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

Vacation rentals in St. Michaels

Browse 236 available vacation homes and compared across 8 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 236 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House St. Michaels
House ∙ 4 guests ∙ 2 bedrooms

House with BBQ | City view

St. Michaels, Talbot County, Maryland, United States
This house rental in Saint Michaels features a fireplace, parking, and pet-friendly policies, perfect for a cozy getaway with friends.
from $629
per night
Outstanding(1 rating)
from $629
per night
View deal
House St. Michaels
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with yard, barbeque & private pool

St. Michaels, Talbot County, Maryland, United States
This waterfront house in Bozman offers a private pool, kitchen, yard, and balcony, perfect for a memorable getaway for 8.
from $914
per night
Outstanding(4 ratings)
from $914
per night
View deal
House St. Michaels
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
This waterfront house in Royal Oak features a private pool, balcony, and yard, perfect for families and pet-friendly getaways.
from $857
per night
from $857
per night
View deal
House St. Michaels
House ∙ 6 guests ∙ 3 bedrooms

Child-friendly vacation home with barbecue & private pool | Nature view | Pet-friendly

St. Michaels, Talbot County, Maryland, United States
This waterfront house rental in Saint Michaels features a private pool, kitchen, and space for six, perfect for a family getaway.
from $837
per night
Outstanding(4 ratings)
from $837
per night
View deal
Apartment St. Michaels
Apartment ∙ 2 guests ∙ 1 bedroom

Apartment | Nature view | Perfect for remote work

St. Michaels, Talbot County, Maryland, United States
This Saint Michaels apartment offers a kitchen and parking, perfect for a getaway for two in a scenic waterfront town.
from $282
per night
Outstanding(58 ratings)
from $282
per night
View deal
House St. Michaels
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with barbeque, garden & terrace

St. Michaels, Talbot County, Maryland, United States
This Neavitt house rental offers waterfront access, a yard, and a fireplace, perfect for a family getaway with pets.
from $405
per night
Outstanding(63 ratings)
from $405
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 $979
per night
Outstanding(14 ratings)
from $979
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 $246
per night
Outstanding(42 ratings)
from $246
per night
View deal
House St. Michaels
House ∙ 8 guests ∙ 5 bedrooms

House with yard, private pool & patio | Nature view

St. Michaels, Talbot County, Maryland, United States
This waterfront house rental in Saint Michaels features a private heated pool, balcony, and ample space for family gatherings.
from $1,224
per night
Outstanding(80 ratings)
from $1,224
per night
View deal
House St. Michaels
House ∙ 6 guests ∙ 3 bedrooms

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

St. Michaels, Talbot County, Maryland, United States
This house rental in Saint Michaels features a kitchen, balcony, and yard, accommodating up to six guests and pets.
from $386
per night
Outstanding(8 ratings)
from $386
per night
View deal
Villa St. Michaels
Villa ∙ 12 guests ∙ 6 bedrooms

Villa with grill, garden & private pool

St. Michaels, Talbot County, Maryland, United States
This Neavitt villa offers a private pool, waterfront access, and ample space for 12, making it perfect for family getaways.
from $942
per night
Outstanding(83 ratings)
from $942
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 $540
per night
Excellent(26 ratings)
from $540
per night
View deal
House St. Michaels
House ∙ 9 guests ∙ 4 bedrooms

Family-oriented spacious vacation home with BBQ, terrace & yard | Good for workation

St. Michaels, Talbot County, Maryland, United States
This waterfront house in Bozman features a private pool, yard, and balcony, perfect for families seeking relaxation and fun.
from $686
per night
Outstanding(55 ratings)
from $686
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 $740
per night
Outstanding(33 ratings)
from $740
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 $625
per night
Outstanding(10 ratings)
from $625
per night
View deal

Vacation rentals and apartments with air conditioning

House St. Michaels
from $1,344
per night
House ∙ 10 guests ∙ 5 bedrooms

Family-friendly pleasant vacation home with terrace, private pool & barbeque

5.0
Outstanding(16 ratings)
St. Michaels, Talbot County, Maryland, United States
Air conditioning
View deal
House St. Michaels
from $730
per night
House ∙ 9 guests ∙ 6 bedrooms

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

4.7
Excellent(154 ratings)
St. Michaels, Talbot County, Maryland, United States
Air conditioning
View deal
House St. Michaels
from $2,934
per night
House ∙ 16 guests ∙ 8 bedrooms

House with terrace, pool & barbecue

5.0
Outstanding(2 ratings)
St. Michaels, Talbot County, Maryland, United States
Air conditioning
View deal
See all offers

Vacation rentals with a balcony

House St. Michaels
from $302
per night
House ∙ 4 guests ∙ 2 bedrooms

House with 2 rooms for 4 persons

St. Michaels, Talbot County, Maryland, United States
Balcony
View deal
House St. Michaels
from $1,536
per night
House ∙ 8 guests ∙ 4 bedrooms

Child-friendly house with patio, BBQ & yard

St. Michaels, Talbot County, Maryland, United States
Balcony
View deal
House St. Michaels
from $1,460
per night
House ∙ 9 guests ∙ 5 bedrooms

House with garden, terrace & grill

4.9
Outstanding(25 ratings)
St. Michaels, Talbot County, Maryland, United States
Balcony
View deal
See all offers

Vacation Rentals With Fireplaces

Cabin St. Michaels
from $350
per night
Cabin ∙ 4 guests ∙ 2 bedrooms

Cottage with pool & BBQ

4.8
Outstanding(7 ratings)
St. Michaels, Talbot County, Maryland, United States
Fireplace
View deal
House St. Michaels
from $350
per night
House ∙ 4 guests ∙ 2 bedrooms

Fully equipped lovely vacation home with yard | Pets are welcome

4.8
Outstanding(9 ratings)
St. Michaels, Talbot County, Maryland, United States
Fireplace
View deal
Cabin St. Michaels
from $383
per night
Cabin ∙ 2 guests ∙ 1 bedroom

Fully equipped pleasant cottage with garden & barbecue | Nature view

5.0
Outstanding(59 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 $620
per night
House ∙ 6 guests ∙ 3 bedrooms

Child-friendly spacious house with jacuzzi, private pool & yard | Pet-friendly

4.4
Very good(26 ratings)
St. Michaels, Talbot County, Maryland, United States
View deal
House St. Michaels
from $1,673
per night
House ∙ 12 guests ∙ 6 bedrooms

House with BBQ, private pool & garden | Nature view

St. Michaels, Talbot County, Maryland, United States
View deal
Cabin St. Michaels
from $712
per night
Cabin ∙ 6 guests ∙ 3 bedrooms

Family-friendly lovely cottage with yard, terrace & BBQ | Nature view | Pets are welcome

5.0
Outstanding(31 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 $430
per night
Cabin ∙ 2 guests ∙ 1 bedroom

Cottage with yard | Nature view

5.0
Outstanding(20 ratings)
St. Michaels, Talbot County, Maryland, United States
View deal
Apartment St. Michaels
from $439
per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Apartment with 2 rooms for 4 persons

4.9
Outstanding(12 ratings)
St. Michaels, Talbot County, Maryland, United States
View deal
House St. Michaels
from $392
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
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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Spend your budget exactly as planned by comparing thousands of providers.

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Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

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, more than half of the vacation rentals offering a pool are within 2 miles of the waterfront.

Information about vacation rentals in St. Michaels

🏡 Vacation rentals available 236 rentals
🌙 Nightly prices starting at $244
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 120 homes
🏊 Vacation rentals with pools 143 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 $244 per night. Average prices for house rentals are $1,134 per night. Cottages in St. Michaels cost $587 per night on average.

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

Currently there are 236 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 143 vacation homes from 8 providers in St. Michaels.

Are pets allowed in vacation rentals in St. Michaels?

Sure, currently there are 120 vacation homes in St. Michaels that allow dogs , with an average nightly rate of $747.

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