Sherwood Vacation Rentals

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Oct 25 - Oct 26
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Vacation Rentals in Sherwood

Property grounds
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
$2,728 nightly
The price is $3,110
Oct 26 - Oct 27
Total with taxes and fees
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
Outdoor pool
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
10.0 out of 10, Exceptional, (48)
"The house was perfect. The view was stunning. The pool was a perfect bonus!"
United States
Jamie A.
$243 nightly
The price is $258
Oct 30 - Oct 31
Total with taxes and fees
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Marina
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
9.6 out of 10, Exceptional, (31)
"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
$252 nightly
The price is $267
Oct 29 - Oct 30
Total with taxes and fees
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Marina
Station House East: Upscale Loft in the Historic District Cambridge, MD
Station House East: Upscale Loft in the Historic District Cambridge, MD
10.0 out of 10, Exceptional, (1)
"Location very convenient, flat beautiful, clean, very friendly, respo sive and accommodating hostess! Thank you!"
United States
Solveig S.
$337 nightly
The price is $357
Oct 27 - Oct 28
Total with taxes and fees
Station House East: Upscale Loft in the Historic District Cambridge, MD
Outdoor dining
Waterfront Getaway, Dock Your Boat & Play!
Waterfront Getaway, Dock Your Boat & Play!
10.0 out of 10, Exceptional, (3)
"Great place to stay. It is clean, comfortable, and not lacking convenience.Quick communication with the host. We would definitely recommend!"
United States
Daniel K.
$291 nightly
The price is $311
Oct 26 - Oct 27
Total with taxes and fees
Waterfront Getaway, Dock Your Boat & Play!
Marina
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
2.0 star property
9.6 out of 10, Exceptional, (10)
"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.
$346 nightly
The price is $367
Oct 27 - Oct 28
Total with taxes and fees
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
8.8 out of 10, Excellent, (5)
"The place was very clean and in the most perfect spot in downtown Cambridge. We had a wedding walking distance from this place. Jen is a very responsive and accommodating host!"
United States
Angie R.
$279 nightly
The price is $296
Oct 26 - Oct 27
Total with taxes and fees
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Beach nearby
Walk to Beach! King Bed & Free Beach Passes
Walk to Beach! King Bed & Free Beach Passes
10.0 out of 10, Exceptional, (16)
"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.
$291 nightly
The price is $321
Oct 26 - Oct 27
Total with taxes and fees
Walk to Beach! King Bed & Free Beach Passes
Marina
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
9.6 out of 10, Exceptional, (17)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
United States
Aaron N.
$350 nightly
The price is $371
Oct 27 - Oct 28
Total with taxes and fees
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Private kitchen
Sailwinds Loft at Cambridge Creek
Sailwinds Loft at Cambridge Creek
9.8 out of 10, Exceptional, (19)
"The location and apartment were perfect. "
United States
Christina B.
$240 nightly
The price is $254
Oct 27 - Oct 28
Total with taxes and fees
Sailwinds Loft at Cambridge Creek
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
10.0 out of 10, Exceptional, (10)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
$347 nightly
The price is $368
Oct 26 - Oct 27
Total with taxes and fees
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Interior
Beautiful Waterfront Retreat in Cambridge!
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (49)
"Property was as listed. We enjoyed are stay."
United States
Jennifer S.
$377 nightly
The price is $400
Oct 28 - Oct 29
Total with taxes and fees
Beautiful Waterfront Retreat in Cambridge!
Marina
Relax on Kent Island in 3 Bedroom Home w/Waterview
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (41)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
$290 nightly
The price is $307
Nov 16 - Nov 17
Total with taxes and fees
Relax on Kent Island in 3 Bedroom Home w/Waterview
Fridge, microwave, oven, stovetop
Cute bungalow blocks to Stadium
Cute bungalow blocks to Stadium
10.0 out of 10, Exceptional, (5)
"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.
$459 nightly
The price is $519
Oct 27 - Oct 28
Total with taxes and fees
Cute bungalow blocks to Stadium
Exterior
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
10.0 out of 10, Exceptional, (4)
"Very comfortable bedrooms and sitting area. Perfect location for the event we were attending. Very clean. Friendly host. "
United States
Mark E.
$376 nightly
The price is $429
Oct 26 - Oct 27
Total with taxes and fees
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Terrace/patio
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
9.8 out of 10, Exceptional, (11)
"Very clean - well equipped - perfect for our relaxing weekend."
United States
Chris J.
$466 nightly
The price is $531
Oct 30 - Oct 31
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Property grounds
Sunset Breezes - quiet waterfront retreat
Sunset Breezes - quiet waterfront retreat
10.0 out of 10, Exceptional, (40)
"Good time with my friends "
United Kingdom
Oleg L.
Sunset Breezes - quiet waterfront retreat
Outdoor spa tub
London Towne Bungalow w/Loft - Walk to the Beach!
London Towne Bungalow w/Loft - Walk to the Beach!
8.0 out of 10, Very Good, (2)
"The water that comes out of the house tastes bad."
United States
Mario A.
$441 nightly
The price is $469
Oct 26 - Oct 27
Total with taxes and fees
London Towne Bungalow w/Loft - Walk to the Beach!
Fridge, microwave, oven, stovetop
Waterfront Getaway with Dock
Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (51)
"Really neat property with everything that you need!"
United States
Hannah K.
$263 nightly
The price is $279
Oct 28 - Oct 29
Total with taxes and fees
Waterfront Getaway with Dock
Microwave, oven, stovetop, dishwasher
Annapolis Retreat - 7 mins from downtown Annapolis!
Annapolis Retreat - 7 mins from downtown Annapolis!
10.0 out of 10, Exceptional, (4)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
$503 nightly
The price is $573
Nov 11 - Nov 12
Total with taxes and fees
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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Top Sherwood Hotel Reviews

Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

10/10 Excellent
"."
Ethan 3-night trip
Posted 21 hours ago
Hampton Inn & Suites Annapolis

Find out more about Sherwood

Everything you need to know about Sherwood vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sherwood vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sherwood vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sherwood vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sherwood. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Sherwood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $307 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sherwood rentals

At Expedia, we put the best Sherwood vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Sherwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sherwood vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sherwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND: This highly rated vacation home rental in Sherwood is located on a river and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a patio, a garden, and a selection of games 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.