Sherwood Holiday Rentals

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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Sherwood holiday rentals

Marina

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
2.0 star property
Downtown Cambridge
9.8 out of 10, Exceptional, (11 reviews)
"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 HK$1,053
HK$2,661 total
includes taxes & fees
2 Feb - 3 Feb
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Marina

Station House East: Upscale Loft in the Historic District Cambridge, MD

Station House East: Upscale Loft in the Historic District Cambridge, MD
Downtown Cambridge
10.0 out of 10, Exceptional, (7 reviews)
"Location very convenient, flat beautiful, clean, very friendly, respo sive and accommodating hostess! Thank you!"
United States
Solveig S.
The price is HK$1,158
HK$2,781 total
includes taxes & fees
29 Jan - 30 Jan
Station House East: Upscale Loft in the Historic District Cambridge, MD
Marina

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
2.5 star property
Downtown Cambridge
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 HK$1,131
HK$2,752 total
includes taxes & fees
2 Feb - 3 Feb
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Exterior

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (32 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is HK$632
HK$2,008 total
includes taxes & fees
22 Jan - 23 Jan
Charming Coastal/Country Home w/3 Acres & Sauna!
Exterior detail

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
2.0 star property
North Beach
9.6 out of 10, Exceptional, (4 reviews)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
The price is HK$1,123
HK$2,306 total
includes taxes & fees
24 Jan - 25 Jan
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.6 out of 10, Exceptional, (20 reviews)
"Very clean, and very comfortable beds."
United States
Edward R.
The price is HK$1,092
HK$2,702 total
includes taxes & fees
2 Feb - 3 Feb
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina

Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.

Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
Edgewater
The price is HK$16,841
HK$24,363 total
includes taxes & fees
29 Jan - 30 Jan
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
Marina

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Downtown Cambridge
8.4 out of 10, Very good, (6 reviews)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is HK$936
HK$2,306 total
includes taxes & fees
3 Feb - 4 Feb
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Private kitchen

Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (24 reviews)
"What a great place to relax after exploring and enjoying the area. Definitely will visit again "
United States
Chris S.
The price is HK$1,208
HK$1,983 total
includes taxes & fees
29 Jan - 30 Jan
Sailwinds Loft at Cambridge Creek
Exterior

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (43 reviews)
"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 HK$589
HK$1,997 total
includes taxes & fees
28 Jan - 29 Jan
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Fridge, microwave, oven, stovetop

Beautiful Waterfront Retreat in Cambridge!

Beautiful Waterfront Retreat in Cambridge!
Cambridge
10.0 out of 10, Exceptional, (50 reviews)
"The house was completely spotless - the location was perfect! And the host included a s'mores kit, and baited crab traps and had them waiting with crabs in them when we arrived! This was an excellent weekend - we would recommend Hudson House to anyone!"
United States
Elizabeth G.
The price is HK$1,228
HK$2,905 total
includes taxes & fees
25 Jan - 26 Jan
Beautiful Waterfront Retreat in Cambridge!
Interior

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (5 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is HK$1,318
HK$4,142 total
includes taxes & fees
22 Jan - 23 Jan
Annapolis Retreat - 7 mins from downtown Annapolis!
Dining

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

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
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 HK$1,949
HK$3,273 total
includes taxes & fees
22 Jan - 23 Jan
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Beach nearby

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (18 reviews)
"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 HK$523
HK$2,386 total
includes taxes & fees
22 Jan - 23 Jan
Walk to Beach! King Bed & Free Beach Passes
Outdoor dining

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (31 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is HK$695
HK$3,084 total
includes taxes & fees
22 Jan - 23 Jan
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Marina

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is HK$1,344
HK$3,781 total
includes taxes & fees
29 Jan - 30 Jan
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Fridge, microwave, oven, stovetop

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (51 reviews)
"Great place, will stay again"
United States
Matt S.
The price is HK$1,793
HK$2,107 total
includes taxes & fees
29 Jan - 30 Jan
Waterfront Getaway with Dock
Fridge, microwave, oven, stovetop

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (8 reviews)
"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 HK$1,333
HK$4,322 total
includes taxes & fees
25 Jan - 26 Jan
Cute bungalow blocks to Stadium
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is HK$1,614
HK$3,226 total
includes taxes & fees
23 Jan - 24 Jan
Waterfront Oasis of Annapolis Star
TV, books, offices

Holly Hill Haven - Sleeps 10

Holly Hill Haven - Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (3 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is HK$1,146
HK$4,357 total
includes taxes & fees
9 Feb - 10 Feb
Holly Hill Haven - Sleeps 10
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

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

10/10 Excellent
"Room was spotless, staff was exceptionally friendly."
Maxwell 6-night trip
Posted 18 hours ago
Hyatt Place Kent Narrows & Marina

Find out more about Sherwood

Search for holiday rentals in Sherwood on Expedia! You can easily find your home rentals, villas, holiday apartments in Sherwood using one of the methods below:

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Look no further and take a look at our great range of rental properties in Sherwood!

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.