Vacation Rentals in Saint Michaels, MD

PRICE PER NIGHT

ACCOMMODATION TYPES

Beautiful Waterfront Home w/ Pool In St. Michaels
9.1

Excellent

·
Saint Michaels
·
4 br
·
Sleeps 8
·
Ocean · Hot Tub · Private Pool ·
From
$660/night
Check availability
Property
House · 4 Beds · 4 baths
Amenities
Ocean
Hot Tub
Private Pool
Waterfront
Pool
Fireplace
Dishwasher
Oven
Other spaces
Kitchen
Stay in the HEART of Saint Michaels!
9.9

Excellent

·
Saint Michaels
·
2 br
·
Sleeps 4
·
Hardwood Floor · Outdoor Space · Dishwasher ·
From
$250/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Hardwood Floor
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Classic Eastern Shore Waterfront Manor House - ST-936
10

Excellent

·
Saint Michaels
·
6 br
·
Sleeps 12
·
Hot Tub · Balcony · Private Pool ·
From
$1,250/night
Check availability
Property
House · 6 Beds · 5 baths
Amenities
Hot Tub
Private Pool
Waterfront
Pool
Fireplace
Dishwasher
Oven
In Unit Laundry
Other spaces
Balcony, Kitchen
St. Michael's Premier In-Town Rental with pool and 2023 Designer updates!
10

Excellent

·
Saint Michaels
·
2 br
·
Sleeps 4
·
Beach · Ski In Ski Out · Ceiling Fan ·
From
$500/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Beach
Ski In Ski Out
Ceiling Fan
Private Pool
Pool
Dishwasher
Oven
In Unit Laundry
Other spaces
Workspace, Kitchen
Beautiful Large 3 Bdrm Luxury suites with outdoor pool & spa

No reviews

·
Saint Michaels
·
3 br
·
Sleeps 10
·
Lake · Smoking Allowed · Private Pool ·
From
$1,025/night
Check availability
Property
Apartment · 3 Beds · 3 baths
Amenities
Lake
Smoking Allowed
Private Pool
Fitness Center
Waterfront
Pool
Dishwasher
Oven
Other spaces
Kitchen
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8

Excellent

·
Saint Michaels
·
2 br
·
Sleeps 5
·
Pool · Dishwasher · Oven ·
From
$357/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Pool
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Swimming Pool
Other spaces
Kitchen
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6

Excellent

·
Saint Michaels
·
2 br
·
Sleeps 5
·
Ceiling Fan · Fitness Center · Outdoor Space ·
From
$341/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Ceiling Fan
Fitness Center
Pool
Fireplace
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Other spaces
Kitchen
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
9.2

Excellent

·
Saint Michaels
·
6 br
·
Sleeps 9
·
Fitness Center · Waterfront · Pool ·
From
$640/night
Check availability
Property
House · 6 Beds · 4 baths
Amenities
Fitness Center
Waterfront
Pool
Fireplace
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Other spaces
Kitchen

The best of Zumper, delivered

Be the first to hear about new listings matching your search.

Email
By clicking submit, I accept Zumper's Terms and Conditions, Privacy Policy, and Community Values.
Private+Cozy /3br+3ba /1 mile to Historic Downtown Saint Michaels
10

Excellent

·
Saint Michaels
·
3 br
·
Sleeps 6
·
Dishwasher · Oven · In Unit Laundry ·
From
$379/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Carpenter Alley - Newly Renovated Cottage in Center of Historic St. Michaels
9.6

Excellent

·
Saint Michaels
·
3 br
·
Sleeps 6
·
Dishwasher · Oven · In Unit Laundry ·
From
$280/night
Check availability
Property
Apartment · 3 Beds · 3 baths
Amenities
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Countryside Manor/3br+2ba/1 mile to Historic Downtown St. Michaels, MD
9.7

Excellent

·
Saint Michaels
·
3 br
·
Sleeps 6
·
Coffee Tea Maker · Outdoor Space · Dishwasher ·
From
$322/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Coffee Tea Maker
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
St. Michaels Inn
7.5

Very good

·
Saint Michaels
·
1 br
·
Sleeps 4
·
Carpet · Free Parking · On Site Laundry ·
From
$77/night
Check availability
Property
Hotel · 1 Bed
Amenities
Carpet
Free Parking
On Site Laundry
Smoking Allowed
Pool
Air Conditioning
Furnished
Wifi
Other spaces
Workspace
Harbor View Suite

No reviews

·
Saint Michaels
·
1 br
·
Sleeps 2
·
Outdoor Space · In Unit Laundry · Kitchen ·
From
$250/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Charming Saint Michaels home

No reviews

·
Saint Michaels
·
3 br
·
Sleeps 7
·
On Site Laundry · Fitness Center · Outdoor Space ·
From
$250/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
On Site Laundry
Fitness Center
Fireplace
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
Waterfront Estate. **WALK TO ST. MICHAELS!**
10

Excellent

·
Saint Michaels
·
6 br
·
Sleeps 12
·
Ev Charging · Private Pool · Waterfront ·
From
$1,485/night
Check availability
Property
House · 6 Beds · 6 baths
Amenities
Ev Charging
Private Pool
Waterfront
Pool
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Other spaces
Kitchen
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.5

Excellent

·
Saint Michaels
·
2 br
·
Sleeps 5
·
Pool · Fireplace · Dishwasher ·
From
$312/night
Check availability
Property
Apartment · 2 Beds · 3 baths
Amenities
Pool
Fireplace
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.4

Excellent

·
Saint Michaels
·
2 br
·
Sleeps 5
·
Fitness Center · Pool · Fireplace ·
From
$327/night
Check availability
Property
Apartment · 2 Beds · 3 baths
Amenities
Fitness Center
Pool
Fireplace
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
Riverview Retreat - Charming Waterfront Cottage in St Michaels!
9.6

Excellent

·
Saint Michaels
·
3 br
·
Sleeps 6
·
Fireplace · Dishwasher · Oven ·
From
$795/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Fireplace
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Dollhouse in Central Historic St Michaels
9.7

Excellent

·
Saint Michaels
·
2 br
·
Sleeps 4
·
Pool · Dishwasher · Oven ·
From
$272/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Pool
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Swimming Pool
Other spaces
Kitchen
Crabber's Cove - Charming Waterfront Near St. Michaels, Kayaks & Bikes!
9.5

Excellent

·
Saint Michaels
·
3 br
·
Sleeps 6
·
Balcony · Fireplace · Dishwasher ·
From
$557/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Fireplace
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Swimming Pool
Other spaces
Balcony, Kitchen
TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT *HEATED POOL*
10

Excellent

·
Saint Michaels
·
5 br
·
Sleeps 8
·
Fitness Center · Outdoor Space · Pool ·
From
$874/night
Check availability
Property
House · 5 Beds · 3 baths
Amenities
Fitness Center
Pool
Fireplace
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
Walk to Everything House
10

Excellent

·
Saint Michaels
·
3 br
·
Sleeps 6
·
Dishwasher · Oven · In Unit Laundry ·
From
$310/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Covey Creek - Peaceful Waterfront Home, BBQ, Kayak & Fire Pit!
10

Excellent

·
Saint Michaels
·
4 br
·
Sleeps 8
·
Fireplace · Dishwasher · Oven ·
From
$560/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Fireplace
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Delightful Close to town
9.7

Excellent

·
Saint Michaels
·
3 br
·
Sleeps 6
·
Waterfront · Fireplace · Dishwasher ·
From
$625/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Waterfront
Fireplace
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Luxury Waterfront with pool and deep water dock, minutes from St Michaels.
10

Excellent

·
Saint Michaels
·
4 br
·
Sleeps 8
·
Ceiling Fan · Workspace · Private Pool ·
From
$1,395/night
Check availability
Property
House · 4 Beds · 5 baths
Amenities
Ceiling Fan
Private Pool
Fitness Center
Waterfront
Pool
Dishwasher
Oven
In Unit Laundry
Other spaces
Workspace, Kitchen
Luxurious studio in heart of historic St Michaels!

No reviews

·
Saint Michaels
·
1 br
·
Dishwasher · Oven · In Unit Laundry ·
From
$250/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Modern Studio in heart of town, walk everywhere!

No reviews

·
Saint Michaels
·
1 br
·
Dishwasher · Oven · In Unit Laundry ·
From
$250/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
The Water House - Unique 3600-SqFt Home Near St. Michaels!
9.8

Excellent

·
Saint Michaels
·
5 br
·
Sleeps 8
·
Balcony · Fireplace · Dishwasher ·
From
$772/night
Check availability
Property
House · 5 Beds · 6 baths
Amenities
Fireplace
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Balcony, Kitchen
Fabulous rates, Luxury Flat, Heart of St Michaels!
10

Excellent

·
Saint Michaels
·
1 br
·
Sleeps 3
·
Assigned Parking · Fireplace · Dishwasher ·
From
$295/night
Check availability
Property
Apartment · 1 Bed · 2 baths
Amenities
Assigned Parking
Fireplace
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Captain's Cove - Fantastic Family Compound Just 1/2 Mile to Historic District!
10

Excellent

·
Saint Michaels
·
5 br
·
Sleeps 10
·
Pool · Fireplace · Dishwasher ·
From
$875/night
Check availability
Property
House · 5 Beds · 5 baths
Amenities
Pool
Fireplace
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Showing 1 - 30 of 30 results
Home > Maryland Vacation Rentals > Saint Michaels Vacation Rentals
Updated: March 29, 2023

Learn about vacation rentals in

Saint Michaels

Explore 30 vacation rentals near Saint Michaels, Maryland. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Saint Michaels, you can see photos of Saint Michaels vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Saint Michaels vacation rentals in specific areas. Whether you’re looking for a Saint Michaels staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Saint Michaels is $77 per night and the highest price is $1,485 per night.
4 of the vacation rentals near Saint Michaels are apartments or condos. The average bathroom count for this property type is 1. The median price for these vacation units is $250 per night. There are currently 3 vacation units under this price. 18 of the vacation rentals near Saint Michaels are houses. The average bathroom count for a vacation house near Saint Michaels is 3. The average price for vacation houses near Saint Michaels is $682 per night. There are 11 vacation homes under this price. The most common amenities for vacation rentals near Saint Michaels are: furnished, wifi, and air conditioning. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.

1 bed rentals

5 available

2 bed rentals

7 available

3 bed rentals

9 available

4+ bed rentals

9 available

Getting around Saint Michaels

Walking

4/10
Fewer daily needs are within walking distance (unless you’re up for a challenge).

Driving

10/10
Commuting is easy with multiple accessible routes and plenty of parking.

Transit

1/10
FYI, there are little to no public transit options within walking distance.

Points of interest in Saint Michaels

Groceries

7/10
At least one grocery store within a 15-minute walk

Shopping

3/10
Some shops within walking distance

Cafes

5/10
Some cafés within walking distance

Restaurants

4/10
Some restaurants within walking distance

Nightlife

3/10
Few or no bars within walking distance

Which price range for vacation rentals is considered a good deal in Saint Michaels, MD area?

Vacation Rental Price Information in Saint Michaels, MD

The graph shows the percentages of vacation homes in each price bucket. Saint Michaels, MD has the largest percentage (48.39%) of homes in $500+ price range.
$0 - $50
1
units
$200 - $250
8
units
$250 - $300
5
units
$300 - $350
2
units
$500+
15
units

Vacation Rentals in Saint Michaels, MD FAQ

How many vacation rentals in Saint Michaels are available?

There are currently 30 vacation rentals in Saint Michaels available. Our vacation rentals in Saint Michaels include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.

Are there any pet friendly vacation rentals in Saint Michaels?

Yes, right now there are 16 pet friendly vacation rentals in Saint Michaels. A pet friendly vacation rental in Saint Michaels means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.

Are there any vacation rentals in Saint Michaels with a pool?

Yes there are vacation rentals with a pool available in Saint Michaels, MD. View more detailed vacation spots on Vacations by Zumper.

Are there any vacation rentals in Saint Michaels with internet access?

As of March 29, 2023, there are vacation rentals with internet access available in Saint Michaels, Maryland. Check out more enjoyable destinations on Vacations by Zumper.

More Options

Compare over 500K vacation listings

Search in one place

Our marketplace is populated with rentals from trusted partners like Vrbo, Booking.com, and more, so you can search a wide selection on a single platform.

City Vacation Rentals In Maryland

Vacation Rentals Woodstock, MD