HomeAway Vacation Rentals
Traveler Login
Owner Login
Viewed
Favorites
Inquired
My Trips
My Profile
Owner Dashboard
Logout
Help
Travelers
How it Works
Community
Help
Homeowners
How it Works
List Your Property
Community
Help
Property Managers
How it Works
Help
List Your Property
Search
You have sent
a request for
information to
this owner.
FILTERS
List View
Map View
Cancel
Apply Filters
Clear Filters
FILTERS
41
Results
Location
St. Michaels
Property Manager
Price
Price Per Week
$
Any
0
750
1,000
1,250
1,500
2,000
3,000
4,000
5,000
6,000
7,000
8,000
9,000
$
Any
750
1,000
1,250
1,500
2,000
3,000
4,000
5,000
6,000
7,000
8,000
9,000
10,000
Clear
Sleeps
Any
1+
(
533,322
)
2+
(
533,064
)
3+
(
509,484
)
4+
(
495,187
)
5+
(
393,228
)
6+
(
357,133
)
7+
(
227,358
)
8+
(
205,756
)
9+
(
121,500
)
10+
(
109,136
)
11+
(
64,618
)
12+
(
58,772
)
13 or more
(
34,617
)
Bedrooms
Any
Studio
(
22,125
)
1
(
88,256
)
2
(
162,293
)
3
(
142,411
)
4
(
76,194
)
5
(
32,079
)
6+
(
23,593
)
Booking
Book Online
(
3
)
Accepts online payments
(
11
)
More Filters
Hide Filters
Price Per Week
$
$
Sleeps
Bedrooms
Bathrooms
Booking Options
Booking Options
Book Online
(
3
)
Accepts online payments
(
11
)
Property Type (Select Multiple)
Property Type
Cottages
Cottages
(
9
)
Estates
Estates
(
9
)
Farmhouses
Farmhouses
(
2
)
Homes
Homes
(
21
)
Apartments
Apartments
(
0
)
Barns
Barns
(
0
)
Bungalows
Bungalows
(
0
)
Cabins
Cabins
(
0
)
Castles
Castles
(
0
)
Chalets
Chalets
(
0
)
Condos
Condos
(
0
)
Hotels
Hotels
(
0
)
Lodges
Lodges
(
0
)
Studios
Studios
(
0
)
Townhomes
Townhomes
(
0
)
Villas
Villas
(
0
)
Yachts
Yachts
(
0
)
Location Type
Location Type
beach
(
5
)
waterfront
(
34
)
near the ocean
(
1
)
lake
(
0
)
downtown
(
3
)
mountain
(
0
)
river
(
9
)
golf
(
39
)
skiing
(
2
)
Even More Filters
Even More Filters
special deals & offers
(
0
)
long term renters welcome
(
10
)
luxury
(
10
)
budget
(
1
)
Featured Listing
(
7
)
1+ reviews
(
30
)
Features
Features
Pool
(
33
)
Internet Access
(
34
)
Satellite or Cable TV
(
40
)
Pets Considered
(
17
)
wheelchair accessible
(
3
)
Hot Tub
(
12
)
Air Conditioning
(
41
)
non smoking only
(
37
)
Fireplace
(
35
)
Parking Included
(
-1
)
Outdoor Grill
(
40
)
Managed By
Managed By
Owner
(
31
)
Property Manager
(
10
)
Any
Cancel
Clear Filters
Apply Filters
Vacation Rentals
>
World
>
USA
>
Maryland
>
Chesapeake Bay
>
St. Michaels
5
BR /
4
BA /
Sleeps
10
From $1,020/nt
Featured
4
BR /
3
BA /
Sleeps
8
From $702/nt
Featured
4
BR /
3
BA /
Sleeps
6
From $340/nt
Featured
4
BR /
2
BA /
Sleeps
8
From $492/nt
Featured
5
BR /
3
BA /
Sleeps
12
Featured
St. Michaels with Parking Included
(41)
sort by
HomeAway Sort
HomeAway Sort
Average Rating
Availability Last Updated
Accepts Online Payments
Bedrooms: Least to Most
Bedrooms: Most to Least
Price: High to Low
Price: Low to High
Number of Reviews
Special Offers First
Historic Waterfront Home in St. Michaels, w/Wi-Fi, Dock & Pet Friendly
4 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 8
$400 - $700
per night
Historic Waterfront Home in St. Michaels, w/Wi-Fi, Dock & Pet Friendly
2 - 3 night Minimum Stay
4
BR,
2
BA,
1
HF BA,
Sleeps
8
Chesapeake Bay
>
St. Michaels House
#123352
(17)
Compare
Luxury Waterfront Home, Sunsets, Pool, 2 miles from Town Center!
5 Bedrooms,
4
Bathrooms
, Sleeps 10
$650 - $800
per night
Luxury Waterfront Home, Sunsets, Pool, 2 miles from Town Center!
2 - 7 night Minimum Stay
5
BR,
4
BA,
Sleeps
10
Chesapeake Bay
>
St. Michaels House
#233398
(13)
Compare
Special $1,000 Off May and June Weeks
4 Bedrooms,
3
Bathrooms
, Sleeps 10
$800
per night
Special $1,000 Off May and June Weeks
2 night Minimum Stay
4
BR,
3
BA,
Sleeps
10
Chesapeake Bay
>
St. Michaels House
#454608vb
Compare
2 Weeks Still Open in June - $2000 Off $6300/Week!
6 Bedrooms,
6
Bathrooms
,
2
Half Baths
, Sleeps 12
$4,900
per week
2 Weeks Still Open in June - $2000 Off $6300/Week!
2 night Minimum Stay
6
BR,
6
BA,
2
HF BA,
Sleeps
12
Chesapeake Bay
>
St. Michaels House
#272472
Compare
Breezy Point Waterfront Cottage-Pool-Dock-Recreation Pavilion
4 Bedrooms,
3
Bathrooms
, Sleeps 6
$340 - $600
per night
Breezy Point Waterfront Cottage-Pool-Dock-Recreation Pavilion
2 night Minimum Stay
4
BR,
3
BA,
Sleeps
6
Chesapeake Bay
>
St. Michaels Cottage
#254824
Compare
Endless Waterfront Sunsets on Eastern Bay!!
3 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 8
$300 - $550
per night
Endless Waterfront Sunsets on Eastern Bay!!
2 - 3 night Minimum Stay
3
BR,
3
BA,
1
HF BA,
Sleeps
8
Chesapeake Bay
>
St. Michaels House
#246578
(6)
Compare
Premium Waterfront Estate Property - $7,500/Week -
5 Bedrooms,
7
Bathrooms
, Sleeps 10
Premium Waterfront Estate Property - $7,500/Week -
5
BR,
7
BA,
Sleeps
10
Chesapeake Bay
>
St. Michaels Estate
#388823
(8)
Compare
Luxury home with pool and deep water dock.
4 Bedrooms,
4
Bathrooms
, Sleeps 8
Luxury home with pool and deep water dock.
4
BR,
4
BA,
Sleeps
8
Chesapeake Bay
>
St. Michaels Estate
#336403
(4)
Compare
Waterfront Home in Historic St. Michaels
4 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 8
Waterfront Home in Historic St. Michaels
4
BR,
2
BA,
1
HF BA,
Sleeps
8
Chesapeake Bay
>
St. Michaels Farmhouse
#410694vb
(5)
Compare
New listing with rural country charm, pool, and a deep water dock
3 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 10
$350 - $550
per night
New listing with rural country charm, pool, and a deep water dock
2 night Minimum Stay
3
BR,
2
BA,
1
HF BA,
Sleeps
10
Chesapeake Bay
>
St. Michaels Estate
#3021814
(4)
Compare
Luxurious and Extremely Private Waterfront Estate
9 Bedrooms,
7
Bathrooms
,
2
Half Baths
, Sleeps 20
$11,500
per week
Luxurious and Extremely Private Waterfront Estate
2 night Minimum Stay
9
BR,
7
BA,
2
HF BA,
Sleeps
20
Chesapeake Bay
>
St. Michaels Estate
#942769
(5)
Compare
Sea Glass Cottage on the Bay - St Michaels MD Area
3 Bedrooms,
1
Bathroom
,
1
Half Bath
, Sleeps 6
$300 - $400
per night
Sea Glass Cottage on the Bay - St Michaels MD Area
2 night Minimum Stay
3
BR,
1
BA,
1
HF BA,
Sleeps
6
Chesapeake Bay
>
St. Michaels Cottage
#3014081
(4)
Compare
Waterfront Country Cottage Close To St Michaels
3 Bedrooms,
3
Bathrooms
, Sleeps 6
$280 - $495
per night
Waterfront Country Cottage Close To St Michaels
2 night Minimum Stay
3
BR,
3
BA,
Sleeps
6
Chesapeake Bay
>
St. Michaels Cottage
#185818
(10)
Compare
Premier Waterfront Vacation Home/St. Michaels (August Availability)
4 Bedrooms,
4
Bathrooms
, Sleeps 8
$250 - $350
per night
Premier Waterfront Vacation Home/St. Michaels (August Availability)
Book it Now!
3 night Minimum Stay
4
BR,
4
BA,
Sleeps
8
Chesapeake Bay
>
St. Michaels House
#3177402
(7)
Compare
'Sandy Pines' 4 BR Home on Harris Creek w/Pool, Dock, Kayaks, Sunfish
4 Bedrooms,
3
Bathrooms
, Sleeps 10
$2,600 - $4,600
per week
'Sandy Pines' 4 BR Home on Harris Creek w/Pool, Dock, Kayaks, Sunfish
2 - 7 night Minimum Stay
4
BR,
3
BA,
Sleeps
10
Chesapeake Bay
>
St. Michaels House
#314049
(7)
Compare
Europa on the Beach - Architectural contemporary home on the Chesapeake Bay
3 Bedrooms,
2
Bathrooms
, Sleeps 6
$500 - $650
per night
Europa on the Beach - Architectural contemporary home on the Chesapeake Bay
3 night Minimum Stay
3
BR,
2
BA,
Sleeps
6
Chesapeake Bay
>
St. Michaels House
#234151
(3)
Compare
Incredible Waterfront Home 'Wye Provence' ' With Pool And Dock
5 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 10
$850
per night
Incredible Waterfront Home 'Wye Provence' ' With Pool And Dock
3 night Minimum Stay
5
BR,
3
BA,
1
HF BA,
Sleeps
10
Chesapeake Bay
>
St. Michaels House
#909433
Compare
St. Michael's premier in town summer vacation cottage!
2 Bedrooms,
2
Bathrooms
, Sleeps 4
St. Michael's premier in town summer vacation cottage!
2
BR,
2
BA,
Sleeps
4
Chesapeake Bay
>
St. Michaels Cottage
#287681
(26)
Compare
St Michaels Premier Waterfront home with pool and dock
5 Bedrooms,
4
Bathrooms
, Sleeps 10
$1,000
per night
St Michaels Premier Waterfront home with pool and dock
3 night Minimum Stay
5
BR,
4
BA,
Sleeps
10
Chesapeake Bay
>
St. Michaels House
#138986
1 Review
Compare
Exquisite 360 acre farm with 5 bedroom Manor, pool and vineyard
5 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 10
$1,000
per night
Exquisite 360 acre farm with 5 bedroom Manor, pool and vineyard
3 night Minimum Stay
5
BR,
3
BA,
1
HF BA,
Sleeps
10
Chesapeake Bay
>
St. Michaels House
#120889
Compare
'Chez Bonheur' magnificent 5 bedroom home on 1000 acre estate with pool and dock
6 Bedrooms,
2
Bathrooms
,
2
Half Baths
, Sleeps 6
$1,200
per night
'Chez Bonheur' magnificent 5 bedroom home on 1000 acre estate with pool and dock
3 night Minimum Stay
6
BR,
2
BA,
2
HF BA,
Sleeps
6
Chesapeake Bay
>
St. Michaels House
#909425
Compare
Sunrises AND Sunsets, Panoramic Views with Pool and Deepwater Dock, Sleeps 10
4 Bedrooms,
5
Bathrooms
, Sleeps 10
$4,500 - $6,500
per week
Sunrises AND Sunsets, Panoramic Views with Pool and Deepwater Dock, Sleeps 10
7 night Minimum Stay
4
BR,
5
BA,
Sleeps
10
Chesapeake Bay
>
St. Michaels House
#254760
Compare
Magnificent Vacation Rental home - 'Compass Rose' with pool and dock
5 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 8
$5,502
per week
Magnificent Vacation Rental home - 'Compass Rose' with pool and dock
7 night Minimum Stay
5
BR,
2
BA,
1
HF BA,
Sleeps
8
Chesapeake Bay
>
St. Michaels Estate
#234152
Compare
St. Michaels Premier Waterfront estate close to town, golfcourse, Harbor,Museum
6 Bedrooms,
5
Bathrooms
,
1
Half Bath
, Sleeps 12
St. Michaels Premier Waterfront estate close to town, golfcourse, Harbor,Museum
6
BR,
5
BA,
1
HF BA,
Sleeps
12
Chesapeake Bay
>
St. Michaels Estate
#113980
Compare
Charming historic farmhouse just minutes from all St. Michaels has to offer
2 Bedrooms,
1
Bathroom
, Sleeps 4
Charming historic farmhouse just minutes from all St. Michaels has to offer
2
BR,
1
BA,
Sleeps
4
Chesapeake Bay
>
St. Michaels Farmhouse
#3001756
Compare
Longview -- Waterfront Estate w/ Pool & 3+ Acres
5 Bedrooms,
3
Bathrooms
, Sleeps 10
Longview -- Waterfront Estate w/ Pool & 3+ Acres
5
BR,
3
BA,
Sleeps
10
Chesapeake Bay
>
St. Michaels Estate
#109333
(3)
Compare
15 More choices from HomeAway International Websites
BOAT HOUSE: New Luxury pool on the water in St. Michaels -
4 Bedrooms,
2
Bathrooms
, Sleeps 9
$380 - $900
per night
BOAT HOUSE: New Luxury pool on the water in St. Michaels -
Book it Now!
2 - 3 night Minimum Stay
4
BR,
2
BA,
Sleeps
9
Chesapeake Bay
>
St. Michaels House
#410948vb
(5)
Compare
Relaxing New Waterfront Retreat W/ Private Pier, Pool & Kayaks
4 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 11
$500 - $700
per night
Relaxing New Waterfront Retreat W/ Private Pier, Pool & Kayaks
Book it Now!
2 - 7 night Minimum Stay
4
BR,
3
BA,
1
HF BA,
Sleeps
11
Chesapeake Bay
>
St. Michaels Estate
#347588vb
(24)
Compare
Perfect for Families! Waterfront, 1 mile from downtown St. M's. Mostly 1 level.
5 Bedrooms,
3
Bathrooms
, Sleeps 10
$300 - $510
per night
Perfect for Families! Waterfront, 1 mile from downtown St. M's. Mostly 1 level.
2 night Minimum Stay
5
BR,
3
BA,
Sleeps
10
Chesapeake Bay
>
St. Michaels House
#399572vb
(16)
Compare
On Harbor and on Park! - Only Large Vacation House in Town
6 Bedrooms, Sleeps 11
On Harbor and on Park! - Only Large Vacation House in Town
6
BR,
Sleeps
11
Chesapeake Bay
>
St. Michaels House
#198445vb
(12)
Compare
1 - 30 of 41
Show
15
30
60
properties
Advertisement