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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$727
includes taxes & fees
6 Nov - 7 Nov
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, (4)
"Great location! Lots of extra items . "
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$541
includes taxes & fees
6 Nov - 7 Nov
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, (264)
"Great location, clean, excellent communication with owner. Everything we needed for a perfect trip to Annapolis."
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!"
The price is AU$499
includes taxes & fees
7 Nov - 8 Nov
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, (136)
"The location was great with lots of restaurants and bars within walking distance. We came to see the Halloween concert at USNA and the condo is in the best location to walk Eastport and old town Annapolis. I chose this condo because of the rooftop (although we didn't take advantage of it) and the easy parking. I would recommend this property."
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, (48)
"Our accommodations were very clean. We’re 4 Senior Citizens using canes so we were thankful for the elevator and the parking spot in the garage. We did feel that the bathrooms were lacking in facilities to hang robes, clothing and wet towels and wash cloths. In the second bathroom it was difficult to get into the tub to shower because there were no safety rails. The beds were very comfortable and we made good use of the ceiling fans. The entrance into and out of the garage was difficulty...
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, (2)
"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$565
includes taxes & fees
19 Nov - 20 Nov
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 Gate One & Steps from the Waterfront
Miscellaneous
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (200)
"Incredible location! The process was easy and the house completely suited our needs! We would definitely stay again!"
Directly Across from Gate One & Steps from the Waterfront
Charming Annapolis WaterVIEW Home
Outdoor dining
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (48)
"This house was perfect for our group of friends especially with infants. Easy check in, comfortable beds and room for pack and plays. Water view is amazing. Definitely worth the rent and would be interested in coming back!"
Charming Annapolis WaterVIEW Home
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Exterior
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (202)
"This was a lovely home. I especially appreciated how clean and well-stocked it was. Liz and Tom were very responsive and accommodating! This truly added to a wonderful reunion weekend with friends and family. Thank you!"
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
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.

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.