Holiday Rentals in Sherwood

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Holiday Rentals in Sherwood

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.8 out of 10, Exceptional, (9)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is €446
includes taxes & fees
8 Jul - 9 Jul
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

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 €332
includes taxes & fees
8 Jul - 9 Jul
Charming 3-bedroom Midcentury modern home, retro vibe and stylish furnishings.

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (42)
"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 €242
includes taxes & fees
9 Jul - 10 Jul
Waterfront Getaway with Dock

Spacious waterfront home with amazing views, private pier, fishing and crabbing.

10.0 out of 10, Exceptional, (21)
"A nice, quiet location on the water. Exactly as advertised. We would definitely stay again if we were in the area."
The price is €777
includes taxes & fees
21 Jul - 22 Jul
Spacious waterfront home with amazing views, private pier, fishing and crabbing.

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 €467
includes taxes & fees
14 Jul - 15 Jul
Beautiful Waterfront Retreat in Cambridge!

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

9.6 out of 10, Exceptional, (9)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is €370
includes taxes & fees
8 Jul - 9 Jul
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

10.0 out of 10, Exceptional, (12)
"very serene, peaceful home on the bay! Amazing getaway! "
The price is €514
includes taxes & fees
9 Jul - 10 Jul
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

#2 Egret Cottage Harris Cove

The price is €335
includes taxes & fees
4 Aug - 5 Aug
#2 Egret Cottage Harris Cove

Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (17)
"Loved the location, the property, and amenities. Would definitely stay again!"
The price is €727
includes taxes & fees
2 Aug - 3 Aug
Waterfront Sunset Bayview: sleeps 6

Room for an Island getaway

2.0 star property
9.0 out of 10, Wonderful, (2)
"Was a nice place for the night we were there. It had everything we needed for the night"
The price is €188
includes taxes & fees
8 Jul - 9 Jul
Room for an Island getaway

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

9.6 out of 10, Exceptional, (28)
"Great place and location. Not far from good food and local hot spots. Would definitely rebook and stay here again. "
The price is €294
includes taxes & fees
13 Jul - 14 Jul
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

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 €297
includes taxes & fees
14 Jul - 15 Jul
Relax on Kent Island in 3 Bedroom Home w/Waterview

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 €1,215
includes taxes & fees
14 Jul - 15 Jul
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

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 €1,133
includes taxes & fees
14 Jul - 15 Jul
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.

9.4 out of 10, Exceptional, (3)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
The price is €477
includes taxes & fees
6 Aug - 7 Aug
Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.

Charming Pet-Friendly Stay - Near Bay & Beaches.

10.0 out of 10, Exceptional, (1)
"Tons of space with lots of amenities! Super nice neighbor hood and neighbors. Very clean as well!"
The price is €450
includes taxes & fees
8 Jul - 9 Jul
Charming Pet-Friendly Stay - Near Bay & Beaches.

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 €428
includes taxes & fees
27 Jul - 28 Jul
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Charming Cottage with Hot Tub 1 Block from the Bay

10.0 out of 10, Exceptional, (9)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is €708
includes taxes & fees
8 Jul - 9 Jul
Charming Cottage with Hot Tub 1 Block from the Bay

Charming Historic Row House in The Heart of Eastport's Horn Point

2.5 star property
10.0 out of 10, Exceptional, (1)
"Gorgeous little house in the heart of Eastport, walking distance to fabulous restaurants and a short hop over the bridge to dwtn Annapolis. The house was clean, well stocked, comfy beds, and the patio was a lovely little oasis to kick back in with a glass of wine at the end of the day. The host was very responsive and accommodating. Highly recommend! "
Charming Historic Row House in The Heart of Eastport's Horn Point

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 €547
includes taxes & fees
8 Jul - 9 Jul
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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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.