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Check prices for these dates

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1 Aug - 3 Aug
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22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Cottages in Sherwood

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

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

3.0 star property
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
Exterior

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

3.0 star property
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
Tilghman Island Retreat By Knapps Narrows!
Front of property

Tilghman Island Retreat By Knapps Narrows!

3.0 star property
Tilghman Island Retreat By Knapps Narrows!
2 Mi to Sandy Point State Park: Home w/ Deck!
Interior

2 Mi to Sandy Point State Park: Home w/ Deck!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house was clean and nice. The beds choices were comfortable and keyless checkin was convenient. "
2 Mi to Sandy Point State Park: Home w/ Deck!
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Interior

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

3.0 star property
8.0 out of 10, Very good, (2)
"The water is well water and it stinks, water treatment could improve that. This is more in the woods than beachy. In a rundown area. Get some Damprid to cut down on musty smell. Cute decor."
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Bayfront Gem w/ Amazing Water Views + Pond!
Interior

Bayfront Gem w/ Amazing Water Views + Pond!

3.0 star property
Bayfront Gem w/ Amazing Water Views + Pond!
Pet-friendly Annapolis Home: Walk to Beach!
Interior

Pet-friendly Annapolis Home: Walk to Beach!

3.0 star property
Pet-friendly Annapolis Home: Walk to Beach!
Tranquil Port Republic Home w/ Water Views!
Property grounds

Tranquil Port Republic Home w/ Water Views!

3.0 star property
Tranquil Port Republic Home w/ Water Views!
Annapolis Home Near Beach & Quiet Waters Park!
Terrace/patio

Annapolis Home Near Beach & Quiet Waters Park!

3.0 star property
Annapolis Home Near Beach & Quiet Waters Park!
Bayfront Maryland Retreat w/ Deck, Near Beaches!
Exterior

Bayfront Maryland Retreat w/ Deck, Near Beaches!

3.0 star property
Bayfront Maryland Retreat w/ Deck, Near Beaches!
Waterfront North Beach Home ~ 2 Mi to Beach!
Interior

Waterfront North Beach Home ~ 2 Mi to Beach!

3.0 star property
Waterfront North Beach Home ~ 2 Mi to Beach!
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
Interior

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

3.0 star property
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
North Beach Cottage - Walk to Chesapeake Bay
Exterior

North Beach Cottage - Walk to Chesapeake Bay

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house condition was very cleran,beautiful. we appreciate the house owner's guidance&help. we made very good memories!"
North Beach Cottage - Walk to Chesapeake Bay
Beautiful Colonial Home on the Choptank River
Terrace/patio

Beautiful Colonial Home on the Choptank River

3.0 star property
Beautiful Colonial Home on the Choptank River
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Interior

Waterfront Annapolis Home: Fire Pit & Fishing Pier

3.0 star property
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Grasonville Home w/ Private Pool on the Water
Interior

Grasonville Home w/ Private Pool on the Water

3.0 star property
Grasonville Home w/ Private Pool on the Water
Updated North Beach Cottage: Pet Friendly!
Exterior

Updated North Beach Cottage: Pet Friendly!

3.0 star property
6.0 out of 10, (1)
"The property needs a severe cleaning. The floors were filthy. "
Updated North Beach Cottage: Pet Friendly!
Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit
Interior

Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit

3.0 star property
Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit
Water-view Deale Home: Walk to Marina, Restaurants
Interior

Water-view Deale Home: Walk to Marina, Restaurants

3.0 star property
Water-view Deale Home: Walk to Marina, Restaurants
Bay Views & Fire Pit: Taylors Island Retreat
Interior

Bay Views & Fire Pit: Taylors Island Retreat

3.0 star property
Bay Views & Fire Pit: Taylors Island Retreat
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.
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Top Sherwood Hotel Reviews

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

10/10 Excellent
"Excellent place only missing the club room !!!"
Zina 2-night trip
Posted 20 hours ago
Hyatt Regency Chesapeake Bay

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 38 cottages in Sherwood. Whether you're travelling 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 holidays 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 favourite people.