Sherwood Holiday Rentals

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Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for Sherwood holiday rentals

Marina

Holiday Home in Cambridge

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
9.6 out of 10, Exceptional, (20 reviews)
"Very nice place in a great location. We would definitely stay there again "
United States
Traci C.
The price is HK$1,212
HK$2,861 total
includes taxes & fees
11 Mar - 12 Mar
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina

Condo in Downtown Cambridge

Station House East: Upscale Loft in the Historic District Cambridge, MD
10.0 out of 10, Exceptional, (7 reviews)
"The property was clean, accurate to the listing and to prior feedback from other visitors. We loved the area; very quaint and cute. We enjoyed our stay and would recommend it to anyone looking for a cozy place to stay. "
United States
Amanda S.
The price is HK$1,162
HK$2,798 total
includes taxes & fees
10 Mar - 11 Mar
Station House East: Upscale Loft in the Historic District Cambridge, MD
Private kitchen

Apartment in Cambridge

Sailwinds Loft at Cambridge Creek
10.0 out of 10, Exceptional, (24 reviews)
"Lovely place, huge rooms, definitely recommend it. "
United States
Lee P.
The price is HK$1,212
HK$1,990 total
includes taxes & fees
10 Mar - 11 Mar
Sailwinds Loft at Cambridge Creek
Marina

Condo in Downtown Cambridge

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
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$1,056
HK$2,438 total
includes taxes & fees
10 Mar - 11 Mar
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Exterior

Holiday Home in Stevensville

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
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$597
HK$2,009 total
includes taxes & fees
10 Mar - 11 Mar
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Exterior

Holiday Home in Stevensville

Charming Coastal/Country Home w/3 Acres & Sauna!
9.6 out of 10, Exceptional, (34 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is HK$597
HK$2,017 total
includes taxes & fees
11 Mar - 12 Mar
Charming Coastal/Country Home w/3 Acres & Sauna!
Marina

Condo in Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
9.8 out of 10, Exceptional, (12 reviews)
"Host was personally accessible during stay, responded quickly, and went the extra mile with wonderful touches left around the place."
United States
John S.
The price is HK$1,291
HK$2,952 total
includes taxes & fees
17 Mar - 18 Mar
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Dining

Holiday Home in Grasonville

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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$1,956
HK$3,292 total
includes taxes & fees
10 Mar - 11 Mar
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Marina

Condo in Downtown Cambridge

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
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$1,369
HK$3,051 total
includes taxes & fees
17 Mar - 18 Mar
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Beach nearby

Holiday Home in North Beach

Walk to Beach! King Bed & Free Beach Passes
10.0 out of 10, Exceptional, (19 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$981
HK$2,957 total
includes taxes & fees
18 Mar - 19 Mar
Walk to Beach! King Bed & Free Beach Passes
Marina

Holiday Home in Annapolis

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
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$1,348
HK$3,793 total
includes taxes & fees
10 Mar - 11 Mar
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Outdoor pool, a heated pool

Apartment in Annapolis

Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is HK$1,619
HK$3,237 total
includes taxes & fees
12 Mar - 13 Mar
Waterfront Oasis of Annapolis Star
Outdoor dining

Holiday Home in Dorchester County

Sunset Breezes - quiet waterfront retreat
10.0 out of 10, Exceptional, (43 reviews)
"Clean, quiet, comfy"
United Kingdom
Deborah V.
The price is HK$2,128
HK$2,677 total
includes taxes & fees
30 Mar - 31 Mar
Sunset Breezes - quiet waterfront retreat
Pool

Holiday Home in Chesapeak beach

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is HK$1,330
HK$3,430 total
includes taxes & fees
15 Mar - 16 Mar
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Fridge, microwave, oven, stovetop

Holiday Home in Admiral Heights

Cute bungalow blocks to Stadium
9.8 out of 10, Exceptional, (8 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is HK$1,103
HK$4,041 total
includes taxes & fees
10 Mar - 11 Mar
Cute bungalow blocks to Stadium
Fridge, microwave, oven, stovetop

Holiday Home in Woolford

Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (53 reviews)
"Great place, will stay again"
United States
Matt S.
The price is HK$1,799
HK$2,114 total
includes taxes & fees
10 Mar - 11 Mar
Waterfront Getaway with Dock
Smart TV

Holiday Home in Cambridge

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
10.0 out of 10, Exceptional, (14 reviews)
"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 HK$2,052
HK$4,140 total
includes taxes & fees
11 Mar - 12 Mar
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Smart TV, books

Holiday Home in Prince Frederick

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
9.6 out of 10, Exceptional, (5 reviews)
"Our family had a great stay. Thank you!"
United States
Colleen G.
The price is HK$1,674
HK$3,134 total
includes taxes & fees
30 Mar - 31 Mar
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Beach nearby, sun-loungers, beach towels

Holiday Home in Arundel on the Bay

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is HK$1,866
HK$4,213 total
includes taxes & fees
17 Mar - 18 Mar
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Beach

Holiday Home in Prince Frederick

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
10.0 out of 10, Exceptional, (8 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is HK$1,916
HK$3,458 total
includes taxes & fees
16 Mar - 17 Mar
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Very clean, great staff, very good communication skills, excellent service, AC could have been turned on sooner, friendly. I just wish they had a restaurant on the premises."
Jeff 1-night trip
Posted 9 hours ago
Historic Inns of Annapolis

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:

  • View our selection of featured holiday rentals in Sherwood
  • Use the map to find apartments and other holiday homes in the Sherwood neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sherwood while they last

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?

Private 2 Acre Waterfront Family Retreat with Pool & Pier: This holiday home rental outside of Sherwood is located on the waterfront, and has an outdoor pool, a balcony 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. You can relax into your holiday with a garden and 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.