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

Hotels in Sherwood

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Dates

November 2026

December 2026

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Where to stay in Sherwood?

A marina with boats docked at wooden piers, surrounded by greenery.

1. Knapps Narrows Marina & Inn

Sherwood

$110 total

includes taxes & fees

Nov 5 - Nov 6

A two-story building with a covered entrance and an American flag.

2. St Michaels Inn

St. Michaels

$94 total

includes taxes & fees

Dec 1 - Dec 2

A waterfront property with a covered patio, a dock, and a boat.

3. Wylder Tilghman Island

Tilghman

$273 total

includes taxes & fees

Dec 1 - Dec 2

A two-story house with a porch, a front door, and a small garden area.

4. The Wildset

Downtown St. Michaels

$244 total

includes taxes & fees

Dec 1 - Dec 2

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

5. Inn at Perry Cabin

Downtown St. Michaels

$538 total

includes taxes & fees

Nov 11 - Nov 12

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

6. Parsonage Inn

Downtown St. Michaels

$231 total

includes taxes & fees

Nov 5 - Nov 6

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

7. George Brooks House B&B

St. Michaels

$219 total

includes taxes & fees

Nov 5 - Nov 6

A covered outdoor seating area with brick walls, two potted plants, and a table and chairs.

8. Baymont by Wyndham Easton

Easton

$90 total

includes taxes & fees

Nov 11 - Nov 12

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

9. Holiday Inn Express Easton by IHG

Easton

$149 total

includes taxes & fees

Nov 19 - Nov 20

A modern hotel dining area with a long table, four chairs, and three pendant lights.

10. Hampton Inn Easton

Easton

$144 total

includes taxes & fees

Nov 9 - Nov 10

A hotel room with a sofa, armchairs, a TV, a bed, and a large window.

11. Quality Inn Grasonville near Kent Island

Grasonville

$93 total

includes taxes & fees

Nov 29 - Nov 30

A hotel room with two beds, a desk, a TV, and a window with curtains.

12. Econo Lodge Easton Route 50

Easton

$89 total

includes taxes & fees

Nov 11 - Nov 12

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.

13. The Oaks Waterfront

Easton

$538 total

includes taxes & fees

Nov 8 - Nov 9

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

14. The Tidewater Inn

Easton

$197 total

includes taxes & fees

Nov 22 - Nov 23

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.

15. Fairfield Inn & Suites by Marriott Easton

Easton

$139 total

includes taxes & fees

Nov 15 - Nov 16

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

16. Best Western Plus Easton Inn & Suites

Easton

$131 total

includes taxes & fees

Nov 15 - Nov 16

A hotel room with a bed, a desk, a chair, a large window with curtains, a wall-mounted painting, and a bathtub.

17. Best Western Kent Narrows Inn

Grasonville

$100 total

includes taxes & fees

Nov 10 - Nov 11

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

18. Rod 'N' Reel Resort

Chesapeake Beach

$202 total

includes taxes & fees

Nov 30 - Dec 1

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

19. Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

$112 total

includes taxes & fees

Nov 29 - Nov 30

A multi-story hotel with a central entrance, a landscaped garden with flowers, and a metal sculpture.

20. Anchored Inn at Hidden Harbour Marina

Deale

$204 total

includes taxes & fees

Nov 29 - Nov 30

View all properties

Go beyond your typical stay in Sherwood

Top landmarks in Sherwood

Goat Island

Goat Island is 1.5 mi (2.4 km) from central Sherwood, why not stop by during your stay.

See properties

Learn more about Sherwood

Sherwood is well-known for its attractions such as Knapp's Narrows Marina & Inn and Goat Island.

See all hotels in Sherwood

Check out reviews of Sherwood hotels guests love

Knapps Narrows Marina & Inn

Sherwood

10/10 Exceptional

Stan and Joan

Wylder Tilghman Island

Tilghman

10/10 Exceptional

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

Inn at Perry Cabin

Downtown St. Michaels

10/10 Exceptional

Norm

St Michaels Inn

St. Michaels

10/10 Exceptional

Lori

Parsonage Inn

Downtown St. Michaels

10/10 Exceptional

The Oaks Waterfront

Easton

10/10 Exceptional

The Oaks Waterfront was exactly the kind of getaway we were looking for. Tucked away in a quiet, secluded setting, it feels like you’re escaping from everything, yet St. Michaels is only a short ride away thanks to their beautiful shuttle. It really gives you the best of both worlds. What stood out most to us was the family-owned and operated feel. Everyone was genuinely friendly, and there was a warmth about the property that made it feel less like a hotel and more like staying with incredibly...

Matthew

Fairfield Inn & Suites by Marriott Easton

Easton

10/10 Exceptional

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

George Brooks House B&B

St. Michaels

10/10 Exceptional

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

A lakeside view with sailboats, grassy areas, and white Adirondack chairs.

Sandaway Suites & Beach

Oxford

10/10 Exceptional

joseph

Anchored Inn at Hidden Harbour Marina

Deale

10/10 Exceptional

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 hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

The Inn at Chesapeake Bay Beach Club

Stevensville

10/10 Exceptional

Chuck

A large, two-story barn-style building with a covered front porch and a garage.

Kent Island Resort

Stevensville

10/10 Exceptional

I stayed here for a quick overnight and did not utilize many of the amenities however, the staff was incredibly kind overall and with tips on dinner. This place is historic, which is a nice way of saying old but classic. Don’t expect a huge room, the photos portray the room accurately. Some things were a little rickety, but everything was clean. Overall I recommend this if you’re solo or a couple looking for a place as you enjoy the bay.

John

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

10/10 Exceptional

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

Hampton Inn Easton

Easton

10/10 Exceptional

Anonymous traveler

Best Western Plus Easton Inn & Suites

Easton

10/10 Exceptional

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 hot tub in a grassy area with a building in the background.

The Inn at Tacaro Estate

Tracys Landing

10/10 Exceptional

Tamara

A large, two-story house with a prominent tower and a covered porch.

Hummingbird Inn

Easton

10/10 Exceptional

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

The Tidewater Inn

Easton

10/10 Exceptional

Maria

Frequently Asked Questions

What hotels do travelers recommend in Sherwood?

Guests like Knapps Narrows Marina & Inn and St Michaels Inn.

Can I book a refundable hotel in Sherwood?

If you're looking for the flexibility to change your plans to Sherwood, most properties offer refundable* bookable rates. You can find these properties by searching our site and using the "fully refundable" filter to narrow down the results.

Where can I stay in Sherwood if I want a vacation home instead of a traditional hotel?

You'll find 6 vacation homes on our site.

What will the weather in Sherwood be like during my vacation?

The warmest months in Sherwood are usually July and August with an average temp of 75°F. January and February are the chilliest months when the average temp is 41°F. The rainiest months are August and October.

Why should I book my Sherwood accommodation with Hotels.com?

There are plenty of reasons to book your Sherwood travel with us: our free cancellations on selected hotels* gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.