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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

Apartments in Sherwood

Private kitchen
Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek

Cambridge
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 SAR 582
SAR 955 total
includes taxes & fees
12 Dec - 13 Dec
Sailwinds Loft at Cambridge Creek
Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star

Annapolis
10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is SAR 777
SAR 1,545 total
includes taxes & fees
10 Dec - 11 Dec
Waterfront Oasis of Annapolis Star
Interior
Dean Street's Lower Deck House!

Dean Street's Lower Deck House!

Historic District
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 SAR 714
SAR 1,606 total
includes taxes & fees
28 Dec - 29 Dec
Dean Street's Lower Deck House!
Fridge, microwave, oven, stovetop
Annapolis Gem: Stylish and Cozy

Annapolis Gem: Stylish and Cozy

Eastport
10.0 out of 10, Exceptional, (3)
"Great spot"
United States
Brian F.
The price is SAR 929
SAR 1,808 total
includes taxes & fees
7 Jan - 8 January 2026
Annapolis Gem: Stylish and Cozy
Terrace/patio
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, (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 SAR 1,483
SAR 1,917 total
includes taxes & fees
6 Jan - 7 January 2026
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 Sherwood Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Rooms are in the different buildings so we needed to check in to find out where we were staying. Parking is difficult so we chose to pay for valet. Loved the location and it was convenient for Midnight Madness shopping and to great restaurants."
Carolyn Alexandra 1-night trip
Posted 3 days ago
Historic Inns of Annapolis

Frequently asked questions

What's it like to stay at an apartment in Sherwood?
There are 8 hotels and other accommodations in Sherwood. Though there aren't many apartments, we can help you find accommodations that are similar. When you search on Expedia, you can filter by amenities you might find in an apartment such as a kitchen. You can also search for similar properties such as condos, vacation homes, or cottages.
Are you thinking about apartments over traditional hotel rooms?
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 a more local feel, but also for families wanting the conveniences of home.
What's the top apartment I should consider for a stay in Sherwood?
Below are some of the favorite apartments in the area: Downtown St. Michaels | Porch + Pet-Friendly: Located 5.3 mi/8.6 km away in St. Michaels. Amenities include private balconies. Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis: Located in Annapolis, 18.3 mi/29.4 km away. Includes free WiFi, sofa beds, and jetted bathtubs. Onsite laundry facilities and a hot tub are on site. Modern Flat in the Heart of St. Michaels – Walk Everywhere: Located 5.4 mi/8.6 km away in St. Michaels. Private balconies and fireplaces are included. Access to onsite laundry facilities is available on site. Waterfront Oasis of Annapolis Star: Located in Annapolis, 19.1 mi/30.7 km from Sherwood. Includes a private pool, free WiFi, and fireplaces. Access to an outdoor pool is available on site.
What can I expect from the weather during my trip to Sherwood?
Weather is only one factor, but it can really affect your travel plans, especially if you are planning a longer stay in Sherwood. 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 Sherwood is 53 inches.
What are the must-see places to visit in Sherwood?
Explore the area and family-friendly sights such as Chesapeake Bay Maritime Museum, or get out into nature at a spot like Goat Island. In the larger area, you'll find Knapp's Narrows Marina & Inn and St. Michaels Winery.
What's the best way to get to and around Sherwood?
Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Easton, MD (ESN-Easton - Newnam), which is located 14.1 mi (22.7 km) from the heart of the city. You can also search for flights into Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional), which is 52.1 mi (83.8 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.