Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Cottages
Estates
Homes
Barns
Boats
Bungalows
Cabins
Castles
Chalets
Condos
Farmhouses
Hotels
Lodges
Studios
Townhomes
Villas
Yachts

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

St. Michaels Vacation Rentals(22)

22 Results
$450 - $750
per night
2 - 4 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 4 night minimum stay
(34)
  • 4 BR,
  • 4 BA,
  • Sleeps 8
3 - 7 night minimum stay
(33)
$400
per night
2 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
(4)
$829 - $950
per night
2 - 7 night minimum stay
  • 5 BR,
  • 6 BA,
  • 2 HF BA,
  • Sleeps 10
2 - 7 night minimum stay
(5)
$350
per night
2 - 3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 3 night minimum stay
(9)
$5,500
per week
7 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 8
7 night minimum stay
(6)
$250 - $400
per night
2 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
2 - 7 night minimum stay
(34)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
(9)
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 12
4 - 7 night minimum stay
(6)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
(7)
$439 - $441
per night
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
(34)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
2 night minimum stay
(18)
  • 5 BR,
  • 4 BA,
  • Sleeps 10
(24)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
3 night minimum stay
(27)
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 night minimum stay
(27)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(34)
  • 5 BR,
  • 5 BA,
  • Sleeps 12
4 night minimum stay
(13)
  • 4 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(43)
  • 5 BR,
  • 7 BA,
  • Sleeps 10
(13)
  • 5 BR,
  • 4 BA,
  • Sleeps 10
2 - 7 night minimum stay
(15)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 3 night minimum stay
(12)
1 more choices from the HomeAway Network
$500 - $800
per night
2 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
2 - 7 night minimum stay
(43)
Advertisement
 

Recent St. Michaels Reviews

What a sensational property!

5 of 5
This home had everything we needed to hold our family Thanksgiving reunion, and, I mean everything. From comfortable bedrooms, social living space and wonderful dining and kitchen space to all of the accoutrements needed to prepare a Thanksgiving feast. The owner is meticulous with the intricacies of managing a vacation rental home, from rental engagement through post occupancy. She was accessible and proactive and made sure the home would fit our specific needs. AND the view is sensational from multiple rooms. A truly peaceful and inspiring setting. My family looks forward to retuning in the future.
  • Submitted: Dec 4, 2014
  • Stayed: Nov 2014

The best week ever.

5 of 5
I can't remember enjoying a week more. The house is beautiful, one can tell great care was used in selecting the furnishings. Everything is of the highest quality and yet comfortable and relaxing at the same time. The kitchen is well-equipped, I found everything I wanted, and the view from the breakfast table is glorious. One feels at home. The water is right at the edge of the property, a stroll to the dock always rewarded the birdwatcher. Total privacy and yet the town of St. Michael's has great restaurants, intriguing shops, and local history to delve into, and it's just minutes away.
  • Submitted: Dec 3, 2014
  • Stayed: Nov 2014

Sisters Weekend

5 of 5
Wonderful weekend, beautiful weather, terrific sail on the Selina, shopping, Gina's Cafe for incredible tacos, and let's not forget Tilghman Island Day with music, food and working boat races!! Harbor Hideaway and St. Michaels is a special jewel on the eastern shore. Our spring visit and return in October exceeded our expectations!
  • Submitted: Oct 25, 2014
  • Stayed: Oct 2014