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Compare 15 Condo Rentals in Sherwood with updated reviews, rates, and availability.

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

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 AED 826
AED 1,733 total
includes taxes & fees
28 Nov - 29 Nov
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Parking

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 AED 624
AED 1,413 total
includes taxes & fees
16 Dec - 17 Dec
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Annapolis Condominium in the heart of the historic center
Deck view

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!
Colorful nautical decor and comfy sofa bed. Unit is not water view.

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!
Waterfront 2-Bedroom Condo on Spa Creek
Brand new kitchen combines white and color for a fun vibe

Waterfront 2-Bedroom Condo on Spa Creek

10.0 out of 10, Exceptional, (5)
"Our unit was comfortable and clean with all the amenities. We loved the outside space overlooking the Bay Area. It was only a very short drive or 15 min walk to all the restaurants and shops. We will return!"
Waterfront 2-Bedroom Condo on Spa Creek
Downtown Annapolis Condo w/ Free Parking + Coffee
Living area

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
Gather around the living with views of the water at Liberty Lookout.

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
Front gate of building

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!
Annapolis Vacation Rental | 2BR | 2BA | 991 Sq Ft | Step-Free Access

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
Miscellaneous

Kent Island Waterfront Cottage

9.2 out of 10, Wonderful, (7)
"My husband and I stayed here for a quick weekend getaway to celebrate our anniversary. We appreciated the host being able to accommodate us an earlier check in and later check out time to maximize our short time away. They only charged us a small fee. The place was clean. So clean that I didn't feel I needed to wipe anything down, which is usually the case when we go to other places. The view was stunning and we had nice weather. We loved being able to walk out onto the dock as well as sit out...
Kent Island Waterfront Cottage
Water-view condo with rooftop pool & balcony - minutes from downtown

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
Upscale Condo in Historic Downtown Cambridge, Maryland
The property is located in the heart of historic downtown Cambridge

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 AED 606
AED 1,281 total
includes taxes & fees
3 Dec - 4 Dec
Upscale Condo in Historic Downtown Cambridge, Maryland
Delightful little Historic District gem - for the antique lover and history buff.
View from entrance into living room and kitchen

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
You can't get much closer to the Chesapeake Bay than this 2-bed/1-bath gem that sleeps 6!

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
A Kozy Waterfront Condo
Property grounds

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!
Private rear courtyard

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
Charming Cottage on a quite creek of the Chesapeake Bay with private pool.

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
3 covered balconies, a ground floor patio, and ceramic and propane grills.

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.

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