Search Vacation Homes in St. Michaels

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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Vacation Homes in St. Michaels

Marina
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Vacation Home in Cambridge

9.6 out of 10, Exceptional, (20)
"In town for a family wedding. This worked out perfectly. Would stay there again "
United States
Barbara V.
The price is SAR 525
SAR 1,300 total
includes taxes & fees
8 Dec - 9 Dec
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Vacation Home in Stevensville

9.8 out of 10, Exceptional, (42)
"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 SAR 295
SAR 977 total
includes taxes & fees
3 Dec - 4 Dec
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Beach nearby
Walk to Beach! King Bed & Free Beach Passes

Vacation Home in 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 SAR 397
SAR 1,329 total
includes taxes & fees
4 Dec - 5 Dec
Walk to Beach! King Bed & Free Beach Passes
Marina
Charming Coastal/Country Home w/3 Acres & Sauna!

Vacation Home in 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 SAR 374
SAR 1,073 total
includes taxes & fees
8 Dec - 9 Dec
Charming Coastal/Country Home w/3 Acres & Sauna!
Terrace/patio
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Vacation Home in 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 SAR 739
SAR 1,671 total
includes taxes & fees
15 Dec - 16 Dec
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Interior
Beautiful Waterfront Retreat in Cambridge!

Vacation Home in Cambridge

10.0 out of 10, Exceptional, (49)
"Just what we were looking for. Appreciated the little touches such as already baited crab traps and the complimentary smores kit. "
United States
Dan K.
The price is SAR 608
SAR 1,420 total
includes taxes & fees
4 Dec - 5 Dec
Beautiful Waterfront Retreat in Cambridge!
Fridge, microwave, oven, stovetop
Waterfront Getaway with Dock

Vacation Home in Woolford

10.0 out of 10, Exceptional, (51)
"Great place, will stay again"
United States
Matt S.
The price is SAR 863
SAR 1,010 total
includes taxes & fees
8 Dec - 9 Dec
Waterfront Getaway with Dock
Property grounds
Sunset Breezes - quiet waterfront retreat

Vacation Home in Dorchester County

10.0 out of 10, Exceptional, (41)
"Good time with my friends "
United Kingdom
Oleg L.
The price is SAR 990
SAR 1,235 total
includes taxes & fees
23 Dec - 24 Dec
Sunset Breezes - quiet waterfront retreat
Exterior
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Vacation Home in 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 SAR 938
SAR 1,571 total
includes taxes & fees
3 Dec - 4 Dec
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Marina
Cozy 2br home w/ parking in downtown Annapolis

Vacation Home in 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 SAR 454
SAR 1,180 total
includes taxes & fees
3 Dec - 4 Dec
Cozy 2br home w/ parking in downtown Annapolis
Interior
Charming Pet-Friendly Stay - Near Bay & Beaches.

Vacation Home in 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 SAR 836
SAR 1,962 total
includes taxes & fees
3 Dec - 4 Dec
Charming Pet-Friendly Stay - Near Bay & Beaches.
Fridge, microwave, oven, stovetop
Cute bungalow blocks to Stadium

Vacation Home in 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 SAR 642
SAR 2,071 total
includes taxes & fees
3 Dec - 4 Dec
Cute bungalow blocks to Stadium
Exterior
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Vacation Home in Shady Side

10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
The price is SAR 540
SAR 1,608 total
includes taxes & fees
3 Dec - 4 Dec
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Fridge, microwave, oven, stovetop
Neptune by the Water - Pet Friendly Fenced Yard

Vacation Home in Cape Saint Claire

9.8 out of 10, Exceptional, (11)
"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 SAR 563
SAR 1,883 total
includes taxes & fees
3 Dec - 4 Dec
Neptune by the Water - Pet Friendly Fenced Yard
Interior
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Vacation Home in 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 SAR 1,296
SAR 2,476 total
includes taxes & fees
7 Dec - 8 Dec
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Interior
Historic Row Home 1 Block from Gate 1 at USNA!

Vacation Home in 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 SAR 597
SAR 2,776 total
includes taxes & fees
3 Dec - 4 Dec
Historic Row Home 1 Block from Gate 1 at USNA!
Property grounds
New! Stylish downtown home w/awesome outdoor area!

Vacation Home in 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 SAR 919
SAR 1,996 total
includes taxes & fees
25 Dec - 26 Dec
New! Stylish downtown home w/awesome outdoor area!
Terrace/patio
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Vacation Home in Arundel on the Bay

9.8 out of 10, Exceptional, (11)
"Very clean - well equipped - perfect for our relaxing weekend."
United States
Chris J.
The price is SAR 658
SAR 1,713 total
includes taxes & fees
9 Dec - 10 Dec
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Beach nearby, sun loungers, beach towels
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Vacation Home in 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 SAR 369
SAR 1,526 total
includes taxes & fees
3 Dec - 4 Dec
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
4 bedrooms, desk, iron/ironing board, travel crib
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Vacation Home in Homewood

9.8 out of 10, Exceptional, (8)
"This house was perfect for us! We love the ease of getting into town without having to drive and park in a parking garage. I would 10/10 recommend this house!"
United States
Elaina H.
The price is SAR 672
SAR 1,733 total
includes taxes & fees
9 Dec - 10 Dec
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
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

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Evening bar staff was exceptional, as was the crew at the check-in desk. Excellent recommendations for places to eat. This hotel is within walking distance of everything we wanted to see and do. So much history here, cool stores, venues, and not far from the bay."
Jan Michael 2-night trip
Posted 2 days ago
Hilton Garden Inn Annapolis Downtown