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

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for St. Michaels apartments

Exterior detail

1. 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.
The price is AED 459
AED 1,181 total
includes taxes & fees
12 Aug - 13 Aug
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Private kitchen

2. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (38 reviews)
"The property was immaculate!! It was more than worth it!"
United States
Randy
The price is AED 569
AED 934 total
includes taxes & fees
6 Aug - 7 Aug
Sailwinds Loft at Cambridge Creek
1 bedroom, iron/ironing board, WiFi, bed sheets

3. Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing

Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
Downtown Cambridge
The price is AED 522
AED 966 total
includes taxes & fees
11 Aug - 12 Aug
Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
Coffee/tea maker, fridge, microwave, oven

4. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (6 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is AED 709
AED 1,746 total
includes taxes & fees
9 Aug - 10 Aug
Pool Loft Suite | Bay Access & Beach Passes
Beach

5. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (27 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is AED 455
AED 1,079 total
includes taxes & fees
18 Aug - 19 Aug
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Outdoor pool, a heated pool

6. Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (87 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is AED 900
AED 1,700 total
includes taxes & fees
1 Sep - 2 Sep
Waterfront Oasis of Annapolis Star
Coffee/tea maker, fridge, microwave, oven

7. 18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.0 out of 10, Wonderful, (14 reviews)
"Jen was an amazing host. The property was meticulously maintained. She made sure we had everything we needed! Shen created an environment where we could socialize with other guests or keep to ourselves. She made plenty of recommendations for local eateries and entertainment. We would definitely stay again!"
United States
Maureens B.
The price is AED 790
AED 1,403 total
includes taxes & fees
5 Aug - 6 Aug
18th Cent. Charm in Historic Downtown Annapolis
Interior

8. Dean Street's Lower Deck House!

Dean Street's Lower Deck House!
Historic District
10.0 out of 10, Exceptional, (4 reviews)
"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 806
AED 1,723 total
includes taxes & fees
31 Aug - 1 Sep
Dean Street's Lower Deck House!
Exterior

9. Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Admiral Heights
10.0 out of 10, Exceptional, (52 reviews)
"Great stay in Annapolis. The property is gorgeous. Everything you need for a great weekend in Annapolis. "
United States
Jennifer G.
The price is AED 1,405
AED 1,807 total
includes taxes & fees
5 Aug - 6 Aug
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

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Super quiet. Great bed."
Gary 1-night trip
Posted 2 hours ago
Graduate by Hilton 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: Neighborhood: Downtown St. Michaels. Includes private balconies. Elegant 2-Bedroom Retreat in Historic Saint Michaels – Walk to Dining & Shops: Neighborhood: Downtown St. Michaels. Downtown St. Michaels Studio – Walk to Waterfront, Dining & Shops: Neighborhood: Downtown St. Michaels. Includes private balconies. Harbor View Suite Talbot County License Number STRN-25-58: Neighborhood: Downtown St. Michaels. Amenities include free WiFi. Access to onsite laundry facilities is available on site.
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. Saint Michaels Town Hall and St. Michaels Marina 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.

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