Search Cottages in Sherwood

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Cottages in Sherwood

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (50)
"Beautiful home with LOTS of attention to detail. The backyard was a beautiful oasis and we LOVED the “swing bed” on the screened-in porch. Mark and Karen add lots of fine touches to make your stay special. Plenty of room for two, cozy for four, and comfortable for four legged friends with the fenced in back yard. Quiet and private with a short 10 minute drive to town. Can’t wait to return!"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (224)
"We had a lovely stay here.Place was VERY clean.Visited St. Michael’s and relaxed on the porch & pier.It met our expectations."
Relaxing Waterfront Cottage Near St Michaels, Maryland

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (184)
"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Waterfront property with private boat ramp and new dock!

9.4 out of 10, Exceptional, (13)
"Thoroughly enjoyed our stay! Cottage was comfortable and very clean with everything we could have needed! "
Waterfront property with private boat ramp and new dock!

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

10.0 out of 10, Exceptional, (11)
"The home was so well appointed and walking distance to stores, restaurants, quaint museums and beautiful nature. The host was so friendly and helpful with quick responses. We had high winds and lots of rain, but stayed cozy and warm. What a friendly Island of people!!"
"Point of View" Waterfront cottage with panoramic views on Tilghman Island

Updated North Beach Cottage: Pet Friendly!

9.8 out of 10, Exceptional, (17)
"Awesome house a very short walk from Herrington Harbour."
Updated North Beach Cottage: Pet Friendly!

Cozy Cottage with access to and partially obstructed views of the bay.

9.2 out of 10, Wonderful, (25)
"Enjoy our time there"
Cozy Cottage with access to and partially obstructed views of the bay.

Perfect location for USNA Commissioning Week

10.0 out of 10, Exceptional, (84)
"Nice small property. Great for get aways and amazing service."
Perfect location for USNA Commissioning Week

Quick walk to the beach! Fire pit, Corn hole, Games & More!

10.0 out of 10, Exceptional, (1)
"We loved EVERYTHING about this place. Right next to the beach, great restaurants and shops. Could not have been better service. "
Quick walk to the beach! Fire pit, Corn hole, Games & More!

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (253)
"Our stay was great and Rob and Clarissa were very welcoming!"
Family and Pet-Friendly, Waterfront with Pier

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

10.0 out of 10, Exceptional, (7)
"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

10.0 out of 10, Exceptional, (213)
"Great views and location. Well furnished and very comfortable. We will definitely be staying here again. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (162)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

9.8 out of 10, Exceptional, (82)
"The cottage was a wonderful place for me and my kids to stay. I really appreciate the thoughtfulness of the owner. We would definitely stay here again."
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Private waterfront cottage with pool on Church Creek

10.0 out of 10, Exceptional, (62)
"Very clean, comfortable, and cozy property with gorgeous view of the water. Would definitely stay here again. Just wish we spent more time on the property this stay, but obligations in Fishing Creek kept us away most of the time. Thank you for sharing your lovely cottage!!"
Private waterfront cottage with pool on Church Creek

North Beach Cottage - Walk to Chesapeake Bay

10.0 out of 10, Exceptional, (37)
"The house was beautiful with everything you could need. We were out all day so didn’t get to use the house much except for sleeping. The bed was super comfortable."
North Beach Cottage - Walk to Chesapeake Bay

Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK

10.0 out of 10, Exceptional, (32)
"Really like this place "
Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK

6 Mi to Dtwn: Family-friendly Home in Annapolis!

3.0 star property
6 Mi to Dtwn: Family-friendly Home in Annapolis!

Charming Waterfront Cottage Retreat near St. Michaels

10.0 out of 10, Exceptional, (7)
"Great weekend get away if you’re just looking for some peace and quiet with some great scenery. The kitchen was immaculate and everything was as listed."
Charming Waterfront Cottage Retreat near St. Michaels

Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!

10.0 out of 10, Exceptional, (88)
"Beautiful property in a great location!"
Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Sherwood Hotel Reviews

Frequently asked questions

How much do cottages in Sherwood cost?
You can expect to pay between and per night for cottages in Sherwood. No matter your budget, an excellent stay is only clicks away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Sherwood?
Choose from 89 cottages in Sherwood. Whether you're traveling with the family or planning a weekend escape with your pals, Expedia can help you find the perfect property to get back to nature.
Why book your cottage in Sherwood with Expedia?
We think that vacations should be stress-free, so if you're chasing cottages in Sherwood at a competitive price, Expedia has you covered. Keep costs down and choose an economical option far from the hustle and bustle, or splurge on an upmarket cottage to really pamper your favorite people.