Sherwood Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Sherwood

Beach Home with King Bed and Beach Passes in a Cute Town

10.0 out of 10, Exceptional, (15)
"We had everything we needed in this townhome in North Beach. Nicely decorated, clean and the beds were comfortable! Perfect spot for our girl's weekend."
The price is NZ$715
includes taxes & fees
20 July - 21 July
Beach Home with King Bed and Beach Passes in a Cute Town

Charming 3-bedroom Midcentury modern home, retro vibe and stylish furnishings.

9.6 out of 10, Exceptional, (5)
"We had a great week in Cambridge. The Retro House has everything you need. It’s neat, clean, bright and very easy to stay in. It’s in a quiet neighborhood just short drive from the center of town. This was our second stay in the Retro House, we love it & will be coming back in the spring for another week!"
The price is NZ$662
includes taxes & fees
21 July - 22 July
Charming 3-bedroom Midcentury modern home, retro vibe and stylish furnishings.

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (37)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is NZ$564
includes taxes & fees
23 July - 24 July
Relax on Kent Island in 3 Bedroom Home w/Waterview

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

10.0 out of 10, Exceptional, (1)
"Stay there while my new home was getting work done, house was clean, perfect size for my family. It’s 50 ft to an ice cream shop and laundry mat. Our hoist even included a gift card to the ice cream shop. Great communication and perfect stay for us, felt like home "
The price is NZ$796
includes taxes & fees
16 July - 17 July
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Dean Street's Lower Deck House!

The price is NZ$752
includes taxes & fees
3 Aug - 4 Aug
Dean Street's Lower Deck House!

Gorgeous Creek Side Ranch-Style Estate With Dock

9.8 out of 10, Exceptional, (8)
"We were in town for a family wedding and throughly enjoyed our stay at this beautiful house. The property is gorgeous and the house has everything you need to make your stay enjoyable. We will definitely be back when visiting family in the area. "
The price is NZ$1,348
includes taxes & fees
24 July - 25 July
Gorgeous Creek Side Ranch-Style Estate With Dock

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.6 out of 10, Exceptional, (10)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is NZ$882
includes taxes & fees
16 July - 17 July
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy Home in Beautiful Annapolis

10.0 out of 10, Exceptional, (13)
"Great property and very clean!"
The price is NZ$475
includes taxes & fees
22 July - 23 July
Cozy Home in Beautiful Annapolis

Cozy Stay in Downtown Naptown -Located in the heart of Annapolis - 3BR, 2 BA

10.0 out of 10, Exceptional, (1)
"Tracy's place was perfect for our trip to Annapolis. The home is very comfortable, clean and quiet. Tracy has the home very well stocked with all your basic necessities. We were able to walk everywhere we went with some great restaurants and shops very close by. We will definitely look into booking here again when we visit Annapolis."
The price is NZ$870
includes taxes & fees
22 July - 23 July
Cozy Stay in Downtown Naptown -Located in the heart of Annapolis - 3BR, 2 BA

3 BR Pet Friendly Beverly Beach Cottage

9.8 out of 10, Exceptional, (7)
" Retreating from a construction project in our home, we landed in Grandma's Cottage. What a delightful semi-vactation. Lovely cottage, kind and friendly commuity srrouned by water and nature parks."
The price is NZ$747
includes taxes & fees
16 July - 17 July
3 BR Pet Friendly Beverly Beach Cottage

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

9.8 out of 10, Exceptional, (11)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is NZ$702
includes taxes & fees
16 July - 17 July
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

9.2 out of 10, Wonderful, (5)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is NZ$799
includes taxes & fees
14 Aug - 15 Aug
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

9.6 out of 10, Exceptional, (28)
"Nice and peaceful stay for a quick local getaway. "
The price is NZ$613
includes taxes & fees
4 Aug - 5 Aug
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

10.0 out of 10, Exceptional, (75)
"Property and Host were exceptional."
The price is NZ$2,225
includes taxes & fees
16 July - 17 July
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

Annapolis Retreat - 7 mins from downtown Annapolis!

10.0 out of 10, Exceptional, (2)
"The house was roomy, perfect for a large group and it was very clean and cozy. They also provided everything that was needed to have a comfortable stay."
The price is NZ$996
includes taxes & fees
22 July - 23 July
Annapolis Retreat - 7 mins from downtown Annapolis!

Waterfront Camper with Dock

10.0 out of 10, Exceptional, (1)
"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. "
The price is NZ$571
includes taxes & fees
16 July - 17 July
Waterfront Camper with Dock

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (45)
"We appreciated the cleanliness of the home and the location was beautiful and convenient to the state/national park, town and Harriet Tubman museum."
The price is NZ$465
includes taxes & fees
23 July - 24 July
Waterfront Getaway with Dock

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (39)
"The house was so cute and the fact that we were able to do early check in was amazing!"
The price is NZ$812
includes taxes & fees
20 July - 21 July
Beautiful Waterfront Retreat in Cambridge!

Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

10.0 out of 10, Exceptional, (38)
"Easy check-in and access to the property. Clean and stocked with everything we needed. Great rental for families!"
The price is NZ$2,332
includes taxes & fees
16 July - 17 July
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

10.0 out of 10, Exceptional, (6)
"This house was perfect for us! We love the ease of getting into town without having to drive and park in a parking garage. I would 10/10 recommend this house!"
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
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

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?

The Cozy Crab- Your Charming Haven in Lovely North Beach!: This holiday home rental outside of Sherwood offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as 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.