Sherwood Vacation Rentals from ￥56,594: Search Short-Term Rentals

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Our top choices for Sherwood vacation rentals

Charming Coastal/Country Home w/3 Acres & Sauna!

Stevensville

Handy M.

￥44,955 total

includes taxes & fees

Jun 9 - Jun 10

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Downtown Cambridge

Sylvie G.

￥81,413 total

includes taxes & fees

Jun 8 - Jun 9

Sailwinds Loft at Cambridge Creek

Cambridge

Lee P.

￥40,707 total

includes taxes & fees

Jun 8 - Jun 9

Waterfront Getaway with Dock

Woolford

Matt S.

￥42,911 total

includes taxes & fees

Jun 7 - Jun 8

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Downtown Cambridge

Kristen S.

￥77,682 total

includes taxes & fees

Jun 8 - Jun 9

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge

Traci C.

￥79,548 total

includes taxes & fees

Jun 8 - Jun 9

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville

"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."

Brian

￥56,594 total

includes taxes & fees

Jun 22 - Jun 23

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Grasonville

Robin

￥66,997 total

includes taxes & fees

Jun 8 - Jun 9

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Top Sherwood Hotel Reviews

Historic Inns of Annapolis

8/10 Good

"Loved the location. Place was historic and beautiful"

Hampton Inn & Suites Annapolis

10/10 Excellent

"Had a great overall experience! Great staff, a/c and clean facility/rooms I had an issue, with my first room, where the toilet would not flush correctly and missing tv remote, but Cherise (front desk) quickly gave me to option to move to a different room, which I did In addition, great communication from staff when checking in via text messaging service about the 1st (bathroom) issue. She had an engineer staff come up within 5min to try and fix the issue, but was not able to Overall, I had a great experience and I would return again"

The Wildset

10/10 Excellent

"My husband and I stayed here one night to celebrate his birthday. The hotel was beautiful and so convenient to everything. The room was immaculate with comfortable bedding, beautiful bathroom and wonderful amenities. Loved the breakfast and staff were efficient and informative about places to see in the area. The garden area and fire pit were a bonus. Park your car in the off street lot and explore beautiful St. Michael’s. Can’t wait to come back."

Rod 'N' Reel Resort

6/10 Okay

"Beautiful setting on the Chesapeake!! Stunning property!! BUT... management needs to instruct their staff who relate to the customers on protocol and service. I experienced it on several levels from check in, to dinning, to the bar, and even asking for directions related to where things were at the hotel. Albeit I'm back 3 weeks later w my wife to buy a boat, and staying at Rod and Reel because of the property, w no expectations on staff treatment towards their guests. Which is why 3 stars and not 1 star"

Hilton Garden Inn Annapolis Downtown

6/10 Okay

"While the staff were very pleasant and helpful—the physical property has seen better days. Our first room had a leaking shower and a non-working refrigerator. We were moved to a different room without question. This room was laid out a little better. But, both rooms had the a/c & heat vents right next to the bed. We had to turn the system off at night so the cold air wouldn’t blast onto the person on that side of the bed."

Find out more about Sherwood

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Frequently asked questions

Can I find a vacation rental in Sherwood?

Yes, you can find vacation rentals close to popular attractions in Sherwood, or you can go with a more secluded option if you'd like a relaxing place to stay. Sherwood is known for its waterfront and restaurants.

What are some of the best vacation rentals that Sherwood has to offer?

Lovely bay views with kayaks, bikes, fire pit, crabbing & more: Visitors like this Sherwood vacation home rental. It offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Sherwood?

With 6 Expedia vacation rentals, you're sure to find just the right place for your Sherwood stay.

What can I see and do in Sherwood?

While exploring the area, visit family-friendly sights like Chesapeake Bay Maritime Museum, or get outside and enjoy nature at Goat Island. In the larger area, you’ll find Knapp's Narrows Marina & Inn and Tilghman Watermen’s Museum.

What are vacation rentals like in Sherwood?

Vacation rentals are privately owned accommodations you can stay in for several days or longer in Sherwood. Vacation rentals offer extras such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from shared hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for families.

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Check prices for these dates

Our top choices for Sherwood vacation rentals

Charming Coastal/Country Home w/3 Acres & Sauna!