Saint Michaels Vacation Rentals

Our Favorite Vacation Rentals in St. Michaels

  • DULCE VIDA AT CHESTER-Ocean View
     Country House
    Booking.com
    From
    $2,100
  • Location Location! St Michaels-- In Town Cottage!
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $243
  • Halo's Haven Guest Quarters
     3br Home/Apartment
    HolidayLettings
    From
    $491
  • RESTORED WATERFRONT COTTAGE
    Excellent3br Cottage
    Flipkey
    From
    $533
  • Historic Waterfront Property with Wi-Fi and Dock
     3br Home/Apartment
    HolidayLettings
    From
    $1,028
  • Sandy Pines: Enjoy Harris Creek w/Pool and Boats
    Excellent4br Boat
    HolidayLettings
    From
    $678
  • Cottage 1a at Grandview Pleasure Point
     Home/Apartment
    HolidayLettings
    From
    $299
  • St. Michaels Area Cottage - Walk to Water & Marina
     2br Home/Apartment
    HolidayLettings
    From
    $346

Check prices for these upcoming dates

St. Michaels Vacation Rentals with a Pool

  • Miles Aweigh
    Excellent3br Cottage
    Airbnb
    From
    $333
  • TRUE SAINT MICHAELS 5.5 ACRE WATERFRONT w/POOL!!!!
    Excellent5br Home/Apartment
    Airbnb
    From
    $663
  • *****Waterfront hs St. Michaels w/ private pool
    Excellent4br Home/Apartment
    Airbnb
    From
    $918
  • Riverslie Estate on the Miles River
    Excellent5br Estate
    Airbnb
    From
    $1,055

St. Michaels Vacation Rentals with Wi-Fi

  • The Farm House at Hunting Creek
    Excellent5br Home/Apartment
    Airbnb
    From
    $480
  • Home Away from home Cottage #1 Lighthouse
    ExcellentHome/Apartment
    Airbnb
    From
    $226
  • Eastern Shore Cape Cod Getaway
    Excellent3br Home/Apartment
    Airbnb
    From
    $331
  • Chesapeake Country Cottage: A Home Away From Home
    Excellent3br Home/Apartment
    Airbnb
    From
    $347

St. Michaels Pet-Friendly Vacation Rentals

  • Waterview Cottage In St. Michaels!
    Excellent2br Cottage
    HolidayLettings
    From
    $302
  • Large Historic Thomas Harrison House on Harbor in St. Michaels Town
    Good7br Home/Apartment
    HolidayLettings
    From
    $486
  • Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!
    Good2br Cottage
    HolidayLettings
    From
    $268
  • Waterfront Tilghman Island Cottage
    Good2br Home/Apartment
    Airbnb
    From
    $176

Saint Micheals Travel Guide

The small waterfront town of Saint Michaels is in the Chesapeake Bay and it's home to pretty marinas as well as some historic architecture, a strong maritime history and many shops, restaurants and popular places to relax.

Things to Do in Saint Micheals

Begin by exploring the town with a walking tour of the historical buildings. Pick up a map at the St. Mary’s Square Museum between Mulberry Street and East Chestnut Street and stroll through the town’s historic streets, lined with 18th and 19th-century houses and stores. You can also see St. Michaels and the surrounding area by boat with various chartered tours, for a different view of the town from the water plus some insight into local nature and wildlife.

An important attraction in town is the Chesapeake Bay Maritime Museum. Here you can see items related to Chesapeake Bay's commercial fishing industry and navigation. The museum incorporates the Hooper Straight Lighthouse and a cannery warehouse, plus a large collection of sail, power and row boats.

You can also rent bicycles to explore the surrounding country roads, or kayaks and paddle boards for fun on the water. With several breweries and a winery in town plus a local farmers market and numerous restaurants, you can discover new tastes and relax with some excellent cuisine.

Best Time to Visit Saint Micheals

If you visit in late spring or early summer you will fall in love with this beautiful sailing town with its mild temperatures, coastal views and welcoming atmosphere.

Price and Availability in St. Michaels

Most expensive
Most availability
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The cheapest day to stay at a vacation rental in St. Michaels tends to be Tuesday, while the most expensive day tends to be Friday. Vacation homes in St. Michaels tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in St. Michaels is in July, while the cheapest month is in April. The most popular time to book a vacation rental in St. Michaels is in the high season in August. St. Michaels has its low season in February, when less people are visiting and the vacation home occupancy rate drops.

The Weather in St. Michaels

Rainy days
93 º57
7
88 º36
4
73 º19
7
66 º23
4
66 º5
3
79 º18
3
75 º27
2
82 º33
3
90 º45
8
93 º52
3
99 º56
5
93 º61
2
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in St. Michaels. The warmest months in St. Michaels are June and July, when temperatures reach 99 ˚F. The coolest month is December, when temperatures drop to 5 ˚F. The wettest month in St. Michaels is August with 7.51 inches of rain, while the driest month is May with 1.68 inches of rain.

What Expert Travelers Think

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    Max Hobbs
    Max HobbsLTL Mandarin School
  • — I love AllTheRooms because it enables me to compare a range of providers in just one search. I'd normally spend time checking prices across a range of platforms by visiting different websites one-by-one, so this helps me to save time on my accommodation searches while planning my upcoming trips

    Kacie Morgan
    Kacie MorganThe Rare Welsh Bit

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