Sherwood Holiday Rentals

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Holiday Rentals in Sherwood

Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (41)
"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 AU$488
includes taxes & fees
16 Nov - 17 Nov
Relax on Kent Island in 3 Bedroom Home w/Waterview
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
2.0 star property
9.8 out of 10, Exceptional, (9)
"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 AU$549
includes taxes & fees
20 Oct - 21 Oct
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
9.6 out of 10, Exceptional, (31)
"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 AU$400
includes taxes & fees
21 Oct - 22 Oct
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
2.5 star property
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 AU$548
includes taxes & fees
20 Oct - 21 Oct
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
9.6 out of 10, Exceptional, (17)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
United States
Aaron N.
The price is AU$549
includes taxes & fees
20 Oct - 21 Oct
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Sailwinds Loft at Cambridge Creek
9.8 out of 10, Exceptional, (18)
"The location and apartment were perfect. "
United States
Christina B.
The price is AU$396
includes taxes & fees
20 Oct - 21 Oct
Sailwinds Loft at Cambridge Creek
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
8.8 out of 10, Excellent, (5)
"The place was very clean and in the most perfect spot in downtown Cambridge. We had a wedding walking distance from this place. Jen is a very responsive and accommodating host!"
United States
Angie R.
The price is AU$465
includes taxes & fees
22 Oct - 23 Oct
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (48)
"Property was as listed. We enjoyed are stay."
United States
Jennifer S.
The price is AU$611
includes taxes & fees
21 Oct - 22 Oct
Beautiful Waterfront Retreat in Cambridge!
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
2.0 star property
The price is AU$431
includes taxes & fees
2 Nov - 3 Nov
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Station House East: Upscale Loft in the Historic District Cambridge, MD
10.0 out of 10, Exceptional, (1)
"Location very convenient, flat beautiful, clean, very friendly, respo sive and accommodating hostess! Thank you!"
United States
Solveig S.
The price is AU$555
includes taxes & fees
22 Oct - 23 Oct
Station House East: Upscale Loft in the Historic District Cambridge, MD
Waterfront Getaway, Dock Your Boat & Play!
10.0 out of 10, Exceptional, (2)
"Lovely stay, don't let the RV aspect.of it scare you. Nicer than most other bnbs ice stayed in. Quiet, clean and beautiful view of the water. "
United States
Aaron D.
The price is AU$472
includes taxes & fees
27 Oct - 28 Oct
Waterfront Getaway, Dock Your Boat & Play!
Walk to Beach! King Bed & Free Beach Passes
10.0 out of 10, Exceptional, (16)
"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 AU$540
includes taxes & fees
20 Oct - 21 Oct
Walk to Beach! King Bed & Free Beach Passes
Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (51)
"Great location with everything you may need. It is close to restaurants and Emily’s produce.2nd time staying and will be back again. "
United States
Edna L.
The price is AU$418
includes taxes & fees
28 Oct - 29 Oct
Waterfront Getaway with Dock
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
10.0 out of 10, Exceptional, (10)
"Very clean - well equipped - perfect for our relaxing weekend."
United States
Chris J.
The price is AU$810
includes taxes & fees
22 Oct - 23 Oct
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Cute bungalow blocks to Stadium
10.0 out of 10, Exceptional, (5)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
The price is AU$795
includes taxes & fees
21 Oct - 22 Oct
Cute bungalow blocks to Stadium
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
9.6 out of 10, Exceptional, (12)
"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$641
includes taxes & fees
20 Oct - 21 Oct
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Annapolis Retreat - 7 mins from downtown Annapolis!
10.0 out of 10, Exceptional, (3)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is AU$862
includes taxes & fees
11 Nov - 12 Nov
Annapolis Retreat - 7 mins from downtown Annapolis!
London Towne Bungalow w/Loft - Walk to the Beach!
8.0 out of 10, Very good, (2)
"The water that comes out of the house tastes bad."
United States
Mario A.
The price is AU$740
includes taxes & fees
30 Oct - 31 Oct
London Towne Bungalow w/Loft - Walk to the Beach!
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
10.0 out of 10, Exceptional, (3)
"Very comfortable bedrooms and sitting area. Perfect location for the event we were attending. Very clean. Friendly host. "
United States
Mark E.
The price is AU$661
includes taxes & fees
20 Oct - 21 Oct
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Charming Pet-Friendly Stay - Near Bay & Beaches.
10.0 out of 10, Exceptional, (5)
"The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here."
United States
Kristina
Charming Pet-Friendly Stay - Near Bay & Beaches.
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 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 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?

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND: This highly rated holiday home rental in Sherwood is located on a river, and has an outdoor pool, a fireplace 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. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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.