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

Vacation rentals in St. Michaels

Browse 224 available vacation homes and compared across 7 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+

  • Booking Options

    • Instant Booking

  • 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 224 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 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 $687
per night
Excellent(26 ratings)
from $687
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 $524
per night
Outstanding(8 ratings)
from $524
per night
View deal
House St. Michaels
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped charming house with private pool, grill & garden | Pet-friendly

St. Michaels, Talbot County, Maryland, United States
This Bozman house rental features a private pool, waterfront access, and a yard, ideal for up to 8 guests and pets.
from $799
per night
Outstanding(52 ratings)
from $799
per night
View deal
House St. Michaels
House ∙ 10 guests ∙ 5 bedrooms

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

St. Michaels, Talbot County, Maryland, United States
This waterfront house rental in Bozman features a private pool, a kitchen, and space for up to 10 guests, making it ideal for families.
from $844
per night
Outstanding(14 ratings)
from $844
per night
View deal
House St. Michaels
House ∙ 16 guests ∙ 6 bedrooms

Vacation home with BBQ, garden & private pool | Nature view

St. Michaels, Talbot County, Maryland, United States
This waterfront house rental in Royal Oak features a private pool, fireplace, and ample space for 16 guests, perfect for families.
from $1,782
per night
Outstanding(104 ratings)
from $1,782
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 $415
per night
Outstanding(115 ratings)
from $415
per night
View deal
Cabin St. Michaels
Cabin ∙ 6 guests ∙ 1 bedroom

Cottage with yard & barbecue

St. Michaels, Talbot County, Maryland, United States
This Bozman cabin features a fireplace, kitchen, yard, and waterfront access, accommodating up to six guests for an unforgettable stay.
from $379
per night
Outstanding(2 ratings)
from $379
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 $765
per night
Outstanding(33 ratings)
from $765
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 $432
per night
Excellent(149 ratings)
from $432
per night
View deal
Cabin St. Michaels
Cabin ∙ 4 guests ∙ 3 bedrooms

Family-friendly pleasant cottage with yard, terrace & barbeque | Dogs allowed

St. Michaels, Talbot County, Maryland, United States
This cabin in Neavitt features a kitchen, fireplace, and yard, making it perfect for families and pets alike.
from $175
per night
Outstanding(67 ratings)
from $175
per night
View deal
House St. Michaels
House ∙ 8 guests ∙ 4 bedrooms

House with garden, grill & private pool

St. Michaels, Talbot County, Maryland, United States
This waterfront house in Bozman features a private heated pool, hot tub, and a yard, perfect for family getaways with pets.
from $491
per night
Outstanding(3 ratings)
from $491
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 $692
per night
Outstanding(41 ratings)
from $692
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 $250
per night
Outstanding(42 ratings)
from $250
per night
View deal
House St. Michaels
House ∙ 8 guests ∙ 4 bedrooms

House with barbeque, terrace & garden | Nature view

St. Michaels, Talbot County, Maryland, United States
This cabin in Saint Michaels features a fireplace, kitchen, and balcony, perfect for families and pets, accommodating up to 8 guests.
from $290
per night
Outstanding(11 ratings)
from $290
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 $736
per night
Outstanding(70 ratings)
from $736
per night
View deal

Vacation houses with Balconies or Patios

Cabin St. Michaels
from $238
per night
Cabin ∙ 5 guests ∙ 2 bedrooms

Cottage with barbeque, pool & patio

4.8
Outstanding(144 ratings)
St. Michaels, Talbot County, Maryland, United States
Balcony/Patio
View deal
House St. Michaels
from $302
per night
House ∙ 6 guests ∙ 3 bedrooms

Child-friendly vacation home with yard & terrace | City view

5.0
Outstanding(12 ratings)
St. Michaels, Talbot County, Maryland, United States
Balcony/Patio
View deal
House St. Michaels
from $686
per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with yard, barbeque & private pool

5.0
Outstanding(4 ratings)
St. Michaels, Talbot County, Maryland, United States
Balcony/Patio
View deal
See all offers

Vacation rentals and apartments with air conditioning

Cabin St. Michaels
from $513
per night
Cabin ∙ 8 guests ∙ 4 bedrooms

Cottage with pool & BBQ

St. Michaels, Talbot County, Maryland, United States
Air conditioning
View deal
House St. Michaels
from $508
per night
House ∙ 8 guests ∙ 4 bedrooms

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

4.9
Outstanding(9 ratings)
St. Michaels, Talbot County, Maryland, United States
Air conditioning
View deal
Cabin St. Michaels
from $381
per night
Cabin ∙ 2 guests ∙ 1 bedroom

Fully equipped pleasant cottage with garden & barbecue | Nature view

5.0
Outstanding(58 ratings)
St. Michaels, Talbot County, Maryland, United States
Air conditioning
View deal
See all offers

Vacation Rentals With Fireplaces

House St. Michaels
from $807
per night
House ∙ 8 guests ∙ 4 bedrooms

Child-friendly lovely vacation home with private pool, yard & grill | Good for workation | Pet-friendly

St. Michaels, Talbot County, Maryland, United States
Fireplace
View deal
Cabin St. Michaels
from $335
per night
Cabin ∙ 2 guests ∙ 1 bedroom

Nice cottage with grill, pool & yard

5.0
Outstanding(6 ratings)
St. Michaels, Talbot County, Maryland, United States
Fireplace
View deal
Cabin St. Michaels
from $329
per night
Cabin ∙ 4 guests ∙ 2 bedrooms

Cottage with pool & BBQ

4.7
Excellent(3 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 $490
per night
House ∙ 8 guests ∙ 4 bedrooms

House with private pool, barbecue & garden | Water view

5.0
Outstanding(1 rating)
St. Michaels, Talbot County, Maryland, United States
View deal
House St. Michaels
from $253
per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with BBQ & yard | Nature view

4.9
Outstanding(74 ratings)
St. Michaels, Talbot County, Maryland, United States
View deal
House St. Michaels
from $924
per night
House ∙ 8 guests ∙ 4 bedrooms

Family-oriented vacation home with garden, terrace & hot tub | Nature view | Pet-friendly

5.0
Outstanding(32 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

House St. Michaels
from $962
per night
House ∙ 8 guests ∙ 5 bedrooms

Beautiful vacation home with terrace & pool

5.0
Outstanding(97 ratings)
St. Michaels, Talbot County, Maryland, United States
View deal
House St. Michaels
from $412
per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with 2 rooms for 4 persons

5.0
Outstanding(20 ratings)
St. Michaels, Talbot County, Maryland, United States
View deal
House St. Michaels
from $687
per night
House ∙ 8 guests ∙ 4 bedrooms

House with garden & barbecue

4.9
Outstanding(20 ratings)
St. Michaels, Talbot County, Maryland, United States
View deal

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Verified reviews

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

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Popular Features & Amenities in St. Michaels

  • Pet-friendly (117)
  • Pool (135)
  • WiFi (216)
  • TV (189)
  • Air conditioning (221)
  • No smoking (215)
  • Fishing (97)
  • Grill (93)
  • Kitchen (122)
  • 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 224 rentals
🌙 Nightly prices starting at $176
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 116 homes
🏊 Vacation rentals with pools 134 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 $176 per night. Average prices for house rentals are $1,275 per night. Cottages in St. Michaels cost $523 per night on average.

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

Currently there are 224 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 134 vacation homes from 7 providers in St. Michaels.

Are pets allowed in vacation rentals in St. Michaels?

Sure, currently there are 116 vacation homes in St. Michaels that allow dogs , with an average nightly rate of $717.

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