Sherwood vacation rentals

We found 183 vacation rentals — enter your dates for availability

Discover a selection of 7 homes and other vacation rentals in Sherwood that are perfect for your trip. Whether you're staying in a vacation rental with family or friends, you'll have the best amenities for spending time at your home away from home, which might include a fireplace and a washer and dryer. You'll be sure to find a rental to meet everyone's needs, including options that are accessible or non-smoking.

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Find out more about Sherwood

Why visit Sherwood

  • Outdoor adventures: Enjoy a range of activities in Sherwood's beautiful parks and scenic areas, perfect for nature lovers.
  • Cultural experiences: Discover local history through museums and cultural sites that reflect Sherwood's rich heritage.
  • Romantic getaways: Experience charming spots ideal for couples seeking a peaceful and romantic atmosphere.
  • Family-friendly neighborhoods: Explore welcoming communities with gorgeous homes and a friendly vibe for families.
  • Variety of accommodations: Choose from cozy cottages, modern apartments, and vacation homes tailored to your needs.

Popular types of accommodation in Sherwood

If you're looking for the perfect getaway in Sherwood, you'll find a variety of comfortable options to suit your needs. Our most popular types of accommodations include houses, charming cottages, and modern apartments. Whether you're searching for sherwood homes for rent or cozy house rentals, we have the ideal rental home in Sherwood for you. Enjoy your stay with us and experience the best that Sherwood has to offer.

  • Houses: The top choice for visitors in Sherwood, these homes offer spacious accommodations perfect for families or groups, featuring all the comforts of home.
  • Cottages: Quaint and charming, cottages provide a cozy retreat, ideal for couples or small families looking to enjoy a peaceful getaway.
  • Apartments: A convenient option for solo travelers or couples, apartments in Sherwood provide essential amenities and easy access to local attractions.
  • Condos: Offering a blend of luxury and comfort, condos are perfect for those seeking modern amenities and a vibrant community atmosphere.
  • Cabins: Nestled in nature, cabins offer a rustic escape for those wanting to unwind in the great outdoors, perfect for a serene vacation.**

Top attractions near Sherwood

Sherwood, Maryland, is a fantastic destination for outdoor enthusiasts, couples seeking romance, and culture lovers. With attractions like history museums, marinas, and urban parks, visitors can enjoy a variety of experiences that cater to families and those interested in local culture. Whether you’re exploring the scenic beauty or diving into the rich history, Sherwood promises memorable adventures for everyone.

  • Chesapeake Bay Maritime Museum: Located 6 miles from Sherwood, this maritime museum offers a deep dive into the rich maritime history of the Chesapeake Bay. With engaging exhibits and cultural vibes, visitors can explore historic boats, learn about local ecology, and enjoy beautiful waterfront views.
  • Tilghman Watermen’s Museum: Situated 4 miles away, this history museum celebrates the life and traditions of watermen in the Chesapeake Bay region. It provides an authentic glimpse into the area's fishing heritage and cultural influences.
  • Tilghman Island Marina: Just 3 miles from Sherwood, this marina is perfect for outdoor adventures. Enjoy boating, fishing, or simply relaxing by the water while soaking up the beach vibes and scenic surroundings.

Things to do recommended for couples

For a romantic getaway in Sherwood, enjoy the charm of St. Michaels Winery, just 5 miles away, for wine tasting. Indulge in relaxation at Talbot Massage, 14 miles away, or embark on an adventurous sailing experience with Annapolis Sailing School, located 16 miles from Sherwood.

Things to do recommended for families

Families visiting Sherwood can have a blast at the Chesapeake Beach Water Park, located 13 miles away. This waterpark offers thrilling slides and fun pools, providing a perfect day of adventure and entertainment for all ages.

Things to do recommended for groups

Explore the charming shops at Saint Michaels Village, enjoy a captivating show at the Avalon Theatre, and challenge your friends to a round of golf at Hog Neck Golf Course. These activities offer a perfect blend of shopping, culture, and outdoor fun for your group adventure in Sherwood.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Sherwood

When traveling with a group, family, or pets, or if you're seeking extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Sherwood with a group: Think about how many bedrooms you'll require and any additional features you might want, like a fully equipped kitchen or outdoor areas for group gatherings. The good news is that you can easily filter for all of these options and more on Vrbo.
  • Traveling to Sherwood with young kids: Traveling with young kids can be demanding. It's important to prioritize their comfort and safety, along with amenities suitable for their age, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Sherwood: For many families, a vacation wouldn’t be the same without their furry companions. If this resonates with you, take a look at Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and cozy beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Sherwood: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Sherwood

Experience the charm of Sherwood, Maryland, where outdoor adventures and romantic getaways await. Explore nearby neighborhoods filled with gorgeous homes and a friendly atmosphere perfect for families. With sunny weather and a rich history, you'll find plenty to enjoy in this relaxing destination. Don't miss the chance to visit nearby cities that offer a delightful blend of culture and business vibes, making your vacation truly memorable.

  • St. Michaels: Nestled about 5 miles from Sherwood, St. Michaels is a charming town that offers a delightful blend of outdoor and family experiences. Known for its picturesque waterfront, visitors can enjoy leisurely strolls along the boardwalk, explore recreational areas, and unwind at the local beach. The town's family-friendly atmosphere makes it perfect for those seeking both relaxation and adventure. Key attractions include the scenic lake, where boating and fishing are popular, along with various outdoor activities that highlight the natural beauty of the area.
  • Tilghman: Located 4 miles from Sherwood, Tilghman is a hidden gem for those looking to immerse themselves in nature's beauty. This tranquil town is perfect for outdoor enthusiasts and romantics alike, featuring stunning scenery and a welcoming community. Visitors can enjoy activities such as walking along the boardwalk or spending time at the beach, where the calm waters are ideal for family outings. The nearby lake also offers opportunities for fishing and kayaking, making it a versatile destination for any traveler seeking a peaceful retreat.
  • Bozman: Just 3 miles from Sherwood, Bozman is a quaint town that captures the essence of Maryland's scenic charm. Known for its beautiful landscapes and outdoor adventures, Bozman is a haven for those who appreciate nature. With access to recreational areas and a lovely boardwalk, visitors can enjoy a variety of outdoor activities. The nearby beach and lake provide a perfect backdrop for family fun, whether it be swimming, picnicking, or simply soaking in the serene atmosphere. Bozman is an ideal spot to unwind and reconnect with nature.

Best time to go to Sherwood

If you're planning a trip to Sherwood, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from March to May, while off-peak times, like February tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January36.3°F (2.4°C)Light RainMostly SunnyAverageSlightly Low
February38.8°F (3.8°C)Light RainMostly SunnyLowSlightly Low
March45.3°F (7.4°C)Light RainMostly SunnyHighSlightly Low
April55.6°F (13.1°C)Light RainMostly SunnyHighAverage
May64.6°F (18.1°C)Light RainMostly SunnyHighAverage
June73.4°F (23.0°C)Light RainMostly SunnyAverageSlightly High
July78.4°F (25.8°C)Light RainMostly SunnyAverageSlightly High
August76.8°F (24.9°C)Light RainMostly SunnyAverageSlightly High
September71.1°F (21.7°C)Light RainMostly SunnyAverageAverage
October61.0°F (16.1°C)Light RainMostly SunnyAverageAverage
November49.5°F (9.7°C)Light RainMostly SunnyAverageAverage
December42.3°F (5.7°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming vacation? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Save more with One Key

Reserve an eligible Vrbo for your group getaway and earn all the OneKeyCash from your booking. Being the planner definitely has its perks. By enrolling in our travel rewards program, OneKey, you can quickly access member discounts and earn as well as redeem OneKeyCash on qualifying bookings. Sign up today to start enjoying savings.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient way to plan new trips, pick up right where you left off, or manage and organize your travel plans. You can easily access properties you've previously saved or booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, just visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Travel to beautiful Sherwood

The island views and riverfront create a pretty picture of Sherwood. This scenic and welcoming city entices travelers with its sailing and restaurants. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Sherwood

Are you hoping to discover things to do while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Sherwood a fun spot to vacation. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • St. Michaels Winery (5.4 mi / 8.7 km)
  • Chesapeake Beach Water Park (12.6 mi / 20.3 km)
  • Paul Reed Smith Guitars (15.6 mi / 25.2 km)
  • Phillips Wharf Environmental Center (3.2 mi / 5.1 km)
  • Talbot Massage (13.8 mi / 22.1 km)
  • Easton Cycle and Sport (13.9 mi / 22.3 km)

Exploring the natural features in Sherwood

Whether you're looking for adventure or just want to appreciate the scenery, Sherwood is a great place to spend some time outside. Here are some of the area’s most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • Chesapeake Bay Environmental Center (13.8 mi / 22.2 km)
  • Northern Chesapeake Bay (14.1 mi / 22.7 km)
  • Breezy Point Beach (14.3 mi / 23 km)
  • Bay Ridge Beach (14.8 mi / 23.9 km)
  • Carrs Beach (15.6 mi / 25.2 km)
  • Maryland Quiet Waters Park (15.9 mi / 25.5 km)

Traveling to and around Sherwood

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 14.1 mi (22.7 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional), which is 52.1 mi (83.8 km) away.

Frequently asked questions

What is the best area to stay in Sherwood, Maryland, United States of America when booking a vacation rental?
When looking for the best area to stay in Sherwood, Maryland, you might consider the neighborhoods surrounding the picturesque waterfront. This area offers a charming blend of natural beauty and local attractions. The proximity to parks and nature trails makes it an ideal spot for outdoor enthusiasts. A popular point of interest nearby is the scenic waterfront, which provides opportunities for kayaking and fishing, making it a great choice for those who enjoy water activities.

Another top attraction is the local community parks, where families can enjoy picnics and sports. The Sherwood area typically has a selection of vacation rentals, ranging from cozy cottages to spacious homes, providing options for different group sizes and preferences. Staying in this vibrant neighborhood allows you to experience the warmth of the community while being close to nature and recreational activities.
How much does it cost to rent a vacation home in Sherwood?
Prices for vacation rentals in Sherwood vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Sherwood to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Sherwood vacation house rentals?
You can find great discounts on house rentals in Sherwood on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Sherwood?
For renting a beach house in Sherwood, Maryland, travelers should explore the nearby coastal areas along the Chesapeake Bay. The vicinity around Sandy Point State Park is particularly attractive, offering easy access to sandy beaches and scenic picnic areas. Many vacation rentals in this area feature amenities such as private decks, outdoor grills, and spacious living areas, providing a comfortable environment for families and groups looking to enjoy the bay's natural beauty.

Additionally, the community of Kent Island, just a short drive away, boasts a variety of waterfront properties that often come equipped with modern kitchens, boat docks, and access to community pools. This area is great for those who enjoy water activities such as kayaking or fishing, with many rentals offering direct access to the water and stunning sunset views.

Further along the bay, the towns of Deale and North Beach also provide excellent beach house options, with accommodations that often include outdoor spaces, fire pits, and proximity to local shops and dining. These beach towns offer a laid-back atmosphere, great for relaxing by the water or engaging in beachside activities.
What is the most popular type of vacation rental accomodation in Sherwood?
In Sherwood, vacation houses are the predominant type of rental accommodation, with several options available throughout the area. These homes typically feature spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups seeking comfort and convenience. Many of these rentals are situated in quiet neighborhoods, providing a relaxing environment while still being accessible to local attractions and outdoor activities.
Are there any family house rentals in Sherwood?
In Sherwood, Maryland, there are several family-friendly house rentals available, making it an excellent choice for those traveling with children. Visitors can find accommodations that offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces great for kids to play. Many properties also include amenities like air conditioning and Wi-Fi to ensure a comfortable stay.

This charming area is close to a variety of parks and recreational spots, providing opportunities for outdoor activities and family outings. The nearby neighborhoods have local attractions, giving families a chance to explore the community and enjoy the natural beauty of the region.
Can I rent a vacation home with a pool or hot tub in Sherwood?
In Sherwood, Maryland, there are several vacation homes available for rent that feature pools and hot tubs. This charming area provides a tranquil setting for travelers looking to unwind. Many of these rentals come equipped with private pools, outdoor seating areas, and hot tubs, ideal for relaxation after a day of exploring. Expect amenities such as fully equipped kitchens, spacious living areas, and sometimes even outdoor grills for entertaining.
Can I find long-stay vacation rentals in Sherwood?
A long-stay vacation rental in Sherwood is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any remote work vacation rentals in Sherwood?
In Sherwood, Maryland, there are several vacation rentals suitable for remote work. These properties often come equipped with dedicated office spaces, desks, and comfortable office chairs, ensuring a productive environment for those working remotely. High-speed Wi-Fi is typically available, allowing for seamless connectivity. Many rentals also feature additional amenities such as printers and comfortable living areas for relaxation after work hours. The peaceful residential setting of Sherwood provides a quiet backdrop for remote work, while also offering proximity to local parks and nature trails for outdoor breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Sherwood vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Sherwood with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Sherwood?
In Sherwood, Maryland, popular vacation rental amenities cater to travelers seeking comfort and convenience. Most rentals include fully equipped kitchens, allowing guests to prepare their own meals. Many properties also feature decks or patios, superb for enjoying the outdoors and taking in the peaceful surroundings. A fireplace is commonly found in these rentals, providing a cozy atmosphere during cooler evenings. Additionally, private pools are available in several properties, offering a refreshing retreat during warmer months. Many rentals also come with a coffee and tea maker, ensuring guests can enjoy their favorite beverages at any time.
How early should I book a Sherwood vacation rental?
Book your Sherwood vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Sherwood, Maryland, United States of America?
In Sherwood, Maryland, visitors can enjoy a variety of attractions that highlight the area's natural beauty and community spirit. The nearby Patuxent River offers opportunities for kayaking and fishing, making it a popular spot for outdoor enthusiasts. The scenic trails around the river are superb for hiking and biking, providing a great way to experience the local flora and fauna.

For those looking to explore local culture, the nearby town of Columbia features a vibrant arts scene, including galleries and theaters. The Merriweather Post Pavilion, an outdoor concert venue, hosts a range of musical performances throughout the year, attracting both locals and visitors alike.

Additionally, Sherwood is conveniently located near several parks, such as Blandair Regional Park, which offers playgrounds, sports fields, and picnic areas, making it an ideal spot for families.
Can I change or cancel my Sherwood home rental booking on Vrbo?
To find Sherwood vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Sherwood vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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