Sherwood Vacation Rentals from $280: Search Short-Term Rentals

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Our top choices for Sherwood vacation rentals

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

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

Stevensville

Anthony P.

$271 nightly

Nov 1 - Nov 2

Total with taxes and fees

A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

2. The Cozy Crab- Your Charming Haven in Lovely North Beach!

North Beach

James L.

$293 nightly

Nov 23 - Nov 24

Total with taxes and fees

A house with a yellow door and a window with a lamp outside.

3. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Deale

Maude H.

$307 nightly

Nov 15 - Nov 16

Total with taxes and fees

A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

4. Beachside Oasis with Beach Passes & King Suite by A Haven Away

North Beach

Johanna S.

$319 nightly

Nov 1 - Nov 2

Total with taxes and fees

An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

5. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

North Beach

Sarah

$427 nightly

Oct 30 - Oct 31

Total with taxes and fees

A lighthouse with a white exterior, a balcony, and a metal roof.

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

Stevensville

Michael V.

$299 nightly

Nov 2 - Nov 3

Total with taxes and fees

A waterfront patio with outdoor seating and umbrellas, overlooking a river with boats and a bridge in the background.

7. Cass-Away Luxury Houseboat

Grasonville

Jamie L.

A living room with a sofa, coffee table, fireplace, and artwork on the wall.

8. 3-bedroom house in Deale located on Bay many amenities and great views

Deale

"Everything at this location was as shown on the listing and it was very clean. We were very satisfied with all elements of this stay. We were there for a weekend and did not use the place heavily, but it suited our needs. It's a quiet location. They had all the major points covered. The only negative comment I have is that the water out of the tap was smelly. I suggest bringing a couple of bottles of water and not drinking the water out of the taps. This is obviously a well maintained home...

Amelia

$383 nightly

Oct 28 - Oct 29

Total with taxes and fees

A deck with outdoor furniture, a red door, and a house with windows.

9. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

Shady Side

David S.

$333 nightly

Nov 18 - Nov 19

Total with taxes and fees

A deck with a view of a marina, including boats and docks.

10. Cass-N-Reel Luxury Houseboat

Grasonville

Yamilet

$254 nightly

Nov 12 - Nov 13

Total with taxes and fees

A dining area with a wooden spiral staircase, a round table with chairs, a chandelier, and a clock on the wall.

11. Rose Haven Coastal Cottage

North Beach

Sodbileg

A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

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

Cambridge

Jill C.

$440 nightly

Oct 29 - Oct 30

Total with taxes and fees

A living room with two grey sofas, a coffee table, and a ceiling fan.

13. Cambridge Apt in Walkable Neighborhood

Cambridge

LOIS

$291 nightly

Oct 28 - Oct 29

Total with taxes and fees

A beach with chairs and a pier in the background.

14. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Arundel on the Bay

Ryan C.

$422 nightly

Nov 3 - Nov 4

Total with taxes and fees

A modern kitchen with a large window, a dishwasher, and a ceiling fan.

15. Sunset Cottage - West River Access and Views!

Shady Side

Michelle H.

$443 nightly

Nov 4 - Nov 5

Total with taxes and fees

A two-story house with a red roof, a brick chimney, and a small porch.

16. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

Stevensville

"The house was clean. It is clear someone lives there full time and vacated the house for our stay. Their food and clothes remained in the property. It did not bother us, but not something we expected. The AC worked well. The owner communicated there were issues before we arrived that they were working to fix and left the number of the contractor in case we experienced issues. We were there the hottest weekend so far this year and did not have any issues. It does look like they are still...

Michele F.

$994 nightly

Oct 29 - Oct 30

Total with taxes and fees

17. EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places

Easton

Lynn G.

$400 nightly

Nov 2 - Nov 3

Total with taxes and fees

18. Cambridge Apt in Walkable Neighborhood

Cambridge

Anonymous traveler

$296 nightly

Oct 28 - Oct 29

Total with taxes and fees

A lakeside view from a deck with a wooden railing, a sandy area with a boat, and a dock extending into the water.

19. 2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

Cambridge

$257 nightly

Oct 28 - Oct 29

Total with taxes and fees

Three birds perched on a wooden structure by the water.

20. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Stevensville

barbara s.

$1,200 nightly

Oct 28 - Oct 29

Total with taxes and fees

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Top Sherwood Hotel Reviews

Baymont by Wyndham Easton

8/10 Good

"Hotel is very run down but is in the process of renovation. Rooms are in need of paint and bathrooms need grout cleaning. Refrigerator only had 3 legs! No safety rail in shower. Door to bathroom very tight and fittiing is wrong. Dining area for breakfast was renovated and very nice."

Best Western Annapolis

8/10 Good

"The room and lobby were incredibly clean. The staff was pleasant and helpful. Overall pleased with the stay. Only downside was that the flush lever of the toilet would get stuck on the lid of the tank. And the chain to the flapper valve likely needs to be shortened. Once I adjusted the lever and tank lid the problem was corrected."

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 $280 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.

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?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: Visitors like this Sherwood vacation home rental. It is located near the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease 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. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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.

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Check prices for these dates

Our top choices for Sherwood vacation rentals

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

2. The Cozy Crab- Your Charming Haven in Lovely North Beach!

3. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

4. Beachside Oasis with Beach Passes & King Suite by A Haven Away

5. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants