Holiday Homes in St. Michaels

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for St. Michaels holiday homes

Beach nearby

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (17 reviews)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
The price is NZ$553
includes taxes & fees
19 Jan - 20 Jan
Walk to Beach! King Bed & Free Beach Passes
Exterior

Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (32 reviews)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
The price is NZ$458
includes taxes & fees
18 Jan - 19 Jan
Charming Coastal/Country Home w/3 Acres & Sauna!
Exterior

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (43 reviews)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is NZ$446
includes taxes & fees
19 Jan - 20 Jan
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.6 out of 10, Exceptional, (20 reviews)
"Very clean, and very comfortable beds."
United States
Edward R.
The price is NZ$600
includes taxes & fees
2 Feb - 3 Feb
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Outdoor dining

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (31 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is NZ$703
includes taxes & fees
22 Jan - 23 Jan
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Fridge, microwave, oven, stovetop

Beautiful Waterfront Retreat in Cambridge!

Beautiful Waterfront Retreat in Cambridge!
Cambridge
10.0 out of 10, Exceptional, (50 reviews)
"Beautiful place! Loved all the activities, will return in the future! Our family and friends had a blast! Thank you so much!!"
United States
Karen L.
The price is NZ$632
includes taxes & fees
18 Jan - 19 Jan
Beautiful Waterfront Retreat in Cambridge!
Fridge, microwave, oven, stovetop

Neptune by the Water - Pet Friendly Fenced Yard

Neptune by the Water - Pet Friendly Fenced Yard
Cape Saint Claire
9.8 out of 10, Exceptional, (11 reviews)
"Very nice home, location, close to our family and activities. Enjoyed our stay and would recommend to other renters looking for spaciousness and holiness that a hotel cannot provide! "
United States
Lisa S.
The price is NZ$1,024
includes taxes & fees
21 Jan - 22 Jan
Neptune by the Water - Pet Friendly Fenced Yard
Fridge, microwave, dishwasher, coffee/tea maker

HGTV quality, private guest suite, country getaway with hot tub & fire pit

HGTV quality, private guest suite, country getaway with hot tub & fire pit
Centreville
10.0 out of 10, Exceptional, (8 reviews)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
The price is NZ$764
includes taxes & fees
19 Jan - 20 Jan
HGTV quality, private guest suite, country getaway with hot tub & fire pit
TV, books, offices

Holly Hill Haven - Sleeps 10

Holly Hill Haven - Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (3 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is NZ$951
includes taxes & fees
9 Feb - 10 Feb
Holly Hill Haven - Sleeps 10
Marina

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is NZ$830
includes taxes & fees
18 Jan - 19 Jan
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Fridge, microwave, oven, stovetop

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (8 reviews)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
The price is NZ$951
includes taxes & fees
26 Jan - 27 Jan
Cute bungalow blocks to Stadium
Marina

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (73 reviews)
"Great location!"
United States
Burton S.
The price is NZ$560
includes taxes & fees
20 Jan - 21 Jan
Cozy 2br home w/ parking in downtown Annapolis
Outdoor spa tub

London Towne Bungalow w/Loft - Walk to the Beach!

London Towne Bungalow w/Loft - Walk to the Beach!
Edgewater
8.8 out of 10, Excellent, (3 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is NZ$860
includes taxes & fees
5 Feb - 6 Feb
London Towne Bungalow w/Loft - Walk to the Beach!
Interior

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (5 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is NZ$915
includes taxes & fees
20 Jan - 21 Jan
Annapolis Retreat - 7 mins from downtown Annapolis!
Dining

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (12 reviews)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is NZ$720
includes taxes & fees
16 Jan - 17 Jan
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Fridge, microwave, oven, stovetop

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (51 reviews)
"Great place, will stay again"
United States
Matt S.
The price is NZ$478
includes taxes & fees
20 Jan - 21 Jan
Waterfront Getaway with Dock
Interior

Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
10.0 out of 10, Exceptional, (5 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
The price is NZ$1,263
includes taxes & fees
28 Jan - 29 Jan
Historic Row Home | Hot Tub - 1 Block from Gate 1!
Smart TV, fireplace, table football, ping pong

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Homewood
9.8 out of 10, Exceptional, (8 reviews)
"Our family gathered for a special celebration and loved the home! It was roomy and had everything we needed for our stay. The location was perfect for getting around."
United States
Jeanie W.
The price is NZ$812
includes taxes & fees
21 Jan - 22 Jan
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Fridge, microwave, oven, stovetop

Golden Anchor Retreat; Lux Living! - Sleeps 7

Golden Anchor Retreat; Lux Living! - Sleeps 7
Edgewater
10.0 out of 10, Exceptional, (2 reviews)
"The property was beautiful with plenty of space to have a getaway with friends. The host was super communicative when we had issues with check in. Would highly recommend staying here!"
United States
Sam A.
The price is NZ$1,164
includes taxes & fees
19 Jan - 20 Jan
Golden Anchor Retreat; Lux Living! - Sleeps 7
Smart TV

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Shady Side
10.0 out of 10, Exceptional, (4 reviews)
"Would stay here again "
United States
Thomas D.
The price is NZ$775
includes taxes & fees
25 Jan - 26 Jan
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top St. Michaels Hotel Reviews

The Wildset

The Wildset

10/10 Excellent
"The room was very clean. The staff was very pleasant and extremely helpful when we needed something @3:30am."
Harry 2-night trip
Posted 18 hours ago
The Wildset

Find out more about St. Michaels

St. Michaels Holiday Homes information

Number of reviews
378
Accommodation
659 Holiday Homes
Lowest Price
NZ$446
Highest Price
NZ$1,263