Search Apartments in St. Michaels

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for St. Michaels apartments

Private kitchen
Sailwinds Loft at Cambridge Creek

Apartment in Cambridge

Sailwinds Loft at Cambridge Creek
10.0 out of 10, Exceptional, (23)
"What a great place to relax after exploring and enjoying the area. Definitely will visit again "
United States
Chris S.
The price is AED 569
AED 934 total
includes taxes & fees
12 Dec - 13 Dec
Sailwinds Loft at Cambridge Creek
Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star

Apartment in Annapolis

Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is AED 760
AED 1,520 total
includes taxes & fees
11 Dec - 12 Dec
Waterfront Oasis of Annapolis Star
Interior
Dean Street's Lower Deck House!

Apartment in Historic District

Dean Street's Lower Deck House!
10.0 out of 10, Exceptional, (3)
"We had a great time—the location is fantastic and our dog loved the backyard! A great base to rest and recover between adventures in Annapolis. "
United States
Nathaniel R.
The price is AED 699
AED 1,571 total
includes taxes & fees
28 Dec - 29 Dec
Dean Street's Lower Deck House!
Fridge, microwave, oven, stovetop
Annapolis Gem: Stylish and Cozy

Apartment in Eastport

Annapolis Gem: Stylish and Cozy
10.0 out of 10, Exceptional, (3)
"Great spot"
United States
Brian F.
The price is AED 909
AED 1,773 total
includes taxes & fees
5 Jan - 6 January 2026
Annapolis Gem: Stylish and Cozy
Terrace/patio
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Apartment in Admiral Heights

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
10.0 out of 10, Exceptional, (48)
"Perfect hideaway for a weekend trip to Annapolis. Great location and had everything we needed for the kids. Host was very accommodating and communicative, would come back!"
United States
Jay B.
The price is AED 1,306
AED 1,668 total
includes taxes & fees
16 Dec - 17 Dec
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Great"
stephen 3-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Annapolis

Frequently asked questions

What's it like to stay at an apartment in St. Michaels?
You can search through 6 apartments in St. Michaels for your vacation. During your trip, you can check out this romantic area's waterfront and shops.
Why would you choose an apartment versus a traditional hotel?
An apartment comes equipped with a kitchen, so you can cook some of your meals, and often has more space than a traditional hotel room. Apartments are a good option for couples who want to live like locals, but also for families who want the conveniences of home.
What's a favorite apartment for a stay in St. Michaels?
Downtown St. Michaels | Porch + Pet-Friendly: Includes private balconies. Modern Flat in the Heart of St. Michaels – Walk Everywhere: Private balconies and fireplaces are included. Access to onsite laundry facilities is available on site. Historic Downtown St. Michaels Studio | Walk to Waterfront, Dining & Shops: Includes private balconies.
How many apartments can I expect to find in St. Michaels?
Expedia has 6 apartments to book in St. Michaels.
What can I expect from the weather during my trip to St. Michaels?
Weather is only one factor, but it can really affect your travel plans, especially when you are planning a longer stay in St. Michaels. The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 41°F. Average annual precipitation for St. Michaels is 53 inches.
What should I see in St. Michaels?
St. Michaels is known for its waterfront and shops. 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. St. Michaels Marina and St. Michaels Winery are other places to visit while you're in town.
What's the best way to get to and around St. Michaels?
Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Easton, MD (ESN-Easton - Newnam), which is located 8.8 mi (14.1 km) from the city center. You can also search for flights into Fort Meade, MD (FME-Tipton), which is 35.5 mi (57.2 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.