A waterfront street lined with trees and a white building with a balcony.

St. Michaels Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for St. Michaels vacation rentals

Living area

1. EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places

EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
Easton
10.0 out of 10, Exceptional, (1 review)
"Fabulous location in town location! It was much larger than we expected - 2 levels. Nice open layout on the main level with 2 BR/BA and a 3rd BR/BA on 2nd floor. Owners are very responsive before and during the trip. We could not connect to the TV, but owner quickly offered assistance. Bathrooms can use some towel racks and shelves. Beds/pillows were comfy! We were very happy with our stay."
United States
Lynn G.
$379 nightly
The price is $402
Nov 16 - Nov 17
Total with taxes and fees
EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
A deck with a view of a marina, including boats and docks.

2. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (54 reviews)
"Love This rental. One of our favorites. Small but everything needed. And the view is absolutely wonderful."
United States
Yamilet
Cass-N-Reel Luxury Houseboat
A lighthouse with a white exterior, a balcony, and a metal roof.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (50 reviews)
"Great stay"
United States
Michael V.
$304 nightly
The price is $328
Nov 23 - Nov 24
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

4. Relax on Kent Island in 4 Bedroom Home w/Waterview

Relax on Kent Island in 4 Bedroom Home w/Waterview
Stevensville
9.8 out of 10, Exceptional, (57 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
$270 nightly
The price is $291
Nov 15 - Nov 16
Total with taxes and fees
Relax on Kent Island in 4 Bedroom Home w/Waterview
A living room with two grey sofas, a coffee table, and a ceiling fan.

5. Cambridge Apt in Walkable Neighborhood

Cambridge Apt in Walkable Neighborhood
3.0 star property
Cambridge
10.0 out of 10, Exceptional, (1 review)
"This apt was built in the 50’s, or back when fewer outlets were needed, and it has window air conditioners. It was just what we were looking for as we visited the ste for family reunions"
United States
LOIS
$291 nightly
The price is $323
Nov 14 - Nov 15
Total with taxes and fees
Cambridge Apt in Walkable Neighborhood
A kitchen with wooden cabinets, a stove, and a dining table with chairs.

6. Family Friendly Cozy 3 Bedroom Duplex

Family Friendly Cozy 3 Bedroom Duplex
Grasonville
$293 nightly
The price is $311
Nov 24 - Nov 25
Total with taxes and fees
Family Friendly Cozy 3 Bedroom Duplex
A living room with two grey sofas, a coffee table, and a ceiling fan.

7. Cambridge Apt in Walkable Neighborhood

Cambridge Apt in Walkable Neighborhood
Cambridge
8.0 out of 10, Very good, (4 reviews)
"great location."
United States
Anonymous traveler
$282 nightly
The price is $312
Nov 14 - Nov 15
Total with taxes and fees
Cambridge Apt in Walkable Neighborhood
A house with a yellow door and a window with a lamp outside.

8. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
$276 nightly
The price is $314
Nov 15 - Nov 16
Total with taxes and fees
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

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

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.4 out of 10, Exceptional, (26 reviews)
"Pet friendly!"
United States
Mary Beth S.
$352 nightly
The price is $373
Dec 13 - Dec 14
Total with taxes and fees
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

10. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (25 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
$298 nightly
The price is $320
Dec 1 - Dec 2
Total with taxes and fees
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

11. The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach
9.6 out of 10, Exceptional, (30 reviews)
"Wonderful place to visit "
United States
James L.
$292 nightly
The price is $310
Nov 15 - Nov 16
Total with taxes and fees
The Cozy Crab- Your Charming Haven in Lovely North Beach!
A lakeside view from a deck with a wooden railing, a sandy area with a boat, and a dock extending into the water.

12. 2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.
Cambridge
$244 nightly
The price is $259
Nov 13 - Nov 14
Total with taxes and fees
2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.
A two-story house with a red roof, a brick chimney, and a small porch.

13. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
Stevensville
8.6 out of 10, Excellent, (7 reviews)
"The place was very clean and Host was ok the shopping was six miles away, not in walking distance, we had no pets on this trip."
United States
Anonymous traveler
$945 nightly
The price is $1,002
Nov 13 - Nov 14
Total with taxes and fees
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
An outdoor seating area with tables and chairs, umbrellas, and a view of the water.

14. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (75 reviews)
"Great stay, exactly as advertised, Donna was great!"
United States
Sam C.
$1,122 nightly
The price is $1,239
Dec 1 - Dec 2
Total with taxes and fees
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

15. WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (17 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
$438 nightly
The price is $464
Nov 16 - Nov 17
Total with taxes and fees
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A beach with chairs and a pier in the background.

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

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
"Super clean, well furnished and in a nice quiet neighborhood close to downtown Annapolis. Great place to stay!"
United States
Ryan C.
$414 nightly
The price is $472
Nov 16 - Nov 17
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

17. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
9.8 out of 10, Exceptional, (6 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
$431 nightly
The price is $436
Dec 1 - Dec 2
Total with taxes and fees
Sunset Cottage - West River Access and Views!
A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

18. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (40 reviews)
"Wonderful place to stay."
United States
Sharon D.
$228 nightly
The price is $242
Nov 16 - Nov 17
Total with taxes and fees
Sailwinds Loft at Cambridge Creek
A marina with boats docked, a water tower, and residential buildings with balconies.

19. Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym

Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym
Cambridge
10.0 out of 10, Exceptional, (2 reviews)
"We only stayed one night but wouldn't hesitate to come back and stay for a few days. Beautiful home overlooking the docks."
United States
mike
$414 nightly
The price is $458
Nov 13 - Nov 14
Total with taxes and fees
Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

20. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Downtown Cambridge
9.8 out of 10, Exceptional, (15 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
$350 nightly
The price is $371
Dec 13 - Dec 14
Total with taxes and fees
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
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

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"1"
David Louis 2-night trip
Posted less than an hour ago
Annapolis Waterfront Hotel, Autograph Collection

Find out more about St. Michaels

Everything you need to know about St. Michaels vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the St. Michaels vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect St. Michaels vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

St. Michaels vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in St. Michaels. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit St. Michaels in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $291 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on St. Michaels rentals

At Expedia, we put the best St. Michaels vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top St. Michaels rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream St. Michaels vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around St. Michaels. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in St. Michaels?

Yes, we have vacation rentals in St. Michaels close to Chesapeake Bay Maritime Museum, or you can choose a more secluded option if you're looking for a relaxing stay. The waterfront and shops are just a few reasons why tourists like St. Michaels. While you're here, grab a bite or have a drink at the seafood restaurants.

What are some of the best vacation rentals in St. Michaels?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: You might want to consider this vacation home rental near St. Michaels, which is located near the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in St. Michaels?

Expedia has 35 vacation rentals for your stay in St. Michaels.

What’s there to see and do in St. Michaels?

Cultural attractions include Chesapeake Bay Maritime Museum and St. Michaels Museum, whereas Church Cove Park and CL Open Field are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Saint Michaels Town Hall and St. Michaels Marina.

What’s a vacation rental in St. Michaels like?

Vacation rentals are private properties where you can stay for short or long periods in St. Michaels. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for small groups.