Compare Sherwood Cottage Rentals

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Featured Sherwood Cottages

Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier

At this cottage, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
Pool
Kitchen
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Pool
Kitchen
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Pool
Kitchen
"Point of View" Waterfront cottage with panoramic views on Tilghman Island

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

At this cottage, guests have access to features like laundry facilities.
Kitchen
Washer
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

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

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Waterfront property with private boat ramp and new dock!

Waterfront property with private boat ramp and new dock!

At this cottage, guests have access to features like laundry facilities.
Kitchen
Washer
The Middle Point Cabin in Saint Michaels

The Middle Point Cabin in Saint Michaels

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK

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

At this cottage, guests have access to a gym, laundry facilities, and barbecue grills. This beach cottage also has a garden.
Kitchen
Washer
Cozy Cottage with access to and partially obstructed views of the bay.

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

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
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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.

Hotel Options in Sherwood

    Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

    Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

    Sherwood
    10/10 Exceptional! (35 reviews)
    Historic Inns of Annapolis

    Historic Inns of Annapolis

    58 State Circle, Annapolis, MD
    $145 nightly
    The price is $166 total per night from Nov 2 to Nov 3
    $166 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.8/10 Excellent! (1,857 reviews)
    Sonesta ES Suites Annapolis

    Sonesta ES Suites Annapolis

    170 Admiral Cochrane Dr, Edgewater, MD
    $113 nightly
    The price is $129 total per night from Oct 19 to Oct 20
    $129 total
    Oct 19 - Oct 20
    Total with taxes and fees
    8.8/10 Excellent! (899 reviews)

Cottages

Book a cottage in Sherwood
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Sherwood. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Sherwood better.

Cottage apartments in Sherwood range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Sherwood
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Sherwood and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Sherwood cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Sherwood. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Sherwood Cottages essential information

Accommodation
87 Cottages
Lowest Price
$129
Highest Price
$166
Popular accommodation
Family and Pet-Friendly, Waterfront with Pier, John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, "Point of View" Waterfront cottage with panoramic views on Tilghman Island, Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly), Waterfront property with private boat ramp and new dock! , The Middle Point Cabin in Saint Michaels, Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK, Cozy Cottage with access to and partially obstructed views of the bay.

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