Sherwood Vacation Rentals

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Check prices for these dates

In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Our top choices for Sherwood vacation rentals

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

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)
"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 ￥11,000
￥38,402 total
includes taxes & fees
Jan 11 - Jan 12
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Exterior
Charming Coastal/Country Home w/3 Acres & Sauna!

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (32)
"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 ￥11,000
￥39,067 total
includes taxes & fees
Jan 11 - Jan 12
Charming Coastal/Country Home w/3 Acres & Sauna!
Marina
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City 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)
"The place was wonderful beautiful views of harbor, extremely clean and well appointed. Great restaurants we ate at RAR, great beer and food. Christopher’ Corner great dinner food fabulous and cocktails, highly recommend. Blackwater Cafe wonderful breakfast. "
United States
deb j.
The price is ￥21,938
￥54,315 total
includes taxes & fees
Jan 12 - Jan 13
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

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)
"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 ￥21,155
￥51,990 total
includes taxes & fees
Feb 2 - Feb 3
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Marina
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

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)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is ￥15,670
￥41,193 total
includes taxes & fees
Jan 12 - Jan 13
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Fridge, microwave, oven, stovetop
Beautiful Waterfront Retreat in Cambridge!

Beautiful Waterfront Retreat in Cambridge!

Beautiful Waterfront Retreat in Cambridge!
Cambridge
10.0 out of 10, Exceptional, (50)
"Beautiful place! Loved all the activities, will return in the future! Our family and friends had a blast! Thank you so much!!"
United States
Karen L.
The price is ￥18,616
￥51,127 total
includes taxes & fees
Jan 13 - Jan 14
Beautiful Waterfront Retreat in Cambridge!
Beach nearby
Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (17)
"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 ￥12,920
￥51,261 total
includes taxes & fees
Jan 25 - Jan 26
Walk to Beach! King Bed & Free Beach Passes
Marina
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

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)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
The price is ￥22,722
￥53,153 total
includes taxes & fees
Jan 12 - Jan 13
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Marina
Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (73)
"Great location!"
United States
Burton S.
The price is ￥19,274
￥48,947 total
includes taxes & fees
Jan 11 - Jan 12
Cozy 2br home w/ parking in downtown Annapolis
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

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is ￥15,341
￥64,161 total
includes taxes & fees
Jan 12 - Jan 13
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Marina
Station House East: Upscale Loft in the Historic District Cambridge, MD

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)
The price is ￥23,270
￥55,727 total
includes taxes & fees
Jan 9 - Jan 10
Station House East: Upscale Loft in the Historic District Cambridge, MD
Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is ￥32,437
￥64,488 total
includes taxes & fees
Jan 9 - Jan 10
Waterfront Oasis of Annapolis Star
Exterior detail
2nd floor Spacious Downtown Getaway- Across from US Naval Academy

2nd floor Spacious Downtown Getaway- Across from US Naval Academy

2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Historic District
9.6 out of 10, Exceptional, (27)
"Very nice place, just two of us stayed but would fit 4 comfortably. "
United States
Brad L.
The price is ￥26,639
￥49,483 total
includes taxes & fees
Jan 11 - Jan 12
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Interior
Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
10.0 out of 10, Exceptional, (5)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
The price is ￥24,915
￥115,936 total
includes taxes & fees
Jan 11 - Jan 12
Historic Row Home | Hot Tub - 1 Block from Gate 1!
Private kitchen
Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (24)
"What a great place to relax after exploring and enjoying the area. Definitely will visit again "
United States
Chris S.
The price is ￥24,289
￥39,865 total
includes taxes & fees
Jan 10 - Jan 11
Sailwinds Loft at Cambridge Creek
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.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
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 ￥39,175
￥66,109 total
includes taxes & fees
Jan 19 - Jan 20
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Fridge, microwave, oven, stovetop
Waterfront Getaway with Dock

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (51)
"Great place, will stay again"
United States
Matt S.
The price is ￥36,041
￥43,685 total
includes taxes & fees
Jan 12 - Jan 13
Waterfront Getaway with Dock
Smart TV
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

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

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Shady Side
10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
The price is ￥24,807
￥70,056 total
includes taxes & fees
Jan 11 - Jan 12
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Microwave, oven, stovetop, dishwasher
Walk to the stadium! - Lighthouse on Glenwood

Walk to the stadium! - Lighthouse on Glenwood

Walk to the stadium! - Lighthouse on Glenwood
Annapolis
9.8 out of 10, Exceptional, (7)
"5 star property with plenty of street parking. Everything was clean and had all of the ammendities"
United States
Tom D.
The price is ￥39,175
￥60,916 total
includes taxes & fees
Jan 11 - Jan 12
Walk to the stadium! - Lighthouse on Glenwood
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.

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)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
The price is ￥22,565
￥46,177 total
includes taxes & fees
Jan 9 - Jan 10
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
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

Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

10/10 Excellent
"Everything was great about my stay. From checking in to checking out! The front desk staff as well as housekeeping were extremely helpful and kind! I look forward to my next visit!"
Tina 3-night trip
Posted 4 days ago
Hampton Inn & Suites 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 vacation rental in Sherwood?

Yes, you can find vacation rentals close to popular attractions in Sherwood, or you can go with a more secluded option if you'd like a relaxing place to stay. Sherwood is known for its waterfront and restaurants.

What are some of the best vacation rentals that Sherwood has to offer?

6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access: This highly rated vacation home rental in Sherwood is located on a river and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Sherwood?

With 7 Expedia vacation rentals, you're sure 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 larger area, you’ll find Knapp's Narrows Marina & Inn and St. Michaels Winery.

What are vacation rentals like in Sherwood?

Vacation rentals are privately owned accommodations you can stay in for several days or longer in Sherwood. Vacation rentals offer extras such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from shared hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for families.