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Featured Condo Rentals in Sherwood

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

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

2.5 star property
10.0 out of 10, Exceptional, (7)
"Attention to detail is everywhere! The location is great. Light and airy. Thank you!"
The price is AU$735
includes taxes & fees
1 Dec - 2 Dec
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Waterfront 2-Bedroom Condo on Spa Creek
Interior

Waterfront 2-Bedroom Condo on Spa Creek

10.0 out of 10, Exceptional, (5)
"We had such an amazing time. It had a beautiful view and easy to walk everywhere :)"
Waterfront 2-Bedroom Condo on Spa Creek
Upscale Condo in Historic Downtown Cambridge, Maryland
1 bedroom, iron/ironing board, free WiFi, bed sheets

Upscale Condo in Historic Downtown Cambridge, Maryland

9.4 out of 10, Exceptional, (3)
"The property itself is lovely, but the neighborhood has seen better days. The city other than the one street with the cafe and mural seems to be vacant and there isn’t much to do for a family with young children other than the park with the light house. But like I said, the home was lovely."
The price is AU$544
includes taxes & fees
4 Dec - 5 Dec
Upscale Condo in Historic Downtown Cambridge, Maryland
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, (265)
"Great location. Clean and very roomy!"
Annapolis Condominium in the heart of the historic center
Eastport Condo in Building with Rooftop Water Views of Spa Creek!
Pool

Eastport Condo in Building with Rooftop Water Views of Spa Creek!

10.0 out of 10, Exceptional, (9)
"We enjoyed our visit with our son at USNA. Easy walk to DTA and great restaurants in Eastport. View from rooftop was spectacular!! Beds were comfortable."
Eastport Condo in Building with Rooftop Water Views of Spa Creek!
Downtown Annapolis Condo w/ Free Parking + Coffee
Property grounds

Downtown Annapolis Condo w/ Free Parking + Coffee

10.0 out of 10, Exceptional, (16)
"Very nice location and nice apartment!"
Downtown Annapolis Condo w/ Free Parking + Coffee
Walk to Main Street from Waterfront Condo w Pool and Parking
Point of interest

Walk to Main Street from Waterfront Condo w Pool and Parking

10.0 out of 10, Exceptional, (14)
"The property was outstanding in proximity to the USNA and downtown Annapolis. We were able to walk to a fabulous bakery and good restaurants. The apartment was well appointed. The King-sized bed was exceptionally comfortable. We will return to this location!"
Walk to Main Street from Waterfront Condo w Pool and Parking
Beautiful Condo - Water View Near City Dock
Outdoor dining

Beautiful Condo - Water View Near City Dock

9.6 out of 10, Exceptional, (137)
"I’ve stayed at several places around Annapolis and Eastport. This is on the top of my list to return. Great location to walk into DTA and Eastport. Just a five minute walk to the market. 7 minute walk to davis pub! Exactly as advertised, ample parking. Great communication. "
Beautiful Condo - Water View Near City Dock
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, (49)
"I love the location of the condo. It was in the downtown district of Annapolis. It can be a bit noisy, especially when you’re trying to sleep. If you like quietness while sleeping, this is not the place for you. I’m a city girl so I’m used to the noise. There are lots of coffee shops, bars and restaurants you can go to within walking distance. The condo was clean had everything I needed and the perk was a garage. Yes, I would definitely stay there again.."
Chic Condo w/ Balcony in the Heart of Annapolis!
Kent Island Waterfront Cottage
Beach

Kent Island Waterfront Cottage

9.2 out of 10, Wonderful, (7)
"We needed to de-stress and this bay-side home gave us all the peace and quiet we needed. It sits on a huge grassy lawn that slopes down to a dock. Geese and osprey kept us company, while motor noise was almost non-existent. It is still close to many amenities and historic towns, but tucked away from the hustle and bustle. There were a few things that needed attention, and Julie, the property manager, responded right away with great courtesy. We loved our stay. "
Kent Island Waterfront Cottage
Water-view condo with rooftop pool & balcony - minutes from downtown
TV

Water-view condo with rooftop pool & balcony - minutes from downtown

9.2 out of 10, Wonderful, (9)
"I recently stayed at the USNA Getaway in Annapolis, MD, and it was fantastic! The location is perfect, right near the Naval Academy and downtown Annapolis. The property is immaculate and beautifully furnished, with a cozy living area, fully equipped kitchen, and a lovely outdoor patio. The bedroom was spacious and super comfortable. The host was incredibly responsive and made sure I had everything I needed. Check-in and check-out were smooth and easy. I highly recommend the USNA Getaway for...
Water-view condo with rooftop pool & balcony - minutes from downtown
Delightful little Historic District gem - for the antique lover and history buff.
Fridge, microwave, oven, stovetop

Delightful little Historic District gem - for the antique lover and history buff.

9.0 out of 10, Wonderful, (4)
"Excellent location for all things USNA and downtown Annapolis. We walked everywhere. The second bedroom was a little warm but it was unseasonably hot while we were there. There is a K cup coffeemaker but you’ll need to bring everything to enjoy a cup. Would definitely stay again!"
Delightful little Historic District gem - for the antique lover and history buff.
Unbelievable beach views for 6
Property grounds

Unbelievable beach views for 6

2.0 star property
10.0 out of 10, Exceptional, (3)
"Very nice place in a great location!!!"
Unbelievable beach views for 6
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Property grounds

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

2.0 star property
9.4 out of 10, Exceptional, (3)
"Our grandparents are interned at the Old Trinity Church in Woolford. When our mother passed away we decided to lay her to rest there also. I looked for a place that the 5 of us would be comfortable. I was not disappointed. The condo was beautiful. We had all the creature comforts of home. Beds were comfortable, place was clean and parking was perfect. We will definitely use this place again. "
The price is AU$600
includes taxes & fees
16 Dec - 17 Dec
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
A Kozy Waterfront Condo
Pool

A Kozy Waterfront Condo

A Kozy Waterfront Condo
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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Other property types in Sherwood

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (202)
"This cozy home was perfect for my coaches & I that were in town for a lacrosse tourney @ the Naval Academy. This home is literally less than 100 steps from the gate of the Naval Base and same distance to dowtown Annapolis city docks, diming, shopping and sight-seeing. We will defintely be back! Thanks John!!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (217)
"Were pleased with the property and surroundings. Very beautiful, ancient trees. Neighborhood was quiet and the river and dock were favorite reading spots. Enjoyed!!!"
Relaxing Waterfront Cottage Near St Michaels, Maryland
Charming Annapolis WaterVIEW Home
Outdoor dining

Charming Annapolis WaterVIEW Home

9.6 out of 10, Exceptional, (49)
"Wonderful location to downtown Annapolis! Beautiful home, well maintained and plenty of room. The porch overlooking the bay has a table for 10 which provided a wonderful setting for our family. This is our second stay and we’ll absolutely stay again "
Charming Annapolis WaterVIEW Home
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.
Beautiful view of the beach with palm trees

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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.