Vacation Rentals by Owner

St. Michaels Vacation Rentals Show this location only Back to top

•   Historic Waterfront Home in St. Michaels, W/Wi-Fi, Dock & Pet Friendly 4BR+/2.5BA – Sleeps 8 – St. Michaels #87481
  17
  $279 - $700 per night

  View details
•   Premier One Level Waterfront Home with Pool, Dock, Every Amenity! 4BR/3BA – Sleeps 8 – St. Michaels #27321
  14
  $429 - $1047 per night

  View details
•   Luxury Waterfront Home, Sunsets, Pool, 2 Miles from Town Center! 5BR/4BA – Sleeps 10 – St. Michaels #231553
  13
  $500 - $929 per night

  View details
•   Ultimate Family Vacation Home! Pool, Dock, Games Barn, Hot Tub and More! 5BR/4BA – Sleeps 10 – St. Michaels #922712ha
  15
  $712 - $1185 per night

  View details
•   Contemporary Cottage on Quiet Creek, Waterside Pool, Tranquil Views 3BR/2BA – Sleeps 8 – St. Michaels #391798
  21
  $326 - $775 per night

  View details
•   Private Cottage Just Outside St. Michaels with Kayak and Bikes Included! 3BR/3BA – Sleeps 6 – St. Michaels #389515
  11
  $252 - $610 per night

  View details
•   2 Weeks Still Open in June - $2000 Off $6300/Week! 6BR/6.5+BA – Sleeps 12 – St. Michaels #284839
  0
  $700 per night

  View details
•   Grandview - Main House 4BR+/2.5BA – Sleeps 13 – St. Michaels #232799
  4
  $2,000-$2750/wk or $530/nt

  View details
•   Elegant Ralph Lauren Waterfront Cottage Nr St Michaels 3BR/2BA – Sleeps 6 – St. Michaels #410268
  4
  2000. wk. Call re: last minute wk ends

  View details
•   Thistle Dew - Will Do!! Waterfront, Pool, Decor, Location 4BR/3BA – Sleeps 8 – St. Michaels #449007
  8
  $327 - $753 per night

  View details
•   Waterfront Getaway Cottage Near St. Michaels, Hot Tub, Kayaks 3BR/2BA – Sleeps 6 – St. Michaels #448997
  25
  $206 - $550 per night

  View details
•   Friends & Family "Crash Pad" - Views, Pool, Kayaks, Bikes, Firepit & More 4BR/3BA – Sleeps 8 – St. Michaels #449003
  6
  $386 - $865 per night

  View details
•   Special $1,000 Off May and June Weeks 4BR/3BA – Sleeps 8-10 – St. Michaels #454608
  0
  $800 per night 2 night min stay

  View details
•   1,000 Off Full Week $3,900 Rental in May and June! 6BR/5.5BA – Sleeps 14 – St. Michaels #452636
  0
  $800 - $900 per night 2 night min stay

  View details
•   Total Privacy and Relaxation! 90 Acre Waterfront Farm with Wraparound Views 4BR/2BA – Sleeps 6-8 – St. Michaels #146900
  26
  $355 - $750 per night

  View details
•   St. Michaels Waterfront-7BR-Indoor Pool-Dock 7BR+/5BA – Sleeps 2-14 – St. Michaels #25129
  0
  $1000 per night 2 night min stay

  View details
•   On Harbor and on Park! - Only Large Vacation House in Town 6BR+/3.5BA – Sleeps 6-11 – St. Michaels #198445
  12
  590- 1845 for 2 or 3 nts;1845-2845 for wk

  View details
•   Premier Waterfront Vacation Home/St. Michaels (August Availability) 4BR/4BA – Sleeps 8 – St. Michaels #432739
  8
  $250 - $350 per night 3 night min stay

  View details
•   Heron Cove *Private Family Retreat* Summer $4000/wk 7BR+/5BA – Sleeps 14-20 – St. Michaels #89088
  6
  $4000/wk

  View details
•   St. Michael's Premier in-Town Summer Vacation Cottage! 2BR+/2BA – Sleeps 4 – St. Michaels #296266
  26
  $235-$260/nt and $1400-1600 wkly

  View details
•   Breezy Point Waterfront Cottage-Pool-Dock-Recreation Pavilion 4BR/2.5BA – Sleeps 6 – St. Michaels #292678
  0
  $340 - $600 per night 2 night min stay

  View details
•   Private Cottage Just Outside St. Michaels with Kayak and Bikes Included! 3BR/3BA – Sleeps 6 – St. Michaels #960147ha
  11
  $252 - $610 per night

  View details
•   Endless Waterfront Sunsets on Eastern Bay!! 3BR+/3.5BA – Sleeps 8 – St. Michaels #246578ha
  6
  $271 - $550 per night

  View details
•   Premium Waterfront Estate Property - $7,500/Week - 5BR+/7BA – Sleeps 10 – St. Michaels #355811
  8
  $5500 - $7500

  View details
•   Acreage, Amenities and All You Need for Family and Friend Gatherings 5BR/5BA – Sleeps 12 – St. Michaels #449016
  3
  $458 - $1135 per night

  View details
•   1900 Circa Duel Cottages Decorated to Die for 3BR/3BA – Sleeps 6 – St. Michaels #449015
  3
  $295 - $768 per night

  View details
•   Location, Location, Location!--Beautiful St. Michaels Cottage 2BR+/1.5BA – Sleeps 4-5 – St. Michaels #359766
  8
  $290-$890 for 2- 3 nt stay--$850-$1450/wk

  View details
•   Boat House: New Luxury Pool on the Water in St. Michaels - 4BR/2BA – Sleeps 9 – St. Michaels #410948
  5
  $480 - $900 per night 2-3 night min stay

  View details
•   Best St. Michaels Cottage in Best Location Walk to Everything 2BR+/1.5BA – Sleeps 4-5 – St. Michaels #229963
  12
  $310-$790/2- 3 Night - $875-$1,575/wk

  View details
• Special offer JUNE DAYS SPECIAL--25% OFF!! Jun 1, 2013 to Jun 30, 2013
    St. Michael's Waterfront Vacation Cottage 3BR+/3BA – Sleeps 6 – St. Michaels #178681
  10
  $280 - $495 per night 2 night min stay

  View details
•   St. Michaels Cozy Waterfront Cottage, Spa, Dock, Pet Friendly 2BR+/1.5BA – Sleeps 4-6 – St. Michaels #94139
  6
  From $250/nt

  View details
•   Waterfront Home in Historic St. Michaels 4BR/2.5BA – Sleeps 8 – St. Michaels #410694
  5
  $550/nt $3,500/wk, monthly rate discount

  View details
•   Luxurious and Extremely Private Waterfront Estate 9BR/7.5+BA – Sleeps 20 – St. Michaels #942769ha
  5
  $993 - $1643 per night

  View details
•   Beautiful, Quiet, Waterfront Home Close to St. Michaels/Easton 5BR+/4BA – Sleeps 10-13 – St. Michaels #304091
  2
  $3000- $5745/wk

  View details
•   Adorable, Affordable Blue Heron Cottage with Shared Pool & Water Views 2BR/2BA – Sleeps 4 – St. Michaels #245608
  29
  $180 per night 2 night min stay

  View details
•   Elegant, Waterfront Cottage on Six Acres in Historic Area 3BR/2BA – Sleeps 6-8 – St. Michaels #43980
  6
  $325-$550/nt - $1200-$3000/wk

  View details
•   Waterfront Home 'Sandy Pines' - Private Waterfront and Pool 4BR+/3BA – Sleeps 10 – St. Michaels #40646
  7
  $2600- $4600/wk

  View details
•   Relaxing New Waterfront Retreat W/ Private Pier, Pool & Kayaks 4BR+/3.5BA – Sleeps 9-11 – St. Michaels #347588
  24
  $500 - $700 per night 2-7 night min stay

  View details
•   Great Amenities---Close to Town, Pool, Dock, Hot Tub! 4BR/3BA – Sleeps 8 – St. Michaels #448999
  18
  $291 - $790 per night

  View details
•   Large Waterfront House Near St. Michael's with Pool & Dock 6BR/3BA – Sleeps 12 – St. Michaels #227037
  1
  $375 - $600 per night 3-7 night min stay

  View details
•   Relaxing Family Retreat with Dock and Pool 6BR/3.5BA – Sleeps 14 – St. Michaels #458864
  0
  $800 per night 2 night min stay

  View details
•   'Forest Cottage' Low Cost, Elegant, Romantic, Cottage Nr St Michaels 2BR/2.5BA – Sleeps 2-4 – St. Michaels #423077
  0
  1300 wk/ 790 wk End/ 300 daily, 3 night

  View details
•   Mountain Meadows Luxury Getaway Near the Heart of Park City 3BR/3BA – Sleeps 8 – St. Michaels #173713ha
  4
  $225 - $525 per night 3-5 night min stay

  View details
•   Single Family Vacation Cottage with Pool, Kayaks, Play Gym and Dock 3BR/1.5BA – Sleeps 6 – St. Michaels #214581
  28
  $288 - $678 per night

  View details
•   Perfect for Families! Waterfront, 1 Mile from Downtown St. M's. Mostly 1 Level. 5BR/3BA – Sleeps 9-10 – St. Michaels #399572
  17
  $300 - $510 per night 2 night min stay

  View details
•   Exceptionally Beautiful Waterfront Property in St. Michaels. 4BR/3BA – Sleeps 11 – St. Michaels #405188
  6
  From $3800- $5300/wk

  View details
•   Charming Waterfront Farmhouse on 70 Acre Farm 4BR/1BA – Sleeps 6-10 – St. Michaels #124154
  7
  $250-$325/nt - $1100-$1600

  View details
•   Eastern Shore Waterfront Estate, Private Beach, Deep Water 8BR/6.5BA – Sleeps 16 – St. Michaels #235779
  0
  $2,500- $6,800/wk

  View details
•   Beautiful St. Michaels House Steps from Water and Town 3BR+/2.5BA – Sleeps 6-10 – St. Michaels #381875
  7
  From $1200 to $2500 wk

  View details
•   Sunrises and Sunsets, Panoramic Views with Pool and Deepwater Dock, Sleeps 10 4BR+/5BA – Sleeps 10 – St. Michaels #254760ha
  0
  $643 - $929 per night

  View details