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Check prices for these dates

Next weekend
11 Rab. II - 13 Rab. II
In two weeks
18 Rab. II - 20 Rab. II
In one month
2 Jum. I - 4 Jum. I
In two months
30 Jum. I - 1 Jum. II

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

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. "
The price is SAR 484
SAR 1,227 total
includes taxes & fees
29 Apr - 30 Apr
Downtown Annapolis Condo w/ Free Parking + Coffee
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
Book for CW 2025 Walk to Main Street restaurants and shops from waterfront Condo w Pool and Parking
Point of interest

Book for CW 2025 Walk to Main Street restaurants and shops from waterfront Condo w Pool and Parking

10.0 out of 10, Exceptional, (15)
"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!"
Book for CW 2025 Walk to Main Street restaurants and shops 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, (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
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!
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, (55)
"We have stayed in this building 3 times, and the location and the set up of the units are excellent. The complex is safe, quiet and is in a great location. It also is very accessible for handicap and having a secure parking spot is advantageous. "
Chic Condo w/ Balcony in the Heart of Annapolis!
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 450
SAR 1,113 total
includes taxes & fees
10 Apr - 11 Apr
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, (6)
"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
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
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 525
SAR 1,368 total
includes taxes & fees
6 Apr - 7 Apr
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
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 1,245 total
includes taxes & fees
6 Apr - 7 Apr
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Waterfront 2-Bedroom Condo on Spa Creek
Interior

Waterfront 2-Bedroom Condo on Spa Creek

10.0 out of 10, Exceptional, (7)
"This is a great location. Walking distance to everything. Near all the sailing clubs! Property manager was the best we have ever experienced."
Waterfront 2-Bedroom Condo on Spa Creek
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
Unique 2-Bedroom Condo in Renovated Church Parish House
Point of interest

Unique 2-Bedroom Condo in Renovated Church Parish House

Unique 2-Bedroom Condo in Renovated Church Parish House
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
Sun loungers, beach towels

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

10.0 out of 10, Exceptional, (33)
"The Chesapeake Mansion was even better than it looks on the VRBO listing. Huge house but still managed to feel warm and inviting, never cold or stand-offish. We cooked big dinners for our group of 12 and the kitchen was perfect for that. Billiards room was fun, amazing bar room, also an exercise room. Walking out on the dock was always a treat. With 12 people, folks could always find a place to chill out when they wanted, but we also had big rooms where we could all get together for chatting and...
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (210)
"We loved our visit to Annapolis, and our stay at 10 Randall was all that we’d imagined it would be.We wish the weather has been a tad warmer, but I don’t think John could have fixed that .We highly recommend this charming home."
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Outdoor dining

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (180)
"This house was so cozy yet spacious! The house was amply stocked with just about everything you would want or need. The owner responded to our inquiries immediately! I hope we go back there again! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
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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