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22 Aug - 24 Aug
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12 Sept - 14 Sept
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Featured Condo Rentals in Sherwood

Annapolis Condominium in the heart of the historic center
Terrace/patio

Annapolis Condominium in the heart of the historic center

9.8 out of 10, Exceptional, (282)
"The location and amenities are great. The host are very friendly, helpful and easy to make contact with. My family used this location for commission week and could not have asked for more. "
Annapolis Condominium in the heart of the historic center
Beautiful Condo - Water View Near City Dock
View from property

Beautiful Condo - Water View Near City Dock

9.6 out of 10, Exceptional, (145)
"Clean, quiet, and very close to both downtown and Eastport restaurants."
Beautiful Condo - Water View Near City Dock
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Marina

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

9.4 out of 10, Exceptional, (3)
"The place was very clean and in the most perfect spot in downtown Cambridge. We had a wedding walking distance from this place. Jen is a very responsive and accommodating host!"
The price is AU$463
includes taxes & fees
19 Aug - 20 Aug
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Marina

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

2.0 star property
9.8 out of 10, Exceptional, (9)
"This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. "
The price is AU$610
includes taxes & fees
17 Aug - 18 Aug
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Waterfront 2-Bedroom Condo on Spa Creek
Smart TV

Waterfront 2-Bedroom Condo on Spa Creek

10.0 out of 10, Exceptional, (8)
"This is a great location. Walking distance to everything. Near all the sailing clubs! Property manager was the best we have ever experienced."
Waterfront 2-Bedroom Condo on Spa Creek
Waterfront Condo with Rooftop Pool, Spa Creek Views & Prime Eastport Location with Parking
Pool

Waterfront Condo with Rooftop Pool, Spa Creek Views & Prime Eastport Location with Parking

10.0 out of 10, Exceptional, (18)
"Can’t have a better location near everything in Eastport and Main St Annapolis!"
Waterfront Condo with Rooftop Pool, Spa Creek Views & Prime Eastport Location with Parking
Kent Island Waterfront Cottage
Fridge, microwave, oven, stovetop

Kent Island Waterfront Cottage

8.8 out of 10, Excellent, (11)
"Enjoyed fishing at the pier and sitting on the porch"
Kent Island Waterfront Cottage
Unbelievable beach views for 6
Property grounds

Unbelievable beach views for 6

2.0 star property
10.0 out of 10, Exceptional, (8)
"It was unbelievable stay with fantastic sunrise and moon rise on the day of the eclipse"
Unbelievable beach views for 6
New Downtown Annapolis Condo With Free Parking
Property grounds

New Downtown Annapolis Condo With Free Parking

10.0 out of 10, Exceptional, (26)
"Clean, modern apartment walking distance from all of Annapolis harbor and restaurants. "
New Downtown Annapolis Condo With Free Parking
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Marina

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

2.5 star property
10.0 out of 10, Exceptional, (10)
"Property was located in heart of Cambridge restaurant district. Easy access to great restaurants. Parking easy and plentiful. Condo was as beautiful as advertised! Stunning penthouse 2 bedroom apartment!"
The price is AU$637
includes taxes & fees
17 Aug - 18 Aug
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Chic Condo w/ Balcony in the Heart of Annapolis!
Interior

Chic Condo w/ Balcony in the Heart of Annapolis!

9.8 out of 10, Exceptional, (58)
"This cute condo is as pictured; charming and clean. Nice bathrooms. Comfortable beds. Great location. Loved the parking ease as well. Host was very receptive and flexible with my arrival/departure times.Would highly recommend and would stay here again."
Chic Condo w/ Balcony in the Heart of Annapolis!
Walkable Condo w/ Drawbridge Views in Cambridge
Living area

Walkable Condo w/ Drawbridge Views in Cambridge

Walkable Condo w/ Drawbridge Views in Cambridge
Unique 2-Bedroom Condo in Renovated Parish House
Marina

Unique 2-Bedroom Condo in Renovated Parish House

Unique 2-Bedroom Condo in Renovated Parish House
Upscale Condo in Annapolis
Terrace/patio

Upscale Condo in Annapolis

Upscale Condo in Annapolis
Waterfront condo. Completely renovated. Walk to Kent Island's best places
TV, fireplace

Waterfront condo. Completely renovated. Walk to Kent Island's best places

Waterfront condo. Completely renovated. Walk to Kent Island's best places
Station House East: Upscale Loft in the Historic District Cambridge, MD
Marina

Station House East: Upscale Loft in the Historic District Cambridge, MD

The price is AU$441
includes taxes & fees
27 Aug - 28 Aug
Station House East: Upscale Loft in the Historic District Cambridge, MD
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

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Great area and it was a perfect hotel for our trip. "
Lauren 3-night trip
Posted 4 hours ago
Graduate by Hilton Annapolis

Frequently asked questions

What is there to do in Sherwood near my condo?
After you've unpacked your bags, head out and explore the awesome things Sherwood has to offer. St. Michaels Winery is a popular attraction to add to your itinerary.