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Compare 16 Condo Rentals in Sherwood with updated reviews, rates, and availability.

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, (46)
"Great apartment, so clean and comfortable! Felt right at home. The hosts are wonderful and very responsive with any questions. Convenient location, would definitely stay again!"
Chic Condo w/ Balcony in the Heart of Annapolis!
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, (1)
"We had a great stay at North Beach. Quiet and relaxing which is what we were looking for. Jen and Mike were great hosts. Communication was excellent. We will be back again soon. "
Unbelievable beach views for 6
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, (259)
"We had a wonderful stay, our second at this prime location in the heart of downtown Annapolis. Host was exceptional, and we look forward to future stays! Thanks again!"
Annapolis Condominium in the heart of the historic center
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
10.0 out of 10, Exceptional, (2)
"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 AED 606
AED 1,285 total
includes taxes & fees
8 Oct - 9 Oct
Upscale Condo in Historic Downtown Cambridge, Maryland
Beautiful Condo - Water View Near City Dock
Front gate of building
Beautiful Condo - Water View Near City Dock
9.6 out of 10, Exceptional, (135)
"This is our second time at this property and it is just perfect for us. Quiet, great location, comfortable, great host!!!!"
Beautiful Condo - Water View Near City Dock
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, (2)
"This location is perfect to walk or enjoy the water taxi to City Dock! The only thing I wish I knew ahead of time was the pool hours. I would have liked if they were open more often. The condo was beautiful and had everything we needed to enjoy our stay. Would definitely consider going back! "
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
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Parking
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
2.0 star property
8.0 out of 10, Very Good, (1)
"Third floor walk up that makes quite an impression when you open the door. Very high ceilings in an open concept living space which makes it feel so grand when in it. The massive doors have stunning brass fittings and trim which I have never seen before. The kitchen is spacious and well appointed. The beds comfy Towels fresh and soft. Massive windows add to the openness of the space. Everything is walking distance to the charming town center. Parking is included. We would definitely...
The price is AED 551
AED 1,335 total
includes taxes & fees
1 Oct - 2 Oct
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Pool, Parking and Walk to Main Street from Waterfront Condo
Gather around the living with views of the water at Liberty Lookout.
Pool, Parking and Walk to Main Street from Waterfront Condo
10.0 out of 10, Exceptional, (11)
"From the property manager to the property itself, this rental and all of the amenities are a 10/10. The Eastport location provides an exquisite view of the water as well as walking distance to upscale restaurants. A 10 to 15 minute walk to downtown Annapolis as well. An unforeseen circumstance caused for us not to complete our stay but this property will be on my list for future trips to come. Go Navy!"
Pool, Parking and Walk to Main Street from Waterfront Condo
Eastport Condo in Building with Rooftop Water Views of Spa Creek!
View from rooftop deck!
Eastport Condo in Building with Rooftop Water Views of Spa Creek!
10.0 out of 10, Exceptional, (7)
"Perfect place to hang out and then walk/uber to DTA! Really enjoyed our stay. "
Eastport Condo in Building with Rooftop Water Views of Spa Creek!
Kent Island Waterfront Cottage
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
Luxury Waterfront home with private pier and guest house
View of main house and pool house (pool closed Oct-May)
Luxury Waterfront home with private pier and guest house
10.0 out of 10, Exceptional, (4)
"We loved our stay - the home was beautiful. We really appreciated the antique artwork, beautiful views, deck, pool, and convenient location in Annapolis. Plenty of space and things to entertain everyone!"
Luxury Waterfront home with private pier and guest house
Water-view condo with rooftop pool & balcony - minutes from downtown
Water-view condo with rooftop pool & balcony - minutes from downtown
9.0 out of 10, Wonderful, (8)
"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.
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.
A Kozy Waterfront Condo
Property grounds
A Kozy Waterfront Condo
A Kozy Waterfront Condo
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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

Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Grill no longer works
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
9.8 out of 10, Exceptional, (83)
"The house was clean and comfortable. Walking distance to a local restaurant. Screened porch was great for watching the sunrise in the morning and the boats coming in and out of harbor "
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Waterfront Cottage on the Eastern Shore
Exterior
Waterfront Cottage on the Eastern Shore
9.6 out of 10, Exceptional, (7)
"We rented the house for the weekend and to host a surprise birthday party. We had the party right at the beach and the host/concierge were able to help us with everything we needed. They really went out of their way for us, and it made a huge difference in the party’s success! Plus, you can’t beat the view and the Chesapeake Bay sunsets !!"
The price is AED 1,282
AED 3,008 total
includes taxes & fees
1 Oct - 2 Oct
Waterfront Cottage on the Eastern Shore
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, (212)
"As always our stay was amazing from kayaking, bird watching, sunsets. The cove is a special place."
Relaxing Waterfront Cottage Near St Michaels, Maryland
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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