Sherwood Vacation Rentals from $266: Search Short-Term Rentals

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

Private 2 Acre Waterfront Family Retreat with Pool & Pier : Visitors like this Sherwood vacation home rental. It is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 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 books.

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In two weeks

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Our top choices for Sherwood vacation rentals

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

Grasonville

Joe C.

$397 nightly

Mar 19 - Mar 20

Total with taxes and fees

WATERFRONT!! HOT TUB 3 bedroom Oasis on 2+ acres - Sleeps 8

Cambridge

Jill C.

$497 nightly

Mar 19 - Mar 20

Total with taxes and fees

Sailwinds Loft at Cambridge Creek

Cambridge

Lee P.

$240 nightly

Mar 19 - Mar 20

Total with taxes and fees

Waterfront Getaway with Dock

Woolford

Matt S.

$263 nightly

Mar 19 - Mar 20

Total with taxes and fees

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

Downtown Cambridge

Sylvie G.

$373 nightly

Mar 23 - Mar 24

Total with taxes and fees

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Downtown Cambridge

John S.

$355 nightly

Mar 25 - Mar 26

Total with taxes and fees

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge

Traci C.

$362 nightly

Mar 23 - Mar 24

Total with taxes and fees

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Shady Side

Thomas D.

$395 nightly

Mar 19 - Mar 20

Total with taxes and fees

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Top Sherwood Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

6/10 Okay

"Size of the room was nice we stayed in a king suite we had room to get dressed and not crash into each other. We also went to the gym it was small but four people were able to work out at the same time if two are on the machines for cardio. The store was great and check in was easy the parking on the side was helpful. Comfy bed. We didn’t have a smart tv so no Netflix but some good movies were on. "

Hyatt Place Kent Narrows & Marina

10/10 Excellent

"This hotel were one of the best, I have stayed at numerous Hyatt regencies and all of them makes the grade. But this Hyatt with the view of the river puts it over the top. The staff was very nice and very knowledgeable and also very helpful. I recommend Hyatt hotels in general but I especially recommend this Hyatt in Kent Narrows "

Graduate by Hilton Annapolis

10/10 Excellent

"The hotel has cute and trendy decor. It’s located centrally nearby many restaurants and coffee shops around. Our room was clean and spacious. Check in was easy and on point. We had no issues with this hotel. This is my second Graduate hotel that I’m staying in and they are very efficient. "

Rod 'N' Reel Resort

2/10 Terrible

"Have to walk clear through the hotel through the lobby to get to the pool. No microwaves in rooms. Only 1 shared old one next to the ice machine. Room floors were dirty. Staff was extremely rude. They were horrible to deal with. Was to scared to go into the casino. Mostly non -guest were using the casino, yelling cussing, playing 3 machines at once. Men sexually harassing women. No employees to help you cash out. I would never waste my money on this place again. "

Find out more about Sherwood

Everything you need to know about Sherwood vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sherwood vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sherwood vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sherwood vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sherwood. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Sherwood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $266 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sherwood rentals

At Expedia, we put the best Sherwood vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Sherwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sherwood vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sherwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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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?

Private 2 Acre Waterfront Family Retreat with Pool & Pier: Visitors like this Sherwood vacation home rental. It is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 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 books.

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 St. Michaels Winery.

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.

Room 1

Check prices for these dates

Our top choices for Sherwood vacation rentals

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