A large brick house with a green roof, surrounded by lush gardens and trees.

Search Apartment Rentals in Sherwood

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Sherwood apartments

A house with a yellow door and a window with a lamp outside.

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 CA $181
CA $459 total
includes taxes & fees
Sep 8 - Sep 9
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

2. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (39 reviews)
"Wonderful place to stay."
United States
Sharon D.
The price is CA $215
CA $350 total
includes taxes & fees
Sep 7 - Sep 8
Sailwinds Loft at Cambridge Creek
A swimming pool with a waterfall feature surrounded by lush greenery.

3. Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (88 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is CA $339
CA $638 total
includes taxes & fees
Sep 8 - Sep 9
Waterfront Oasis of Annapolis Star
A kitchen counter with a marble top, a striped basket, a tissue box, and a potted plant.

4. 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 CA $282
CA $618 total
includes taxes & fees
Sep 8 - Sep 9
Dean Street's Lower Deck House!
A kitchen with a wooden countertop, a stove, and a refrigerator.

5. 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 CA $323
CA $589 total
includes taxes & fees
Sep 8 - Sep 9
18th Cent. Charm in Historic Downtown Annapolis
A two-story house with a covered patio, a garage, and a well-maintained lawn.

6. 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, (54 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 CA $530
CA $688 total
includes taxes & fees
Sep 8 - Sep 9
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sherwood Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"We come in every year for the Annapolis10 mile race and have stayed here for the past two years. It's a wonderful hotel that's located in such a convenient place in Annapolis. You can walk everywhere, and are a little out of the mainstream so it's not too crazy. The room we had this year was very large. The beds are comfortable and everything is clean. We will stay here again next year."
Karen Glou 2-night trip
Posted 2 hours ago
Historic Inns of Annapolis

Find out more about Sherwood

Sherwood Apartments information

Number of reviews
212
Accommodation
67 Apartments
Lowest Price
CA $350
Highest Price
CA $688

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?
Listed below are some of the favorite apartments in the area: Waterfront Oasis of Annapolis Star: Located in Annapolis, 19.1 mi/30.7 km from the heart of Sherwood. Includes a private pool, free WiFi, and fireplaces. Access to an outdoor pool is available on site. Downtown St. Michaels | Porch + Pet-Friendly: Located 5.3 mi/8.6 km away in St. Michaels. Amenities include private balconies. Annapolis Spa Retreat, Sauna, Jacuzzi, King Bed Couples Quiet Loft Apt. Getaway: 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. New Loft w/South River view from treehouse deck!: 19.5 mi/31.4 km away in Riva. Free WiFi, private patios, and premium mattresses are included.
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.

Explore a world of travel with Expedia