Sherwood Holiday Rentals

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Our top choices for Sherwood holiday rentals

10.0 out of 10, Exceptional, (7)
The price is NZ$445
includes taxes & fees
12 Jan - 13 Jan 2026
Station House East: Upscale Loft in the Historic District Cambridge, MD
10.0 out of 10, Exceptional, (10)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
The price is NZ$608
includes taxes & fees
6 Jan - 7 Jan 2026
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
9.8 out of 10, Exceptional, (11)
"This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. "
United States
Lauren V.
The price is NZ$610
includes taxes & fees
14 Jan - 15 Jan 2026
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
9.8 out of 10, Exceptional, (43)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is NZ$449
includes taxes & fees
5 Jan - 6 Jan 2026
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
9.6 out of 10, Exceptional, (32)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
The price is NZ$472
includes taxes & fees
5 Jan - 6 Jan 2026
Charming Coastal/Country Home w/3 Acres & Sauna!
9.6 out of 10, Exceptional, (20)
"The place was wonderful beautiful views of harbor, extremely clean and well appointed. Great restaurants we ate at RAR, great beer and food. Christopher’ Corner great dinner food fabulous and cocktails, highly recommend. Blackwater Cafe wonderful breakfast. "
United States
deb j.
The price is NZ$602
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Apartment in Cambridge

Sailwinds Loft at Cambridge Creek
10.0 out of 10, Exceptional, (24)
"What a great place to relax after exploring and enjoying the area. Definitely will visit again "
United States
Chris S.
The price is NZ$436
includes taxes & fees
31 Dec - 1 Jan 2026
Sailwinds Loft at Cambridge Creek
8.4 out of 10, Very good, (6)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is NZ$480
includes taxes & fees
12 Jan - 13 Jan 2026
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
10.0 out of 10, Exceptional, (17)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
The price is NZ$553
includes taxes & fees
14 Jan - 15 Jan 2026
Walk to Beach! King Bed & Free Beach Passes
10.0 out of 10, Exceptional, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is NZ$672
includes taxes & fees
3 Jan - 4 Jan 2026
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
10.0 out of 10, Exceptional, (50)
"Beautiful place! Loved all the activities, will return in the future! Our family and friends had a blast! Thank you so much!!"
United States
Karen L.
The price is NZ$642
includes taxes & fees
4 Jan - 5 Jan 2026
Beautiful Waterfront Retreat in Cambridge!
The price is NZ$5,323
includes taxes & fees
9 Jan - 10 Jan 2026
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
9.6 out of 10, Exceptional, (4)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
The price is NZ$472
includes taxes & fees
1 Jan - 2 Jan 2026
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
10.0 out of 10, Exceptional, (48)
"We love this place!"
United States
Joan K.
The price is NZ$532
includes taxes & fees
8 Jan - 9 Jan 2026
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Holiday Home in Woolford

Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (51)
"Great place, will stay again"
United States
Matt S.
The price is NZ$478
includes taxes & fees
6 Jan - 7 Jan 2026
Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is NZ$709
includes taxes & fees
3 Jan - 4 Jan 2026
Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (14)
"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 NZ$910
includes taxes & fees
12 Jan - 13 Jan 2026
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Condo in Historic District

Upscale Condo in Annapolis
10.0 out of 10, Exceptional, (2)
"Great condo! Very clean and convenient to everything in Annapolis. We will definitely be back."
United States
Scott P.
The price is NZ$914
includes taxes & fees
13 Jan - 14 Jan 2026
Upscale Condo in Annapolis
10.0 out of 10, Exceptional, (6)
"Very clean and very convenient location for our trip. "
United States
Greg S.
The price is NZ$964
includes taxes & fees
4 Jan - 5 Jan 2026
Charming Pet-Friendly Stay - Near Bay & Beaches.
10.0 out of 10, Exceptional, (5)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is NZ$908
includes taxes & fees
19 Jan - 20 Jan 2026
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.
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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 favorite 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 depends 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 NZ$479 per night. Entering your travel dates in the search wizard you might find 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?

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA: This holiday home rental outside of Sherwood is located in the city centre, and offers a selection of games, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Sherwood?

With 7 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.