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Check prices for these dates

In two weeks
Dec 12 - Dec 14
In two months
Jan 23 - Jan 25
In three months
Feb 20 - Feb 22
In four months
Mar 20 - Mar 22

Vacation Homes in St. Michaels

Marina
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, (42)
"Wonderful home and host. Very easy to check-in and communication was excellent. "
United States
Ann T.
The price is ￥13,012
￥41,729 total
includes taxes & fees
Dec 1 - Dec 2
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Marina
Charming Coastal/Country Home w/3 Acres & Sauna!

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

Stevensville
9.6 out of 10, Exceptional, (32)
"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 ￥14,617
￥43,514 total
includes taxes & fees
Dec 1 - Dec 2
Charming Coastal/Country Home w/3 Acres & Sauna!
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, (16)
"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 ￥13,345
￥51,354 total
includes taxes & fees
Dec 1 - Dec 2
Walk to Beach! King Bed & Free Beach Passes
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, (72)
"Great little house easy to walk to West St, Main St & the Yard (USNA). Has parking included which is nice. Great communication we owner. Will stay again. "
United States
Sheldon E.
The price is ￥18,354
￥48,464 total
includes taxes & fees
Dec 1 - Dec 2
Cozy 2br home w/ parking in downtown Annapolis
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, (19)
"In town for a family wedding. This worked out perfectly. Would stay there again "
United States
Barbara V.
The price is ￥22,679
￥55,209 total
includes taxes & fees
Dec 8 - Dec 9
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Interior
Beautiful Waterfront Retreat in Cambridge!

Beautiful Waterfront Retreat in Cambridge!

Cambridge
10.0 out of 10, Exceptional, (49)
"Wonderful stay. The Crab Shack and dock were the highlights. We spent most of our time there. It was awesome. Highly recommend. "
United States
Christopher D.
The price is ￥25,338
￥59,188 total
includes taxes & fees
Nov 30 - Dec 1
Beautiful Waterfront Retreat in Cambridge!
Beach nearby, sun loungers, beach towels
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)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is ￥22,298
￥72,293 total
includes taxes & fees
Dec 1 - Dec 2
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Fridge, microwave, oven, stovetop
Waterfront Getaway with Dock

Waterfront Getaway with Dock

Woolford
10.0 out of 10, Exceptional, (51)
"Great place, will stay again"
United States
Matt S.
The price is ￥35,974
￥42,112 total
includes taxes & fees
Dec 1 - Dec 2
Waterfront Getaway with Dock
Interior
Historic Row Home 1 Block from Gate 1 at USNA!

Historic Row Home 1 Block from Gate 1 at USNA!

Historic District
10.0 out of 10, Exceptional, (5)
"Wonderful location. Easy walking to downtown restaurants, shops, city docks and USNA. Enjoyed spending time on front porch and swing.Comfortable beds and home like atmosphere.No need for a vehicle, but if you have one, parking garage is just a few blocks away. "
United States
Katie S.
The price is ￥24,942
￥116,062 total
includes taxes & fees
Dec 1 - Dec 2
Historic Row Home 1 Block from Gate 1 at USNA!
Microwave, oven, stovetop, dishwasher
Walk to the stadium! - Lighthouse on Glenwood

Walk to the stadium! - Lighthouse on Glenwood

Annapolis
10.0 out of 10, Exceptional, (5)
The price is ￥39,103
￥60,803 total
includes taxes & fees
Dec 7 - Dec 8
Walk to the stadium! - Lighthouse on Glenwood
3 bedrooms, iron/ironing board, travel crib, WiFi
★ Midcentury Modern Getaway ★ Prime Location ★

★ Midcentury Modern Getaway ★ Prime Location ★

Historic District
10.0 out of 10, Exceptional, (35)
"This is our second time staying in the property and it’s adorable and so convenient to everything. Ryan was very responsive and easy to work with. "
United States
shannon r.
The price is ￥29,790
￥89,934 total
includes taxes & fees
Dec 9 - Dec 10
★ Midcentury Modern Getaway ★ Prime Location ★
Property grounds
Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat

Dorchester County
10.0 out of 10, Exceptional, (41)
"Good time with my friends "
United Kingdom
Oleg L.
The price is ￥34,355
￥43,455 total
includes taxes & fees
Dec 23 - Dec 24
Sunset Breezes - quiet waterfront retreat
Terrace/patio
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)
"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 ￥30,828
￥70,148 total
includes taxes & fees
Dec 3 - Dec 4
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Fridge, microwave, oven, stovetop
vacation home in Historic Annapolis, 17-minute walk to U.S. Naval Academy

vacation home in Historic Annapolis, 17-minute walk to U.S. Naval Academy

Historic District
9.4 out of 10, Exceptional, (15)
"Very clean rooms, and very convenient to the historic district and waterfront in Annapolis. "
United States
Gary S.
vacation home in Historic Annapolis, 17-minute walk to U.S. Naval Academy
Interior
Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Pet-Friendly Stay - Near Bay & Beaches.

Annapolis
10.0 out of 10, Exceptional, (6)
"The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here."
United States
Kristina
The price is ￥34,840
￥86,257 total
includes taxes & fees
Dec 2 - Dec 3
Charming Pet-Friendly Stay - Near Bay & Beaches.
Interior
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Cambridge
8.8 out of 10, Excellent, (9)
"This home was everything we needed and more! It was spacious, clean and a beautiful location! There was a leak in the ceiling and the owners were very responsive and fixed it right away. Definitely recommend this stay."
United States
Priscilla A.
The price is ￥54,041
￥103,208 total
includes taxes & fees
Dec 4 - Dec 5
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Exterior
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)
"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 ￥39,103
￥65,987 total
includes taxes & fees
Nov 26 - Nov 27
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Fridge, microwave, oven, stovetop
Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium

Admiral Heights
9.8 out of 10, Exceptional, (6)
"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 ￥26,746
￥86,338 total
includes taxes & fees
Nov 30 - Dec 1
Cute bungalow blocks to Stadium
Property grounds
New! Stylish downtown home w/awesome outdoor area!

New! Stylish downtown home w/awesome outdoor area!

Stevensville
9.8 out of 10, Exceptional, (26)
"The house was spacious, clean, and in a great location. The owners were available, and easy to communicate with."
United States
Marjorie N.
The price is ￥38,433
￥83,474 total
includes taxes & fees
Dec 25 - Dec 26
New! Stylish downtown home w/awesome outdoor area!
Outdoor dining
Chesapeake Bay Harbor View in a central location to events/restaurants

Chesapeake Bay Harbor View in a central location to events/restaurants

2.5 star property
Rock Hall
10.0 out of 10, Exceptional, (2)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
United States
Todd W.
The price is ￥35,192
￥42,609 total
includes taxes & fees
Dec 7 - Dec 8
Chesapeake Bay Harbor View in a central location to events/restaurants
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 Westin Annapolis

The Westin Annapolis

10/10 Excellent
"The room was clean and the amenities were great! I loved the lobby and valet very fast and professional. I will stay here again. "
Scott 3-night trip
Posted 2 days ago
The Westin Annapolis

Find out more about St. Michaels

St. Michaels Vacation Homes information

Number of reviews
469
Accommodation
659 Vacation Homes
Lowest Price
￥41,729
Highest Price
￥116,062

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