House vacation rentals in Saint Michaels
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Top-rated house rentals in Saint Michaels
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Saint Michaels house rentals
House rentals with a pool
Home in Stevensville
5.0 out of 5 average rating, 101 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
Dec. 25 – Jan. 1
Home in Tracys Landing
4.99 out of 5 average rating, 166 reviewsThe Little Gypsy BoHome
Dec. 15 – 22
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
Nov. 20 – 27
Home in Montross
5.0 out of 5 average rating, 121 reviewsBeach Please! River cottage w/private beach & dock
Nov. 11 – 18
Home in Chesapeake Beach
4.91 out of 5 average rating, 111 reviewsIndoor pool/spa nestled in Southern Md. woods.
Jul. 12 – 19
Home in Montross
4.93 out of 5 average rating, 166 reviewsThe Glebe
Dec. 4 – 11
Home in Shady Side
4.88 out of 5 average rating, 174 reviewsCattail Landing- Photographer's Waterfront Retreat
Sep. 16 – 23
Home in Severn
4.81 out of 5 average rating, 102 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
Mar. 25 – Apr. 1
Weekly house rentals
Home in Woolford
4.93 out of 5 average rating, 118 reviewsWaterfront Getaway with Dock
Oct. 21 – 28
Home in Woolford
4.99 out of 5 average rating, 198 reviewsNewly Renovated Modern 3 bed 2 bath Water Front
Aug. 17 – 24
Home in Rock Hall
5.0 out of 5 average rating, 105 reviewsBayside Beach House
Sep. 30 – Oct. 7
Home in Saint Michaels
5.0 out of 5 average rating, 36 reviewsShipwrights Cottage in Town!
Jan. 5 – 12
Home in Saint Michaels
4.91 out of 5 average rating, 22 reviewsPrivate&Cozy/3br+2ba/1mi to town
Dec. 31 – Jan. 7
Home in Tilghman Island
4.97 out of 5 average rating, 32 reviewsTilghman Retreat: A house on the Chesapeake Bay.
Aug. 23 – 30
Home in Cambridge
4.96 out of 5 average rating, 26 reviewsWaterfrontQuietHotTubPvtPierFirePitKayakGrillCasa
Jul. 24 – 31
Home in Greensboro
4.96 out of 5 average rating, 48 reviewsCozy 2 bedroom home on wooded private lane
Feb. 23 – Mar. 2
Private house rentals
Home in Newcomb
5.0 out of 5 average rating, 30 reviewsSaint Michaels Waterfront Home
Aug. 8 – 15
Home in Oxford
5.0 out of 5 average rating, 37 reviewsStunning Chesapeake waterfront home
Nov. 10 – 17
Home in Easton
5.0 out of 5 average rating, 40 reviewsTuckaway Cove Relaxing waterfront property
Sep. 25 – Oct. 2
Home in Chester
5.0 out of 5 average rating, 12 reviews*Waterfront Sunset Bayview* sleeps 6
Sep. 5 – 12
Home in Cambridge
4.89 out of 5 average rating, 9 reviewsHigh St. Art Gallery Suite
Nov. 3 – 10
Home in Easton
5.0 out of 5 average rating, 19 reviewsCozy, convenient, Easton home
Mar. 26 – Apr. 2
Home in Cambridge
5.0 out of 5 average rating, 54 reviewsEntire Updated Waterview Home in Cambridge, MD
Dec. 8 – 15
Home in Cambridge
4.92 out of 5 average rating, 51 reviewsOsprey's Retreat - Waterfront with private beach!
Sep. 4 – 9
Quick stats about house rentals in Saint Michaels
Total rentals
20 properties
Wifi availability
20 properties include access to wifi
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.5K reviews
Nightly prices starting at
$246 CAD before taxes and fees
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