Sherwood Holiday Rentals

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Holiday Rentals in Sherwood

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (202)
"This cozy home was perfect for my coaches & I that were in town for a lacrosse tourney @ the Naval Academy. This home is literally less than 100 steps from the gate of the Naval Base and same distance to dowtown Annapolis city docks, diming, shopping and sight-seeing. We will defintely be back! Thanks John!!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (217)
"Were pleased with the property and surroundings. Very beautiful, ancient trees. Neighborhood was quiet and the river and dock were favorite reading spots. Enjoyed!!!"
Relaxing Waterfront Cottage Near St Michaels, Maryland

Charming Annapolis WaterVIEW Home

9.6 out of 10, Exceptional, (49)
"Wonderful location to downtown Annapolis! Beautiful home, well maintained and plenty of room. The porch overlooking the bay has a table for 10 which provided a wonderful setting for our family. This is our second stay and we’ll absolutely stay again "
Charming Annapolis WaterVIEW Home

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (47)
"Everything close by!"
The Blue Crab Beach House - Free beach passes

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

9.6 out of 10, Exceptional, (17)
" October 11-14, 2024, we rented the “Willoughby” for a family reunion. Let me start out by saying this home is amazing. It looks exactly as pictured based on the website photos. It was even better than I expected. If you are considering this property, I highly recommend booking it! Believe me when I say the Willoughby is a rare gem. The location of the home is perfect and extremely private. The grounds are pristine and the view of the water is breathtaking. The home sits on the Hudson...
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

3 Story Stunner in Murray Hill <1 mile from USNA!

10.0 out of 10, Exceptional, (18)
"Very nicely renovated property in the heart of downtown Annapolis. Highly recommend for groups / families and very kid friendly. Great location to walk to all that Annapolis has to offer. "
The price is AU$1,357
includes taxes & fees
9 Dec - 10 Dec
3 Story Stunner in Murray Hill <1 mile from USNA!

Amazing views, short walks to great dining!

10.0 out of 10, Exceptional, (73)
"Perfect for a romantic weekend away!"
Amazing views, short walks to great dining!

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (35)
"The groomsmen and their families attending my daughter's nearby wedding stayed at this spectacular property. I heard nothing but high praise for its beauty, amenities, and comfort. So glad this all worked out for the dates we needed it for!"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (30)
"Excellent experience."
The price is AU$404
includes taxes & fees
2 Dec - 3 Dec
Relax on Kent Island in 3 Bedroom Home w/Waterview

2-story, riverfront home with private dock, inviting deck & dog-friendly yard

9.6 out of 10, Exceptional, (12)
"We appreciate the hospitality and responsiveness of our gracious host. We would stay again and look forward to our next visit. Recommend staying to all looking for a tranquil getaway in the Annapolis area."
2-story, riverfront home with private dock, inviting deck & dog-friendly yard

421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!

10.0 out of 10, Exceptional, (100)
"We absolutely loved staying in this property. It’s comfortable, charming and so well appointed. It’s situated in a great location, within walking distance of all the special things Annapolis has to offer. The host was so easy to communicate with, and we really appreciate that she shares this beautiful home. We will’s definitely be back!"
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (32)
"Four of my friends and I stayed at this cute home for a ladies' weekend (two nights) in St. Michaels. We are in our early 40's and all agreed that the location of this home is superb. We walked to dinner each night (Limoncello and Ruse, both great) and enjoyed the wonderful shops in the lovely downtown area. The location of this home cannot be beat if you want to park your car upon arrival and not have a need to use it again during your stay. We had three cars, two of which fit in the driveway...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (71)
"We had an amazing time! Beth and Andy are wonderful hosts! We are looking forward to another stay!"
The price is AU$692
includes taxes & fees
1 Dec - 2 Dec
Waterfront Oasis of Annapolis Star

USNA Quintessential Charm ~ Downtown Annapolis.

9.8 out of 10, Exceptional, (6)
"Limited living room seating for family of 5"
USNA Quintessential Charm ~ Downtown Annapolis.

Cass-Away Luxury Houseboat

10.0 out of 10, Exceptional, (87)
"All as advertised Wonderful option to a hotel"
Cass-Away Luxury Houseboat

Pool and Bay Views on wrap around deck in Kent Island

9.6 out of 10, Exceptional, (24)
"We loved everything about the Kent Island House! Would book again in a hot minute"
Pool and Bay Views on wrap around deck in Kent Island

Your Annapolis Adventure Starts Here!!

10.0 out of 10, Exceptional, (136)
"My family and I love staying here! It's clean, beautiful, spacious, and comfortable. It's home away from home. I love all the special touches--lots of cozy blankets, the beautiful decor, the comfortable beds. And, of course, it's close to anything you want to do in Annapolis or the surrounding areas. During this stay, we were able to enjoy the patio, which was especially wonderful to be able to do in November. My favorite spot is the sitting area next to the kitchen; it's a perfect place to...
Your Annapolis Adventure Starts Here!!

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

10.0 out of 10, Exceptional, (204)
"Very cozy and clean. Beautiful surroundings with direct view of the water. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (38)
"The Lazy Crab was such a delightful home to visit. The kitchen was fully stocked and the house had everything any traveler could need, including a washer and dryer! It was evident that the owners put a lot of love into making sure guests enjoyed their stay. I highly recommend! You will feel right at home."
The Lazy Crab Beach House - Free beach passes

Mid-Century Modern and Marvelous on the Bay

10.0 out of 10, Exceptional, (70)
"The house was amazing! From the moment the front door opened it was a visual feast. The views are incredible, it's quiet, private and very relaxing. There were personal elements reflecting the current and original owners which we found very interesting and the attention to detail throughout was superb! Everything was incredibly well stocked with a multitude of extras. "
Mid-Century Modern and Marvelous on the Bay
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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Other types of properties in Sherwood you may be interested in

Lowes Wharf Marina Inn

3.0 star property
7.8 out of 10, Good, (71)
"Very relaxing ( we were there midweek). Incredible location and sunsets."
Lowes Wharf Marina Inn

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1774)
"The Maryland was quaint, clean and comfortable."
The price is AU$247
includes taxes & fees
23 Dec - 24 Dec
Historic Inns of Annapolis

Graduate by Hilton Annapolis

4.0 star property
9.4 out of 10, Exceptional, (1044)
"The staff was the best always checking to see if I needed anything. "
The price is AU$235
includes taxes & fees
25 Dec - 26 Dec
Graduate by Hilton 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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Rockhold Creek Cottage, Water Front, Vacation Home, Docks: This holiday home rental outside of Sherwood is located on a river, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Sherwood?

With 8 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 Shadyside Park. In the wider area, you’ll find St. Michaels Winery and Rod n Reel Charter Fishing.

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.