Sherwood Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Sherwood holiday rentals

9.6 out of 10, Exceptional, (12 reviews)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is AU$584
includes taxes & fees
19 Mar - 20 Mar
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
10.0 out of 10, Exceptional, (14 reviews)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is AU$732
includes taxes & fees
29 Mar - 30 Mar
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Apartment in Cambridge

Sailwinds Loft at Cambridge Creek
10.0 out of 10, Exceptional, (24 reviews)
"Lovely place, huge rooms, definitely recommend it. "
United States
Lee P.
The price is AU$358
includes taxes & fees
19 Mar - 20 Mar
Sailwinds Loft at Cambridge Creek

Holiday Home in Woolford

Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (53 reviews)
"Great place, will stay again"
United States
Matt S.
The price is AU$393
includes taxes & fees
19 Mar - 20 Mar
Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (10 reviews)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
The price is AU$548
includes taxes & fees
23 Mar - 24 Mar
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
9.8 out of 10, Exceptional, (12 reviews)
"Host was personally accessible during stay, responded quickly, and went the extra mile with wonderful touches left around the place."
United States
John S.
The price is AU$525
includes taxes & fees
23 Mar - 24 Mar
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
9.6 out of 10, Exceptional, (20 reviews)
"Very nice place in a great location. We would definitely stay there again "
United States
Traci C.
The price is AU$534
includes taxes & fees
23 Mar - 24 Mar
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
10.0 out of 10, Exceptional, (4 reviews)
"Would stay here again "
United States
Thomas D.
The price is AU$618
includes taxes & fees
19 Mar - 20 Mar
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
9.8 out of 10, Exceptional, (43 reviews)
"We had a wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!"
United States
Supriya V.
The price is AU$403
includes taxes & fees
19 Mar - 20 Mar
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
The price is AU$4,278
includes taxes & fees
22 Mar - 23 Mar
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
10.0 out of 10, Exceptional, (7 reviews)
"The property was clean, accurate to the listing and to prior feedback from other visitors. We loved the area; very quaint and cute. We enjoyed our stay and would recommend it to anyone looking for a cozy place to stay. "
United States
Amanda S.
The price is AU$509
includes taxes & fees
19 Mar - 20 Mar
Station House East: Upscale Loft in the Historic District Cambridge, MD
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is AU$760
includes taxes & fees
24 Mar - 25 Mar
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
10.0 out of 10, Exceptional, (19 reviews)
"Delightful one-night stay! Place was clean, quiet, convenient and very comfortable. Especially grateful that our beloved dog was welcomed"
United States
Elaine D.
The price is AU$459
includes taxes & fees
19 Mar - 20 Mar
Walk to Beach! King Bed & Free Beach Passes

Apartment in Eastport

Annapolis Gem: Stylish and Cozy
10.0 out of 10, Exceptional, (3 reviews)
"Great spot"
United States
Brian F.
The price is AU$679
includes taxes & fees
22 Mar - 23 Mar
Annapolis Gem: Stylish and Cozy
9.6 out of 10, Exceptional, (5 reviews)
"Our family had a great stay. Thank you!"
United States
Colleen G.
The price is AU$561
includes taxes & fees
30 Mar - 31 Mar
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
9.0 out of 10, Wonderful, (4 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is AU$641
includes taxes & fees
19 Mar - 20 Mar
London Towne Bungalow w/Loft - Walk to the Beach!
The price is AU$599
includes taxes & fees
19 Mar - 20 Mar
40' Bristol sailboat with spectacular views
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is AU$564
includes taxes & fees
22 Mar - 23 Mar
Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (4 reviews)
"Great location, easy check in/out. Everything we needed was available! Very comfortable bed, super cute property. "
United States
MJ S.
The price is AU$500
includes taxes & fees
22 Mar - 23 Mar
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is AU$761
includes taxes & fees
22 Mar - 23 Mar
Annapolis Retreat - 7 mins from downtown Annapolis!
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

Find out more about Sherwood

Everything you need to know about Sherwood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sherwood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sherwood holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Sherwood holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sherwood. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sherwood holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sherwood holiday rentals we have selected for you start as low as AU$385 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Sherwood rentals

At Expedia, we put the best Sherwood holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Sherwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sherwood holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sherwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Sherwood?

Yes, there are holiday rentals close to the most popular sights in Sherwood, or you can select a more secluded option if you're looking for a relaxing stay. Sherwood is known for its waterfront and restaurants.

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

Private 2 Acre Waterfront Family Retreat with Pool & Pier: This holiday home rental outside of Sherwood is located on the waterfront, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of books.

How many holiday rentals will I find in Sherwood?

With 6 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Knapp's Narrows Marina & Inn and St. Michaels Winery.

What are holiday rentals like in Sherwood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Sherwood. Holiday rentals offer extras like WiFi and washers and dryers so you'll feel right at home. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for small groups.