House holiday rentals in Saint Michaels
Find and book unique houses on Airbnb
Top-rated house rentals in Saint Michaels
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Saint Michaels
House rentals with a pool
Home in Stevensville
5.0 out of 5 average rating, 101 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
26 Feb – 5 Mar
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
18–25 Nov
Home in Tracys Landing
4.99 out of 5 average rating, 166 reviewsThe Little Gypsy BoHome
12–19 Dec
Home in Harwood
4.94 out of 5 average rating, 117 reviewsLuxury Home, Sleeps 15, Private Pool, Close to DC
15–22 Jun
Home in Chesapeake Beach
4.91 out of 5 average rating, 111 reviewsIndoor pool/spa nestled in Southern Md. woods.
29 Jan – 5 Feb
Home in Shady Side
4.88 out of 5 average rating, 174 reviewsCattail Landing- Photographer's Waterfront Retreat
30 Mar – 6 Apr
Home in Montross
5.0 out of 5 average rating, 121 reviewsBeach Please! River cottage w/private beach & dock
13–20 Jan
Home in Montross
4.93 out of 5 average rating, 166 reviewsThe Glebe
4–11 Dec
Weekly house rentals
Home in Woolford
4.93 out of 5 average rating, 118 reviewsWaterfront Getaway with Dock
21–28 Oct
Home in Woolford
4.99 out of 5 average rating, 198 reviewsNewly Renovated Modern 3 bed 2 bath Water Front
24–31 Jul
Home in Saint Michaels
5.0 out of 5 average rating, 36 reviewsShipwrights Cottage in Town!
16–23 Jan
Home in Saint Michaels
4.91 out of 5 average rating, 22 reviewsPrivate&Cozy/3br+2ba/1mi to town
6–13 Jan
Home in Cambridge
4.96 out of 5 average rating, 26 reviewsWaterfrontQuietHotTubPvtPierFirePitKayakGrillCasa
24–31 Jul
Home in Cambridge
4.89 out of 5 average rating, 9 reviewsHigh St. Art Gallery Suite
12–19 Dec
Home in Easton
5.0 out of 5 average rating, 19 reviewsEastern Shore Retreat!
18–25 Jan
Home in Tilghman Island
4.97 out of 5 average rating, 32 reviewsTilghman Retreat: A house on the Chesapeake Bay.
6–13 Sep
Private house rentals
Home in Bozman
5.0 out of 5 average rating, 7 reviewsGrace Creek Cottage
14–21 Jun
Home in Cambridge
5.0 out of 5 average rating, 6 reviewsMagical Waterfront Home-Dock, Firepit, family fun!
25 Mar – 1 Apr
Home in Oxford
5.0 out of 5 average rating, 37 reviewsStunning Chesapeake waterfront home
4–11 Dec
Home in Newcomb
5.0 out of 5 average rating, 30 reviewsSaint Michaels Waterfront Home
19–26 Sep
Home in Saint Michaels
4.89 out of 5 average rating, 9 reviewsWaterfront - 3 luxury Bdrms w/ outside pool & spa
14–21 Mar
Home in Chester
5.0 out of 5 average rating, 12 reviews*Waterfront Sunset Bayview* sleeps 6
13–20 Jan
Home in Cambridge
5.0 out of 5 average rating, 54 reviewsEntire Updated Waterview Home in Cambridge, MD
10–17 Jun
Home in Easton
5.0 out of 5 average rating, 40 reviewsTuckaway Cove Relaxing waterfront property
20–27 Oct
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
1.5T reviews
Nightly prices starting at
₹15,036 before taxes and fees
Destinations to explore
- Baltimore Holiday rentals
- Ocean City Holiday rentals
- Cape May Holiday rentals
- Wildwood Holiday rentals
- Rehoboth Beach Holiday rentals
- Arlington Holiday rentals
- Washington Holiday rentals
- Deep Creek Lake Holiday rentals
- Philadelphia Holiday rentals
- Jersey City Holiday rentals
- New York Holiday rentals
- The Hamptons Holiday rentals
- Lighthouse rentals United States
- House rentals United States
- Guest house rentals United States
- Townhouse rentals United States
- Earth house rentals United States
- House rentals Washington
- Townhouse rentals Washington
- Guest house rentals Washington
- House rentals Philadelphia
- Townhouse rentals Philadelphia
- Townhouse rentals Baltimore
- Guest house rentals Baltimore
- House rentals Baltimore
- Guest house rentals Maryland
- Tiny house rentals Maryland
- Townhouse rentals Maryland
- Beach house rentals Maryland
- House rentals Maryland
- Lakehouse rentals Maryland
- Monthly Rentals Saint Michaels
- Rentals with outdoor seating Saint Michaels
- Family-friendly rentals Saint Michaels
- Pet-friendly rentals Saint Michaels
- Rentals with a patio Saint Michaels
- Cottage rentals Saint Michaels
- Rentals with a washing machine and dryer Saint Michaels
- House rentals Talbot County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom