooms,
  • 2 Bathrooms, 
  • 1 Half Bath
    • , Sleeps 8
    1. Chesapeake Bay  >
    2. St. Michaels House
    #123352

    C$411 - C$719
    per night (C$)
    2 - 3 night Minimum Stay
    Premier Waterfront Vacation Home/St. Michaels (August Availability)
      4 Bedrooms,
    • 4 Bathrooms
      • , Sleeps 8
    • Viewed

    Premier Waterfront Vacation Home/St. Michaels (August Availability)

    4 Bedrooms,
  • 4 Bathrooms
    • , Sleeps 8
    1. Chesapeake Bay  >
    2. St. Michaels House
    #3177402

    C$257 - C$360
    per night (C$)
    3 night Minimum Stay
    BOAT HOUSE: New Luxury pool on the water in St. Michaels -
      4 Bedrooms,
    • 2 Bathrooms
      • , Sleeps 9
    • Viewed

    BOAT HOUSE: New Luxury pool on the water in St. Michaels -

    4 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 9
    1. Chesapeake Bay  >
    2. St. Michaels House
    #410948vb

    C$391 - C$925
    per night (C$)
    2 - 3 night Minimum Stay

    Premier One Level Waterfront Home with Pool, Dock, every Amenity!
      4 Bedrooms,
    • 3 Bathrooms
      • , Sleeps 8
    • Viewed

    Premier One Level Waterfront Home with Pool, Dock, every Amenity!

    4 Bedrooms,
  • 3 Bathrooms
    • , Sleeps 8
    1. Chesapeake Bay  >
    2. St. Michaels House
    #27321vb

    C$711 - C$1,076
    per night (C$)
    2 - 7 night Minimum Stay
    Relaxing New Waterfront Retreat W/ Private Pier, Pool & Kayaks
      4 Bedrooms,
    • 3 Bathrooms, 
    • 1 Half Bath
      • , Sleeps 11
    • Viewed

    Relaxing New Waterfront Retreat W/ Private Pier, Pool & Kayaks

    4 Bedrooms,
  • 3 Bathrooms, 
  • 1 Half Bath
    • , Sleeps 11
    1. Chesapeake Bay  >
    2. St. Michaels Estate
    #347588vb

    C$514 - C$719
    per night (C$)
    2 - 7 night Minimum Stay
    Total Privacy and Relaxation! 90 Acre Waterfront Farm with wraparound views
      4 Bedrooms,
    • 2 Bathrooms
      • , Sleeps 8
    • Viewed

    Total Privacy and Relaxation! 90 Acre Waterfront Farm with wraparound views

    4 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 8
    1. Chesapeake Bay  >
    2. St. Michaels House
    #146900vb

    C$505 - C$719
    per night (C$)
    2 - 7 night Minimum Stay
    Ultimate family vacation home! Pool, dock, games barn, hot tub and more!
      5 Bedrooms,
    • 4 Bathrooms
      • , Sleeps 10
    • Viewed

    Ultimate family vacation home! Pool, dock, games barn, hot tub and more!

    5 Bedrooms,
  • 4 Bathrooms
    • , Sleeps 10
    1. Chesapeake Bay  >
    2. St. Michaels House
    #922712

    C$1,048 - C$1,218
    per night (C$)
    3 - 7 night Minimum Stay
    Perfect for Families! Waterfront, 1 mile from downtown St. M's. Mostly 1 level.
      5 Bedrooms,
    • 3 Bathrooms
      • , Sleeps 10
    • Viewed

    Perfect for Families! Waterfront, 1 mile from downtown St. M's. Mostly 1 level.

    5 Bedrooms,
  • 3 Bathrooms
    • , Sleeps 10
    1. Chesapeake Bay  >
    2. St. Michaels House
    #399572vb

    C$308 - C$524
    per night (C$)
    2 night Minimum Stay
    Single family vacation cottage with pool, kayaks, play gym and dock
      3 Bedrooms,
    • 1 Bathroom, 
    • 1 Half Bath
      • , Sleeps 6
    • Viewed

    Single family vacation cottage with pool, kayaks, play gym and dock

    3 Bedrooms,
  • 1 Bathroom, 
  • 1 Half Bath
    • , Sleeps 6
    1. Chesapeake Bay  >
    2. St. Michaels Cottage
    #214581vb

    C$533 - C$696
    per night (C$)
    2 - 7 night Minimum Stay
    Great amenities---close to town, pool, dock, hot tub!
      4 Bedrooms,
    • 3 Bathrooms
      • , Sleeps 8
    • Viewed

    Great amenities---close to town, pool, dock, hot tub!

    4 Bedrooms,
  • 3 Bathrooms
    • , Sleeps 8
    1. Chesapeake Bay  >
    2. St. Michaels House
    #448999vb

    C$644 - C$812
    per night (C$)
    2 - 7 night Minimum Stay
    'Sandy Pines' 4 BR Home on Harris Creek w/Pool, Dock, Kayaks, Sunfish
      4 Bedrooms,
    • 3 Bathrooms
      • , Sleeps 10
    • Viewed

    'Sandy Pines' 4 BR Home on Harris Creek w/Pool, Dock, Kayaks, Sunfish

    4 Bedrooms,
  • 3 Bathrooms
    • , Sleeps 10
    1. Chesapeake Bay  >
    2. St. Michaels House
    #314049

    C$2,672 - C$4,728
    per week (C$)
    2 - 7 night Minimum Stay
    Luxury Waterfront Home, Sunsets, Pool, 2 miles from Town Center!
      5 Bedrooms,
    • 4 Bathrooms
      • , Sleeps 10
    • Viewed

    Luxury Waterfront Home, Sunsets, Pool, 2 miles from Town Center!

    5 Bedrooms,
  • 4 Bathrooms
    • , Sleeps 10
    1. Chesapeake Bay  >
    2. St. Michaels House
    #233398

    C$668 - C$822
    per night (C$)
    2 - 7 night Minimum Stay
    Contemporary Cottage on quiet creek, waterside pool, tranquil views
      3 Bedrooms,
    • 2 Bathrooms
      • , Sleeps 8
    • Viewed

    Contemporary Cottage on quiet creek, waterside pool, tranquil views

    3 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 8
    1. Chesapeake Bay  >
    2. St. Michaels House
    #391798vb

    C$659 - C$797
    per night (C$)
    2 - 7 night Minimum Stay
    Thistle Dew - Will Do!! Waterfront, Pool, Decor, Location
      4 Bedrooms,
    • 3 Bathrooms
      • , Sleeps 8
    • Viewed

    Thistle Dew - Will Do!! Waterfront, Pool, Decor, Location

    4 Bedrooms,
  • 3 Bathrooms
    • , Sleeps 8
    1. Chesapeake Bay  >
    2. St. Michaels Cottage
    #449007vb

    C$550 - C$704
    per night (C$)
    3 - 7 night Minimum Stay
    Private Cottage just outside St. Michaels with kayak and bikes included!
      3 Bedrooms,
    • 3 Bathrooms
      • , Sleeps 6
    • Viewed

    Private Cottage just outside St. Michaels with kayak and bikes included!

    3 Bedrooms,
  • 3 Bathrooms
    • , Sleeps 6
    1. Chesapeake Bay  >
    2. St. Michaels Cottage
    #389515vb

    C$606 - C$781
    per night (C$)
    2 - 3 night Minimum Stay
    Private Cottage just outside St. Michaels with kayak and bikes included!
      3 Bedrooms,
    • 3 Bathrooms
      • , Sleeps 6
    • Viewed

    Private Cottage just outside St. Michaels with kayak and bikes included!

    3 Bedrooms,
  • 3 Bathrooms
    • , Sleeps 6
    1. Chesapeake Bay  >
    2. St. Michaels Cottage
    #960147

    C$606 - C$781
    per night (C$)
    2 - 3 night Minimum Stay
    Waterfront getaway cottage near St. Michaels, hot tub, kayaks
      3 Bedrooms,
    • 2 Bathrooms
      • , Sleeps 6
    • Viewed

    Waterfront getaway cottage near St. Michaels, hot tub, kayaks

    3 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 6
    1. Chesapeake Bay  >
    2. St. Michaels Cottage
    #448997vb

    C$411 - C$565
    per night (C$)
    2 - 7 night Minimum Stay
    Friends & Family "Crash Pad" - Views, Pool, Kayaks, Bikes, Firepit & More
      4 Bedrooms,
    • 3 Bathrooms
      • , Sleeps 8
    • Viewed

    Friends & Family "Crash Pad" - Views, Pool, Kayaks, Bikes, Firepit & More

    4 Bedrooms,
  • 3 Bathrooms
    • , Sleeps 8
    1. Chesapeake Bay  >
    2. St. Michaels House
    #449003vb

    C$721 - C$889
    per night (C$)
    2 - 7 night Minimum Stay
    Sea Glass Cottage on the Bay - St Michaels MD Area
      3 Bedrooms,
    • 1 Bathroom, 
    • 1 Half Bath
      • , Sleeps 6
    • Viewed

    Sea Glass Cottage on the Bay - St Michaels MD Area

    3 Bedrooms,
  • 1 Bathroom, 
  • 1 Half Bath
    • , Sleeps 6
    1. Chesapeake Bay  >
    2. St. Michaels Cottage
    #3014081

    C$308 - C$411
    per night (C$)
    2 night Minimum Stay
    Europa on the Beach - Architectural contemporary home on the Chesapeake Bay
      3 Bedrooms,
    • 2 Bathrooms
      • , Sleeps 6
    • Viewed

    Europa on the Beach - Architectural contemporary home on the Chesapeake Bay

    3 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 6
    1. Chesapeake Bay  >
    2. St. Michaels House
    #234151

    C$514 - C$668
    per night (C$)
    3 night Minimum Stay
    Acreage, Amenities and All You Need for Family and Friend Gatherings
      5 Bedrooms,
    • 5 Bathrooms
      • , Sleeps 12
    • Viewed

    Acreage, Amenities and All You Need for Family and Friend Gatherings

    5 Bedrooms,
  • 5 Bathrooms
    • , Sleeps 12
    1. Chesapeake Bay  >
    2. St. Michaels House
    #449016vb

    C$663 - C$1,166
    per night (C$)
    2 - 7 night Minimum Stay
    Luxurious and Extremely Private Waterfront Estate
      9 Bedrooms,
    • 7 Bathrooms, 
    • 2 Half Baths
      • , Sleeps 20
    • Viewed

    Luxurious and Extremely Private Waterfront Estate

    9 Bedrooms,
  • 7 Bathrooms, 
  • 2 Half Baths
    • , Sleeps 20
    1. Chesapeake Bay  >
    2. St. Michaels Estate
    #942769

    C$11,819
    per week (C$)
    2 night Minimum Stay
    Waterfront Home 'Sandy Pines' - Private Waterfront and Pool
      4 Bedrooms,
    • 3 Bathrooms
      • , Sleeps 10
    • Viewed

    Waterfront Home 'Sandy Pines' - Private Waterfront and Pool

    4 Bedrooms,
  • 3 Bathrooms
    • , Sleeps 10
    1. Chesapeake Bay  >
    2. St. Michaels House
    #40646vb

    Waterfront Home in Historic St. Michaels
      4 Bedrooms,
    • 2 Bathrooms, 
    • 1 Half Bath
      • , Sleeps 8
    • Viewed

    Waterfront Home in Historic St. Michaels

    4 Bedrooms,
  • 2 Bathrooms, 
  • 1 Half Bath
    • , Sleeps 8
    1. Chesapeake Bay  >
    2. St. Michaels Farmhouse
    #410694vb

    St. Michael's Waterfront Vacation Cottage
      3 Bedrooms,
    • 3 Bathrooms
      • , Sleeps 6
    • Viewed

    St. Michael's Waterfront Vacation Cottage

    3 Bedrooms,
  • 3 Bathrooms
    • , Sleeps 6
    1. Chesapeake Bay  >
    2. St. Michaels Cottage
    #178681vb

    C$288 - C$509
    per night (C$)
    2 night Minimum Stay
    1900 Circa Duel Cottages Decorated to Die For
      3 Bedrooms,
    • 3 Bathrooms
      • , Sleeps 6
    • Viewed

    1900 Circa Duel Cottages Decorated to Die For

    3 Bedrooms,
  • 3 Bathrooms
    • , Sleeps 6
    1. Chesapeake Bay  >
    2. St. Michaels Cottage
    #449015vb

    C$609 - C$763
    per night (C$)
    2 - 7 night Minimum Stay
    2 Weeks Still Open in June - $2000 Off $6300/Week!
      6 Bedrooms,
    • 6 Bathrooms, 
    • 2 Half Baths
      • , Sleeps 12
    • Viewed

    2 Weeks Still Open in June - $2000 Off $6300/Week!

    6 Bedrooms,
  • 6 Bathrooms, 
  • 2 Half Baths
    • , Sleeps 12
    1. Chesapeake Bay  >
    2. St. Michaels House
    #272472

    C$5,036
    per week (C$)
    2 night Minimum Stay
    Elegant Ralph Lauren Waterfront Cottage Nr St Michaels
      3 Bedrooms,
    • 2 Bathrooms
      • , Sleeps 6
    • Viewed

    Elegant Ralph Lauren Waterfront Cottage Nr St Michaels

    3 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 6
    1. Chesapeake Bay  >
    2. St. Michaels Cottage
    #410268vb

    On Harbor and on Park! - Only Large Vacation House in Town
      6 Bedrooms, Sleeps 11
    • Viewed

    On Harbor and on Park! - Only Large Vacation House in Town

    6 Bedrooms, Sleeps 11
    1. Chesapeake Bay  >
    2. St. Michaels House
    #198445vb

    New listing with rural country charm, pool, and a deep water dock
      3 Bedrooms,
    • 2 Bathrooms, 
    • 1 Half Bath
      • , Sleeps 10
    • Viewed

    New listing with rural country charm, pool, and a deep water dock

    3 Bedrooms,
  • 2 Bathrooms, 
  • 1 Half Bath
    • , Sleeps 10
    1. Chesapeake Bay  >
    2. St. Michaels Estate
    #3021814

    C$360 - C$565
    per night (C$)
    2 night Minimum Stay
    1 2 3
    Sort Properties By: 
    Compare Selected