Vacation rentals in St. Michaels - HomeToGo base64Hash Vacation rentals in St. Michaels - HomeToGo

Vacation rentals in St. Michaels

Browse 203 available vacation homes and compared across 6 trusted partners
Anytime
Guests
Anytime
Guests

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • House
    • Farmhouse
    • Apartment

  • Rating

    • 4.5+
    • 4+

  • Services

    • Pool
    • WiFi
    • TV
    • Air conditioning
    • Kitchen
    • Dishwasher
    • Microwave
    • Yard
    • Balcony/patio
    • Washing machine
    • Hot tub
    • Fireplace
    • Crib
    • Sauna
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • No pets
    • Wheelchair access

  • Activities

    • Fishing
    • Grill

Top 15 most Recommended Vacation Rentals in St. Michaels

Discover your ideal St. Michaels vacation rental with real-time comparisons of 204 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House St. Michaels
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped vacation home with terrace, jacuzzi & private pool | Nature view | Pet-friendly

St. Michaels, Talbot County, Maryland, United States
This waterfront house rental in Saint Michaels features a private pool, hot tub, and a kitchen, perfect for up to 8 guests.
from $565
per night
Very good(5 ratings)
from $565
per night
View deal
House St. Michaels
House ∙ 6 guests ∙ 3 bedrooms

House with BBQ, private pool & yard | Good for workation

St. Michaels, Talbot County, Maryland, United States
This waterfront house rental in Saint Michaels features a private pool, hot tub, and a balcony for unforgettable family gatherings.
from $988
per night
Outstanding(13 ratings)
from $988
per night
View deal
House St. Michaels
House ∙ 10 guests ∙ 5 bedrooms

Family-oriented house with yard, grill & patio | Pets allowed

St. Michaels, Talbot County, Maryland, United States
This St. Michaels house rental features a private pool, hot tub, and waterfront access, perfect for family getaways with pets.
from $676
per night
Outstanding(34 ratings)
from $676
per night
View deal
House St. Michaels
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with patio, barbeque & garden | Nature view | Good for workation

St. Michaels, Talbot County, Maryland, United States
This Neavitt house rental features a waterfront yard, fireplace, and kitchen, perfect for family gatherings and pets.
from $432
per night
Outstanding(25 ratings)
from $432
per night
View deal
House St. Michaels
House ∙ 4 guests ∙ 2 bedrooms

House with 2 bedrooms for 4 persons

St. Michaels, Talbot County, Maryland, United States
This cozy house rental in Neavitt offers a fireplace, balcony, and kitchen, perfect for a family getaway with pets.
from $300
per night
Outstanding(1 rating)
from $300
per night
View deal
House St. Michaels
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped lovely house with BBQ, patio & hot tub | Nature view | Pet-friendly

St. Michaels, Talbot County, Maryland, United States
This waterfront house rental in Royal Oak features a hot tub, fireplace, and yard, perfect for up to 8 guests and their pets.
from $586
per night
Excellent(26 ratings)
from $586
per night
View deal
House St. Michaels
House ∙ 10 guests ∙ 5 bedrooms

House with BBQ, patio & yard | Nature view

St. Michaels, Talbot County, Maryland, United States
This waterfront house rental in Bozman features a kitchen, yard, and parking, perfect for a family getaway with up to 10 guests.
from $392
per night
Outstanding(120 ratings)
from $392
per night
View deal
Cabin St. Michaels
Cabin ∙ 14 guests ∙ 4 bedrooms

Cottage with garden, hot tub & patio

St. Michaels, Talbot County, Maryland, United States
This Royal Oak cabin accommodates 14 guests, offering a perfect retreat for family gatherings and unforgettable adventures.
from $1,169
per night
Outstanding(1 rating)
from $1,169
per night
View deal
House St. Michaels
House ∙ 6 guests ∙ 3 bedrooms

Child-friendly house with pool & BBQ | Pet-friendly

St. Michaels, Talbot County, Maryland, United States
This waterfront house rental in Saint Michaels features a pool, fireplace, and balcony, perfect for a family getaway with pets.
from $561
per night
Outstanding(41 ratings)
from $561
per night
View deal
House St. Michaels
House ∙ 8 guests ∙ 4 bedrooms

House with garden & barbecue

St. Michaels, Talbot County, Maryland, United States
This waterfront house rental in Saint Michaels features a fireplace, kitchen, yard, and parking, perfect for family gatherings.
from $592
per night
Outstanding(22 ratings)
from $592
per night
View deal
House St. Michaels
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly vacation home with BBQ & yard | Nature view | Pet-friendly

St. Michaels, Talbot County, Maryland, United States
This waterfront house rental in Royal Oak features a kitchen, fireplace, and yard, perfect for family gatherings and pets.
from $537
per night
Outstanding(11 ratings)
from $537
per night
View deal
Cabin St. Michaels
Cabin ∙ 6 guests ∙ 3 bedrooms

Cottage with barbeque, private pool & terrace

St. Michaels, Talbot County, Maryland, United States
This Neavitt cabin features a private pool, a fireplace, and waterfront access, perfect for a family getaway of six.
from $239
per night
Outstanding(45 ratings)
from $239
per night
View deal
House St. Michaels
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with barbecue, yard & hot tub | Nature view

St. Michaels, Talbot County, Maryland, United States
This house rental in Saint Michaels features a private pool, hot tub, kitchen, and yard, perfect for family getaways.
from $636
per night
Excellent(9 ratings)
from $636
per night
View deal
House St. Michaels
House ∙ 9 guests ∙ 6 bedrooms

Child-friendly house with pool, patio & garden | Nature view | Dogs allowed

St. Michaels, Talbot County, Maryland, United States
This waterfront house rental in Saint Michaels offers a pool, fireplace, and yard, perfect for families and pets alike.
from $627
per night
Excellent(158 ratings)
from $627
per night
View deal
House St. Michaels
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with terrace, BBQ & jacuzzi

St. Michaels, Talbot County, Maryland, United States
This waterfront house in Saint Michaels features a private pool, hot tub, and ample space for up to eight guests, perfect for families.
from $761
per night
Outstanding(72 ratings)
from $761
per night
View deal

Vacation rentals and apartments with air conditioning

House St. Michaels
from $620
per night
House ∙ 8 guests ∙ 4 bedrooms

House with terrace | Nature view

4.9
Outstanding(15 ratings)
St. Michaels, Talbot County, Maryland, United States
Air conditioning
View deal
Cabin St. Michaels
from $338
per night
Cabin ∙ 4 guests ∙ 2 bedrooms

Cottage with pool & BBQ

4.8
Outstanding(7 ratings)
St. Michaels, Talbot County, Maryland, United States
Air conditioning
View deal
House St. Michaels
from $1,393
per night
House ∙ 10 guests ∙ 5 bedrooms

Family-friendly pleasant house with yard, grill & private pool | Good for workation

St. Michaels, Talbot County, Maryland, United States
Air conditioning
View deal
See all offers

Vacation rentals with a balcony

House St. Michaels
from $2,212
per night
House ∙ 10 guests ∙ 5 bedrooms

House with patio, yard & barbecue | Nature view | Perfect for remote work

5.0
Outstanding(2 ratings)
St. Michaels, Talbot County, Maryland, United States
Balcony
View deal
House St. Michaels
from $393
per night
House ∙ 4 guests ∙ 1 bedroom

Vacation home | City view

5.0
Outstanding(2 ratings)
St. Michaels, Talbot County, Maryland, United States
Balcony
View deal
House St. Michaels
from $6,268
per night
House ∙ 50 guests ∙ 1 bedroom

House with yard, barbecue & pool

St. Michaels, Talbot County, Maryland, United States
Balcony
View deal
See all offers

Vacation Rentals With Fireplaces

Cabin St. Michaels
from $266
per night
Cabin ∙ 2 guests ∙ 1 bedroom

Cottage with pool

4.7
Excellent(8 ratings)
St. Michaels, Talbot County, Maryland, United States
Fireplace
View deal
House St. Michaels
from $279
per night
House ∙ 4 guests ∙ 2 bedrooms

Fully equipped house with barbecue & yard | City view

5.0
Outstanding(489 ratings)
St. Michaels, Talbot County, Maryland, United States
Fireplace
View deal
House St. Michaels
from $338
per night
House ∙ 4 guests ∙ 2 bedrooms

Fully equipped lovely vacation home with yard | Suitable for remote work | Pets are welcome

4.9
Outstanding(10 ratings)
St. Michaels, Talbot County, Maryland, United States
Fireplace
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in St. Michaels offering exceptional value for money

House St. Michaels
from $694
per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with patio, barbecue & garden

5.0
Outstanding(53 ratings)
St. Michaels, Talbot County, Maryland, United States
View deal
House St. Michaels
from $748
per night
House ∙ 6 guests ∙ 3 bedrooms

House with patio, grill & yard | Nature view

5.0
Outstanding(7 ratings)
St. Michaels, Talbot County, Maryland, United States
View deal
House St. Michaels
from $933
per night
House ∙ 10 guests ∙ 5 bedrooms

Family-friendly house with grill, patio & private pool | Nature view | Pets allowed

4.8
Outstanding(15 ratings)
St. Michaels, Talbot County, Maryland, United States
View deal

Top-Rated Vacation rentals in St. Michaels

Book the highest-rated St. Michaels vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

Cabin St. Michaels
from $356
per night
Cabin ∙ 5 guests ∙ 2 bedrooms

Cottage with patio, yard & pool

4.9
Outstanding(244 ratings)
St. Michaels, Talbot County, Maryland, United States
View deal
Cabin St. Michaels
from $315
per night
Cabin ∙ 5 guests ∙ 2 bedrooms

Cottage with barbeque, pool & yard | Nature view

4.8
Outstanding(149 ratings)
St. Michaels, Talbot County, Maryland, United States
View deal
House St. Michaels
from $361
per night
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped vacation home with terrace & garden | Nature view | Pet-friendly

5.0
Outstanding(110 ratings)
St. Michaels, Talbot County, Maryland, United States
View deal

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Verified reviews

Verified reviews

Trust in the quality and comfort of your stay with verified guest reviews.

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Price clarity, no surprises

Spend your budget exactly as planned by comparing thousands of providers.

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Popular Features & Amenities in St. Michaels

  • Pet-friendly (117)
  • Pool (135)
  • WiFi (215)
  • TV (189)
  • Air conditioning (222)
  • No smoking (215)
  • Fishing (95)
  • Grill (93)
  • Kitchen (123)
  • Dishwasher (95)
  • Microwave (106)
  • Yard (147)

You will find a great selection of accommodations to choose from if you are looking for a vacation rental including a pool in St. Michaels. Additionally, more House rental have pools than any other property type. They are an excellent choice if you go in a group of 3, as that is the number of people they can welcome on average. If you would also like to be close to the water, many of the vacation rentals offering a pool are within 2 miles of the waterfront.

Information about vacation rentals in St. Michaels

🏡 Vacation rentals available 204 rentals
🌙 Nightly prices starting at $148
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 109 homes
🏊 Vacation rentals with pools 119 homes

Frequently Asked Questions

What is the average price per night for a vacation home in St. Michaels?

Prices for vacation rentals in St. Michaels start from $148 per night. Average prices for house rentals are $1,106 per night. Cottages in St. Michaels cost $543 per night on average.

How many vacation homes are available to book in St. Michaels?

Currently there are 204 vacation rentals available for booking for your trip.

What amenities are most popular for vacation homes in St. Michaels?

Most travelers look for Pool, Pets allowed, and Internet when booking a vacation rental in St. Michaels.

How many vacation homes with a pool are in St. Michaels?

There are 119 vacation homes from 6 providers in St. Michaels.

Are pets allowed in vacation rentals in St. Michaels?

Sure, currently there are 109 vacation homes in St. Michaels that allow dogs , with an average nightly rate of $785.

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