Sherwood holiday lettings

We found 190 holiday rentals — enter your dates for availability

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

Holiday rentals with weekly discounts - Sherwood

Showing deals for:13 Mar - 20 Mar

Image gallery for Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

House and Garage as seen from above (pool on left)
10 out of 10, Exceptional, (90 reviews)
Exceptional
(90 reviews)

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

Royal Oak, MD

8% off
Price is £11,309
for 7 nights, 1 home
£1,616 per night
includes taxes & fees
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

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Why visit Sherwood

  • Outdoor Adventures: Enjoy a range of activities in Sherwood Forest, perfect for nature lovers and thrill-seekers alike.
  • Cultural Experiences: Visit the intriguing history museum to learn about the local heritage and culture.
  • Scenic Marina: Relax and unwind at the marina, offering picturesque views and leisurely strolls.
  • Family-Friendly Atmosphere: Explore charming neighbourhoods that cater to families, providing a welcoming environment.
  • Charming Accommodation: Choose from delightful cottages or private holiday homes for a cosy retreat.

Popular types of accommodation in Sherwood

Looking for the perfect getaway in Sherwood? You’re in the right place! Our top accommodation options include charming houses, delightful cottages, and modern apartments. Whether you fancy a cosy lodge or a picturesque holiday cottage in Sherwood Forest, we have something for everyone. Explore our range of Sherwood Forest holiday rentals and find the ideal base for your adventures, all with the transparency and reassurance you deserve.

  • Houses: The top choice for visitors in Sherwood, offering spacious and comfortable stays ideal for families or groups.
  • Cottages: A delightful option for those seeking a quaint and charming retreat amidst beautiful surroundings.
  • Apartments: Convenient and versatile, these rentals provide a home-away-from-home experience in the heart of Sherwood.
  • Condos: Perfect for those who prefer modern amenities and shared facilities, ideal for a hassle-free getaway.
  • Cabins: A rustic escape for nature enthusiasts, combining comfort with a touch of adventure.**

Top attractions near Sherwood

Sherwood, Maryland, offers a delightful blend of outdoor adventures and cultural experiences, perfect for a romantic getaway or family holiday. Visitors can explore the intriguing history museum, unwind at the marina, or enjoy leisurely strolls in the urban park. Don't miss the chance to visit Sherwood Forest and its fun park, where outdoor activities abound, making it an ideal destination for those seeking both relaxation and adventure.

  • Chesapeake Bay Maritime Museum: This captivating maritime museum, located 3.7km from Sherwood, immerses you in the rich maritime heritage of the Chesapeake Bay, featuring exhibits on boat building and regional history, all set against scenic waterfront views.
  • Tilghman Watermen’s Museum: Situated 2.5km away, this history museum offers a unique glimpse into the lives of local watermen, showcasing their traditions and the vital role they play in the community's culture and economy.
  • Phillips Wharf Environmental Center: Just 1.9km from Sherwood, this eco-friendly centre provides enlightening experiences on marine life and conservation, promoting sustainability and environmental awareness through interactive exhibits and educational programmes.

Things to do recommended for couples

Planning a romantic getaway in Sherwood? Embrace the charm of St. Michaels Winery for a delightful tasting, unwind at Talbot Massage for some soothing relaxation, or embark on an exhilarating adventure with Annapolis Sailing School. Each experience promises to create lasting memories together.

Things to do recommended for families

Your family will delight in a visit to Chesapeake Beach Water Park, a fantastic waterpark located 8.1km from Sherwood. With thrilling slides and fun-filled attractions, it offers the perfect blend of entertainment and adventure for all ages.

Things to do recommended for groups

Groups visiting Sherwood can enjoy a delightful evening at the Avalon Theatre, indulge in a round of golf at Hog Neck Golf Course, or explore the Bay Bridge Market Place Shopping Centre for a mix of shopping and entertainment, all within a short drive.

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

If you’re travelling with a group, as a family, bringing your pets along, or seeking extended stays, ensure you filter your options according to your key priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Sherwood with a group: Think about how many bedrooms you require, as well as features like a fully-equipped kitchen or outdoor areas for group gatherings. Thankfully, you can refine your search for all these options and more on Vrbo.
  • Traveling to Sherwood with young kids: Journeying with young children can present its own set of challenges. It's essential to prioritise their comfort and safety, along with ensuring access to suitable amenities like a private swimming pool. Additionally, it's wise to take into account your closeness to family-friendly attractions.
  • Taking your pets with you to Sherwood: For many families, a holiday isn’t truly complete without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Sherwood: If you're seeking holiday rentals with offers for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include features like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Sherwood

Sherwood, Maryland, offers a delightful blend of outdoor adventures and romantic getaways, perfect for those seeking a cultural retreat. Explore the enchanting Sherwood Forest, where you can indulge in forest holidays and discover the charm of a tranquil escape. Nearby, you’ll find family-friendly neighbourhoods that provide a relaxing atmosphere, ideal for sunny days. Whether you're on a holiday or a short getaway, Sherwood promises memorable experiences amidst its scenic beauty and friendly locals.

  • St. Michaels: Located 3.1km from Sherwood, St. Michaels is a charming town renowned for its outdoor and romantic offerings, making it a perfect getaway for families and couples alike. The picturesque waterfront features a delightful boardwalk and recreational areas where visitors can enjoy leisurely strolls. St. Michaels is also home to beautiful beaches and serene lakes, providing ample opportunities for water activities and relaxation. The local dining scene is vibrant, with several restaurants offering fresh seafood and stunning views of the Chesapeake Bay.
  • Tilghman: Situated 2.5km from Sherwood, Tilghman is a quaint town that captivates visitors with its stunning scenery and outdoor experiences. The area is ideal for those seeking romantic escapes or family adventures. Explore the scenic boardwalk and recreational spaces, where you can engage in various outdoor activities. Nearby beaches and tranquil lakes serve as perfect spots for a family day out or a leisurely afternoon by the water, making Tilghman a delightful destination for nature lovers.
  • Bozman: Just 1.9km from Sherwood, Bozman is a tranquil town that offers a scenic retreat for outdoor enthusiasts and romantics. With its access to recreational areas and inviting boardwalks, it's an ideal location for leisurely exploration. The beautiful local beaches and shimmering lakes are perfect for a day of fun in the sun or a peaceful picnic. Visitors can immerse themselves in the natural beauty of the area while enjoying a relaxed atmosphere that encourages unwinding and reconnecting 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 a breeze

Are you keen to save on your upcoming trip? Being flexible with your travel dates can really pay off, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To help you discover the perfect Vrbo property that fits your budget, make use of our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient platform to plan new getaways, pick up right where you left off, or manage and organise your travel arrangements. You can easily locate properties you’ve saved and booked in the sections for Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Travel to scenic Sherwood

The island views and riverfront create a pretty picture of Sherwood. This scenic and welcoming city entices travellers with its sailing and restaurants. A holiday 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 searching for attractions to visit while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Sherwood has to offer. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • St. Michaels Winery (5.4 mi / 8.7 km)
  • Chesapeake Beach Water Park (12.6 mi / 20.3 km)
  • Phillips Wharf Environmental Center (3.2 mi / 5.1 km)
  • Hog Neck Golf Course (14.8 mi / 23.8 km)
  • Paul Reed Smith Guitars (15.6 mi / 25.2 km)
  • Talbot Massage (13.8 mi / 22.1 km)

Exploring the natural features in Sherwood

Whether you're looking for adventure or just want to take in the scenery, Sherwood is a great spot to appreciate mother nature. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Shadyside Park (12.1 mi / 19.5 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)
  • Maryland Quiet Waters Park (15.9 mi / 25.5 km)
  • Romancoke Wharf County Park (8.3 mi / 13.3 km)

Travelling to and around Sherwood

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 14.1 mi (22.7 km) from the city centre. If you can't find a flight that's convenient for your trip, 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 when booking a holiday rental?
When considering a holiday rental in Sherwood, Maryland, a popular area to stay in is the neighbourhood of Glenmont. This charming community is well-positioned for visitors who wish to explore both the natural beauty and cultural attractions of the region. Glenmont is not only family-friendly but also offers a variety of rental properties, making it a convenient base for your holiday.

One of the top attractions nearby is the Wheaton Regional Park, which features sprawling green spaces, walking trails, and the beautiful Brookside Gardens. This park is superb for a leisurely afternoon picnic or a scenic stroll among vibrant floral displays. Additionally, the nearby National Capital Trolley Museum provides a unique glimpse into the history of transportation in the area, making it a delightful outing for families and history enthusiasts alike.

Another excellent area to consider is the community of Silver Spring, which boasts a vibrant blend of urban and suburban living. Silver Spring is known for its lively downtown area, rich with shops, restaurants, and entertainment options. The AFI Silver Theatre and Cultural Centre is a must-visit for film lovers, showcasing both classic and contemporary films in a historic setting. With a range of properties available, Silver Spring offers an exciting atmosphere while still being close to the tranquil landscapes of Sherwood.
How much does it cost to rent a holiday home in Sherwood?
Prices for holiday 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 holiday 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, the nearby Chesapeake Bay area provides excellent options. One of the most appealing spots is around the extensive shoreline of Sandy Point State Park, where holiday rentals often boast spectacular views of the bay and direct access to sandy beaches. Many properties in this area come with amenities such as spacious decks for outdoor dining, private piers for fishing or boating, and fully equipped kitchens ideal for self-catering.

Further along the bay, the community of Cape St. Claire features charming waterfront homes, some with private beach access and amenities like fire pits and outdoor showers. This neighbourhood is known for its family-friendly atmosphere, with local parks and playgrounds, making it a great choice for those travelling with children.
What is the most popular type of holiday rental accomodation in Sherwood?
In Sherwood, holiday houses and cottages are the most popular types of rental accommodation, with several options available throughout the area. These properties typically offer a homely atmosphere, with amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces for relaxing. Many of the holiday houses feature multiple bedrooms, making them ideal for families or groups. Cottages, on the other hand, often provide a charming, rustic vibe and can include features like fireplaces and gardens.
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 travelling with children. This area offers spacious homes with amenities that cater to families, such as fully equipped kitchens for preparing meals together, ample living spaces for relaxation, and outdoor areas where kids can play safely.
Can I rent a holiday home with a pool or hot tub in Sherwood?
In Sherwood, Maryland, there are several holiday homes available for rent that feature pools and hot tubs, making it an appealing option for travellers seeking relaxation and leisure. The area offers a blend of suburban charm and proximity to outdoor activities, with many properties located in quiet neighbourhoods that provide a serene retreat.
Can I find long-stay holiday rentals in Sherwood?
A long-stay holiday rental in Sherwood is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Sherwood?
In Sherwood, Maryland, there are several pet-friendly house rentals available for travellers looking to enjoy a comfortable stay with their furry companions. Many of these properties offer amenities such as spacious backyards, allowing pets to roam freely, as well as fully equipped kitchens and comfortable living areas for relaxation after a day of exploring the area.
Are there any remote work holiday rentals in Sherwood?
In Sherwood, Maryland, there are several remote work-friendly holiday rentals available, making it a suitable destination for those looking to blend work and leisure. Many of these properties come equipped with essential amenities for remote work, such as dedicated office spaces, comfortable desk chairs, and reliable Wi-Fi, ensuring a productive environment. Additionally, some rentals may offer features like computer monitors and quiet settings that are ideal for concentration. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Sherwood holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Sherwood with parking available—perfect for families or travellers 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, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals with ease. Many properties feature dishwashers and microwaves for added convenience, making post-meal clean-up and quick snacks straightforward. Additionally, most rentals come with outdoor patios, providing a pleasant space for guests to enjoy the fresh air and relax. Coffee makers are also commonly found in the accommodations, ensuring that travellers can start their day with a freshly brewed cup.
When is the best time to visit Sherwood for a holiday rental?
March marks the beginning of the peak season in Sherwood, attracting visitors eager to experience the charm of this quaint Maryland town. From March to May, you can immerse yourself in the vibrant local culture, enjoy blossoming landscapes, and partake in various outdoor activities as the weather warms up.

During this period, average temperatures in March hover around the mid-teens Celsius, creating a pleasant environment for exploring the picturesque surroundings. Whether you're wandering through the scenic parks or enjoying leisurely strolls along the waterfront, the mild climate makes it an ideal time for outdoor adventures and sightseeing.

If you're looking for a more budget-friendly option, consider planning your visit in February. This month offers the tranquillity of fewer tourists while still allowing you to appreciate the serene beauty of Sherwood. You might find delightful local events and hidden gems that are less crowded and more intimate.
How early should I book a Sherwood holiday rental?
Book your Sherwood holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Sherwood home rental booking on Vrbo?
To find Sherwood holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, 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 organising 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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