Sherwood Vacation Rentals from AED 330: Search Short-Term Rentals

A large brick house with a green roof, surrounded by lush gardens and trees.

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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 4 Bedroom Home w/Waterview

Stevensville

Anthony P.

AED 1,068 total

includes taxes & fees

15 Nov - 16 Nov

A wooden deck with red railings, surrounded by lush green trees.

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

Deale

Maude H.

AED 1,154 total

includes taxes & fees

15 Nov - 16 Nov

A marina with boats docked, a city skyline in the background, and a calm water surface reflecting the lights.

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

Stevensville

Michael V.

AED 1,206 total

includes taxes & fees

23 Nov - 24 Nov

A rocky shoreline with a pier extending into calm waters.

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

North Beach

Johanna S.

AED 1,177 total

includes taxes & fees

1 Dec - 2 Dec

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

5. 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

AED 1,604 total

includes taxes & fees

13 Nov - 14 Nov

An outdoor patio with a round table and chairs, a yellow umbrella, and a wooden deck.

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

North Beach

James L.

AED 1,137 total

includes taxes & fees

15 Nov - 16 Nov

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

7. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

Shady Side

"the house was clean and fully stocked with all linens. there are some staples in the refrigerator and cabinets. All cookware and eatery are provided. there is only one grocery store in the area, so plan ahead. Fast food is not readily available. Nick responded quickly and thoroughly to all messages, that was great. It's a quiet neighborhood. It was the perfect place for a family and pet. we will return"

Jenny A.

AED 1,323 total

includes taxes & fees

16 Nov - 17 Nov

A beach with a canopy, lounge chairs, and a table. Boats are visible in the water.

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

North Beach

Sarah

AED 1,671 total

includes taxes & fees

16 Nov - 17 Nov

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

9. Sunset Cottage - West River Access and Views!

Shady Side

Michelle H.

AED 1,601 total

includes taxes & fees

1 Dec - 2 Dec

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

10. Cass-N-Reel Luxury Houseboat

Grasonville

Yamilet

A hammock and swing set by a lake with a clear sky.

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

Cambridge

Jill C.

AED 1,844 total

includes taxes & fees

19 Nov - 20 Nov

12. Family Beach House: Spacious Deck, Grill & Views

Chesapeak beach

Ben W.

AED 1,404 total

includes taxes & fees

2 Dec - 3 Dec

A sandy beach with lounge chairs and a small pond.

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

Arundel on the Bay

Ryan C.

AED 1,734 total

includes taxes & fees

16 Nov - 17 Nov

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

14. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

Stevensville

Anonymous traveler

AED 3,679 total

includes taxes & fees

14 Nov - 15 Nov

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

Easton

Lynn G.

AED 1,476 total

includes taxes & fees

16 Nov - 17 Nov

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

16. 2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

Cambridge

AED 954 total

includes taxes & fees

13 Nov - 14 Nov

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

17. Cambridge Apt in Walkable Neighborhood

Cambridge

LOIS

AED 1,185 total

includes taxes & fees

14 Nov - 15 Nov

A beach with a wooden fence and a pier in the distance.

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

Stevensville

Sam C.

AED 4,552 total

includes taxes & fees

1 Dec - 2 Dec

19. Cambridge Apt in Walkable Neighborhood

Cambridge

Anonymous traveler

AED 1,146 total

includes taxes & fees

14 Nov - 15 Nov

A modern kitchen with white cabinets, a microwave, and a sink. There is a dining area with a wooden table and chairs.

20. Family Home on Mayo Peninsula | Deck | Sleeps 10

Edgewater

Kristin G.

AED 2,471 total

includes taxes & fees

13 Nov - 14 Nov

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Find vacation rentals that suit your style

Top Sherwood Hotel Reviews

A marina with several boats docked, a building with multiple levels, and a calm water surface reflecting the structures.

Knapps Narrows Marina & Inn

Sherwood

10/10 Excellent

Stan and Joan

A wooden sauna with a central heating unit, two benches with towels, and a small table with bottles and a container.

Wylder Tilghman Island

Tilghman

10/10 Excellent

We had a great time at the Wylder Inn on Tilghman Island (20-21 May). This is a great spot for a quick getaway, and there are many things to do on site and in the area if you want to stay longer. The staff was welcoming and responsive from our arrival to departure when our key was collected from our car so we didn't have to get out in the rain. The Continental Breakfast had a variety of items to start the day right and the fire pits provided a relaxing venue at the end of the day. We look...

Alan

A room with a fireplace, a dining area with chairs, a large window with a view of the outside, and a cabinet with bottles.

Inn at Perry Cabin

Downtown St. Michaels

10/10 Excellent

Norm

A two-story house with a front porch, white siding, and a black front door.

The Oaks Waterfront

Easton

10/10 Excellent

William

A Victorian-style building with a prominent tower, a porch with outdoor seating, and a sign indicating it is a bed and breakfast.

Parsonage Inn

Downtown St. Michaels

10/10 Excellent

A beach with clear water, sandy shore, and some vegetation.

Sandaway Suites & Beach

Oxford

10/10 Excellent

joseph

A modern lobby with a stone fireplace, a blue patterned rug, a blue sofa with colorful cushions, a brown leather chair, and a round coffee table.

Fairfield Inn & Suites by Marriott Easton

Easton

10/10 Excellent

The Fairfield Inn on US50 has become our go-to mid-range hotel in Easton. We have stayed here several times in recent years, and once again had a great experience during this Christmas stay. The facilities are clean and in good condition. The staff is friendly, welcoming, and accommodating. When I booked our stay this time through a third-party, I got a little confused about room options, and took the only king-bed room that I saw. The manager didnt know I had any concerns, and when the staff...

Richard

A two-story house with a swimming pool, outdoor seating, and a covered patio area.

George Brooks House B&B

St. Michaels

10/10 Excellent

Excellent B&B with a pool! the pool was clutch because we were there probably on the hottest days of the year so going in after a long day of walking around was nice. Used the pool until 10pm. Food was good, room was clean, people were nice. What else could you ask for. The only thing I noticed (and it wasn't a big deal) was the mirror in the room was too low on the wall (I'm 5'8 and still had to bend a little) and there was only one mirror so if you're in a hurry getting ready with your spouse...

Anonymous traveler

An indoor swimming pool with lounge chairs and a no diving sign.

Holiday Inn Express Easton by IHG

Easton

10/10 Excellent

Belinda

A modern kitchen with a large island, bar stools, and a wine rack.

Anchored Inn at Hidden Harbour Marina

Deale

10/10 Excellent

We needed overnight accommodations before heading out for a day of sailing on the bay and Hidden Harbour popped up as the closest venue geographically and we're glad it did. The accommodations are new, with quality and fixtures and bathrooms that you wouldn't mind taking home with you. The price seemed fair and as we watched the full moon rising from our deck we wished that we were spending a week.

Rico

A lobby with a fireplace, multiple seating areas, a television, and framed pictures on the walls.

Hampton Inn Easton

Easton

10/10 Excellent

Anonymous traveler

A group of people toasting at a round table in a room with large windows and artwork on the walls.

Hummingbird Inn

Easton

10/10 Excellent

My wife and I were celebrating our 15th anniversary and the Hummingbird Inn was the perfect relaxing and romantic getaway. Eric and Michael are gracious and accommodating hosts. The Inn is gorgeous. Our room was elegant yet comfortable. There are plenty of restaurants within walking distance and lots of cool shops to check out. I also want to throw a shout out to Storm and Daughters Ice Cream which we walked to after dinner because it’s maybe the best ice cream we’ve ever had. Then back to the...

Robert

A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.

Best Western Plus Easton Inn & Suites

Easton

10/10 Excellent

Everything was good with checkin ,check out, and the room. The only complaint I can voice is with the breakfast service attendant. She was not very warm or inviting, did not speak to guest. She did have everything out and the area clean, but at the end of breakfast time, she removed all plates and bowls first so no one could get anything else to eat. We were late eating on our 3rd morning, but were in time to get our food before she started putting away. But then put chairs on the tables so...

Nancy

A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.

St Michaels Inn

St. Michaels

10/10 Excellent

Lori

Two Adirondack chairs facing a calm body of water with a clear sky above.

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

10/10 Excellent

The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...

Christina

A large, multi-story building with a prominent red cylindrical tower, a covered patio area, and a well-maintained garden.

The Inn at Chesapeake Bay Beach Club

Stevensville

10/10 Excellent

Chuck

A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.

Rod 'N' Reel Resort

Chesapeake Beach

10/10 Excellent

Huge resort in a small, well kept town! Our room was right on the bay and was clean and nice. The beds and pillows were super comfortable. There is not a place for breakfast but if you go a little further south on the main road, there is a shopping center with a McDonalds (and a CVS and some other things)... We were in a hurry to get home so did not try any of the breakfast places that the desk clerk recommended. The staff guy that checked us in was SUPER nice and helpful!

Kathie

A large, stately house with a grand entrance, multiple windows, and a symmetrical facade.

The Tidewater Inn

Easton

10/10 Excellent

Maria

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.

Sherwood Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Sherwood vacation rentals

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

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

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

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

5. 3-bedroom house in Deale located on Bay many amenities and great views

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

7. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

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

9. Sunset Cottage - West River Access and Views!

10. Cass-N-Reel Luxury Houseboat

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

12. Family Beach House: Spacious Deck, Grill & Views

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

14. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

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

16. 2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

17. Cambridge Apt in Walkable Neighborhood

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

19. Cambridge Apt in Walkable Neighborhood

20. Family Home on Mayo Peninsula | Deck | Sleeps 10

Find vacation rentals that suit your style

Top Sherwood Hotel Reviews

Knapps Narrows Marina & Inn

10/10 Excellent

Frequently Asked Questions

Can I find a vacation rental in Sherwood?

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

How many vacation rentals will I find in Sherwood?

What can I see and do in Sherwood?

What are vacation rentals like in Sherwood?

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