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Check prices for these dates

Next weekend
14 Rab. I - 16 Rab. I
In two weeks
21 Rab. I - 23 Rab. I
In one month
4 Rab. II - 6 Rab. II
In two months
2 Jum. I - 4 Jum. I

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

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, (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
Outdoor dining

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!
Interior

Chic Condo w/ Balcony in the Heart of Annapolis!

9.8 out of 10, Exceptional, (53)
"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!
Pool

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
Exterior

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 SAR 488
SAR 1,316 total
includes taxes & fees
4 Mar - 5 Mar
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
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
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Property grounds

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

2.0 star property
9.8 out of 10, Exceptional, (6)
"This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. "
The price is SAR 488
SAR 1,248 total
includes taxes & fees
4 Mar - 5 Mar
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
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 SAR 375
SAR 1,018 total
includes taxes & fees
4 Mar - 5 Mar
Upscale Condo in Historic Downtown Cambridge, Maryland
Unbelievable beach views for 6
Property grounds

Unbelievable beach views for 6

2.0 star property
10.0 out of 10, Exceptional, (5)
"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
Point of interest

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
Beach

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
Interior

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
Property grounds

Downtown Annapolis Condo w/ Free Parking + Coffee

10.0 out of 10, Exceptional, (19)
"Great condominium at a great location. Reserved parking. We were impressed with the owners’ approach—a lot of very nice small details. Beautifully decorated. "
Downtown Annapolis Condo w/ Free Parking + Coffee
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.
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

Cozy Cottage with access to and partially obstructed views of the bay.
Miscellaneous

Cozy Cottage with access to and partially obstructed views of the bay.

9.4 out of 10, Exceptional, (18)
"My wife and I stayed two nights to visit family. Cottage was as described, very roomy and comfortable. Great location. Host was very kind. Only dislike was smell from oil heat, I've never had oil heat and not sure if that is normal."
Cozy Cottage with access to and partially obstructed views of the bay.
Cass-N-Reel Luxury Houseboat
Smart TV

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (21)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat
Sweet Bamboo Beach Cottage
Fridge, microwave, oven, stovetop

Sweet Bamboo Beach Cottage

9.8 out of 10, Exceptional, (70)
"Couldn’t be happier with our stay. The house was exactly as pictured. Neighborhood was quiet with a small town feel. Most of the major appliances appeared relatively new, the beds were comfortable and the house was staffed with an abundance of linens and towels. Front and back yards are completely fenced in which is perfect for those with small dogs. North Beach is only a short drive from College Park, Baltimore and Annapolis. Check in was a breeze. Would definitely consider staying there...
Sweet Bamboo Beach Cottage
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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