Search Vacation Homes in St. Michaels

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Vacation Homes in St. Michaels

Spacious Modern Annapolis Retreat, Near Downtown, Firepit + Bar, Sleeps 12

2.0 star property
Cape Saint Claire
$330 nightly
The price is $376
Nov 20 - Nov 21
Total with taxes and fees
Spacious Modern Annapolis Retreat, Near Downtown, Firepit + Bar, Sleeps 12

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.
$333 nightly
The price is $353
Dec 8 - Dec 9
Total with taxes and fees
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

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
$251 nightly
The price is $266
Nov 23 - Nov 24
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!

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.
$420 nightly
The price is $445
Dec 1 - Dec 2
Total with taxes and fees
HGTV quality, private guest suite, country getaway with hot tub & fire pit

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.
$357 nightly
The price is $378
Nov 30 - Dec 1
Total with taxes and fees
Beautiful Waterfront Retreat in Cambridge!

Relax on Kent Island in 3 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.
$246 nightly
The price is $261
Nov 25 - Nov 26
Total with taxes and fees
Relax on Kent Island in 3 Bedroom Home w/Waterview!

Waterfront Getaway with Dock

Woolford
10.0 out of 10, Exceptional, (51)
"Great place, will stay again"
United States
Matt S.
$255 nightly
The price is $270
Nov 23 - Nov 24
Total with taxes and fees
Waterfront Getaway with Dock

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.
$284 nightly
The price is $315
Nov 20 - Nov 21
Total with taxes and fees
Walk to Beach! King Bed & Free Beach Passes

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

Shady Side
10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
$376 nightly
The price is $429
Nov 20 - Nov 21
Total with taxes and fees
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Family Beach House: Spacious Deck, Grill & Views

Chesapeake Beach
9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
$397 nightly
The price is $416
Dec 18 - Dec 19
Total with taxes and fees
Family Beach House: Spacious Deck, Grill & Views

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.
$395 nightly
The price is $419
Nov 20 - Nov 21
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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.
$615 nightly
The price is $651
Nov 20 - Nov 21
Total with taxes and fees
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Arundel on the Bay
9.8 out of 10, Exceptional, (11)
"Very clean - well equipped - perfect for our relaxing weekend."
United States
Chris J.
$421 nightly
The price is $479
Nov 20 - Nov 21
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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.
$271 nightly
The price is $309
Dec 2 - Dec 3
Total with taxes and fees
Cozy 2br home w/ parking in downtown Annapolis

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.
$257 nightly
The price is $272
Nov 20 - Nov 21
Total with taxes and fees
Chesapeake Bay Harbor View in a central location to events/restaurants

Edgewater/Mayo Gateaway w/ Hot Tub

Edgewater
9.8 out of 10, Exceptional, (24)
"Very clean, had everything we needed for our stay!"
United States
Jackie R.
$541 nightly
The price is $580
Nov 20 - Nov 21
Total with taxes and fees
Edgewater/Mayo Gateaway w/ Hot Tub

Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere
10.0 out of 10, Exceptional, (4)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
$480 nightly
The price is $547
Dec 9 - Dec 10
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown Annapolis!

Neptune by the Water - Pet Friendly Fenced Yard

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.
$482 nightly
The price is $514
Nov 20 - Nov 21
Total with taxes and fees
Neptune by the Water - Pet Friendly Fenced Yard

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.
$492 nightly
The price is $557
Nov 23 - Nov 24
Total with taxes and fees
Cute bungalow blocks to Stadium

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
$463 nightly
The price is $528
Nov 20 - Nov 21
Total with taxes and fees
Charming Pet-Friendly Stay - Near Bay & Beaches.
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

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St. Michaels Vacation Homes information

Number of reviews
372
Accommodation
693 Vacation Homes
Lowest Price
$261
Highest Price
$651

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