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Check prices for these dates

Next weekend
14 Feb - 16 Feb
In two weeks
21 Feb - 23 Feb
In one month
7 Mar - 9 Mar
In two months
4 Apr - 6 Apr

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

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, (269)
"This property is just steps from Main Street. It was the perfect location for exploring town and enjoying all that Annapolis had to offer during the holiday season. "
Annapolis Condominium in the heart of the historic center
Beautiful Condo - Water View Near City Dock
Front gate of building

Beautiful Condo - Water View Near City Dock

9.6 out of 10, Exceptional, (140)
"I currently live in this complex, and I rented this condo for my parents to come stay a few days while I recovered from surgery. Joe and Beth were extremely accommodating and kept communication with my parents while they stayed (but also didn't bug them!). I was thankful to have such an easy process for my older parents and they are already talking about coming back down again because they enjoyed their stay so much!"
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, (52)
"Chip's place is very well located on West Street. We stayed over Christmas and it was easy to walk to my sister's house on Spa View and super nice to be above the top-notch coffee and baked goods at Curate. The place is perfectly laid out for two people/couples to each have their own space and bathroom. "
Chic Condo w/ Balcony in the Heart of Annapolis!
Prime Viewing for Blue Angels -Rooftop Deck and Water Views of Spa Creek!
View from rooftop deck!

Prime Viewing for Blue Angels -Rooftop Deck and 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."
Prime Viewing for Blue Angels -Rooftop Deck and Water Views of Spa Creek!
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, (8)
"Beautiful historic place and great location and vibe in the heart of downtown. Great beds, nice quality sheets, fun games, stellar wood doors. Wonderful place! 10 stars!"
The price is AED 496
AED 1,312 total
includes taxes & fees
11 Feb - 12 Feb
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
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
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Parking

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

2.0 star property
9.6 out of 10, Exceptional, (4)
"Our 3 night stay was absolutely perfect for our family of six! As a native of the area I was thrilled to be able to come back to my home town and stay right in the heart of downtown Cambridge. There are several restaurants and shops within walking distance and great views of downtown. The space was great, comfortable beds, and modern updates. Our host Jen was responsive and made sure we had everything we needed. We will definitely be back! "
The price is AED 477
AED 1,223 total
includes taxes & fees
11 Feb - 12 Feb
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
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 349
AED 977 total
includes taxes & fees
9 Feb - 10 Feb
Upscale Condo in Historic Downtown Cambridge, Maryland
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, (4)
"This was our 5th trip to North Beach and our 4th time at a condo in Southwinds, and we have never been disappointed. Jenn and Mike, our hosts this time, provided all the information we needed to feel comfortable in their home. We found it exactly as pictured. NB has 5 good restaurants within walking distance and at least 2 more within a 5 minute drive. The boardwalk is great for walking at anytime of day. The new library is a jewel with special sections for all ages and a “makers” room. Teens...
Unbelievable beach views for 6
Available for CW 2025 Walk to Main Street from spacious waterfront Condo w Pool and Parking
Gather around the living with views of the water at Liberty Lookout.

Available for CW 2025 Walk to Main Street from spacious 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!"
Available for CW 2025 Walk to Main Street from spacious waterfront Condo w Pool and Parking
Kent Island Waterfront Cottage
Miscellaneous

Kent Island Waterfront Cottage

9.4 out of 10, Exceptional, (8)
"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
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, (6)
"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, (17)
"I had such a wonderful time in Annapolis celebrating Thanksgiving week with college friends. The location is perfect for anyone that wants to explore Annapolis. The condo was exactly as described, but what was so wonderful were the personal touches. I cannot wait to book this condo again. If I could give 11 stars I would."
Downtown Annapolis Condo w/ Free Parking + Coffee
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
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

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Exterior

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

10.0 out of 10, Exceptional, (32)
"Perfect large space on a quiet and pretty area. Really great space. "
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Exterior

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (38)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
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, (206)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
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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